Angelo's calling card
The Triple A Foundation
Three things that underpin everything else. Before pipeline reviews, before frameworks, before tactics, this is the standard every rep and every manager is held to. This foundation was born from a moment when a team was underperforming and needed something to rebuild from. The sales team needed an emergency roadside vehicle, and the Triple A foundation was exactly that. It also works proactively, as assurance that you never find yourself stranded again.
The one thing you always control
The attitude you present is felt by your prospects and your peers. Having awareness of the attitude that you possess is a super power.
The numbers game is real
When you're not in a meeting, you're trying to get one or move the pipeline forward. Revenue generating activity is the priority.
Own everything in your circle
Yourself. Your prospects. Your peers. It's a skill, not assumed, developed.
First A
Attitude: the one thing you always control
Sales puts so much outside your control. The prospect's timing, the budget cycle, the competitor who just lowered their price, the deal that fell apart on a Friday afternoon. You can't control any of that. But your attitude? That's entirely yours. And it's contagious, in both directions. A leader who brings it every day, no matter what, gives the team permission to do the same.
"No matter how many obstacles you face, showing up consistently with a positive attitude helps you to drive the team forward and work through issues together. That example will ultimately become your team identity."
This is where emotional intelligence lives. High EQ is what lets you feel the frustration, and still show up right. It's not about being happy all the time. It's about being present, regulated, and consistent. That's what the team reads every single day.
EQ in practice: the four capabilities
Self-awareness
Know your own mindset
Before you walk into a coaching session: what are you carrying? Name it. Don't bring it in unchecked.
Self-regulation
Respond, don't react
A rep has a bad attitude. A deal blows up. How you respond in that moment is the standard the team internalizes.
Empathy
Understand before you solve
The person in front of you has a context you don't fully see. Slow down. Ask. Listen for what's underneath.
Social awareness
Read the room
Energy in a team meeting, tension between two reps, a prospect who says yes and means no, high EQ picks this up.
Attitude standards
- Come with a good attitude: non-negotiable, and it applies to the manager first
- Handle adversity in front of the team the way you want them to handle it
- Call negativity out early: a bad attitude is a behavior, and behaviors define culture
- If someone's attitude shifts, ask what's driving it before you address the symptom
- If you're struggling, communicate it, don't let it become the team's burden
Second A
Activity: the numbers game is real
There is no shortcut here. Sales is a volume game with a skill multiplier. The skill multiplier matters, but you need the volume first. When you're not in a meeting, you should be trying to get one or moving a deal forward. Not admin. Not prospecting ADD. Not circling back on someone once and calling it follow-up. The job.
"When you're not in a meeting, you're trying to get another meeting or move your pipeline forward."
As a manager, your job isn't to be the most active person on the team, it's to create an environment where activity is the standard, not the exception. That means protecting money hours, making KPIs visible, and having the conversation early when volume dips instead of waiting for the month-end miss.
Activity standards
- Protect Monday: it's 20% of the sales week. Nothing interrupts it.
- Calls first, paperwork last, every single day.
- 10 calls before 10 AM. This sets the foundation for 50 calls per week, no matter what comes your way.
- One extra call a day = 200 additional opportunities a year, teach your reps this math
- Make KPIs visible to the full team: transparency creates the right kind of pressure
- "I've been really busy": busy doing what? Always the follow-up question.
Activity diagnostic: when numbers are down
- "Walk me through your last three days, hour by hour." You'll find the leak in five minutes.
- "What time of day do you feel sharpest?" Use that window for outreach, not admin.
- "How many times have you followed up on your last 10 prospects?" One touch is not a pipeline.
- "What's eating the most time right now?" Then decide together if that's the right thing.
Third A
Accountability: own everything in your circle
Accountability isn't just holding your reps to their numbers. It's three-directional: holding yourself accountable to your commitments as a manager, holding your prospects accountable to the process they agreed to, and holding your peers accountable to the standards the team built together.
"Whether holding yourself accountable, your prospects accountable, or your peers accountable, it's an important skill set to develop and do effectively."
The hardest part is it has to start with you. A manager who misses their own commitments loses the right to hold their team to theirs. Own your results first. Then hold the standard.
1
Holding yourself accountable
Did you do the 1:1s you committed to? Send the follow-up you said you would? Have the hard conversation instead of delaying it? Own your miss before you address anyone else's.
2
Holding your prospects accountable
A deal without a dated next step is a wish, not a pipeline. Clear next steps and specific close dates are how you hold the prospect to the process they agreed to, not by being pushy, by being clear.
3
Holding your peers accountable
Letting a teammate's bad attitude or low activity slide tells the team the standard is negotiable. It isn't. Call it early, directly, and privately first.
Accountability in the coaching session
- Every session ends with a written commitment: what will they do and by when?
- The next session opens by revisiting that commitment, no exceptions
- If they didn't follow through, that's the first conversation before any new content
- Own your role in the miss, "What could I have done to set you up better?"
At a glance
A
Attitude: the one thing you always control
High EQ. Consistent. Contagious. How you show up sets the standard for how the team shows up.
A
Activity: the numbers game is real
When you're not in a meeting, you're trying to get one. Protect money hours. Make volume visible.
A
Accountability: own everything in your circle
Yourself. Your prospects. Your peers. It starts with you, and it applies in all three directions.
The operator behind the playbook
Angelo R. Frangiosa
There is a pattern to his career. He joins organizations at an inflection point, a team that's underperforming, a company scaling faster than its infrastructure can support, a market that needs someone who can build the system and coach the people at the same time. He does not inherit finished things. He builds them. Then they grow.
"My goal is predictable sales, not hero sales. Build the system, coach the people, run the process. Then the wins stop being lucky and start being expected."
The arc
The Leyton build
The operator's edge
By the numbers
The person
The pattern: what he walks into, and what he leaves behind
At Staples, he was a top-performing individual contributor, back-to-back President's Club, largest customer acquired in the Boston Metro territory two years running. When he was promoted to Area Sales Manager, he inherited a team that was underperforming and demoralized. Within his first year, they were a top New England team. Within three years, they were at 150% of annual revenue targets. The team didn't change, the structure around them did.
At Leyton, the mandate was bigger. He was recruited as the first outside sales manager and 40th US employee into a company with real ambition and almost no sales infrastructure to support it. The product was strong. The market opportunity was clear. What was missing was the system, the process, the people framework, the technology, the operating rhythm that turns individual effort into scalable, predictable revenue. He built all of it. In under 26 months he was Head of Sales. In under five years the organization went from $7M to $42M.
At IANS Research, he stepped back into a frontline leader role to lead their SMB segment. The goal was to prove the playbook was replicable, and that a great operator can also execute. 244% of ARR goal in Q1. 173% in Q2. Ranked 2nd across the entire sales organization for 2025. 2025 President's Club at 113% ARR. The same principles. The same discipline. Different seat.
What every chapter has in common
1
He joins before the structure exists
Not after the playbook is written: before it. The value he adds isn't executing someone else's system. It's building the system that didn't exist, in the time frame the business needs it, without losing the people in the process.
2
He scales through people, not in spite of them
The $7M-to-$42M growth at Leyton wasn't driven by headcount alone. It was driven by raising the floor of what every rep on the team was capable of, through coaching, structure, incentive design, and a culture built around Attitude, Activity, and Accountability.
3
He connects data to behavior before he connects behavior to outcomes
Most sales leaders manage to the number. He manages to the behaviors that produce the number, and builds the infrastructure that makes those behaviors visible, measurable, and coachable at scale. That's the difference between a sales manager and a revenue architect.
Leyton USA: building a sales organization during rapid growth
Leyton is a global innovation funding consultancy: a highly technical, complex sale into mid-market and enterprise companies. When Angelo joined in January 2020 as the 40th US employee and first outside sales hire, the US business was doing approximately $7M in revenue. There was no formal sales process. No tech stack. No RevOps function. No commission plan architecture. No performance framework. Just a team with strong subject matter expertise and a market that was ready to buy, if someone could build the machine to reach it.
He started as Senior Sales Manager with six Account Executives on a new business team. Within his first full fiscal year he delivered a 50% increase in sales. Within his first quarter he was appointed to the Senior Leadership Team. Within 26 months he was Head of Sales, overseeing 10 direct reports across sales leadership, ICs, and revenue operations, and directing a 150-person organization spanning the US, Canada, France, and Morocco.
By the time he left in January 2025, the business was at $42M, a 6x expansion, with four new product lines launched, a fully operational RevOps function that had never existed before, and a sales culture built on the same Triple A foundation that anchors this playbook.
What he built at Leyton: the infrastructure layer
1
Founded the first Revenue Operations function in the company's 25-year history
Before RevOps existed, performance visibility was reactive, leadership found out about problems after they became problems. He built the function from the ground up: oversaw the full US sales tech stack, implemented Salesloft as the primary automation platform, built Salesforce workflows in collaboration with global teams in Casablanca, and introduced companywide KPI tracking that gave leadership real-time performance data for the first time.
2
Redesigned incentive architecture to connect motivation to behavior
Designed, modeled, and maintained all US sales commission plans in Captivate IQ. Rebuilt the new business bonus structure to reward the behaviors that produce results, not just the results themselves. Established the company's first President's Club program to create aspirational targets and recognize top performers.
3
Built the people framework that scaled with the org
Formalized performance management standards and career pathing frameworks across all sales roles. Built the coaching infrastructure, the 1:1 system, the competency framework, the onboarding ramp, that allowed the team to grow without losing consistency. The playbook you're reading is the distillation of what was built and refined across that five-year period.
4
Launched four new product lines during peak growth
Each new product required a new sales motion, new training, and new positioning, all while the core business was scaling. He built the enablement infrastructure that allowed the team to hold multiple complex products simultaneously without losing discipline or conversion quality.
"You don't scale from $7M to $42M by working harder. You scale by building the system that makes the right behaviors repeatable, across 150 people, in 4 countries, with 4 different products."
The operator's edge: where most sales leaders stop short
Most sales leaders can coach. Fewer can build the system underneath the coaching. The rarest are the ones who can do both simultaneously, who can develop individual reps and rebuild organizational infrastructure in the same quarter, without losing either.
The differentiator in Angelo's career has consistently been the ability to connect data to performance, not just reading dashboards but designing the infrastructure that makes the right behaviors visible, measurable, and repeatable before leadership even knows to ask for it.
What that looks like in practice
1
Revenue Operations & forecasting infrastructure
Built Leyton's first RevOps function from scratch. Implemented Salesloft. Built Salesforce workflows with global teams. Introduced the companywide KPI tracking that created real-time performance visibility for the first time in the company's history. At IANS: built performance visibility frameworks across Outreach, Sales Navigator, Copilot, ZoomInfo, and Salesforce.
2
Commission plan architecture
Designed, modeled, and maintained all US commission plans in Captivate IQ at Leyton. Rebuilt the bonus structure to connect incentives to behaviors, not just outcomes. The principle: if the plan rewards the right activity, the right outcomes follow. If it only rewards outcomes, you get shortcuts.
3
AI-driven sales innovation
Spearheading IANS's company-wide AI initiative: deploying Claude and Microsoft Copilot to drive outbound production efficiency, accelerate pipeline generation, and increase revenue output. Leading the AI development program across the new business team. This isn't a side project. It's a core operating belief: the sales organizations that build AI into their workflow in the next 24 months will have a structural advantage that is very difficult to close.
4
GTM strategy & new business development
Architected and executed GTM strategy across multiple segments, products, and market conditions. Launched four new product lines at Leyton. Built the Channel Sales Initiative and sales playbook development program at IANS. The throughline: a structured approach to market entry that doesn't rely on heroics, it relies on process, positioning, and people who know exactly what they're building toward.
Core competencies
VP-Level Sales Leadership · Revenue Operations & Forecasting · GTM Strategy & Execution · Commission Plan Architecture · Team Building, Coaching & Mentorship · AI-Driven Sales Innovation · Pipeline Management & Acceleration · Sales Forecasting & Data Analysis · Sandler & Challenger Methodologies · Salesforce · Salesloft · Outreach · ZoomInfo · Copilot
The proof points: impact in numbers
| Organization | Starting condition | Result |
Leyton USA Head of Sales | $7M ARR · No RevOps · No tech stack · No commission framework · No performance infrastructure | $42M ARR · 6x revenue expansion · 150-person org · 4 countries · 4 product lines · First RevOps function in 25-year history |
Leyton USA Sr. Sales Manager | First outside sales hire · 6-person new business team · No formal process | 50% revenue increase in first full fiscal year · Sr. Leadership team in first quarter · Promoted to Head of Sales in 26 months |
Staples Advantage Area Sales Manager | Inherited underperforming team · SE Massachusetts & Rhode Island territory | Top New England team within year 1 · 150% of annual revenue targets within 3 years · Back-to-back President's Club |
IANS Research Regional Sales Director | Inaugural year of territory segmentation · New business SMB | 244% ARR Q1 · 173% ARR Q2 · Ranked 2nd org-wide for 2025 · 2025 President's Club at 113% ARR |
"Every number on that table came from the same place, a clear system, consistently run, by people who understood what they were building toward and why it mattered."
He leads with personal before professional: on purpose
You can't coach someone you don't trust, and you can't earn trust without being real first. So before the frameworks and the numbers: he's married, lives in Walpole, has a three-year-old daughter named Cameron Mary and a red lab named Lucky. He grew up in Norwood. He's been a Patriots season ticket holder for over twenty years. He is motivated by recognition, competition, money, and seeing the people around him succeed, in that order of honesty.
The work ethic is inherited, not manufactured. His father owned a residential masonry company and worked in the field from age 20 to 80. Angelo worked alongside him for over a decade. His father was the son of Italian immigrants who came to the US just before the Great Depression and spent their entire lives in Massachusetts. There was no trust fund, no safety net, no plan B. There was just the work, and the standard that came with it.
That's the foundation underneath everything in this playbook. Not a methodology borrowed from a business school case study, a standard that was lived in before it was ever taught.
What drives him as a leader
1
Family first, and giving the team the same permission
Everything is built on a foundation. His is Cameron Mary and the standard set by the men who came before him. The drive to provide a good life for his family and to model what hard work looks like for his daughter is what gets him up early and keeps him sharp. He carries that perspective into how he leads, because a manager who understands what people are actually working for creates an environment where the team can bring their whole motivation to the job, not just their quota.
2
Seeing the team succeed
"My goal is to help each of you make as much money as possible in your current role, and prepare you for the next step." That's not a recruiting line. It's the actual measure. When a rep he developed gets promoted, or closes their first enterprise deal, or finally cracks the discovery conversation they've been working on, that is the win. More than any personal quota.
3
Building something that outlasts him
The goal of servant leadership is to make yourself unnecessary. The best version of any team he's ever run is the one that performs at a high level whether or not he's in the room. That's the measure he holds himself to, not whether people need him, but whether they're equipped.
4
The bigger picture over the individual scoreboard
No matter the role, the motivation has always been to contribute to the advancement of the entire organization, not just his team's number. That bigger-picture mindset drives strategy, drives cross-functional relationships, and is the reason this playbook exists: so that what was built across 15 years doesn't stay in one place.
Philosophy
Management tenants
These go on the table on day one. Not because they sound good, because they define the relationship before the work starts. You can't hold people accountable to a standard they never agreed to.
1
Ownership
Own your results. Own your attitude. Own your business. No excuses, but also no silence. If something isn't working, say so.
2
Challenge: but back it up
Challenge me. Challenge your prospects. But be ready to back any challenge with a reason. Pushback without reasoning is just noise.
3
Consistent, open, honest communication
Not just when things are good. Not just in 1:1s. All the time, in both directions. If you're going to be late, just let me know.
"I will never ask you to do anything I haven't done myself or wouldn't do myself."
Week 1 goals: with any new team
- Get to know everyone on a personal level before anything professional
- Establish a team identity: start with a team name
- Invite me to anything and everything, I want to hear what's happening out there
- Set expectations clearly: for them and for me
- Plan the team outing
Foundations
The IC-to-leader shift
This is the biggest jump you will likely make in your sales career. Everything that made you successful as an individual contributor, your instincts, your drive, your way of doing things, now has to be redirected toward making other people successful. That's not a small adjustment. For most people, it's a complete identity rebuild. The ones who make it cleanly are the ones who see it coming.
"You were a top performer. You got promoted because you could sell. Now your job is to build people who can sell, not to sell for them. The sooner you accept that your number lives inside theirs, the sooner you become a real leader."
The identity shift
Peer to boss overnight
Not everyone is you
The player-coach trap
Early warning signs
Your scoreboard just changed: and that's disorienting
As an IC, your identity was tied to your number. You knew every morning whether you were winning or losing. The feedback loop was immediate, a call booked, a deal closed, a quota hit. That certainty felt like control. As a leader, that's gone. Your results now live in other people's behaviors, and the feedback loop is slower, murkier, and far less satisfying in the short term.
Most new managers don't fully reckon with this. They miss the immediate gratification of the close. They get antsy in months where the team is underperforming. They start second-guessing whether they made the right call. What's actually happening is an identity adjustment, one that takes longer than most leadership books will tell you.
Give yourself that adjustment period. And be honest with yourself when you're acting out of personal ego, wanting to be the one who closes the deal, wanting to be seen as the smartest person in the room, versus acting in the best interest of your reps' development.
What success looks like now: redefine it early
1
Your win is their win
A rep who closes their first big deal because you coached them through it is worth more to you than a deal you closed yourself. One builds a rep. The other builds your ego. Know the difference, and choose the rep every time.
2
Your number is the team's number
You don't have a quota anymore. You have a team quota. That means five or ten individual journeys, each with different timelines, different challenges, and different ceilings. Your job is to raise all of them, not to substitute for them.
3
Your development goal is building leaders, not staying sharp as a seller
The skills that got you promoted: cold calling, closing, handling objections, are no longer your core job. Your core job is coaching, developing, removing friction, and building the environment where others can do those things at a high level.
"The hardest part of the IC-to-leader shift isn't the tactical stuff, it's watching someone struggle with something you could fix in 30 seconds and choosing to coach them through it instead. That restraint is the job."
Yesterday you were their peer. Today you can fire them.
This is the part that doesn't get talked about enough. The people you were sitting next to last week, going to lunch with, venting to, competing against, now report to you. You now carry authority over their livelihood in a way you never did before. That shift is real, and it changes every relationship on the team whether you acknowledge it or not.
Some peers will be genuinely happy for you. Some will be silently resentful. Some will test the boundaries, shrugging off assigned tasks, treating you like a peer in team meetings, coming to you with complaints about the company expecting you to commiserate the way you used to. You can't play that role anymore. It's not personal. It's structural.
The authority that comes with the title is not something you asked for, but it's something you have to own. Whether you like it or not, in the eyes of your team, you are now the person who has the ability to end their employment with your company. That is a heavy burden, and being aware of it changes how you show up, how you communicate, and how you earn trust. Pretending it doesn't exist doesn't make the team more comfortable. It makes you less effective.
How to handle the transition with former peers
1
Address it directly and early
Don't wait for awkwardness to accumulate. In your first 1:1 with each person on the team, acknowledge it: "I know this is a transition for both of us. I want to be your biggest advocate. I also need you to know my job has changed, and that means some things about our dynamic will too." Said once, clearly. Then move forward.
2
Don't try to be everyone's friend
You can be warm, approachable, and human: and still be their manager. The leaders who try to be the buddy first and the boss second lose credibility the first time they have a hard conversation. You can care deeply about the people on your team without needing them to like you at every moment.
3
Apply the standard consistently: no exceptions for former peers
If you hold one person to a different standard than another because of history, it will be noticed by everyone else on the team immediately. Consistency is the foundation of credibility. Former friends get the same standard as everyone else, and they'll respect you more for it in the long run.
4
Expect some relationships to change: and let them
Not everyone who was your peer will become a seamless direct report. Some friendships will cool. Some will deepen. Some will end professionally. That's not failure, that's the cost of taking on leadership. The reps who earn your respect over time are usually different from the ones you were closest to as a peer.
Not everyone is wired like you: and that's not a problem to fix
You were likely promoted because you were intrinsically motivated. You didn't need a manager to push you. You tracked your own numbers. You came in early, stayed late, and outworked the room because that's just how you're built. That's great. It also means you have almost no frame of reference for how the other half of your team experiences this job.
Here's the reality, not everyone on your team will care about the job the way you did. Some will. Most won't, at least not in the same way. Some are motivated by money and nothing else. Some want recognition more than they want to win. Some are coasting until the next thing. Some need structure before they can perform. Some are terrified of rejection in a way that never occurred to you.
None of that makes them bad reps. It makes them different from you. Your job is not to replicate yourself across the team, it's to understand what each person needs in order to perform at their ceiling. That requires patience, curiosity, and a willingness to coach people in a way that works for them, not just a way that would have worked for you.
The individual motivational lever: how to find it and use it
1
Ask directly, "What motivates you?"
Most reps have never been asked this question directly. Do it in the first 1:1. Then listen for what lights them up, not the polished answer. The rep who talks about their mortgage, their kid's school, and their commission tracker is telling you something different than the one who talks about being recognized as the best on the team. Both are right. Both need something different from you.
2
Watch behavior, not just words
A rep who says they're motivated by growth but never asks a development question is telling you something. A rep who says they don't care about recognition but lights up when you call them out in a team meeting is telling you something. What people do consistently is more honest than what they say they want.
3
Tie every coaching conversation to their specific motivator
For the money-motivated rep: "One extra discovery meeting a week over a quarter is roughly X in commission." For the recognition-motivated rep: "If you hit this, I'm calling you out in the next all-hands by name." For the advancement-motivated rep: "This is exactly the kind of result we'd point to when we talk about your next step." Same coaching. Different framing. Completely different impact.
4
Revisit it, motivators change
What drives a rep in their first six months is often different from what drives them at 18 months. Life changes, goals shift, and people outgrow what used to work. The motivation check-in isn't a one-time exercise, it's a quarterly conversation.
"The mistake most new managers make is coaching the way they would have wanted to be coached. Your job isn't to lead people the way you would have wanted to be led. It's to lead them the way they actually need to be led."
The player-coach trap: the most common failure mode for new managers
You're in a stalled deal meeting. The rep is fumbling the discovery questions. You can feel the prospect losing interest. Every instinct in your body is telling you to take over, because you know exactly what to say, you've been here a hundred times, and you could close this in ten minutes. So you do. You jump in, you save the deal, the rep looks at you with a mix of gratitude and relief, and you both leave feeling good.
Here's what actually happened: you coached the rep that they can't handle it. You removed an opportunity for real learning from real pressure. You positioned yourself as the closer instead of the developer. And the next time they're in a tough moment, they're going to look at you and wait to be rescued instead of finding their own way through.
The player-coach trap feels like helping. It is, in the short term. In the long term it creates dependency, stalls development, and means your team can only perform when you're in the room. That's not a team. That's a territory you're running yourself with extra steps.
How to avoid it
1
Pre-brief, don't co-pilot
Before any call you're joining, tell the rep exactly what you're there to do: "I'm observing today. You're running the call. After, we'll debrief on one thing." Then hold to it. Your job is to watch, not to talk. The harder it is to stay quiet, the more the rep needs the practice, not the rescue.
2
Use a hard signal for the exception
Pre-agree with the rep on one signal: a word, a phrase, a look, that means "I'm stepping in now and you're handing the wheel." Use it sparingly. When you do use it, debrief why immediately after. The signal should feel like a last resort, not a safety net.
3
Let the rep fail in a low-stakes room before they fail in a high-stakes one
Role play creates the safe failure environment. If they fumble the objection handling in a mock call with you, they learn it there instead of in front of a $50K prospect. The time you invest in letting them struggle in practice is the time you save recovering deals in the field.
4
Ask yourself honestly: am I doing this for them, or for me?
Sometimes stepping in is the right call: a relationship at risk, a deal in genuine freefall, a rep who isn't ready for that stage of deal. But sometimes you're stepping in because it feels good to close. That's ego. Check it before you open your mouth.
Early warning signs you haven't made the shift yet
Most new managers don't know they're stuck in IC mode. They think they're being helpful. Here are the signs to watch for in yourself, and what to do when you catch them.
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You know every deal in the pipeline better than any rep does
You're running the pipeline: they're watching you run it. The goal is for them to own every detail of their pipeline and you to ask the right questions. If you're doing the tracking, you've taken the accountability away from them.
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You regularly speak more than your reps do in their 1:1s
The 1:1 belongs to them. If you're filling most of the airtime with advice, downloads, and direction, you're not coaching, you're lecturing. Ask more. Talk less. The ratio should be at least 70/30 in their favor.
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You're frustrated that no one works as hard as you did
This one is common and dangerous. The moment you start measuring your team against your own IC standard, you've stopped coaching and started resenting. Your standard for them is their ceiling, not yours. Calibrate accordingly.
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You're more comfortable in front of a prospect than in front of your team
Leading people is harder than selling to them. If you find yourself energized by customer calls but dreading team meetings and hard conversations, you're still an IC emotionally. The work is on the leadership side now.
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You can't name the individual motivator of every person on your team right now
If you don't know what drives each person, not their job, their people, you're managing a team on average. You need to know them individually. The rep who is motivated by money needs something different than the one who is motivated by recognition. If you can't name it, you can't use it.
The reset: one question to ask yourself every week
"Did I make any of my reps better this week: or did I just make things easier for myself?"
Easier for yourself means: you closed something, you jumped in on a call, you gave an answer instead of asking a question. Better for your reps means: they learned something, they handled something they couldn't before, they moved closer to not needing you for that skill. Those are different things. The weekly question keeps you honest.
"The goal is to build a team that performs because they're equipped, not because you're watching. When they can run without you in the room, you've done the job. That's the measure."
Leadership situation
Inheriting a new team
You don't get to manage people you don't know. Before you change anything, strategy, targets, structure, spend 30 days in pure receive mode. The Diagnose phase exists for a reason. Don't skip it because you're eager to make your mark.
"The biggest mistake a new manager makes is trying to prove they belong before they've figured out what's actually broken. Earn the right to change things. You do that by understanding them first."
First 30 days
Days 31–60
Days 61–90
Diagnose: listen before you lead
- 1:1s with every person on the team: personal first, professional second
- Shadow calls and meetings: observe before you coach
- Establish team name and identity in week 1
- Share your management tenants openly: ownership, challenge with reason, honest communication
- Identify the top performers and understand what's driving them
- Understand the pipeline, not to fix it yet, to understand it
Strategize: now you have context
- Set team goals collaboratively: bring them into the process
- Run the 9-box exercise: map every person on the team across performance and potential. Identify future leaders, recognize top performers, and pinpoint where coaching investment will generate the highest return. Do this before you make any structural decisions.
- Establish QBR rhythm and pipeline review cadence
- Co-create the team mission statement
- Start TASC delegation: match authority level to readiness
- Identify coaching focus per rep, not the same for everyone
Execute: now you lead
- Running full coaching sessions with each rep: structured, documented
- First QBR completed: forecast, SWOT, team performance reviewed transparently
- Performance conversations started for anyone below standard
- Recognition and incentive structure in place
- Team outing done: relationships built outside the office
Leadership situation
Hiring a full-cycle seller
You're not hiring a BDR who might become a closer. You're hiring someone who can prospect, run discovery, manage a multi-stakeholder evaluation, and close, without a handoff. That's a different bar. The good news: the filter is the same one that runs everything else here. Attitude. Activity. Accountability. In that order.
"Don't stop at the first answer. Give me a specific example. Then give me another one. Attitude can't be faked for a whole interview, watch how they respond when you push."
The AAA filter
Attitude questions
Activity questions
Accountability questions
Red flags
A
Attitude: the non-negotiable
Everything in sales can be taught: process, product, methodology. Attitude cannot. You either show up every day ready to compete or you don't. A full-cycle seller who carries their own pipeline lives and dies by this more than anyone. When the deal falls apart on a Friday, Attitude is what determines whether they dial on Monday.
What you're looking for: someone who has been knocked down, in sales, in sport, in life, and came back with intent, not excuses. How they talk about failure tells you everything. How they talk about past managers and companies tells you the rest.
A
Activity: the hunter's proof
A full-cycle seller is responsible for creating their own pipeline. No SDR safety net. That means you need someone who is internally driven to prospect, not someone who will wait to be handed opportunities. Activity separates the hunter from the order-taker.
What you're looking for: someone who can describe their prospecting system in specific terms. Not "I make a lot of calls", but how they segment, how they sequence, how they prioritize their time. If they can't articulate it in the interview, they're not running it in the field.
A
Accountability: own the number
A full-cycle seller has nowhere to hide. They own pipeline creation, conversion, and close. The rep who blames the market, the product, or the price is a liability. The rep who says "here's what I learned from that loss and here's what I'm doing differently" is the one you build around.
What you're looking for: ownership language. Not "the deal fell through", but "I missed the economic buyer early and it cost me the deal." Accountability is a skill that's developed, not assumed. Hire people who have already started developing it.
Full-cycle non-negotiables
- Can self-source pipeline: has done it before and can describe exactly how
- Runs their own discovery, not just qualifying, but uncovering pain and building a case for change
- Manages multi-stakeholder deals: knows what a champion looks like and how to build one
- Can close: and can explain their closing philosophy without using the word "close"
- Coachable: asks a real question during the interview itself, not a rehearsed one
Attitude: what you're testing for
Push past the first answer on every one of these. The first answer is prepared. The second answer is real.
- Q"Tell me about your absolute worst day in sales. What happened, and what made you come back the next morning?"
- Q"Tell me about a time you lost a deal you thought you had. What did you do with that?"
- Q"How do you handle a week where nothing is going right, pipeline is stalled, calls aren't landing, and your number is at risk?"
- Q"What did you learn from the manager you disagreed with most? What would they say about you?"
- Q"Tell me about something outside of work that you've competed at seriously. What did losing teach you?"
- Q"Walk me through a time you got critical feedback. What did you do with it?"
"How they talk about past employers is how they'll talk about you. Listen for ownership, not bitterness, not deflection. Ownership."
Activity: what you're testing for
A full-cycle seller has to generate their own pipeline. You need proof they've done it, and a specific system for how.
- Q"Walk me through exactly how you'd build a territory from scratch, no warm leads, no SDR support. Where do you start?"
- Q"What does your prospecting process look like day-to-day? How do you decide who gets your attention?"
- Q"What percentage of your pipeline last year was self-sourced? Walk me through how you built it."
- Q"Tell me about a creative prospecting move that worked. What made you try it?"
- Q"How do you protect your prospecting time when the rest of the day is pulling at you?"
- Q"You're a business owner selling B2B services into the enterprise. Walk me through how you go to market, specific steps, first three weeks."
"Vague answers here are a tell. 'I make a lot of calls' is not a prospecting system. Press for specifics, account segmentation, sequence length, channel mix. The rep who can describe it clearly is the rep who's actually running it."
Accountability: what you're testing for
You're listening for ownership language. Not excuses, not blame, not "the market was tough." The question is: when it went wrong, what did you own?
- Q"Tell me about a quarter where you missed your number. What happened, and what did you change?"
- Q"Walk me through a deal you lost. What did you miss, and when did you miss it?"
- Q"How do you track your own performance outside of what your manager shows you?"
- Q"What's the gap between where you are right now and where you want to be? What are you doing about it?"
- Q"If I called your last manager right now, what would they say is the one area you still need to develop?"
- Q"What did you do to prepare for this interview specifically? What did you find that surprised you?"
"The rep who says 'I missed it because the territory was underpenetrated' and the rep who says 'I didn't get to the economic buyer early enough and it cost me the deal', those are two completely different people. Hire the second one."
Walk away if you see these
- Negativity about past employers, how they talk about the past is how they'll talk about you. One flag is human. A pattern is a character trait.
- No preparation, if they didn't research you before the interview, they won't research their prospects before a cold call
- Can't describe a prospecting system, a full-cycle seller who can't explain how they build pipeline is not a full-cycle seller
- Deflects blame on lost deals, "the product wasn't competitive," "the timing was bad," "my manager didn't support me." Walk away.
- Refuses or hesitates to role play, if they can't do it here, they won't do it in the field
- No follow-up within 24 hours, the thank-you email is a data point. They know the game. If they don't send it, they chose not to.
- Passive energy in the room, weak questions, distracted answers, no curiosity about what "good" looks like here. A hunter walks in hungry. You'll feel it.
Nice to haves: signals, not requirements
These aren't dealmakers. But they're signals. Someone who's competed at something, worked with their hands, or served customers face-to-face usually has the foundation you're building on top of.
- Former athlete or competitive background: knows what losing a game and coming back Monday feels like
- Blue-collar background: the work ethic is usually baked in, not developed
- Customer-facing service jobs: they've been on the other side of the table
- Experience at a company where they had to build their own pipeline, no SDR, no inbound. Just a territory and a phone.
Leadership situation
Hiring a manager
Same core traits as a rep: plus attention to detail, a real coaching framework, and a mentor they can name. Anyone can say they're a leader. Ask them to prove it with specifics.
"Behaviors define culture. The manager you hire will set the standard for every behavior on their team, whether they mean to or not."
Manager-specific questions
- Q"What tools do you rely on to aid in your coaching sessions? Walk me through a recent one."
- Q"Tell me about your most recent mentor: how did you seek them out, and what's the biggest thing they gave you?"
- Q"Tell me about a time you made an ask from an organization and couldn't get it. What did you do?"
- Q"What have you found to be a good structure for your team and yourself?"
- Q"What are the key areas you're actively working on to be a better sales leader right now?"
- Q"Give me a tagline for yourself as a manager: how would your team describe you in one sentence?"
Non-negotiables beyond the rep standard
- Attention to detail: sloppy managers run sloppy pipelines
- Has a coaching framework, not just "I ride along and give feedback"
- Has had a mentor and can articulate the specific impact
- Talks about team wins, not just personal wins
Leadership situation
Ramping a new hire
A slow ramp is almost always a manager problem. The structure of the first six weeks determines everything. Knowledge first. Outreach second. Live selling third, never the other way around. The operating rhythm gets established here. If a rep learns from day one that there is a cadence and a standard, they run inside it. If there's no structure in week one, you'll be chasing it in month six.
"Ask questions. There are never too many. It's likely everyone on the team has the same ones."
Week-by-week sequence
1
Week 1: Product and industry knowledge
Deep knowledge first. No outreach yet. They need to understand what they're selling before they sell it.
2
Week 2: Outreach training
Cold call practice, meeting shadowing, pattern interrupt and call structure drilled until it sounds natural.
3
Week 3: Mock meetings + first prospecting blocks
Role play every scenario before they go live. The first impression in the field comes from here.
4
Weeks 4–6, Live selling
BDR allocation begins week 4. Spot incentive: $100 for every self-gen attended meeting over quota. Still debrief every call.
KPI ramp expectations
Set your full-production targets first, then work backwards. Month 1 is a training month, reps are learning the product, the process, and the motion. Month 2 is half-ramp, they're in the field but still building. Month 3 is full production. By the end of month 3, there should be no ramp adjustment in how you evaluate their output.
| KPI | Month 1 · Training | Month 2 · Half Ramp | Month 3 · Full Production |
| Appointments set | 0, focus on learning, shadowing, and role play | 50% of full goal | 100% of full goal |
| Opportunities created | 0, no expectation until process is understood | 50% of full goal | 100% of full goal |
Define your full-production targets based on your team's current averages before setting the rep's Month 3 goal. The formula is consistent, only the numbers change.
Leadership situation
Coaching vs. managing
Managing gives people the answer. Coaching leads them to it. That distinction sounds small. The difference in outcome is enormous. A rep who arrives at the answer themselves owns it, they're more likely to use it, repeat it, and teach it to someone else. A rep who was just told what to do will execute it once and come back to you the next time with the same question. Your job is to make yourself progressively less necessary, not more indispensable.
"The urge to tell is real. Every time. Resist it. Ask the question instead. The rep who figures it out in the room with you will figure it out in the field without you. The one you told the answer to will wait for you next time."
The philosophy
Running the session
Individual coaching plans
The coaching questions
Role play
Why leading to the answer matters more than giving it
Think about the last time someone told you the answer versus the last time someone walked you through a problem until you got there yourself. Which one stuck? Which one changed how you approached the next similar situation? The answer you arrived at yourself became yours. The answer you were handed remained theirs.
That's what coaching is. It's not a softer version of managing. It's a more demanding one. It requires patience, real patience, not performed patience, to sit with a rep who is circling the answer and not jump in. The restraint is the work. And it pays off in a way that telling never does: a rep who can solve it themselves at 9am on a Tuesday when you're not available.
Managing is faster in the short term. Coaching wins in the long term. Every time.
Indirective before directive: the coaching hierarchy
1
Indirective first, draw it out of them
"What do you think went well on that call?" "What would you do differently?" "What do you think the prospect was really trying to tell you when they said that?" Let them go first. Always. Your instinct is to coach what you observed. Their instinct is to tell you what they experienced. Get their version before you offer yours, it's almost always closer to right than you'd expect, and the gaps are where the real coaching lives.
2
Directive when needed, but earn it
There are moments where the rep genuinely can't find it, where the situation is time-sensitive, or where the gap is technical enough that discovery questions won't close it efficiently. That's when you shift to directive. "Here's what I heard, here's why it matters, here's what I'd try differently." But this is the exception, not the default. If you're being directive more than indirective, you're managing, not coaching.
3
One thing at a time, always
You heard six things on that call that could be better. Coaching all six changes nothing. Pick the one that will move the needle most, the one that, if fixed, makes two of the others easier. Go deep on that and only that. Come back to the others over the next few sessions. A rep who walks out of a coaching session with one clear, specific thing to work on will do something with it. A rep who walks out with six will do nothing with any of them.
"We figure it out together. That's not a slogan. That's literally how the session runs, I'm not sitting across from you with the answer already written down. We're working through it in real time. That's the point."
How to run a coaching session: structure it or it drifts
An unstructured coaching session becomes a conversation. Conversations are fine. They don't change behavior. Give every session a frame from the start so the rep knows what they're walking into and what they'll walk out with.
The session structure
1
Set the frame, use the UFA
"My goal today is to leave you with one thing you can apply on your next call. We'll look at the call from Tuesday together, you'll tell me what you saw, I'll add what I heard, and we'll land on one thing to work on. Sound good?" One minute of setup means the whole session runs more productively. The rep knows what's coming and why.
2
Their take first, always
"Walk me through that call. What happened?" Then: "What do you think went well?" Then: "If you could run that one section again, what would you do differently?" You're not fishing for a specific answer. You're genuinely listening to how they experienced it, because what they noticed and what you noticed are often different things, and both matter.
3
Add your layer, specifically and behaviorally
"Here's what I noticed." Not "you need to be more confident", that's a judgment. "When the prospect said they needed to loop in the team, you moved on without asking what that process looks like, that's the moment I want to talk about." Specific, behavioral, observable. Not a character assessment.
4
Land on one thing together
"Of everything we talked about, what's the one thing you want to focus on before your next call?" Let them name it if they can. If their answer matches yours, great, you're aligned. If it doesn't, have the conversation: "I'd push on one thing first, here's why I think this is the lever." But give them the chance to get there first.
5
Close with a commitment and a date
"What's one thing you're going to do differently on the next three calls this week?" Specific, time-bound, theirs. You're not telling them what to do, you're asking them to commit to what they just decided. Then follow up in the next session: "You said you were going to work on X, how did that go?" The follow-through is what separates a coaching culture from a coaching conversation.
Individual coaching plans: no two reps are the same
This is where most managers take the shortcut. They have one coaching approach, usually the approach that would have worked for them as a rep, and they apply it to everyone. Some reps respond to it. Most don't. And the manager concludes the rep isn't coachable when the reality is the approach wasn't right for that person.
Every rep brings a different experience level, a different motivation, a different confidence profile, and a different skill set. The coaching plan that moves one rep forward might stall another. Your job is to build the plan around the individual, not to run everyone through the same program and see who survives.
Building an individual coaching plan: what to consider first
1
Where are they in their development?
A rep in month two needs fundamentals: call structure, objection handling, qualification basics. A rep in year two who's plateaued needs something completely different, advanced discovery, multi-threading, closing discipline. The same coaching conversation delivered to both is useful to neither. Know the stage before you design the plan.
2
What's the gap: skill, will, or awareness?
Some reps don't know what they don't know. They're not resistant, they're genuinely unaware that the discovery question they skipped was the one that cost them the deal. That's an awareness problem. It responds to observation and specific feedback. A rep who knows what to do and isn't doing it is a different problem, and needs a different conversation entirely.
3
How do they receive feedback?
Some reps want it direct: "Here's what I heard, here's what I'd change." Others shut down when they feel criticized and need more Socratic coaching, questions that lead them to the insight rather than delivering it directly. Neither is a character flaw. They're just different people. Ask them early: "How do you prefer to receive coaching?" Then honor the answer.
4
What motivates them to apply it?
The money-motivated rep needs to see the coaching tied to commission: "This one change in your close rate is worth X per quarter." The recognition-motivated rep needs to see it tied to visibility: "When you get this right consistently, it's the kind of thing we call out in team meetings." The coaching is the same. The framing that makes them actually use it is completely different.
The individual coaching plan: what it contains
- One primary development area: the skill or behavior most likely to move their results if improved
- The specific gap in observable, behavioral terms, not "needs to improve discovery" but "doesn't ask follow-up questions after the prospect states a surface pain"
- The coaching approach that fits this rep: directive, indirective, or a mix
- A weekly practice commitment: what they're working on between sessions, not just in them
- A success marker: how you'll both know the gap has closed
- A timeline: typically 30 to 60 days on one area before moving to the next
"The rep who has been told the same thing twelve times and isn't changing isn't stubborn. You probably haven't found the right entry point yet. Change the angle. Try a different question. The answer is in there, your job is to find the key that unlocks it for that specific person."
The coaching questions: your most important tool
The quality of your coaching is almost entirely determined by the quality of your questions. Not your observations, not your experience, not your advice, your questions. A great question creates a moment of real reflection. A poor one gets a surface answer that closes the conversation instead of opening it.
The goal of every question is the same: get the rep thinking about their own behavior, their own choices, and their own answers. Not yours.
Opening questions: start the session
- Q"Walk me through that call from your perspective. What happened?"
- Q"What do you think went well on that one?"
- Q"If you could run that one section again, what would you do differently, and why?"
- Q"What's the one thing on your mind coming into today?"
Deepening questions, don't stop at the first answer
- Q"Say more about that."
- Q"What do you think was actually happening for the prospect in that moment?"
- Q"You said you weren't sure what to do next: what options did you consider?"
- Q"What would have had to be true for that conversation to go differently?"
- Q"If your top-performing peer had been in that call, what would they have done differently at that point?"
Commitment questions: end every session with one
- Q"What's the one thing you're going to do differently on your next three calls?"
- Q"What does applying this look like in practice: walk me through exactly how you'd handle it?"
- Q"What might get in the way of doing this, and how will you handle that?"
- Q"When we talk next week: what do you want to be able to tell me you did?"
The AWE question: use it whenever the rep gets stuck
One question that cuts through almost every coaching stall:
"And what else?"
When a rep gives you their first answer, they've given you the polished answer, the one they thought you wanted to hear. "And what else?" gets you past it. Ask it two or three times in a row. The third answer is almost always the most honest one, and the most useful one to coach to.
Role play: non-negotiable, no exceptions
You can talk about a cold call for 45 minutes. The rep will nod, take notes, and agree with everything you say. Then they'll pick up the phone, hit the same wall they always hit, and revert to every habit they had before your session. Talking about selling doesn't change selling. Doing it in a room where it's safe to fail, that changes it.
Role play is where coaching becomes real. It's where the rep finds out whether they actually internalized what you discussed, or whether they just understood it conceptually. Those are very different things. The field is the wrong place to find out which one it was.
How to run a role play that actually works
1
Give the rep a specific scenario, not a generic one
"You're calling into a VP of Finance at a 300-person manufacturing company. They've never heard of us. You have 20 seconds before they hang up." The more specific the scenario, the more real the practice. Generic role plays produce generic behavior. Real scenarios build real muscle memory.
2
Play the prospect as they actually are, not as an easy version
The temptation is to be a cooperative prospect so the rep feels good. Resist it. Play the skeptical version. Ask the hard question. Cut them off when the pitch goes long. If they can handle the difficult prospect in practice, the real call is easier. If they can only handle the easy prospect in practice, you've coached them for a scenario that doesn't exist.
3
Debrief with their take first
"How did that feel? What did you think worked? Where did you lose it?" Same framework as the call debrief. Let them assess before you add. The rep who can accurately self-diagnose a role play will accurately self-diagnose in the field, and correct themselves without needing you in the room.
4
Run it again, immediately
One rep of a role play is an exercise. A second rep right after, incorporating the specific feedback from the debrief, is practice. The repetition is the point. "Let's run that same scenario again. This time, when they push back on timing, try this." Then watch whether the coaching translated into behavior. That's the only real test.
"If a rep is uncomfortable with role play, that's the most important information you could have. The discomfort they feel in a room with you is a fraction of what they feel on a live call. The practice is the gift, even when it doesn't feel like one."
Leadership situation
Setting great goals: the SMART framework
Most reps' goals are project plans: a list of things to do, not a promise of what they'll deliver. SMART goals change that. They create a shared definition of success that both the manager and the rep can hold each other to. For a new sales leader, this is foundational: if you can't build goals that are specific, measurable, and time-bound, every accountability conversation is going to be a negotiation about what you meant.
"Fewer. Bigger. Stronger. None of us has more than four truly meaningful things to get done in a year. Find those four, then make sure every single one of them passes the SMART test before you leave the room."
SMART: what each letter actually means
S
Specific
Not "improve pipeline." What pipeline metric, by how much, in which segment? Specific enough that if two people read it, they'd agree on what success looks like.
M
Measurable
There must be a number attached. If you can't measure it at the end of the period, it's not a goal, it's a direction. Progress has to be trackable, not interpretable.
A
Achievable
The goal should push the rep beyond their comfort zone, but it has to be within reach with full effort. Unreachable goals don't motivate. They detach. Calibrate with the team, not just your instincts.
R
Relevant
Tied to something that actually moves the business, not activity for activity's sake. A goal that doesn't connect to a business outcome is a task list in disguise.
T
Time-bound
A deadline is not optional. Without a time constraint, there's no urgency and no accountability. Every goal needs a clear review date, whether that's 30, 60, or 90 days out.
Building the goal
Common mistakes
Goal conversation
How to build a SMART goal: step by step
1
Start with the outcome, not the activity
Ask: what does winning look like at the end of this period? Revenue closed, conversion rate, pipeline created, meetings booked. Start there. The activities follow from the outcome, not the other way around.
2
Attach a number and a date
Every goal lives or dies on this step. "Improve discovery-to-opportunity conversion" is not a goal. "Move discovery-to-opportunity conversion from 58% to 65% by end of Q2" is a goal. Write it that way every time.
3
Gut-check achievability with the rep
Present the goal, then ask: "On a scale of 1–10, how confident are you that you can hit this with full effort?" If they say 5 or below, you either have a calibration problem or a support gap. Find out which before you finalize it.
4
Connect it to the bigger picture
Tell them why this goal matters beyond their number. "This goal contributes to X at the team level, which is one of the three things we need to hit to get to Y this year." Reps who know why their goals matter are more committed to them.
5
Build the check-in cadence in at the start
Don't set a goal and revisit it in 90 days. Schedule the 30 and 60-day check-ins when you set the goal. If it's not on the calendar, it doesn't happen. Goals without check-ins are just intentions.
Goal-setting checklist
- 1–4 goals max: if it's more than four, you haven't prioritized
- Every goal has a number and a date: no exceptions
- Rep has confirmed the goal is achievable with full effort
- Each goal connects explicitly to a team or business outcome
- 30 and 60-day check-ins are on the calendar at time of goal-setting
- No pure behavioral goals: if behavior needs to change, that's a coaching conversation, not a goal
- Calibrate across the team: read goals aloud, check that challenge level is consistent
The most common goal-setting mistakes new managers make
1
Setting activity goals instead of outcome goals
"Make 50 calls a day" is an activity. "Book 8 qualified discovery meetings per week" is an outcome. Both require calls, but only one tells you if the work is actually working. Always lead with the outcome.
2
Setting goals without rep buy-in
A goal handed down without discussion is a target, not a commitment. Before you finalize anything, ask: "Is there anything that would prevent you from hitting this?" That question surfaces real obstacles, and creates real ownership.
3
Too many goals
If everything is a priority, nothing is. Four goals max. Rank them. The rep should be able to recite their top goal without looking it up, if they can't, there are too many.
4
No check-ins until review time
A goal without mid-period check-ins isn't being managed, it's being measured. The check-in is where coaching happens. By the time the review comes, it should have no surprises.
5
Treating SMART as a box to check
SMART is a filter, not a form. Run every goal through it before finalizing, and if it doesn't pass all five, it's not ready. The 10 minutes you spend tightening the goal upfront saves you 90 minutes of unclear accountability conversations later.
How to run the goal-setting conversation
This conversation works best as a collaborative draft, not a presentation from the manager to the rep. Bring a starting point; invite them to sharpen it.
- Q"What are the two or three things you want to be able to say you accomplished by the end of this quarter?", Let them go first. Their answer tells you a lot about their self-awareness.
- Q"Here's what I'm seeing in the data that I think should be a priority, how does that land for you?", Share your view. Check for alignment before setting the direction.
- Q"If you hit this goal, what changes for you in your business? In your career?", Connect the goal to their motivation. Make it personal, not just professional.
- Q"What would stop you from hitting this?", This surfaces real obstacles early. Handle them now, not at the 90-day review.
- Q"On a scale of 1–10, how confident are you that this is achievable with full effort?", Anything below 7 needs re-calibration before you finalize.
"The goal should terrify them slightly. That's right. But 'terrifying' and 'impossible' are different things, a great SMART goal lives in the space between comfort and can't. That's where growth happens."
Leadership situation
Managing performance
High standards and high support are not opposites. The mistake most managers make is picking one. Performance management isn't a process you run when someone is failing, it's a discipline you maintain from day one. By the time you're considering a formal plan, there should be no surprises. Not for you, not for the rep, and not for HR.
"Own your results. If a rep isn't hitting, I want to know what I could have done differently as a manager before I decide anything else. Then I want to know what they're willing to do differently. The answer to both questions determines what happens next."
The weekly 1:1
Calling it out early
The activity plan
The PIP
Documentation
The 1:1: your most important performance management tool
One hour. Once a week. Every week. This is a religiously held meeting. It does not get rescheduled. It does not get shortened to 20 minutes because the week got busy. When a rep knows their 1:1 is protected, that no matter what is happening, that hour belongs to them, it signals something important: that you take them seriously as individuals, not just as quota-carrying headcount.
This is also your primary vehicle for performance management. Every coaching moment, every performance observation, every early warning sign, it surfaces here first. If you're not running consistent 1:1s, you don't have a performance management system. You have a reaction system.
What you cover: every week
1
Personal check-in, always first
Two to three minutes. How are they doing as a person, not as a rep. Ask about their weekend, their family, whatever is real for them. This isn't small talk. It's the foundation of the relationship that makes every harder conversation possible. You can't coach someone you don't know.
2
Performance KPIs: their number and the activities behind it
Review their KPIs against target: pipeline created, meetings booked, meetings attended, conversion rates, revenue. Don't just read the numbers, discuss what the numbers are telling you. "Your conversion from disco to opp is at 52%. Last month it was 64%. Walk me through what's changed." Data first, always.
3
Deal strategy: the open pipeline
Pick 2–3 active deals and go deep. What's the pain? Who's the economic buyer? What's the next step and when? This is where you coach, not just collect updates. The deal review and the coaching session are the same conversation, not two separate ones.
4
Individual development: one thing they're working on
Every rep should be actively working on one development area. Reference it weekly. "Last week you were working on your discovery questioning, how did that land on Tuesday's call?" Development isn't a quarterly event. It's a weekly thread you maintain in every session.
5
Their agenda: what did they bring?
Always leave time for what they came to discuss. If they didn't bring anything, that's the coaching moment. "I want you coming in here with questions, roadblocks, or things you want to get better at. If you have nothing, I'm going to wonder why." Ownership starts with how they show up to their own 1:1.
"The rep who knows their 1:1 will never be cancelled, and that you will come prepared and present, that rep trusts you. Trust is the foundation every hard conversation is built on."
Call it out early: the 1:1 is where performance issues are born and killed
The single biggest mistake new managers make in performance management is waiting too long to say something. They see the warning signs, activity dropping, pipeline stagnating, calls getting shorter, energy changing, and they hope it self-corrects. It almost never does. And every week you wait is a week you're not documenting, not coaching, and not giving the rep a real chance to turn it around.
The 1:1 is where you surface it. Calmly, specifically, and early, not after three bad months when you're already frustrated and they're already defensive.
How to call it out: the conversation
1
Start with data, not judgment
"Here's what I'm seeing in the numbers over the last three weeks. I want to understand it before I draw any conclusions, walk me through what's happening from your side." You're not accusing. You're opening a conversation. The rep's response tells you whether this is a skill problem, a will problem, or a circumstance problem. Don't diagnose before you hear the answer.
2
Name it specifically, not generally
"Your activity is down" is not feedback. "You've had fewer than 8 outreach blocks this week for the last four weeks, and your meeting-to-conversation ratio has dropped from 18% to 11%" is feedback. Be specific enough that there's no room for the rep to interpret what you're seeing differently than you are.
3
Diagnose the root cause: skill, will, or circumstance?
These require completely different responses. A skill problem means more coaching and role play. A will problem means a candid conversation about commitment and fit. A circumstance problem, personal situation, territory challenge, tool friction, means you removing the obstacle. Treating a will problem like a skill problem is one of the most common and most costly mistakes a manager can make.
4
Agree that a problem exists, before you talk about solutions
Don't skip this step. Before you build a plan, get alignment that you're both seeing the same thing. "Do we agree that the last six weeks represent a trend that needs to change, not just a bad patch?" If the rep doesn't agree a problem exists, no plan you build will have their real buy-in. Address the disagreement first.
The coaching conversation checklist: at the first sign of underperformance
- Identified the specific KPIs or behaviors that are off, with numbers, not impressions
- Asked the rep to explain what's happening before drawing a conclusion
- Diagnosed: skill, will, or circumstance?
- Got explicit alignment that a problem exists
- Documented the conversation: date, what was said, what was agreed
- Set a clear check-in date to revisit progress
The activity plan: the bridge between coaching and a formal PIP
Before you ever put someone on a formal Performance Improvement Plan, there should be an activity plan. This is an informal, co-built document that focuses exclusively on the behaviors the rep can control, not outcomes, not revenue targets, not quota attainment. Its purpose is to answer one question: is this an effort problem, or something else?
If a rep follows the activity plan with full effort and still isn't producing, you now have real information. It might be a skill gap that needs a different kind of support. It might be a territory or product issue that needs to be escalated. It might be a fit problem. But at least you know, and so do they. The activity plan removes the guesswork and proves the diagnosis before you escalate.
What makes a good activity plan
1
Tie it only to KPIs the rep controls
Outreach volume. Call attempts. Prospecting blocks completed. Discovery meetings held. Follow-up emails sent within 24 hours. These are effort metrics, the rep can hit them regardless of how the market is behaving or what the prospect decides. Do not put revenue or quota attainment on an activity plan. You're testing effort, not outcome.
2
Make the targets specific and weekly
Not "increase outreach." "Eight outreach blocks of 45+ minutes per week, resulting in a minimum of 60 call attempts and 20 personalized emails." Specific enough that at the end of every week, you can both look at the data and agree on whether the standard was met, no interpretation required.
3
Set a timeline, typically 30 days
30 days is enough time to show real effort and generate meaningful data. Too short and you're not giving them a real chance. Too long and you're dragging out a conversation that should be resolved. Set the start date, the end date, and the weekly check-in cadence at the beginning.
4
Co-build it, don't hand it down
"Here's what I think the standard should be. Do you think it's achievable with full effort?" If they say no, that's important information. If they say yes and then don't hit it, you have a documented commitment they agreed to. Either way, you need their buy-in before the plan starts.
5
Review it weekly in the 1:1, without exception
The activity plan lives in the 1:1. Every week: here's what we agreed to, here's what the data shows, here's what I'm seeing. No surprises at the 30-day mark. If week 2 is off-track, say so in week 2, not at the end of the month.
"If someone completes every activity on the plan and still isn't producing, you've ruled out effort. Now you can have a completely different conversation, and you have the data to back it up."
The PIP: it should never be a surprise
Where PIPs fail is almost always the same place: the rep experiences it as an ambush. The manager calls them into a room, slides a document across the table, and the rep has no context for what they're looking at, because the coaching conversations that should have preceded it either didn't happen or weren't documented clearly enough to be referenced.
By the time a formal PIP is presented, a rep should already know: what the specific performance issues are, what the expectations are, that an activity plan was run and the results of it, and that the next step if performance doesn't improve is a formal plan. None of those things should be news on the day the PIP is presented.
"The toughest conversations become easy when you've been giving good feedback all along." If you've run consistent 1:1s, called out issues early, and executed the activity plan, the PIP conversation is a formality, not a confrontation.
Before the PIP: the checklist
- Multiple documented coaching conversations referencing the specific performance issues
- An activity plan was run, minimum 30 days, and the results are documented
- The rep has been explicitly told that a formal plan is the next step if improvement doesn't occur
- HR has been brought in, before the PIP is drafted, not after
- You are clear on your role in the PIP process and what HR's role is
- The PIP is metric-driven, specific numbers, specific timelines, no ambiguity
Bring HR in early, not as a formality, as a resource
Most first-time managers wait until they've already decided to put someone on a PIP before they call HR. That's backwards. Your HR partner should be in the conversation as soon as the activity plan is underway, ideally earlier. They can tell you whether your documentation is sufficient, what the company's standard is for a PIP at this stage, and what your specific obligations are as the manager running it.
HR is not there to make the process harder. They're there to protect the rep, protect you, and protect the company. A PIP that's built with HR from the beginning is far more defensible, and far more likely to actually drive the outcome you want, than one assembled at the last minute.
1
Loop in HR when the activity plan starts
Brief them on the situation, what you've observed, what conversations have happened, and what the activity plan is designed to test. Ask: "Is there anything I should be doing differently right now?" That question alone will surface things you wouldn't have thought to ask.
2
Ask HR to review your documentation before the PIP is presented
Your notes from 1:1s, the activity plan document, the outcomes, the specific conversations you've had. HR can tell you whether what you have is sufficient or whether there are gaps. Better to find gaps before the PIP than after.
3
Understand exactly what your role is during the PIP period
Who owns the weekly check-ins? What does a missed metric trigger? What's the decision framework at the end of the PIP period? Who makes the final call? These are questions HR answers, and you need the answers before you start, not mid-process.
"A PIP is not a punishment. It's a final, structured opportunity to turn things around, with full clarity on both sides about what success looks like and what happens if it isn't achieved. If you've done everything right, the rep knows all of that before the document is placed in front of them."
Documentation: the discipline that protects everyone
Most managers don't document because it feels bureaucratic. What they discover, usually at the worst possible moment, is that without documentation, every performance conversation becomes your word against theirs. Documentation isn't about building a case against someone. It's about creating a clear, shared record of what was said, what was agreed, and what happened next.
It also protects the rep. A manager who documents consistently can show a rep exactly where the conversation started, how it evolved, and what was agreed at each step. That's not punitive, that's accountable leadership.
What to document: after every performance-related conversation
1
Date and format of the conversation
Was it in the weekly 1:1? A separate conversation? An email follow-up? The format matters. A verbal warning in a 1:1 followed by a written email summary is far more defensible than a verbal warning alone.
2
The specific performance issues discussed: with data
Not "we discussed performance concerns." Specific: "Discussed discovery-to-opportunity conversion rate of 41% against a team average of 58% for the trailing six weeks. Rep acknowledged the gap and attributed it to X." Numbers. Dates. Their acknowledgment. All of it.
3
What was agreed: specifically
What does the rep commit to doing differently? What support did you commit to providing? What is the check-in date? Write it down and follow up with a written summary to the rep after the conversation: "Just wanted to capture what we discussed today." That email is documentation the rep has implicitly acknowledged.
4
What happened at the next check-in
Did the rep follow through on what was agreed? If yes, document that too, not just the misses. A record that shows coaching, effort, and response is far more complete and far more fair than a record that only captures the failures.
Documentation checklist: the minimum standard
- Every formal performance conversation has a written summary sent to the rep within 24 hours
- Activity plan outcomes documented weekly, not summarized at the end
- Any verbal warning followed immediately by a written record
- HR is copied or briefed on documentation that may support a PIP
- Positive progress documented alongside performance concerns, not just the misses
- All documentation stored in a consistent place, not scattered across email threads and notebook pages
"Document every conversation that matters. A note that takes two minutes after a 1:1 is worth hours of scrambling to reconstruct a timeline when HR asks for it later. Do it in the moment. Every time."
Leadership situation
Time management
The real issue is awareness: knowing when your best hours are and protecting them. The biggest time killer on a sales team isn't distraction. It's prospecting ADD: bouncing between tasks without finishing any of them.
"Treat your time like it's money. Know your peak performance window, and protect it like money hours."
1
Find your peak performance time
Break the day into 3–4 slots. Over a week, rank them most to least productive. Schedule your hardest selling activity in the top slot, every day.
2
Fixed time vs. discretionary time
Fixed = must-do's. Discretionary = want-to's. Most reps live in discretionary time during money hours. Flip that.
3
Avoid the sunk cost fallacy
When you've been on something too long, ask: "How valuable is this outcome? Who's affected if it's not finished?" Then decide. Don't just keep going because you've already started.
4
Take a future time perspective
Before you start something: "How does this affect next week?" Tasks that make next week harder are usually the wrong priority right now.
Common time killers: diagnose these with your reps
- Prospecting ADD: bouncing between tasks, never finishing the outreach block
- Taking too long to write emails: if it takes more than 5 minutes, it's too long
- Only hitting prospects once: follow-up is the job, not the exception
- Breaking the day into one category and falling into a hole
- Meetings that could have been emails: be ruthless about this
Sales fundamental
The cold call
Most reps open with the same three lines and get the same result: a click. The pattern interrupt exists because your prospect has already been called by every salesperson alive. Stop sounding like one. The reps who dial the most aren't always the ones who book the most, the ones who sound different are.
"Bob, this is Angelo from Leyton. Does my name sound familiar? … I'm glad I caught you, is it a bad time?"
1
Pattern interrupt
"Does my name sound familiar?" Forces them to think instead of activating their wall. Even a split second of curiosity is everything.
2
No "how are you"
It signals you're a salesperson. Skip it. Go straight to the reason for the call.
3
The reason for my call today is…
"I noticed your team recently won an award and wanted to see how you're planning to handle [X]." Direct. Specific. Not a pitch, a reason.
4
Solution statement
Short. Tied to their world. About what they gain, not what you sell.
5
Trigger statement: date and time, always
Give them a specific binary choice. "Next Thursday, 9 or 11?" Not "sometime next week?"
Strong vs. weak trigger statements
Strong
What works better: morning or afternoon?
Next Thursday, 9 or 11?
I'm available Thursday the 12th at 1. What's the best email for the invite?
Weak
Do you have some time in the future?
Would you want to set up a call sometime next week?
Let me know when works for you.
Sales fundamental
Clear next steps
Buyers aren't committed to your sales cycle. They showed up to decide if they want to be. If you leave a meeting without a concrete next step, you don't have a deal, you have a conversation that happened once. Closing discipline starts here, not at the end of the quarter.
"Touching base next week doesn't count. That's not a next step. That's a ghost waiting to happen."
The Up-Front Agreement (UFA): use this at the start of every meeting
"By the end of this meeting, I'd like you to be in a position where you're either interested and we plan the next logical step, or you're not interested, you tell me that candidly, and we avoid wasting each other's time. Is that fair?"
Take the leadership position
Selling is an act of leadership. If you're constantly waiting for the buyer to suggest the next step, your pipeline is full of deals about to go dark.
"I have some ideas about what a next step could look like. But I'd love to hear your thoughts first.", You lead, they feel in control. Both things can be true.
Coaching exercise for your reps
- Have them write 2–3 concrete next steps before every meeting
- Debrief: "What was the specific next step you agreed on?" If the answer is vague, that's the conversation.
- Role play the UFA until it sounds natural, not scripted
- Pipeline review standard: no deal advances without a dated, named next step
Sales fundamental
Selling to pain
Most reps hear the pain indicator and sprint to the solution. That's why deals fall apart. The real pain is the emotion behind the symptom. Find that and you have a deal. Miss it and you're just hoping price wins.
"Do you have any clue why they'd be motivated to buy from you? Take the time to find the why, and you will be more successful in sales."
Indicator vs. real pain: know the difference
IndicatorI have no idea how much we spend on supplies
PainMad about being over budget / afraid of losing their job
IndicatorAll of our locations use different vendors
PainWorried about not having supplies when needed / letting the team down
IndicatorMy delivery was late / my rep never calls me
PainNervous about losing their best customer / afraid of looking incompetent
People buy based on how it affects them: in this order
1. Them personally, their career, their stress, their job security
2. Their department, their team's headaches and performance
3. Their company, the org-level impact is last, not first
End-of-meeting check: did you find the real pain?
- Did I uncover reasons to buy beyond price?
- Did I stop at the pain indicator instead of digging for the emotion behind it?
- If pricing were equal, would they still choose me?
- Can they recall why they'd move forward: at the end of the meeting, without prompting?
Sales fundamental
Educator vs. seller
The reps who build lasting books of business aren't pitching, they're teaching. When you help someone be better at their job, you become a trusted advisor. That's a sticky customer. That's a relationship. In complex B2B sales, where buyers are sophisticated, skeptical, and bombarded with pitches, being the rep who adds value before asking for anything is the only sustainable strategy.
"Show that you know me before I care what you know. Deals are won during discovery, and discovery starts before you pick up the phone."
The educator mindset: one question to reset your reps
"How does this meeting make this person better at their specific job?" Not their company, them, personally, in their role, today. If the rep can't answer that, the pitch isn't ready.
Educator-style solution statements
- →"I'd love to discuss not only how I can help your company save time, but how I can help you be more efficient in your current role."
- →"I know you wear a lot of hats. We've made changes specifically to save you time during the day, not just the company's time."
- →"Your accountant is your general physician. We're more like a heart surgeon, one specific specialty, and we're very good at it."
Sales fundamental
Rule of 78
Q1 urgency isn't a motivational speech: it's math. In a recurring revenue model, a deal closed in Q1 bills for 33 of the year's 78 periods. A deal closed in Q4 bills for 6. Show your reps this chart once and their relationship with January changes permanently. Once Q1 is gone, it's gone forever.
"73% of your revenue is determined before July 31st. The year is won or lost in the first half."
78 billing periods: where the money actually lives
Q1: 33 periods = 42% of annual revenue
Q2: 24 periods = 31% of annual revenue
Q3: 15 periods = 19% of annual revenue
Q4: 6 periods = 8% of annual revenue
H1 combined
73%
of annual revenue determined before July 31st
Q1 alone
42%
of annual revenue in just 13 weeks
When to pull this out in coaching
- Share it in onboarding week 1: urgency needs to be a belief, not a reminder
- Pull it out in Q1 pipeline reviews when reps are comfortable with a slow start
- Use it to justify contest weighting toward early-year activity
Sales fundamental
Sales Tough, 8 fundamentals
When activity drops, it's almost never strategy. It's one of these eight things. Use this as a coaching checklist, not wall art. If someone's numbers are off, start here before you start elsewhere. The answer is usually staring back at you from row three.
"Monday is 20% of your sales week. Two slow Mondays a month is one full slow month. Once it's gone, it's gone forever."
1
Nothing interrupts money hours
Monday = 20% of your week. Protect it. Full stop.
2
Start early, go long
15 min earlier + 15 min later = 10 extra money hours per month. That's 2+ full sales days.
3
Calls first, paperwork last
One extra call a day = 200 additional opportunities a year. Save admin for after.
4
Open strong
Know your solution statement cold. Be ready before you pick up the phone, not during.
5
Know everyone
Referrals live in relationships. Build them constantly, not just when you need them.
6
Close comfortably
Closing is the natural conclusion when both parties benefit. If it feels forced, the discovery was wrong.
7
Solve, don't share, problems
During sales time, you have no problems. You solve them, and you love what you do.
8
Evaluate your values
Do your actions make customers excited to refer you? Would your employer cringe at losing you?
Sales fundamental
Negotiation, Chris Voss
The person across the table is your partner, not your enemy. The situation is the adversary. Angelo built his own training deck around Voss because the underlying psychology works in a sales negotiation exactly like it works in a hostage negotiation.
"Tone is 5x more important than what someone says. If their words don't match their body language, trust the body language."
Techniques
Voices & tone
Strategies
Mirroring
Repeat 1–3 key words your counterpart just said, with an upward inflection. Forces them to elaborate. You learn more from the follow-up than from any direct question.
"Covid has made this year really difficult financially." → "Difficult financially?"
Labeling
Give voice to their feelings without using "I." Start with "It seems like…" or "It looks like…" Deactivates negative emotions. Reinforces positive ones.
"It seems like the timeline is more of a concern than the fee right now."
Mislabeling
Intentionally misidentify their concern. They'll correct you, and reveal what's actually going on. Then use dynamic silence.
"It seems like you disagree with the payment terms." → "No, I'm fine with the terms, it's the audit clause."
Calibrated questions
"How" and "what" instead of "why." Why triggers defensiveness. What and how keep them thinking, not defending.
"What are you hoping to accomplish by having unlimited audit defense?" vs. "Why do you want that?"
Dynamic silence
After a mirror, label, or mislabel: stop talking. What they say next is almost always the most important thing in the conversation.
Three tones: know which one to use
- Playful/accommodating (80% of the time), warm, collaborative, the default. Promotes working together.
- Late-night FM DJ (10–20%), calm, low, soothing. Use only when establishing something non-negotiable. Fee floor. Payment terms. Timeline.
- Assertive: never. Comes across like a punch to the nose. Always counterproductive.
7–38–55 rule
7% of meaning comes from words. 38% from tone. 55% from body language. Schedule video calls for anything that matters, you need to see the full picture.
Yes and no questions
There are three types of yes: commitment, confirmation, and counterfeit. You can't always tell which one you're getting. A "no" is more valuable because it's always real. Reframe your questions to invite no:
"Is this a good idea?" → "Is this a ridiculous idea?"
"Can you sign by Friday?" → "Do you think it's unreasonable to sign by Friday?"
Accusations audit: before every tough negotiation
Write down every negative thing the prospect might think, feel, or say about your engagement, your price, your contract. Get out ahead of each one. You want them to say "you're being too hard on yourself."
Sales fundamental
Shortening your pitch
Your rep has 30 seconds of real attention on a cold call. Maybe less. The longer the pitch, the less lands. Specialists command more than generalists, and they charge more too. If a rep can't say what they do and why it matters in two sentences, they're not ready to dial.
"Your accountant is your general physician. We are more like a heart surgeon, we focus on one specific specialty. You don't shop around for a heart surgeon."
The compression exercise
- Have them write out their full pitch: no limit, everything they'd say
- "What's the one thing a prospect absolutely must understand?" That's your anchor.
- Cut everything that isn't that anchor or directly supporting it
- Time them: 60 seconds max, 30 seconds goal
- Record it. Play it back. Does it sound like a person or a pitch?
Motivation
Give 'em a cathedral
Three stonemasons. Same job. Same sun. Same stone. Three completely different experiences of their work. As a leader, your job is to make sure every person on your team knows which cathedral they're building, and that you know it too, for each of them individually.
The parable: three stonemasons
A traveler comes upon a medieval building site and stops to ask three stonemasons what they're doing.
1
The first mason: the task
"Can't you see I'm cutting stone? My back is killing me, the sun is scorching, and I have too much work to be answering questions from strangers." He never looks up. The work is a sentence he's serving.
2
The second mason: the paycheck
"I'm a stonemason. I smooth the sides of large blocks so they can be used in construction. It's how I provide for my family." Dignified. Honest. But the work begins and ends with the block in front of him.
3
The third mason: the cathedral
He puts his tools down. Runs his hand over the stone almost like a caress. Jumps to his feet. "Come, I'll show you." He leads the traveler through the chaos of the construction site, then spreads his arms wide: "I am building a cathedral. It will stand for a thousand years and be a place of sanctuary for people long after I'm gone. I may never see it finished. But I know what I'm building."
"All three are doing exactly the same work. The difference is one has a sense of purpose. He feels like he belongs. He comes to work to be part of something bigger than the job he's doing. Simply having a sense of WHY changes his entire view of it."
Why this parable is personal
Angelo's father was a mason. Started in the field at 20. Worked until he was 80. Six decades of building things with his hands, the son of Italian immigrants who came to this country just before the Great Depression and spent their entire lives in Massachusetts. Angelo worked alongside him for over a decade before moving into sales. When he tells this story, he's not reading it from a leadership book. He knows exactly what it feels like to lay a stone and wonder what it's for, and what it feels like to lay a stone knowing you're part of something that will outlast you. That's why purpose isn't motivational language to him. It's the difference between someone who shows up and someone who builds something that lasts.
The three types of rep: which one is on your team?
1
Cutting stone: showing up for the paycheck
Does the work. Hits a floor. Doesn't go above it. Drains energy from the team. Will leave for $5K and a better title.
2
Building a wall: focused on their number
Solid contributor. Hits quota. Takes care of their accounts. But it's transactional, the work stops at their desk. Doesn't pull others forward.
3
Building a cathedral: connected to the why
Outperforms because the work means something. Mentors peers without being asked. Stays late not because they have to but because they care what gets built. This person is created, not found, and the manager's job is to do the creating.
What this means in practice
- Create a team mission statement together, not handed down, co-built
- Connect individual KPIs to team purpose, not just company quotas
- When someone asks "why does this matter," have a real answer ready
- Celebrate the why publicly, not just the numbers
- Recognize when someone is laying bricks vs. building something, and have the conversation
Angelo's team mission statement
"As a team, we aim to share our strengths, battle our weaknesses, and learn from each other and our customers constantly. We understand that our success isn't based off today's results, rather, today's growth, for the results of our future. We are partners for our customers, and as their trusted advisor, we will constantly work to solidify our relationships."
Challenger Sale · Week 1 of 4
Intro, The 5 types of rep
The research behind the Challenger Sale set out to answer one question: what do top-performing reps do that average performers don't? The answer wasn't relationship-building, product knowledge, or hustle. It was something most managers weren't coaching at all.
"The need to understand what top-performing reps are doing drove the research, and what they discovered may be the biggest shock to conventional sales wisdom in decades."
Why the old model is breaking down, 4 trends
1
Consensus-based buying
Widespread support across the organization is now required to make any change. One champion is no longer enough. Your deal needs to survive a room of skeptics you'll never meet.
2
Increased risk aversion
Buyers are more afraid of making a bad decision than they are excited about making a good one. You're selling against inertia as much as competition.
3
Greater demand for customization
Generic solutions don't move anyone. Every stakeholder wants to know how this specifically affects their world, not the company's world.
4
Rise of third-party consultants
Buyers have more advisors between them and you. Your pitch is no longer the only voice in the room, and it may not even be the loudest.
The 5 rep profiles
Which type dominates your team?
1
The Hard Worker
Shows up early, stays late. High activity, high call volume. Doesn't give up easily. Self-motivated but plateaus without a differentiated approach.
2
The Relationship Builder
Invests heavily in customer relationships. Generous with time, focused on harmony. The most common profile, and the least likely to be a top performer.
3
The Lone Wolf
Follows their own instincts, not the playbook. Difficult to manage. Can perform well individually but doesn't scale and often causes team friction.
4
The Reactive Problem Solver
Detail-oriented, responsive. Excellent at service and follow-through. Gets stuck in reactive mode, spending selling time on support instead of pipeline.
5
The Challenger ★
Offers unique perspectives. Strong two-way communication. Knows the customer's value drivers and the company's economic drivers. Comfortable discussing money. Can pressure the customer constructively. The only profile that dominates the high-performer category.
The two critical findings
1
No single profile dominates the average category
Average performers come from every profile. But there is one dominant way to be a star, and it's the Challenger. In complex, solution-based sales, Challengers make up the majority of top performers.
2
The Challenger is the solution seller
The model is sustainable because it makes the customer think differently about how they operate, not just about your product. That shift in thinking is what creates preference before price ever enters the conversation.
Coaching questions for your team, Week 1
- Q"Which of the 5 profiles do you most naturally fall into? Which do you think your best customers would say you are?"
- Q"How do your meetings today compare to meetings your prospects have had with every other vendor? What makes yours different?"
- Q"Where in your sales cycle do you feel the most resistance, and which of the 4 trends do you think is driving it?"
Challenger Sale · Week 2 of 4
Building an insight-led conversation
The top reason buyers choose one vendor over another isn't price or product, it's that the rep offered them a perspective they hadn't considered. Quality insight beats everything else. The 6-step teaching pitch is how you build that into every conversation.
"Challengers teach customers new perspectives, specifically tailored to their most pressing business needs, in a way that not only resonates but actually drives action."
7 attributes: why buyers actually choose you
- Rep offers unique and valuable perspectives on the market
- Rep helps me navigate alternatives
- Rep provides ongoing advice or consultation
- Rep helps me avoid potential landmines
- Rep educates me on new issues and outcomes
- Supplier is easy to buy from
- Supplier has widespread support across my organization
Notice where "best price" and "best product" aren't. The Challenger earns preference through insight, before the conversation ever reaches the solution.
The 6-step teaching pitch
"Where does the supplier first enter the conversation? Step 6. Everything before that is about making the customer think differently, not about selling them anything."
1
The Warmer
Share anecdotes from similar companies. Tell stories. Ask for feedback. Build credibility. Lead with a hypothesis based on your own research, not a generic opener. This is also where your UFA lives, but with a teaching lean: you're setting up that you have something worth hearing.
2
The Reframe
The central pivot moment. The "aha." You're not agreeing with how they currently see their problem, you're showing them a new frame for it. This is the Challenger's signature move. Done right, they lean forward. Done wrong, they get defensive.
3
Rational Drowning
Why the reframe matters: backed by numbers. "Wow, I had no idea we were wasting that much." This is data-driven rationale tied to their specific business. An ROI calculator is not enough here, the data has to feel relevant to their situation, not generic.
4
Emotional Impact
Does the customer see themselves in the story? This is where you move from indicator to real pain. Storytelling that makes the cost personal, their career, their team, their stress. They need to feel it, not just understand it intellectually.
5
A New Way
Present the solution concept, not the supplier yet. How would the process be better if they operated differently? You're selling a better world, not a product. The customer should be nodding before your company name is mentioned.
6
Your Solution
Now demonstrate why your solution is the only one that can deliver the new world you just made them want. By this point, the preference is already built. You're confirming, not convincing.
Building your commercial teaching message: start here
- Start at the end: what do you want them to believe by the close of the meeting?
- Identify the "aha moment": the one reframe that changes how they see their problem
- Ask: "What's currently costing our customers more money than they realize, that only we can fix?"
- Create a logical, compelling path from the warmer to your solution
- Make sure steps 1–5 could apply to any competitor's solution, step 6 is what makes it yours
Coaching questions, Week 2
- Q"What unique perspective do we offer that no other vendor in our space does? If you can't name it, neither can your prospect."
- Q"Walk me through your last discovery meeting using the 6-step structure. Where did you skip a step?"
- Q"What's the reframe you're leading with: and how do you know it lands?"
Challenger Sale · Week 3 of 4
Tailoring for resonance
The same insight delivered to a CFO and a VP of Operations lands completely differently. Challengers don't have one pitch. They have one message, tailored to the specific value drivers of every stakeholder in the room, and the ones who aren't.
"Mining for information vs. empowering: that's the difference between how average reps and Challengers treat stakeholders. One extracts. The other teaches."
The new reality: why one champion isn't enough
In complex sales, widespread support across the organization is now required to close. Your deal has to survive stakeholders you've never met, in rooms you'll never be in. That means every key influencer needs to have been taught something, not just sold to.
1
Be viewed as a resource, not a nuisance
Stakeholders who feel educated and empowered by a rep become internal champions. Stakeholders who feel sold to become blockers.
2
Teach them something of value, don't just sell them something they need
The teaching comes first. The need follows naturally from the insight. Flip the order and you're just another vendor pitching.
The 4 levels of tailoring: go from broad to specific
Industry
What trends, pressures, and dynamics are affecting their entire sector right now?
Company
What is this specific organization trying to accomplish, their goals, growth stage, known challenges?
Role
What does this function care about? A CFO's value drivers are different from an ops leader's, even in the same room.
Individual
What does this specific person care about: their career, their stress, their team? This is where personal pain lives.
Why tailoring works: outcomes are predictable
Customer outcomes remain fairly stable across time and similar roles. That means you can develop a short list of desired outcomes per role and focus your message on the two or three things that person cares about most, without starting from scratch every time.
"Decrease the number of clicks it takes to place an order" lands for an ops manager. The same line does nothing for a CFO. Know the role. Know the person. Then tailor.
Coaching questions, Week 3
- Q"Who are the stakeholders in your top 3 open deals: and do you have a tailored message for each one?"
- Q"What does each stakeholder in this deal care about personally, not their company, them?"
- Q"If the deal went to a vote today across all their stakeholders, how would it go, and who haven't you gotten to yet?"
- Q"Are you educating the influencers or just the decision-maker? What are the influencers being told when you're not in the room?"
Tailoring checklist: before every multi-stakeholder meeting
- Identify every stakeholder who will influence this deal, including ones you haven't met
- Map their role-level value drivers: what does someone in this function care about?
- Identify 1–2 individual-level concerns: career, team, reputation
- Adapt the reframe (step 2) and emotional impact (step 4) for each stakeholder
- Prepare a summary showing how the solution affects each stakeholder, share it with the economic buyer
Challenger Sale · Week 4 of 4
Taking control of the sale
Being #1 in the prospect's mind is great. Nobody cares. Deals don't close because you were liked, they close because someone took control of the process. Taking control isn't aggression. It's confidence in the value you deliver, and the discipline to protect it.
"Sell a deal, not just have a good meeting. A rep who walks out thinking 'that went really well' without a signed next step just had an expensive conversation."
3 misconceptions about taking control
✗
Misconception 1: Taking control = negotiating on price
Wrong. Taking control starts at first contact and runs through every stage of the sale. It's about "verification efforts", pressing for the right access, the right stakeholders, the right commitments. Only 20% of it happens around money.
✗
Misconception 2: Reps only need to control matters of money
Control is about reframing how the customer thinks about their world, not just the invoice. When a prospect says "our company is different," the Challenger response isn't to agree: "You're right, it probably is, and so are the other companies we work with who've rethought their approach."
✗
Misconception 3: Teaching reps to take control will make them aggressive
The opposite is usually true. Without a control framework, Relationship Builders proactively offer discounts before the customer even asks, because the perceived power imbalance sends them into appeasement mode. A Challenger doesn't back down before finding out why the customer is making the request.
Anatomy of a controlled negotiation, 4 steps
1
Acknowledge & Defer
Get permission to defer the objection. "That's an important point, can I come back to that once we've covered X?" Defuses without dismissing. Sounds familiar, it's a close cousin of the UFA.
2
Deepen & Broaden
"What are you looking to achieve with a 20% price reduction?" Get underneath the ask. The stated request is rarely the real concern. Expand the conversation beyond price to surface what's actually driving the pushback.
3
Explore & Compare
Introduce other forms of value beyond price. Implementation support, timeline flexibility, access, terms. A concession on price isn't the only move, and it's often the most expensive one to make.
4
Concede According to Plan
If you concede, do it deliberately. Start with a meaningful concession, then move to smaller ones. Never "take it or leave it." Never concede without getting something in return. Have this mapped before the meeting, not in the moment.
Pre-meeting control prep: do this before every negotiation
- Write down the tough questions you'll likely face: and your answer to each
- List every objection that's likely to come up: and how you'll redirect each
- Identify your concessions: what are you willing to give, and what do you want in return?
- Score the value of each potential concession: know what's cheap and what's expensive before you're in the room
- Define the minimum acceptable outcome: and know when to walk
"Taking control has to happen throughout the sale, not just at close. From the first call: 'We need the economic buyer in the room for the next meeting. Is that something we can make happen?'"
Coaching questions, Week 4
- Q"In your last three deals that stalled: what control move did you not make that might have changed the outcome?"
- Q"Have you ever offered a discount before the customer asked for one? What were you afraid of?"
- Q"What does your pre-negotiation prep look like right now? Walk me through it."
- Q"When the prospect said your company was too expensive, what did you say? What could you have said instead?"
The 4-week program: how Angelo ran it
Session structure
Each week was a team kickoff session built around an audiobook excerpt from The Challenger Sale by Dixon & Adamson. Format: listen together → discuss → connect to your specific role → commit to one thing to try.
- Be engaged, eliminate distraction: this is active learning, not a lecture
- Be open-minded: challenge yourself to try something different before you decide it won't work
- Ask yourself after every excerpt: "How does this apply to my specific role?"
- Take notes. Leave with one implementation commitment, not a list of ten.
Week 5+: Rep-run implementation
After the 4-week program, Angelo handed implementation to the reps themselves. Three follow-on sessions, each rep-led:
1
6 steps of a teaching pitch: in practice
Using real deals from their own pipeline. Not hypothetical, live opportunities workshopped by the team.
2
Tailoring for resonance
Gaining widespread support: mapping stakeholders in actual open deals and building tailored messages for each.
3
Taking control: negotiation role play
Preparation templates, live role play, debrief. Assertiveness takes practice and planning, you can't wing a negotiation and call it strategy.
Advanced Sales
Deep discovery: the 4 layers of pain
Most reps hear the surface pain and sprint to their solution. That's why deals stall and pipeline stays stuck at stage 2. Real pain is buried. The rep who gets to layer 3 before their competitor gets to layer 1 wins, every time. This is where the Challenger rep lives. Not in the pitch. In the diagnosis.
"Surface level pains + knowledge dump = feature selling and a disconnected prospect. Deep role/business/personal pains + the right features = value selling and a connected prospect."
Why we focus on educational selling: the mindset first
Prospects buy based on the value derived from your solution, not because of all the features you drop or the knowledge you demonstrate. Pain and goals are more closely related than most reps realize. To get to the true goal or true pain, you need to ask more than surface-level questions. Most reps know this. Almost none actually do it.
"Think about your recent meetings: is there a time where you could have asked one more question that would have uncovered something deeper?" That's the coaching question. One more question changes everything.
The 4 layers: go deeper every time
L0
Surface Pain: where most reps stop
Challenges with the current solution or process, usually related to features or functionality. "Their vendor is unresponsive." "The price went up." "The process takes too long." These are real, but they're the path in, not the destination. The rep who hears "unresponsive vendor," writes it in Salesforce, and immediately pivots to their differentiator has already lost the value conversation.
L1
Role Pain: how it affects their job
Negative consequences of the surface pain that prevent the prospect from doing their job effectively. "I spent an hour going through my outbox trying to figure out the last time I emailed them." That's a role pain. An hour is real. Now you have something to work with, but you're not done yet.
Questions to get here: "How has that affected your day-to-day?" / "How much time are you spending on this?" / "What does that interrupt for you?"
L2
Business Pain: the impact on the organization
The impact of role pain on the business as a whole: in terms of lost revenue potential or exposure to risk. This is what moves the economic buyer. A VP of Finance isn't moved by "my vendor is slow to respond." They're moved by "we're bleeding $80K a quarter in audit risk because our current vendor misses deadlines." Surface and role pains are often seen as "part of the employee's job." Business pain speaks directly to the decision maker.
Questions: "How would you quantify the impact of that wasted time?" / "What would your ideal relationship with a partner look like, and what's the cost of not having it?"
L3
Personal Pain: the emotional consequence
The emotional consequence that role and business pain cause on the private life of the prospect. "It annoys me to no end, and it makes me look bad as the person who chose this vendor." Not every issue leads here. Not every prospect will share it. But when you get here, you've built a true advocate. If you can attach an emotion, "annoyed," "embarrassed," "stressed," "afraid", to the personal pain, you've created a champion, not just a contact.
Questions: "How does this affect your priorities?" / "What does this mean for you personally when things go wrong here?"
Discovery goals: what you're leaving the meeting with
- Understanding of their decision-making process
- Whether they can actually benefit from your solution based on their situation
- Level of interest: real urgency or just curious?
- A follow-up meeting scheduled with clear expectations, not "I'll reach out to find a time"
- At least one layer of pain below whatever they opened with
The SPIN framework: how to structure the questions
S
Situation
The lay of the land. "What does your current process look like?" "How do you measure this today?" Don't over-index here, reps who spend too long in Situation bore the prospect.
P
Problem
What's not working. "What's the biggest challenge with your current vendor?" "Where does the process break down?" Get specific, don't accept vague answers.
I
Implication
Probing the full impact. "You mentioned the vendor is slow, how has that affected your deadline?" This is where the rep earns their money. Most skip it. Don't.
N
Need Payoff
"If we were able to address that: how would that help you?" The prospect articulates the value in their own words. Now you're selling to what they've told you they need.
"If you want to increase someone's desire for a solution, you must first increase their awareness of the problem.", Neil Rackham, SPIN Selling
Coaching exercise: run this with your team
- Start with one surface-level pain your prospects commonly share
- As a team: brainstorm the role, business, and personal pain it causes, spend 3 minutes per layer
- For each layer: what's the pain itself, and what question would uncover it?
- Debrief: where does the team naturally stop: and why?
- Pick the one question that the team agrees would most reliably get to layer 2 or 3, and practice it
Advanced Sales
MEDDICC: qualifying to win
MEDDICC isn't a sales process. It's a qualification framework that ensures your process is fully executed. Every element you skip shows up later as a forecast miss, a surprise loss, or a deal that goes dark. By Day 90, forecast accuracy is the measure. MEDDICC is the discipline that gets you there.
"Why do we win? Why do we lose? Why do deals slip? MEDDICC was created to answer those three questions, and make sure the answer is never 'I don't know.'"
The 7 elements: what each one means for the deal
M
Metrics
The quantifiable proof. What does success look like in numbers? Without this, you can't defend your price or your value. Deals without metrics end in "no decision" or discount.
E
Economic Buyer
The final "yes" authority. Have you met them? Do they know you? No economic buyer = wasted time addressing a non-priority need at the wrong level.
Dc
Decision Criteria
The customer's requirements. No documented criteria = no consensus. It gets political. Chaos ensues. Influence this early, don't just respond to it.
Dp
Decision Process
How they evaluate, select, and purchase. No clarity here = deal slippage. Every deal that slips in Q4 usually has an unknown decision process behind it.
I
Identified Pain
Compels action. Without real pain, not indicators, real pain, there's no urgency. No urgency = no compelling event = deal slippage.
Ch
Champion
Trusted, respected, influential. Economic buyers need champions, agents of change who advocate internally when you're not in the room. No champion = no deal.
Co
Competition
All alternatives: including "do nothing." If you don't know who you're competing against, you're reacting to them. You're losing. Know the field before you get to the table.
MEDDICC through the lens of strategic alignment
To capture the attention of business leaders, you must first demonstrate that you understand their business. Research before you engage. Earn the right to ask strategic questions.
1
Corporate objectives
Annual reports, investor presentations, letter from the chairman. What is this company trying to accomplish?
2
Headwinds
What's causing the business to react? Competitive pressure, organizational change, business performance, macro trends.
3
Business initiatives
Shorter-range tactical plans in support of their strategy. This is where the budget is. This is what you attach your solution to.
4
Execution gaps
Where their initiatives are at risk. This is where your identified pain lives, and where you earn the right to influence their decision criteria.
"Informed curiosity: do your homework and you'll earn the right to strategically align. Then ask 'How?' instead of 'Why?' Why triggers defensiveness. How opens the conversation."
MEDDICC deal review: questions to ask on every pipeline call
- M"What's the specific business outcome they're trying to achieve, in numbers? What does success look like to them?"
- E"Have you met the economic buyer? Do they know your name? What's their sense of urgency?"
- Dc"What are their stated criteria for choosing a vendor, and have we influenced any of them?"
- Dp"What does the evaluation process look like, and who's involved at each step?"
- I"What happens if they don't solve this problem by end of quarter? Is there a compelling event?"
- Ch"Who is internally selling for you when you're not in the room? How do you know?"
- Co"Who else are they looking at: including doing nothing? What's their impression of the alternatives?"
Advanced Sales
The Sandler selling system
Sandler flips the traditional sales dynamic. Instead of the rep chasing the deal, Sandler positions the seller as a trusted advisor, someone who diagnoses problems and invests time only with prospects who are a genuine fit. The goal isn't to pitch everyone harder. It's to qualify ruthlessly early, so that closing becomes easy. Qualify hard. Close easy.
"Prescription without diagnosis is malpractice. You wouldn't let a doctor write a prescription after a 90-second conversation. Don't let your reps pitch after one either."
The system
Up-Front Contract
The Pain Funnel
Surface → Emotional
Trial closes
The Sandler submarine, 7 stages
Sandler uses a submarine as its visual metaphor: each compartment must be sealed before you move to the next. Skipping a stage doesn't save time. It creates leaks that sink deals at the close.
1
Bonding and rapport
Build a genuine connection before you talk business. Research the person, not just the company. Find real common ground. The prospect needs to feel like a peer in a conversation, not a prospect in a pitch. Forced small talk is worse than none at all.
2
Up-Front Contract
Establish mutual expectations at the start of every interaction. What's the purpose, the agenda, and the possible outcomes, including "no." This is where control of the process is either established or lost. (See the UFC tab for full detail.)
3
Pain discovery
Uncover the real problem, not the surface symptom. The Pain Funnel drives this stage. You're not just identifying what's wrong; you're connecting what's wrong to what it costs them personally and professionally. Buyers act on emotion. Logic comes after. (See Pain Funnel and Surface → Emotional tabs.)
4
Budget
Discuss money early, not at the end. If the budget doesn't align, every hour spent on discovery, demos, and proposals is wasted. Ask about budget before you build a solution. Sandler treats this as a qualification gate, not a negotiation lever.
5
Decision process
Who decides, how, and when? Get explicit clarity on the decision-making process before you invest in a formal presentation. Who needs to be in the room? What does approval look like? How long does procurement take? Deals die here when reps assume instead of ask.
6
Fulfillment
Present your solution only after all five prior stages are complete. This is not a demo or a pitch, it's a targeted presentation that directly addresses the specific pain, budget, and decision criteria already established. Solve, don't sell.
7
Post-sell
Reinforce the commitment and proactively prevent buyer's remorse. Confirm expectations, re-establish value, and set the tone for the implementation relationship. Most reps disappear at this stage. The Sandler rep shows up harder after the close than before it.
"Sandler vs. Challenger: Sandler qualifies first: then teaches. Challenger teaches first, then challenges assumptions. Both are right. The difference is the entry point. In an outbound motion, Sandler's qualification-first approach often wins."
The Up-Front Contract (UFC): what it is and why it matters
The UFC is a simple verbal agreement made at the start of every interaction. It establishes the agenda, the timeframe, and, critically, the possible outcomes, including the prospect's right to say no. It's not a legal document. It's a mutual promise that this conversation will be honest, productive, and respectful of both sides' time.
Most reps skip this because it feels formal or awkward. But the reps who don't set a UFC are the ones who end every call with "sounds great, let's circle back soon", and then chase ghosts for three weeks.
The four elements of every UFC
1
Purpose: why are we here?
State the goal of the meeting explicitly. Not assumed, stated. "The purpose of today is to understand your current environment and figure out together whether there's a problem worth solving." One sentence. Does the prospect agree? Confirm it.
2
Time: how long do we have?
Agree upfront and respect it. "We have 30 minutes: does that still work?" If something comes up mid-call that warrants more time, ask: "I want to be respectful of your time. Would it be worth taking another 10 minutes to get into this deeper?" Never assume you can go over.
3
Agenda: what will we cover?
Walk through the 2–3 things you plan to cover and give the prospect a chance to add to it. This creates buy-in and prevents end-of-call surprises. "Here's what I was thinking we'd get through, does anything else need to be on this agenda?"
4
Outcome: what are the possible results?
This is the most important element. State the possible outcomes, including "no." "By the end of our conversation, one of three things will be true: you'll see enough to want to take a next step, I'll see something that tells me this isn't the right fit, or we'll both agree there's no match here, and that's a completely fine outcome too." Giving permission to say no increases honest engagement.
UFC example: cold outreach to first call
"Thanks for making time today. I want to make sure this is worth 30 minutes for both of us.
Here's what I was thinking: I'll spend a few minutes learning about what's on your plate right now, specifically around [problem area]. Then I'll share a bit about how we work with teams like yours and whether there's a fit worth exploring.
By the end, you might say 'this isn't relevant right now', and that's totally fine. Or we might both see something worth taking a step further. Either way, I'll be straight with you.
Does that work for you?"
"UFCs eliminate 'I need to think about it' stalls: because you've already agreed upfront that 'no' is a valid outcome. A prospect who knows they can say no is more likely to say yes."
The Pain Funnel: from symptom to real problem
The Pain Funnel is Sandler's structured questioning approach for discovery. It starts broad and gets progressively more specific, moving from surface symptoms to the business impact to the personal, emotional cost of the problem. Most reps stop at layer one. The rep who reaches layer three is the one who wins the deal.
Think of it like a doctor. The first question is: "What brought you in today?" Ten questions later, they know exactly what's wrong, not from assumptions, but from a disciplined line of questioning. That's the Pain Funnel.
The three levels of pain
1
Surface pain: the symptom
What the prospect mentions first. Generic, shared with every rep who calls. "Our reporting is slow." "We lose deals to competitors." "Ramp time is too long." This is the entry point, not the destination. Don't pitch here.
2
Business impact pain: the consequence
What is the symptom actually costing the business? Time, revenue, headcount, churn? "That slow reporting is delaying board reviews by 3–5 days." "Those lost deals represent $400K in pipeline walked out the door last quarter." Quantify it. Numbers create urgency that words don't.
3
Emotional pain: the personal stakes
This is the layer that closes deals. Who is frustrated? Who is under pressure? What happens to this person professionally if the problem doesn't get solved? "The CFO is frustrated with me." "I've been asked to fix this twice. A third failure would be a problem for my role." This is where buying decisions actually happen. Buyers buy emotionally and justify logically.
Pain Funnel question sequence: start broad, narrow down
- Q"What are some of the biggest challenges you're facing in [area] right now?", Open the funnel wide.
- Q"Can you tell me more about that?", Never assume you understand. Make them expand.
- Q"How long has this been going on?", Time adds weight. A problem that's been around 18 months has more urgency than one that showed up last week.
- Q"What have you tried to fix it?", Shows what's been attempted. Reveals how serious they are.
- Q"What happened when you tried that?", They tell you why it failed. Now you understand the real gap.
- Q"What's the impact of this on your team / business?", Move from symptom to consequence.
- Q"Can you put a number on what this is costing you?", Quantify the business pain.
- Q"How does this affect you personally?", This is the move into emotional pain. Don't rush to it. Earn it.
- Q"What happens if this doesn't get resolved in the next six months?", Creates urgency without pressure.
- Q"So if I have this right...", Summarize their pain back in their own words. A resounding "yes" means you've found it.
Taking surface pain and making it emotional: the skill most reps skip
People buy emotionally and justify logically. This isn't a sales trick, it's human psychology. When your prospect feels the pain personally, the urgency to solve it is intrinsic. When the pain stays at the business level, it's someone else's problem. Your job as a rep is to move it from abstract to personal.
This requires patience. Most reps sprint to the pitch the moment they hear a surface pain. Slow down. The deal is in the depth of the diagnosis, not the speed of the solution.
The surface → emotional progression: how it works in practice
1
Acknowledge the surface pain, don't pitch it
When a prospect says "our ramp time is too long," the instinct is to say "great, we solve that." Don't. Instead: "Can you tell me more about that?" You've acknowledged it without claiming it. Now dig.
2
Quantify the business consequence
"How many reps are you ramping per quarter? What does a rep generate in their first 90 days once productive? So what's the gap costing you per head, per quarter?" Now it's a number. A $200K problem gets attention. "Long ramp time" doesn't.
3
Connect it to the person, not just the business
"Who owns this problem internally?" Whoever answers that question is the person with the most skin in the game. Follow up: "How long have you been working on this? What happens if it doesn't get better?" Now the problem belongs to someone, not just to the company.
4
Let the emotional weight sit, don't fill the silence
After a prospect describes real personal stakes: the pressure they're under, what's at risk for them, resist the urge to jump in with a solution. Pause. Let it land. "That's a lot to be carrying." The silence after an emotional admission is where trust is built. Don't interrupt it.
5
Confirm you've found it: use their words back
"So if I'm hearing you correctly, [symptom] is causing [business impact], and the pressure that creates for you personally is [emotional consequence]. Is that right?" If they say yes, that's the pain. That's what you're solving. Don't start the pitch until you can finish that sentence in their words.
"When you break your arm, you don't shop around for the best price on getting it fixed. You just fix it. That's what emotional pain does to price sensitivity, it eliminates it. Get to layer three and you're no longer competing on price."
Trial closes: temperature checks, not hard closes
A trial close is not asking for the deal. It's checking where the prospect is in their thinking, so you can identify objections early, confirm alignment, and avoid the end-of-process surprise. Think of it as a barometer reading, not a pressure move.
The Sandler philosophy: move closing to the beginning of the process. If you've qualified pain, budget, and decision process correctly, the close shouldn't be a dramatic moment, it should be the natural next step the prospect already agreed to.
Trial close question bank: use throughout the process
1
After pain discovery
"Based on what you've shared, does it sound like what we do could be relevant to what you're working through?", Simple, non-pressured, reveals commitment level.
2
After presenting a concept or feature
"How does that land for you?" / "Does that address what you described earlier?", Confirms you're on track. If they say "sort of," you have a gap to close before going further.
3
After the demo or fulfillment stage
"On a scale of 1–10, how relevant is what you've seen to the problem you described?" Anything below 7 opens a real conversation. "What would make it a 9?" surfaces the hidden objection without confrontation.
4
Testing commitment to next steps
"If this checks out from a [budget / stakeholder / technical] standpoint, is there any reason we wouldn't move forward?", The Sandler "negative reverse." If they hesitate, now is the time to find out why, not at the contract stage.
5
The soft close: when you're ready to ask
"Based on everything we've covered: the pain you described, the business impact, and what you've seen from us, does it make sense to take a next step?" Let them guide the answer. A soft close that follows a fully qualified discovery rarely gets rejected. If it does, something was missed earlier in the funnel.
Clear next steps: the Sandler connection
Every interaction should end with a UFC for the next interaction. What happens next, who owns it, and by when. This is where Sandler and clear next steps discipline overlap completely.
- Never leave a call without a defined next step: date, owner, purpose
- Use the Up-Front Contract structure to open the next conversation before you close this one
- If a prospect won't commit to a next step, the deal isn't as far along as it appeared, that's your signal
- "Touching base" is not a next step. A specific date with a specific purpose is a next step.
- The rep who controls the next step controls the deal. The rep who says "I'll follow up" has already lost control.
"Qualify hard, close easy. If the close feels hard, something was skipped earlier, pain wasn't real, budget wasn't confirmed, or the decision process wasn't mapped. Go back. Find the gap. Don't push harder on a broken foundation."
Leadership tool
The 1:1 system, 3 types, each with a different purpose
Most managers run one kind of 1:1 and call it everything. They don't. The standard 1:1, the career development conversation, and the pipeline review serve completely different purposes, and confusing them makes all three worse.
"Transparency → Trust → Hard work → Coaching → Success. The 1:1 is where all of it starts."
Standard 1:1
Career development
Pipeline review
"Their time": the standard weekly 1:1
This meeting belongs to the rep. They set the agenda. They come prepared. Your job is to listen, ask questions, and coach, not to download updates or run the pipeline.
1
Format
30–45 minutes. Same time, same day every week: preferably early in the week, afternoons. Non-negotiable cadence. Block it. Never cancel unless you've already made the make-up.
2
Their responsibilities
They fill out the agenda template you've sent in advance. Their topics, their priorities, their questions. If they come unprepared, that's the first conversation.
3
Your responsibilities
Come prepared. Listen to their calls before the session. Know why they're succeeding or struggling before you walk in. Ask questions to discover, don't fill the silence with advice. Indirective coaching before directive coaching.
4
Why it works
Dedicated time for communication. Alignment on goals. Accountability. And most importantly, it builds the relationship that makes every harder conversation easier.
"Lead with questions first, recommendations second. Be a human."
"Both of your time": the career development 1:1
Monthly or quarterly. Separate from the standard 1:1, don't try to sneak this into the last five minutes of a pipeline review. It signals that you're invested in them beyond their number.
1
What you cover
Their current goals in role. Their long-term goals. What support they need from you. Where they see themselves in 12 months. What they'd need to see to want to stay.
2
Their responsibilities
Come ready to discuss current and long-term goals. Come ready to articulate what support they need. Everything should be documented, by them.
3
Your responsibilities
Speak to their current goals in role, don't wing it. Work with them to set goals for future roles. Be explicit: "Here's what I see as the path, and here's how I'll help you get there."
4
Why it matters
Improves engagement and retention. The rep who knows their manager cares about where they're going is the rep who doesn't quietly shop the market. How often are you talking to your reps about their future?
"My time": the pipeline review
This is not their time. This is your time to understand their pipeline and forecast accurately. You drive. They come prepared with clean data. Separate this completely from the standard 1:1, they serve different purposes and mixing them ruins both.
1
Format (AEs)
Start with the largest deal every time: no exceptions. "Quick hits" stay on schedule. Yes/no answers, avoid stories. Next steps field must have a date, tactical next step, and goal. If it doesn't, the deal doesn't advance.
2
Format (SDRs/BDRs)
Start with top accounts. Dig into weekly activity. Assess whether it's the right activity, not just any activity. Ask about strategy and focus. Offer specific assistance.
3
Their responsibilities
CRM is clean and current before the session. All opportunities updated. Prepared to speak to every open opp, its next step, and its close date.
4
Your responsibilities
Come prepared. Ask questions to uncover gaps, not just collect updates. Coach to help progress. Gather intel to report up. A pipeline review where you only listen is just a status update meeting.
"1:1s are for them. Pipeline reviews are for me. Both matter, but don't confuse them."
Leadership tool
SaaS metrics 101
You can't lead a recurring revenue business without speaking the language of it. These are the metrics investors, CEOs, and CFOs use to evaluate your team's performance, and your own. Know them cold before you walk into your next exec review.
"If you think management is for you: these are the metrics your organization's quota, goals, and budget will be determined by."
Revenue
Retention
Growth
Unit economics
Bookings, Billings, Revenue, not the same thing
B
Bookings
Total contract value that will become revenue over time. Includes multi-year commitments. Not the same as revenue or ARR. Not typically used for quota contribution.
B
Billings
Amount invoiced in a specific period. May be monthly, quarterly, or annual depending on contract terms. Not the same as bookings or GAAP revenue, but often used as the basis for comp payments.
R
GAAP Revenue
Revenue recognized per accounting standards. Subject to ASC 606 guidelines. A primary metric investors use to value the company. Do not confuse with ARR.
Recurring revenue: the three forms
ARR
Annual Recurring Revenue
The hallmark of SaaS. Any subscription agreement: monthly, annual, or multi-year, that recurs. Calculated as MRR × 12. The predictability of ARR is why SaaS companies command premium valuations.
MRR
Monthly Recurring Revenue
More common in low-ACV or monthly agreement businesses. MRR × 12 = ARR. Use this to track momentum month-to-month.
CARR
Contracted ARR
All contracted recurring revenue including deals not yet live. Includes deals in implementation. Does not include known churn not yet incurred. Forward-looking view of ARR.
Contract value metrics
TCV
Total Contract Value
Full value of a contract including subscription, professional services, and multi-year value. Sometimes used interchangeably with Bookings, confirm how your company defines it.
ACV
Annual Contract Value
Value of the annual revenue in a subscription. Used by leadership to understand the average annual value of new customers. A 2-year deal at $100K/year = $100K ACV in Year 1, $100K in Year 2.
Retention: the numbers that tell you if you have a real business
GDR
Gross Dollar Retention
% of ARR renewed from existing customers, not including upsells. The floor metric. 100% GDR means you retained every dollar you had. Below 85% is a serious signal. Benchmark: best-in-class SaaS is 90%+.
NDR
Net Dollar Retention
GDR + expansion revenue from upsells and cross-sells. NDR above 100% means your existing customer base is growing without any new logos. This is the metric investors love most. World-class NDR is 120%+.
Logo
Logo Retention / Churn
% of customers (by count) that renew. A useful leading indicator, but less meaningful than dollar retention, because not all logos are the same size.
"If your NDR is above 100%, your existing customer base grows itself. If it's below 100%, you're filling a leaky bucket, and new logo acquisition is just slowing the leak."
Expansion: growing what you have
↑
Expansion ARR
Increase in ARR from existing customers through upsells, cross-sells, or usage-based pricing increases. Does not include new logos.
↑
Up-sell
Selling more of the same product to an existing customer, higher tier, more seats, more volume.
↑
Cross-sell
Selling a different product or service to an existing customer. Typically requires a separate relationship within the account.
Average metrics: understanding your model
ASP
Average Sales Price
Used by sales management to determine how many new customers are needed to hit a revenue target. Tells you your new logo math: if your quota is $1M and your ASP is $50K, you need 20 wins.
ARPA
Average Revenue Per Account
Total ARR ÷ average number of customers on contract. Tracks over time to show whether your customer base is getting larger or smaller on average.
Unit economics: the two metrics every leader needs
CAC
Customer Acquisition Cost
Total fully-loaded sales and marketing expense ÷ number of new customers. Includes salary, incentive comp, tools, facilities. Used by investors to assess ROI on growth investment. High CAC isn't always bad, if CLTV is much higher.
CLTV
Customer Lifetime Value
ARPA × Gross Margin ÷ ARR Churn Rate. Measures the total value of a customer over their lifetime with you. The ratio of CLTV to CAC is the most important unit economics metric: 3:1 or higher is healthy. Below 1:1 means you're destroying value with every customer you acquire.
"These are the GPS coordinates for your business: whether you're running a team or eventually running the company."
Quick reference: the ratios that matter
| Metric | Healthy | World-class |
| Gross Dollar Retention (GDR) | > 85% | > 90% |
| Net Dollar Retention (NDR) | > 100% | > 120% |
| CLTV : CAC ratio | 3:1 | 5:1+ |
| Logo churn (annual) | < 10% | < 5% |
Leadership tool
Forecasting: the executive review
Walking into a budget or forecast review with leadership isn't a status update meeting. It's your opportunity to hold the organization accountable to the inputs that drive your revenue number, marketing, headcount, product, and HR. Know what to ask before you walk in.
"My goal is predictable sales, not hero sales. Predictability comes from asking the right questions upstream, not just managing the team downstream."
Marketing
Headcount
Product
HR
Marketing budget: what to ask and what to watch for
1
Fixed or % of trending revenue?
If trending: ask a lot of questions. A % of trending revenue means that when your revenue number drops, so does your marketing investment. You don't want this, it's a self-reinforcing downward spiral.
2
Events, tradeshows, advertising spend
Review line by line. How are you promoting the brand, what is the call to action, and what does this specifically do for lead creation? Spend without measurable lead outcome is exposure.
3
MQL expectations: monthly and annual
Do they follow the cyclicality of the business? How are MQLs qualified? What action is taken when the minimum MQL KPI isn't hit, and how does that affect your revenue number? Get specific.
4
New product rollouts
What is the marketing plan, total investment, projected outcome, and timeline? Marketing and sales need to be aligned on this before the number is baked in.
Headcount: human capital budget questions
1
Review support staff carefully
Any department that directly supports sales: ops, service, technology, admin, management. Reductions mean your team does more with less. Adds mean they need to produce more revenue to maintain EBITDA. Know which is happening.
2
Revenue to sales headcount ratio
Classic benchmark: $1M revenue per sales headcount. If your team of 50 is forecasted to deliver $50M, that's a 1:1M model. Too low means too much non-quota-carrying headcount, expensive model. Too high means you can afford to add support roles.
3
Revenue to total company headcount
Always ask about this. Gives you visibility into whether the overall organizational structure is sustainable against the revenue plan.
4
Budget for internal promotions
Non-negotiable visibility item. Internal promotions affect quota-carrying transitions, ramp timelines, and team morale. Know the plan before the people do.
Product: how growth assumptions are built in
1
New product launches and timelines
Ask about them. Then ask how the team is held accountable to those timelines, because if a product launch misses, and revenue was built against it, your number takes the hit and you need a plan.
2
Timeline accountability
"If they miss a launch timeline, what's the plan?" If there isn't one, you're the contingency. Get aligned at the table, not after the miss.
3
Anticipated growth by product or enhancement
"How was that growth number calculated?" If it's a round number with no methodology behind it, push back. Revenue assumptions from product need to be grounded in something.
HR, the questions most heads of sales skip
1
Performance Improvement Plans
Present current PIPs and discuss termination timing based on performance, gain alignment, transparency, and consistency at the table. Surprises here are expensive.
2
Open headcount requisitions
Time-to-fill requirement. Investment in tools and assessments. Internal promotion impact on quota-carrying transition timelines. All of this affects your ramp math.
3
Maternity/paternity leave policy
Ask about leave policy and the impact on quota and headcount, before someone on your team goes on leave and you find out mid-quarter that nobody planned for it.
"The head of sales owns all revenue responsibility. That means the inputs matter as much as the outputs. Hold the organization accountable to the levers that feed your number."
Leadership tool
The Eisenhower matrix: protect your time
Nearly everything is noise. Most reps treat their calendar like a suggestion. This matrix, built on real-world sales categories, forces a hard conversation about where your time actually goes and what to eliminate, delegate, or automate so your peak hours stay on revenue-generating activity. Your best thinking has a window. Protect it.
"When you're not in a meeting, you're trying to get another meeting or move your pipeline forward. Everything else is a question."
The 4 quadrants: where does your time actually go?
Q1
Urgent + Important, Do Now
Pipeline review · Forecast · Discovery meetings · Lead management · Pipeline meetings · Follow-up emails on active deals · Meeting invites for follow-ups · Post-meeting follow-up emails · Meeting prep
Q2
Not Urgent + Important, Plan
Professional development · Prospecting for new contacts · Review non-current FY report · Top 50 account strategy · Stretch assignments · Mental health breaks · 1:1s · Custom emails · LinkedIn InMails
Q3
Urgent + Less Important, Delegate or Automate
Salesforce admin · Event registration/list BCIs · Upload monthly engagement plan · Responding to content asks · Update campaigns you own · PMB · Ad-hoc asks from direct leadership · Responding to internal emails that don't impact deals
Q4
Not Urgent + Less Important, Eliminate
Attending webinars not aligned with current goals · Strategy for deals not in pipeline · Over-customizing messaging for low-priority prospects · In-person events with no prospects or ROI · Attending internal meetings with no clear purpose · Office chats that drag on · Worrying about things outside your control
How to run this exercise with your team
- Have each rep fill out the matrix for their actual week, not their ideal week
- Compare to the standard above: what's in the wrong quadrant?
- Identify the single biggest Q3 item they can automate or delegate this week
- Identify the single biggest Q4 item they can eliminate, and hold them to it
- Revisit quarterly: calendar drift is real, especially when things get busy
The time audit question: run this in your next 1:1
- Q"Walk me through the last three days hour by hour. What did you actually spend your time on?"
- Q"What time of day are you sharpest: and are you doing cold calls or Salesforce admin during that window?"
- Q"What's eating the most time in your week right now that isn't advancing a deal?"
- Q"If we could give you back 5 hours a week: what would you do with them?"
IANS Research
IANS sales meeting structure
The IANS sales process is a structured, multi-stage evaluation journey designed to transform interest into committed intent. Each meeting has a defined goal, a defined structure, and a defined next step, because leaving a meeting without all three means you don't have a deal, you have a conversation. This is an example of how to adapt a structured sales process to your specific product and segment. Every stage has a clear goal, a defined structure, and a required next step. Use this as a template, then build your own version specific to your product's evaluation journey.
"Sell a deal, not just have a good meeting. Every stage has a goal and a next step. If you leave without both, you haven't advanced anything."
Discovery
Deep Dive
AAE Scoping
POC
Go/No Go
Discovery: first meeting, qualify and set the next step
Goal: Qualify the opportunity, gauge interest, deliver the value prop, and set up the Use Case meeting.
1
Agenda structure
Catalyst for the call → Projects on security roadmap → Understanding of IANS → Value proposition → Questions and what they find valuable (Need) → Gauge interest → Mention price range $40–60K (do not show packaging slide yet, Authority & Budget) → Next step discussion, tease the POC process
2
What you're qualifying (BANT)
Budget: Gauge with price range mention, don't show packaging. Authority: Who else needs to be involved? Need: What projects are on their security roadmap? Timing: When are they looking to make decisions?
3
Success criteria
Leave with: discovered projects, delivered value prop, uncovered interest, gauged budget with $40–60K range, agreement to Use Case meeting, scheduled ASAP, before any internal socialization.
Use Case / Deep Dive: align timing, scope the POC
Goal: Provide specific use case examples, get full BANT clarity, and establish the trial/evaluation plan.
1
Agenda structure
Feedback on services since last call → Light value prop → Walk through use case and advanced/add-on features → Walk through pricing and packaging → Introduce trial process → Scope the AAE or schedule scoping time
2
What you need to confirm
Full BANT clarity: all four elements confirmed. Who needs to be involved in the process? Do they agree to submit to budget if the trial is successful?
3
Success criteria
Leave with: specific AAE topic, questions, success criteria, clear mutual expectations, 3 x 1-hour blocks scheduled for the AAE call, and a plan for when the portal trial will go live.
AAE Scoping: define the trial, set success criteria
Goal: Narrow the scope of the Ask-An-Expert call, find a project with business-level impact, and define measurable success criteria for the trial.
1
Scoping questions to ask
What topic would you like to discuss? → What's the driver/business context? → What specific questions do you want answered? → What's your team's knowledge level on this topic? → What are you hoping to achieve from this interaction? → Is there a specific project, deadline, or rollout associated with this?
2
What you're building
4–5 discussion points/questions for the faculty member, any nuances about the org or environment, a clear topic, and the boundary conditions for the trial (time, participants, access).
3
Success criteria
Leave with: specific AAE topic + questions + success criteria + trial boundaries + important contacts + 3 x 1-hour blocks to schedule the call + 30-min portal walkthrough meeting to kick off the trial.
Proof of Concept: transform interest into intent
Goal: Allow the prospect to be treated like an IANS client for a defined period. Socialize the value across their team. Make hypothetical features tangible.
1
POC elements
Daily Dive trial access · Peer Community event access · Portal access with curated links to their specific topics · Security Academy / Leadership Development · Work with SME on relevant areas · Reference call · Trial Ask-An-Expert call · Access to hot topic briefings
2
Team introduction (if needed)
If more than one person is involved in the buying process, run a separate team introduction meeting. Full value prop for the new audience. Reinforce trial timeline, POC question, and expectations. Goal: gain buy-in from everyone, not just your primary contact.
3
Success criteria
Solidify the Go/No Go debrief date: scheduled for 1 day following the trial AAE call. The trial must end with a clear next step, not a "we'll be in touch."
Go / No Go: ask for the business
Goal: Win the business, or get a clear no. Leave with a defined procurement path and next step scheduled.
1
Meeting structure
Review all elements of the trial experience → Reinforce positive feedback from the AAE call → Ask if anything else came to mind since then → Ask for the business → Solidify: pricing and packaging, anticipated start date, MSA agreement, procurement process and timeline
2
What you must leave with
A clear answer, not "we'll discuss internally." A defined procurement process. Clear ownership of who does what next. A specific next step scheduled for a procurement check-in, not "I'll follow up."
3
Stage definitions (for reference)
Stage 1–2: Qualifying → Stage 3: Evaluation Started (AAE scheduling begins) → Stage 4: Evaluation Completed (after AAE, before procurement) → Stage 5: Procurement (reviewing paperwork, eval complete)
Leadership tool
Building & sustaining culture, 6 pillars
Culture is behaviors. Not perks, not ping-pong tables, not your values slide in the all-hands deck. It's the consistent, observable patterns of how your team operates, how you give feedback, run meetings, handle conflict, and recognize performance. Behaviors define culture. And 80% of a rep's perception of the company is shaped by their direct manager. That's both a responsibility and an opportunity.
"Building culture is the most important part of your job. When things aren't good, when people stress out, burn out, then opt out, it starts here."
Trust
Motivation
Metrics
Recognition
Development
Hiring
Pillar 1: Trust & psychological safety
Google's 2-year research study of 180+ teams found that psychological safety, not IQ, education, or work ethic, was the #1 attribute of top-performing teams. When people feel safe, they take risks, fail, and get creative. When they don't, they manage up instead of solving problems.
1
No one cares what you have to say unless they know you care about them
Share your personal failures and shortcomings first. Use self-deprecating humor. Build personal relationships with no agenda. How you say something is more important than what you say. Honor your word, "hold me accountable."
2
Microculture is established by everything you do
The energy you show. The values you demonstrate. The questions you ask. The outcomes you reward. The criticism you deliver. The people you fire. The stuff you tolerate. When the team wins, they get the credit. When you lose, it's your fault.
3
Confident humility
"Having faith in our capability while appreciating that we may not have the right solution or even be addressing the right problem." Enough doubt to reexamine. Enough confidence to pursue. That's the leadership posture.
Pillar 2: Motivation
Two types: extrinsic (money, trophies, rewards) and intrinsic (enjoyment, growth, purpose). Most sales leaders assume everyone is motivated like they are. That's how you miss half your team.
1
Know the difference
The rep who doesn't care about spiffs isn't low-motivation, they're intrinsically driven. Ask them directly: "What drives you? What would make this the best job you've ever had?" Then document it. Build a spreadsheet: rep name, strengths, development areas, how they're motivated, what you're working on together.
2
Competitions: do them right
Ask: what behavior do you want to motivate? Competitions break monotony, build relationships, and are fun. Get weird. Zero-cost rewards work (half-day Friday, meeting with the CEO). Do one large cross-team competition a year. Monthly: most meetings booked, highest close rate. Whale hunting. Shark week. Quota club.
Pillar 3: Metrics & operating rhythm
1
Create standards of excellence: roll out on day one
Every rep should know their individual KPIs, the team metrics, and company-level metrics. Align with your manager. Set the expectation: change is the only constant. Review benchmarks quarterly and adjust. The rep who doesn't know the standard can't be held to it.
2
Operating rhythm: analyze how your team actually spends their time
Meetings should be a mix of: Updates (process/product), Development (training/coaching), Collaboration (brainstorming), and Team-building (ice-breakers, peak of the week). Review your meeting cadence quarterly, with the team. Before you tell someone to fix their time management, know their calendar.
3
Effective sales meetings
Start with an energizer. Simplify the agenda and goal. Build recognition into every meeting. Sample agenda: Energizer → Alignment on goals/KPIs → Team updates → Collaboration topic → Rewards/recognition. End on energy, not admin.
Pillar 4: Rewards & recognition
1
Recognition rules
Peer-to-peer recognition. Use a leaderboard to show performance publicly. Company-wide shout-outs for personal bests. Weekly team shout-outs. Tell your team leads it's expected of them to recognize peers, culture can't just come from the top.
2
The three magic words
"I'm proud of you." Think about the last time someone said this to you. It's probably your mom or dad. It triggers an emotional response that strengthens the connection. Say it to your team when it's earned, and mean it.
3
Share best practices publicly
Post snapshots of objections and wins in Slack. Prospecting huddles. Weekly deal reviews where the team teaches each other. Recognize people who go out of their way to share, make it an explicit part of the culture, not just something you hope happens.
Pillar 5: Personal & professional development
83% of Gen Z want to learn skills to perform better in their role. They will leave if they don't feel they're being developed. 25–40% of your time should be spent coaching. Not reviewing pipeline, coaching.
1
The monthly development conversation
15 minutes, monthly, separate from the standard 1:1. One question: "In the next 6–12 months, how can you become a better version of yourself toward your career goals?" Track it. Follow up on it. Show them you remembered.
2
Providing feedback: the framework
Real time, not at quarterly reviews. Ask how they like to receive it. Be specific, not "you talk too much on calls" but "in yesterday's discovery with X, we never got to their timeline because we spent 12 minutes on features they didn't ask about." Focus on behavior, not personality. Let people coach themselves with the right questions.
Pillar 6: Hiring for culture
1
Write down your values: then hire to them
Create a hiring scorecard that measures candidates against the same criteria every time. Eliminate bias. Create interview questions aligned with each value. Test coachability in the interview, it's the most reliable predictor of long-term performance.
2
Hire people who will stand out, not fit in
Diverse teams: in personality, background, and experience, see higher revenue and higher returns. Don't hire more of you. The introverts are often the better listeners. A blend of personalities builds the best teams. Stop looking for the rep who reminds you of yourself at their age.
3
Culture fit interview questions
Growth mindset: "In what ways do you invest in your own development?" Collaboration: "Tell me about a time you had a conflict with a peer, how did you solve it?" Coachability: "What's the toughest piece of feedback you've received, and what did you do with it?"
Leadership tool
The art of feedback & tough conversations
We forget 87% of new information within 30 days. Feedback is how learning sticks. But most managers avoid it, because they're afraid, don't know how, or hope the problem resolves itself. It never does. The toughest conversations become easy when you've been giving good feedback all along. The Fierce Conversations framework gives you the structure to stop avoiding them.
"Vulnerability is the mother of trust. Giving and getting feedback is an act of vulnerability. The best way to create trust is to encourage and give feedback, especially when it's tough."
5 rules
Fierce conversations
In practice
PIPs & firing
Coach, don't advise
5 rules of effective feedback: positive and constructive
1
Remember your why
Trust is the goal. You're investing in the person's success. You're investing in a high-performing culture where everyone can win. Feedback without that intention reads as criticism. Feedback with it reads as coaching.
2
Be timely, within 24 hours
The longer you wait, the harder it is to be specific. Overdue feedback is feedback that's been withheld, and the recipient will feel you've been holding out on them. The toughest conversations become easy when you've followed this rule on the smaller ones.
3
Be relevant
Is this behavior actually blocking them from being their best, or blocking you from being yours? If neither, you don't need to give it. And if you decide not to, you've also decided to stop letting it distract you.
4
Be specific
Not: "I've noticed you show up unprepared for client meetings." Yes: "This morning in your discovery with X, you asked two questions already covered in the SDR notes, and showed no evidence of researching their company. Let's talk about prep." When you're timely, being specific is easy.
5
Never via Slack or email
The only role for written communication in feedback is to recap mutual commitments, summarize what was said, and create an HR record. Feedback always happens face-to-face or on a call. Always.
Signs you need to give it, don't wait for certainty
1
A performance or behavior pattern, not a one-time incident
One bad call is an observation. Two bad calls is a coaching moment. Three is a pattern you're now responsible for addressing. The moment you notice it for the second time, the clock starts.
2
A gut feeling, it's visceral
Your instincts are usually ahead of your data. If something feels off, it probably is. Don't wait for the spreadsheet to confirm what your gut already knows. The conversation you're avoiding is almost always the one that matters most.
3
You're talking about them to someone else first
This is the clearest signal. The moment you find yourself discussing a rep's behavior with a peer before discussing it with the rep, you've already had the conversation once. Have it with the right person.
The Fierce Conversations framework: a structure Angelo has relied on for nearly a decade
Most tough conversations fail because the manager walks in with emotion and no structure, or with structure and no humanity. Fierce Conversations solves both. It gives you a seven-step framework that ensures you name the real issue, make it specific, own your part in it, and invite a real response, without letting the conversation drift into a lecture or devolve into a reaction.
The framework works for performance conversations, behavior conversations, culture conversations, and development conversations. The steps are the same every time. The content changes. That consistency is what makes it trainable, and what makes it feel less like an ambush and more like an honest conversation between two adults.
The 7 steps: in order, every time
1
Name the issue
State clearly and directly what the conversation is about. No warm-up, no easing in, no "I just wanted to check in about a few things." The rep deserves to know immediately what they're walking into. One sentence. Specific. "I want to talk about your activity over the last three weeks and whether the effort matches the expectation for this role."
2
Select specific examples
Name the actual instances. Not a general impression, specific, observable, datable events. "On Tuesday you said you'd complete your outreach block after lunch. Your activity tracker showed zero calls that afternoon. On Thursday your CRM had no updates from the previous two days." Specificity is what separates feedback from opinion. Opinion can be argued. Specifics cannot.
3
Describe your emotion
This is the step most managers skip: and it's the one that makes the conversation land. Not "I've noticed" or "the data shows", how does this make you feel as their manager? "I feel like I've been clear with the expectations and that you haven't held up your end of the agreement." Expressing the emotion is not weakness. It's the signal that this conversation is real, not performative.
4
Clarify what's at stake
Be explicit about the consequences: for them, for the team, for their career. Not a threat. A fact. "Your role on this team is at stake." "This pattern is affecting how you're being perceived by leadership and what opportunities open up for you." "The team's ability to hit their number is being affected by this." The rep needs to understand that this isn't just a coaching conversation. The stakes are real.
5
Acknowledge your contribution
Own your part: always. This is not optional and it is not lip service. "I should have addressed this after the first time I saw it, and I didn't, that's on me." "I've been focused on the new reps and I haven't invested enough time in development conversations with you." This step does two things: it's honest, and it removes the rep's ability to make the conversation about your failure instead of theirs. You've already named it.
6
State your resolution wish
Tell them clearly what you want to see. Not what they need to stop, what you want to see them do. "My goal is to get you to a place where we're talking about big wins instead of minimum expectations." "I want to see you demonstrate that you want this role, not just that you need the paycheck." "My wish is that over the next 30 days you close this gap so we can start the new year clean."
7
Invite them to respond
End with a genuine, open question: and then stop talking. "What are your thoughts?" "What's your perspective on this?" The conversation up to this point has been yours. This step hands it to them. Their response tells you whether the message landed, whether they're aligned, whether there's context you didn't have, and whether this is a person who is going to fight for the role or quietly check out. Listen to all of it before you respond.
"The Fierce Conversations framework doesn't make tough conversations comfortable. It makes them honest. And honest is what actually moves people, in both directions."
The framework in practice: real conversations, real situations
These are examples of the Fierce Conversations framework applied to actual situations a sales manager will face. The names are changed. The structure is real. Study the pattern, the framework is the same in every one.
Scenario 1: Activity and commitment gap
1
Name the issue
"I want to talk today about your performance on activity metrics and the expectations for this role as you move into your quota period."
2
Specific examples
"We had a conversation where you committed to completing your outreach block that afternoon, you didn't. Your activity tracker went untouched for two days. You weren't logged into the CRM on Friday or the following Monday."
3
Emotion
"I feel like I've been clear with the expectations of this role, and that you haven't held up your end of the agreement."
4
What's at stake
"Your role on this team is at stake. However: if you turn this around over the next three weeks, that changes."
5
Your contribution
"I should have been more consistent in following up after each commitment you made. I let it go too long."
6
Resolution wish
"My goal is to see you demonstrate that you want this role and that you're willing to do what it takes to succeed in it."
7
Invite response
"What are your thoughts?"
Scenario 2: Image and team dynamic
1
Name the issue
"I want to talk about your image: specifically how it's being perceived by the team and the region, and what it means for your career development."
2
Specific examples
"You've said yourself that you're polarizing: that people either love you or hate you. I'm going to take you at your word on that and tell you I'm concerned about what the 'hate you' side means for your advancement."
3
Emotion
"I'm genuinely concerned, not frustrated. I think you have real ability and I don't want this pattern to close doors that should be open to you."
4
What's at stake
"Career advancement. How leadership sees you. Team morale. These aren't small things."
5
Your contribution
"Honestly: some of this is on me. I've been focused on the newer and underperforming reps and I should have been having these development conversations with you earlier. I didn't, and that's on me."
6
Resolution wish
"I'd like us to spend time today on concrete next steps, things we can both do, to improve your relationships on the team and position you better for what comes next."
7
Invite response
"What are your thoughts on this?"
Scenario 3: Over-reliance on the manager
Note the tone shift here: this conversation opens with genuine acknowledgment before pivoting. The rep isn't in trouble. They're being coached to independence.
1
Name the issue
"I'm pumped to be your mentor and it's been awesome watching you grow. That said, this is a super busy time of year and I'm having trouble keeping up with my own work while fielding questions throughout the day. That's the conversation I want to have."
2
Specific examples
"The texts and calls have become more frequent: and they're often about the same topics we've already covered. I've noticed the pattern."
3
Emotion
"I feel like you've reached a point where you can handle most of these on your own, and I want you to start trusting that."
4
What's at stake
"Your growth. If you always have someone to call, you never build the confidence that comes from solving it yourself. That confidence is what makes people see you as a leader, not just a strong rep."
5
Your contribution
"I could have set a clearer boundary earlier. I was accessible because I wanted to support you, but I didn't realize it was working against your independence."
6
Resolution wish
"My goal is to make you more independent. Before you reach out, try to answer it yourself first. Come to our weekly 1:1 with what you figured out, and with what you couldn't. That's a much better version of this relationship."
7
Invite response
"What are your thoughts?"
PIPs: before, during, and the conversation itself
1
Before the PIP, check your clarity first
Are your performance expectations clear? Are your effort expectations clear? Do you have clear expectations for how they "show up", qualitative behavior? If the answer to any of these is no, that's where you start, not with the PIP.
2
Still before the PIP, align that a problem exists
"Are you happy here? Do you feel this role is the best fit for your skills?" If they say no, you talk about an exit. Offer to make intros. Decide a reasonable notice timeline. Help them for real. A willing exit is better for everyone than a managed PIP.
3
The PIP itself
Must align to known performance expectations. Must be metric-driven, not exclusively results-based. Needs effort metrics too. A great manager puts in what the rep puts in. "This plan is mine too. I will work hard to help you, but I will only put in the effort that you do."
4
Use the Fierce Conversations framework to open the PIP meeting
The PIP is a document. The conversation is what makes it land. Walk through all 7 steps before you slide the paperwork across the table. Name the issue. Name the examples, with dates, with specifics. Own your contribution. State what you want to see. Then hand it to them. "What are your thoughts?" is still the most important question, even here.
Firing: if you've done everything right, this isn't a surprise
By the time you're firing someone, they should not be shocked. If you expect them to be, you've mismanaged it. Consult HR. Be direct: "This is going to be difficult to take in. Today is your last day." Per your agreement, expectations were not met. HR will walk through the details. Wish them well, mean it, and keep your door open. If you've given timely, specific feedback and run a real activity plan and a real PIP, this conversation is the cleanest one in the whole sequence.
- HR is in the room or on the call
- The message is delivered in the first sentence, no preamble
- The documentation trail supports every point if challenged
- You've prepared for the emotional response, let it happen, don't fill the silence
- You close with genuine well-wishing, this person is not your enemy
Are you addicted to giving advice? Coach instead.
Most managers are advice machines. Someone brings them a problem and they immediately dispense a solution. That's training people to need you, not to grow. Great coaching lets the rep solve their own problems.
Q
The Kickstart Question: "What's on your mind?"
Open-ended. Lets them surface what's most pressing. You learn more in the first 30 seconds than you would in 10 directive questions.
Q
The AWE Question: "And what else?"
The most powerful three words in coaching. Encourages deeper exploration. The first answer is rarely the real one.
Q
The Focus Question: "What's the real challenge here for you?"
Cuts through surface-level venting to the actual issue. Prompts them to clarify their own thinking.
Q
The Foundation Question: "What do you want?"
Forces articulation of goals and aspirations. You can't coach someone toward a goal they haven't named.
Q
The Lazy Question: "How can I help?"
Empowers them to define the support they need. They take ownership of the solution, you support it.
"Your job as a manager is to improve the performance of the individual. Your opportunity as a leader is to lift the effectiveness of the whole team. First, you model it. Then, you teach it."
Leadership tool
Mindset & motivation for leaders
Everything begins with what you believe about yourself and your ability to grow. A fixed mindset avoids challenges. A growth mindset embraces them. As a leader, your mindset is contagious, it shapes how your team responds to adversity, feedback, and hard weeks.
"The egoic mind is like a giant snowman that melts away under the light of conscious awareness.", Eckhart Tolle. Name the limiting belief. Then watch it lose its power.
Fixed vs. growth mindset: which one is running your team?
Fixed
Avoids challenges ("It's too hard") · Expects reward without effort · Ignores feedback · Feels threatened by the success of others · Intelligence is seen as static, you either have it or you don't
Growth
Embraces challenges ("I can train my brain") · Believes effort is the path to mastery · Learns from feedback · Is inspired by the success of others · Intelligence can be developed through work and experience
Overcoming limiting beliefs: the 5-step process
1
Awareness
Name it. "I'm not good enough." "I'm not smart enough for this role." Limiting beliefs are beliefs disguised as facts, they feel true but are not.
2
Unpacking
Where did this belief come from? What specific experience created it? Most limiting beliefs trace back to a handful of moments, not an objective reality.
3
Being objective
Is this actually true: or does it feel true? What evidence contradicts it? What would you tell a rep on your team who said this about themselves?
4
Challenging
Push back on it directly. Ask: "What would have to be true for this belief to be wrong?" Then find examples where it is wrong.
5
New narrative
Rewrite it deliberately. Not "I'm not a good closer" → "I'm developing my closing skills, and here's specifically what I'm working on."
Accountability: what it actually looks like
1
Clearly communicate expectations: start with why
A rep can't be held accountable to a standard they don't know exists. Before you manage performance, confirm the expectation has been explicitly stated.
2
Invite commitment, don't just assign
Ask them to commit to the action, not just receive the directive. "Will you do X by Friday?" vs. "Do X by Friday." The ask creates ownership.
3
Find out what could get in their way
Before the commitment is made: "What might prevent you from doing this?" Surface the obstacle before it becomes an excuse.
4
Create a culture of transparency
Psychological safety and accountability aren't opposites, they require each other. People only hold themselves accountable when they believe they can be honest about failures without punishment.
What to do when you get rejected, Hal Elrod's 5-minute rule
Give yourself 5 minutes: and only 5 minutes, to feel the rejection. Be frustrated. Be disappointed. Then it's over. After 5 minutes, you've already decided it's done. Teach this to your team. Rejection isn't personal, it's data. The rep who can reset fastest will out-compound everyone else over a quarter.
"The best leaders are ducks: calm on the surface, paddling hard underneath. Mindfulness. Boundaries. Detachment. Practice. It's lonely at the top, and also in the middle. Build your support network."
Leadership situation
The 90-day plan, Diagnose, Strategize, Execute
The first 90 days as a new sales leader aren't about proving yourself with announcements. They're about earning credibility through understanding, and then driving measurable improvement with a plan built on facts, not assumptions. The intent is not simply to observe. It's to drive meaningful improvement across people, process, and performance in a structured and sustainable way.
"The Triple A Foundation drives a shared philosophy across the team. Attitude, Activity, and Accountability, not just as an individual posture, but as the operating identity of the organization."
Day 1
Days 1–30 · Diagnose
Days 31–60 · Strategize
Days 61–90 · Execute
Day 1: Assumptive wins you don't need permission for
Before the first team meeting, there are moves you can make immediately that signal the tone, build early credibility, and start generating data for the diagnosis that follows. These aren't grand gestures, they're precision moves.
1
Sales and AI tool adoption audit
Understand what's in the stack, what's actually being used, and where reps are losing time to friction. Efficiencies at the top of the funnel compound quickly, this is a Day 1 look, not a 30-day project.
2
Disco-to-Opp conversion analysis
Pull the data immediately. At IANS Enterprise, the discovery-to-opportunity conversion rate was running at 61%. The target: 65%. That 4-point gap translates to roughly $200K in additional ARR. Know the number before you walk into the first team meeting.
3
RD empowerment and collaboration signal
The first message to regional directors should be about partnership, not hierarchy. Set the vision for what an elite enterprise channel looks like, and make clear they're co-authors of that vision, not just recipients of it.
4
Fortune 500 deep dive
Less than 20% of current prospects above $7.4M in deal size have had a completed discovery. That's the whitespace. Know it on Day 1 so you can build toward it deliberately.
Phase 1: Diagnose: assess strengths, gaps, pipeline health, culture, and process
1
Establish coaching cadence and operating rhythm: immediately
Weekly 1:1s, leadership meetings, pipeline reviews, and team meetings. Biweekly skill development sessions. Monthly skip-level and peer coaching roundtables with other new business leaders. Quarterly cross-functional updates and RD QBRs. Set the rhythm first, everything else runs on it.
2
Shadow late-stage calls: diagnose negotiation acumen
Don't just read the notes. Get in the room. Watch how deals are being run at the close. Identify patterns in negotiation behavior, discount habits, and where control is being lost. This is the diagnostic data you can't find in Salesforce.
3
Cross-functional interviews and expectation setting
Marketing, RevOps, Enablement: understand perception gaps and alignment points. Where does the handoff break down? Where are the teams pointing at each other? These are the systemic problems that no single rep can solve alone.
4
Review closed-lost deals and meeting outcomes
Identify recurring friction points. What are the patterns in how we lose? Are we losing early (qualification problem), late (negotiation problem), or to "no decision" (urgency problem)? The data tells the story, read it before you write the plan.
5
Outputs by Day 30
Identify 3 critical friction points limiting scale. Identify 1 high-impact area to solve immediately for early buy-in. Have a clear view of forecast accuracy aligned with best practices. Have trend data from lost opportunities and prospect feedback.
Phase 2: Strategize: translate findings into an aligned, executable plan
1
Draft and align the directional plan
Built on the insights from the diagnostic period, not assumptions. Align with executive leadership on priorities, expectations, and success metrics. Create a unified view of where we are, where we're going, and how we'll get there. Reduce ambiguity. Reinforce extreme ownership at every level.
2
9-box exercise with leaders
Map every person on the leadership team across performance and potential. Identify future leaders, recognize top performers, and pinpoint where development investment will generate the highest return. This has produced real clarity with every team Angelo has run it with.
3
Launch 1–2 small initiatives that demonstrate the approach
Proof points matter early. Pick initiatives that are data-driven, cross-functional, and produce visible results within 30 days. These aren't about the outcome, they're about establishing the methodology. Show how focused effort + accountability + alignment produce measurable results.
4
Design incentive tied to motivators
Work with Enablement, Finance, and HR to build a recognition framework that rewards both results and the behaviors that drive sustainable success. Know what motivates each person on the team, and build the incentive around that, not around what motivates you.
5
Outputs by Day 60
Improved visibility and alignment on team goals. 1–2 small initiatives launched with early results. Future leaders and top performers identified. Coaching cadence evaluated and adjusted. Quarterly rhythm with cross-functional teams established.
Phase 3: Execute: drive forecast accuracy, closing discipline, and scale
1
Get in the field: regional events, in-territory meetings, late-stage negotiations
Observe behaviors. Reinforce best practices. Model the level of rigor expected at the enterprise level. A leader who only coaches from the conference room loses credibility. Show up where the deals are.
2
Establish guidelines and guardrails: define what "good" looks like
Provide a common language for performance across every stage of the sales process. Reduce subjectivity in deal reviews. Ensure every person in the org knows what is expected of them, not just what their quota is.
3
Forecast as the operational compass
By Day 90, forecast accuracy and cadence should align with enterprise standards: supported by weekly pipeline inspections, forecast validations, and deal-stage accountability. Predictability is the output. Discipline is the input.
4
Build the living playbook
Capture proven processes, effective talk tracks, and key performance indicators. The playbook evolves continuously as the team tests new approaches, documents learnings, and replicates success. Start capturing it as early as Day 60. It compounds fast.
5
Outputs by Day 90
Improved forecast accuracy and conversion. Living playbook foundation in place. Every Fortune 500 account identified and mapped. A high-performing enterprise sales organization with a clearly defined vision of "good", built on precision, transparency, and trust.
"By the end of this journey, we'll have an elite enterprise channel ready to grow predictably, execute with excellence, and serve as a model for what the rest of the organization AND the industry looks like."
Leadership tool
Core competency framework
A competency framework makes development conversations concrete and removes ambiguity from coaching. 'You need to get better at pipeline management' means nothing. 'You're at level 2, here's what level 3 looks like and here's exactly what we're working on to get you there' means everything. When stepping into a new leadership role, embed this framework into your 90-day plan as a Day 31–60 deliverable. Clarity on where each person stands is not a management luxury: it's a management requirement.
"Behaviors define culture. The competency framework is how you make the behaviors you want visible, measurable, and coachable, for everyone on the team."
IC competencies
Manager competencies
How to use it
Individual contributor competencies: rated 1 (Basic) to 5 (Expert)
| Competency | Level 3, Proficient | Level 5, Expert |
| Time Management | Manages personal time efficiently; provides input on broader team time management improvements | Coaches others on maximizing time; proactively looks for org-level time efficiency opportunities |
| Pipeline Management | Proactive coverage; makes strategic decisions based on deal age and momentum | Coaches and mentors others on firm pipeline control and coverage discipline |
| Communications | Communicates with impact and persuasion to move clients through the sales process | Coaches and mentors others on best practices for effective communication |
| Forecasting | Track record of accuracy; flags risks to leadership appropriately and in advance | Coaches team members on accurate forecasting and recommends methodology shifts |
| New Business Sales Process | Consistently high conversion rate; owns all key touchpoints including the evaluation process | Coaches team on how to leverage the sales process to win |
| Client Lifecycle | Proficient account management; consistently builds strong relationships with key contacts | Coaches team on leveraging the client lifecycle for renewal retention and expansion |
| Sales Tools | Power user with forward-thinking mindset to continuously improve tool leverage | Coaches team on day-to-day tool efficiency and revenue growth |
| InfoSec IQ | Ties InfoSec issues to products/faculty; analyzes industry trends from research and events | Coaches team on continuously building InfoSec knowledge |
Manager competencies: rated 1 (Basic) to 5 (Expert)
| Competency | Level 3, Proficient | Level 5, Expert |
| Managing/Coaching | Proactively seeks self-improvement and collaboration with other managers to improve principles | Builds and manages thriving teams; continually identifies coaching opportunities to make the business stronger |
| Issue Identification | Takes proactive responsibility to identify, contextualize, quantify issues, and propose multiple solutions | Owns coaching other managers on how to work through issue identification strategically |
| External Networking | Proactively deepens connections while uncovering business opportunities for growth | Acts as a peer and strategic advisor to clients/prospects; brand ambassador in all settings |
| Executive Presence | Actively listens, analyzes situations, gains high trust; commands respect of peers and leaders | Consistently demonstrates self-confidence, assertive communication, focus, and calm under pressure |
| Negotiation | Comes to the table with multiple negotiation strategies to create positive results for the company | Proactively makes strategic decisions by running an efficient negotiation strategy across their team/region |
| Change Management | Gathers data and information to inform leadership on areas needing focus during change | Advises leadership on best practices; unifies company support from all sides on the path forward |
How to use the competency framework in coaching
1
Rate each rep together, not for them
Run the assessment collaboratively. Ask the rep to rate themselves first, then you share your rating. The gap between their self-assessment and yours is the coaching conversation. Reps who consistently over-rate need a candor conversation. Reps who consistently under-rate may have an confidence or visibility issue.
2
Identify the growth edge
Focus on one or two competencies per quarter, not all eight. "Here's where you are today. Here's what level 4 looks like. Here's what we're going to work on specifically in the next 90 days." Specific. Measurable. Time-bound.
3
Tie competencies to promotion criteria
Promotion is cleaner when it's rooted in demonstrated competency levels, not tenure or relationship. "You need to be at level 4 across these 3 competencies to be eligible for this role. Here's where you are today." That's a conversation anyone can have productively.
4
Use it in performance conversations too
When a PIP is needed, ground it in competencies. "You're at level 1 on pipeline management, here's what level 2 requires in concrete behavioral terms, and here's what I need to see by X date." Removes subjectivity. Protects both of you.
"The rep who doesn't know where they are can't navigate to where they're going. This framework makes the map visible."
Framework
TASC
Most delegation problems aren't people problems: they're clarity problems. TASC forces you to be specific about what you're asking, who owns it, what success looks like, and how you'll verify it. Accountability without clarity is just pressure. Clarity without accountability is just hope.
TASC: how to delegate with clarity
T
Task
What exactly needs to be done? Specific enough that there's no interpretation.
A
Authority
What decisions can they make on their own? Where do they need to escalate?
S
Success
What does "done well" look like? Give them a clear target, not a direction.
C
Checklist
How will you follow up? What does the verification loop look like?
"Created TASC with my team at Leyton because I kept having delegation conversations where everyone thought they understood, and then didn't."
Framework
Servant leadership
Servant leadership isn't being nice to everyone all the time. It's putting your team's development ahead of your own recognition. The goal is to make yourself unnecessary, to build a team that performs because they're equipped, not because you're watching. When the team wins, they get the credit. When you lose, that's yours.
"My goal is to help each of you make as much money as possible in your current role, and prepare you for the next step."
1
Build the person, not just the performer
Know what motivates each individual. Know where they want to go. Your job is to help them get there, even if that means they outgrow your team.
2
Remove obstacles, don't just report them
If something is slowing your team down, fix it before they have to ask twice. That's the job.
3
Share the credit, own the failures
When the team wins, they win. When the team misses, you're the first one who answers for it. That's how trust gets built.
4
Be inclusive: team first, always
No favorites. No inner circles. Everyone on the team deserves the same access to your coaching and attention.
Framework
Motivating individual reps
The stonemason who builds a cathedral isn't more talented than the one laying bricks. He just knows why he's there. Build a spreadsheet: every rep, their strengths, their development areas, how they're motivated, and what you're actively working on together. Then use it. Your job as a leader is to figure out what the "why" is for every person on your team, and make sure the work connects to it. Make sure they feel it every day.
"My goal as a manager is to help each of you make as much money as possible in your current role, and prepare you for the next step. That's my why. You need to find yours."
Know your rep
Recognition
Contests
Mission
Generic motivation doesn't work. A rep who is driven by money needs to see their commission tracker, not a team pizza party. A rep who is driven by recognition needs to be called out by name in front of the group, not a private Slack message. Before you can motivate someone, you have to know what actually moves them.
The five motivators: figure out which one drives each rep
1
Money
Commission tracker visible and updated in real time. Tie every activity back to what it means in their pocket. "That one extra meeting a week is $X by year-end." Make the math personal.
2
Recognition
Public, specific, and tied to behavior you want replicated. Not "great quarter", "here's exactly what Sarah did on that call and why it worked." Name. Story. Impact. In front of the team.
3
Competition
Leaderboards, head-to-head contests, rankings visible to everyone. Former athletes especially, they want to know where they stand relative to the field at all times. Give them that visibility.
4
Growth & advancement
They want a path, not just a role. Be explicit: "Here's what getting to the next level looks like, and here's exactly how I'll help you get there." Career conversations aren't annual reviews, they're monthly check-ins.
5
Team & belonging
Some reps are wired to win together. They're energized by the group, the mission call, the team channel, pulling someone else through a tough week. Give them a team identity to be proud of and responsibility within it.
How to find out: just ask
- Q"What motivates you? What is your why?", Ask it directly. Listen for what lights them up, not the polished answer.
- Q"On your very best day at work: the day you come home and think you have the best job in the world, what did you do that day?"
- Q"What environment do you prefer: everyone paid the same, or performance-based?", Tells you everything about money motivation.
- Q"Where do you want to be in 3–5 years? How does this role get you there?", Tells you if they're growth-driven.
- Q"What would make you leave?", The answer to this is the answer to what keeps them.
The motivation check-in: do this every quarter
- Revisit what each rep told you motivates them: does it still hold?
- Is your recognition approach matching their preference, not yours?
- Have you made their career path explicit and recent?
- Do they know where they stand on the team: and does that visibility energize or discourage them?
- When did you last recognize them for something non-revenue? Effort, growth, team behavior?
Recognition is not a reward program. It's a signal to the entire team about what behavior looks like when done right. When you recognize someone publicly and specifically, you're not just making them feel good, you're setting the standard for everyone else in the room.
"Recognition must be specific and public. 'Good quarter everyone' does nothing. 'Here's exactly what this person did and why it worked' changes the team."
Recognition done right: the three rules
1
Name it publicly
Slack messages don't count for recognition-motivated reps. They need to hear their name in front of the group. Team meeting, all-hands, QBR, wherever the team is together, that's where it happens.
2
Tell the story, not just the result
"Sarah hit 130% this month" is a number. "Sarah had a prospect go dark for six weeks, followed up five times with different angles, and finally got the meeting that turned into our biggest Q3 deal" is a story. Stories travel. Numbers don't.
3
Match the recognition to the person
Some reps love the spotlight. Others find public praise uncomfortable and prefer a direct, private acknowledgment that you noticed. Know which one you're dealing with before you put them in front of the room.
Recognition checklist
- Recognize non-revenue behaviors: coachability, attitude, helping a peer, not just quota attainment
- Spot bonuses for specific behaviors you want replicated, tie the incentive to the action
- Protect President's Club: never dilute it, never move the bar after the fact
- Real-time dashboards: transparency creates healthy competition and surfaces who deserves recognition before you have to dig for it
- Don't wait for end-of-quarter: recognize in the moment, when it's still connected to the behavior
Contests work because they tap into competition, recognition, and belonging all at once. Done right, a well-structured contest changes the energy of an entire month, and sometimes a full quarter. The structure matters as much as the incentive. Reps need to know it's fair, the stakes are real, and leadership takes it seriously.
"Week 1 is seeding week: it prevents sandbagging and means the bracket is earned, not assigned. After that, single elimination. Every week has stakes."
The March Madness model: full blueprint
1
Week 1: Conference play (seeding)
All reps compete individually to earn their team's seed. Most points wins the #1 seed. This prevents teams sandbagging in week 1 and makes the bracket reflect real performance.
2
Weeks 2–4, Single elimination tournament
Teams seeded from week 1. Head-to-head points battle each week. Lose and you're out. Tiebreaker is total points on the month. Urgency every single week, not just at month-end.
3
Points structure: weighted by role
Example structure: BDR/SDR: Booked meeting = 2pts, Attended = 3pts, Signed contract = 5pts. AE/Full-cycle: Booked = 1pt, Attended = 2pts, Signed contract = 10pts. Every role contributes, adjust weights to match what you need to drive on your team right now.
4
Team identity: school & mascot
Each team picks a school and mascot in week 1. Creates belonging and banter. A team with a name and identity fights harder than a team with a number.
5
Weekly best practice call: team-led
Each team holds a weekly best practice call and creates their own channel. The team captain runs it, not the manager. Ownership stays with the reps.
Incentive structure
- Tournament winner: company-sponsored half-day team lunch. Shared, celebrated, visible.
- Runner-up, Half day off in April "to think about your loss." Keeps the stakes light but real.
- Most Outstanding Player, Most total points across the entire contest. Gift card or spot bonus. One BDR/SDR, one AE. Rewards individual effort inside a team competition.
What makes contests fail: avoid these
- No seeding week: sandbagging tanks the integrity of the whole bracket
- Monthly cadence only: no weekly stakes means no weekly urgency
- Manager-run team calls: reps disengage when leadership does everything for them
- Leaderboard hidden or delayed: visibility is the engine of competition
- Same incentive every time: vary the reward, keep the structure consistent
A mission statement isn't a poster. It's a commitment the team makes to each other, and a standard they can hold themselves and each other to. When it's co-built instead of handed down, it means something. When it's referenced in accountability conversations, it has teeth.
A leader's mission statement: write yours first
Model the format before asking your team to do it. Here's an example to build from:
"As a sales leader, my priorities are to first and foremost provide every rep with the support they need to make as much money as possible in their current role. Secondly, to create a culture of internal advancement while fostering an inclusive team-first environment where people are genuinely excited to come to work every day."
Replace the framing with your own. The structure stays the same: what you prioritize for your people → the culture you're committed to creating.
Example team mission statement: adapt and co-build with your team
"As a team, we aim to share our strengths, battle our weaknesses, and learn from each other and our customers constantly. We understand that our success isn't based on today's results, it's today's growth, for the results of our future. We are partners to our customers, and as their trusted advisors, we will constantly work to solidify our relationships with them."
This is a starting point, not a template to copy. Pull your team into the drafting process. The words they choose will tell you a lot about how they see themselves.
How to build one with your team
- Co-create it, not handed down. Bring the team into the drafting.
- Start with: "What does winning together look like for this team?"
- Write the manager mission statement first: model the format before asking for theirs
- Read it aloud at the first team meeting every month, out loud, not referenced in a doc
- When an accountability conversation happens, tie it back: "Is this the team we said we'd be?"
The cathedral connection
The third stonemason knew what he was building. The mission statement is how your team knows what they're building. It's not the words, it's the shared understanding of why the wall matters. A manager who can articulate that, and who built it with their team instead of handing it down, has something that no contest or commission structure can replicate: a team that shows up for each other.
"Have our team be recognized nationally for our contributions to the company, with results and with internal promotions. That's the cathedral we were building."