How to Build a Winning Sales Team Culture
Estimated reading time: 39 minutes
How to create the environment where explosive revenue growth becomes inevitable.
Most Sales Teams fail because they’re optimizing for the wrong things. They obsess over skills training, meaningless metrics, and individual talent. Meanwhile, they completely ignore the thing that actually drives performance: culture.
Then they wonder why success feels so random, why some quarters crush it while others crash and burn, and why they can’t scale profitably.
Here’s what I figured out: Winning isn’t about having the best salespeople. It’s about creating systems and a culture that make any salesperson with the right mindset and behaviour exceptional. Individual talent matters less than team dynamics. What matters is creating an environment where people genuinely want to crush it together.
Most leaders either throw people into sink-or-swim situations or hope natural talent carries the day. I do the opposite. I build teams that systematically develop people rather than just hire them. Resulting in a culture where success becomes inevitable instead of accidental, and revenue compounds because the system works, not because of luck.
The secret? Exceptionally high standards paired with a culture of excellence and fun where winning becomes contagious. Teams bond through shared impossible goals instead of competing against each other. People develop the right behaviors and mindset because the culture demands it while making it fun as hell.
At my last two companies, we smashed records in my first quarter. This is what I do. I just fucking win. Not because I’m magic, but because I built a systematic approach to creating the cultural norms, behaviours, mindsets, and expectations that most leaders leave to chance.
What follows may seem unorthodox. I’ll outline how you can start building the kind of sales culture where salespeople help each other obliterate wild stretch goals, all while having the time of their lives.
If you implement what I’m about to share, you’ll build a sales organization that compounds success quarter after quarter, develops people into their best selves, and creates the kind of winning momentum that becomes self-sustaining. Your team won’t just sell, they’ll become unstoppable.
The Foundation: Empowered Sales Leadership
Before diving into team dynamics, there’s a critical prerequisite for building a winning Sales Team culture: the sales leader must be truly empowered by their CEO.
The Sales Team culture is fundamentally different from any other team at a startup. We might do wild things like Sales Team trips, tattoo bets, or unconventional incentives that would seem “highly unusual” to other departments.
Sales can feel like “black magic” to non-sales executives. Sales Leaders make many decisions based on feel, experience, and intuition developed over years of selling and leading salespeople. There needs to be trust from the CEO, not asking you to justify every decision. I call this, Trust-based leadership.
You need a CEO who is supportive of this culture, excited about the Sales Team, and wants to empower you to build something special. Trust-based leadership, where the sales leader has the autonomy to make decisions without constant justification, is non-negotiable when building a winning Sales Team culture.
How I Build Winning Sales Team Cultures
High-performing Sales Teams don’t rely on individual talent or charisma. They win because the right mindsets and behaviours are systematized into culture. When you build a system that develops people, success becomes the norm.
The approach: Systematic excellence that any team can implement. Instead of hoping you hire the right people, you create an environment that makes any salesperson with the right mindset and behaviours exceptional.
The result: Teams that compound success quarter after quarter because the system works, not because they got lucky.
1. We All Win Together
Most SaaS Sales Teams prioritize the individual over the collective. Leading to varying levels of the same toxic patterns: AEs looking down on BDRs, cliques forming around tenure or roles, hoarding leads and insights, and toxic competition instead of celebrating wins. There’s silos everywhere: SDRs vs AEs, Enterprise vs SMB, territories treating each other like rivals.
The result? High turnover, negative environments, and teams performing well below potential. When people focus on individual pursuits instead of collective success, it’s impossible to build something greater than the sum of its parts.
I do the opposite. I build teams that win together.
As an example, we set outrageous team goals together. When we smash them, everyone enjoys the reward together. My favorite tradition? The BIG sales team trip we all take when we hit our stretch goal. Some recent ones: The Calgary Stampede, skiing the Rocky Mountains, and escaping winter in sunny Florida.
It’s incredible when everyone becomes so obsessed with winning the trip that they focus more on our team target than their individual quotas. Everyone helps each other because our epic trip depends on collective success. The trip becomes a transformative rallying point
On my teams, we sell together. We win together. We celebrate together. We either all go on the trip together or no one does. This is the mindset that drives everything.
Most Sales Teams do the opposite. They segregate with things like President’s Club where only top performers get rewarded while everyone else watches from the sidelines. That’s literally the opposite of team building.
When I was at Together, this mindset ran so deep I printed “We Sell Together” on tanks, t-shirts, and sweaters. It wasn’t just a slogan, it was how we operated. And it worked.
Here’s why this approach drives performance: When people know their success is tied to everyone else’s success, behaviour changes immediately. Information gets shared instead of hoarded. Top performers become teachers instead of competitors. New hires get support from everyone. The entire team becomes invested in each other’s development. Everyone on the team becomes a cheerleader where we celebrate the AE when they close a deal and the BDR who set the Discovery Call.
More importantly, your salespeople want this. People love work when they’re part of something bigger than themselves. They see success as a growing pie, not a zero-sum game. Instead of competing for limited rewards, everyone understands that collective success creates more opportunities for all.
People stay longer, performance soars, and create the kind of positive energy that makes winning sustainable and inevitable. And it’s so much more fun and meaningful for me as a leader.
2. Belief Over Pressure
If you treat your team like they’re losers, don’t be surprised when they play like it.
One of the biggest mistakes I used to make was pushing too hard and treating my salespeople like they didn’t want to win. And I see so many other sales leaders doing this.
Your team already wants to win, your job is to show them how. Most salespeople genuinely want to perform and be the best. When sales leaders push with pressure instead of purpose, it doesn’t drive performance, it just kills morale.
You wouldn’t pester Tom Brady about if he was going to score a touchdown. You wouldn’t micromanage Michael Jordan on his way to a championship.
Treat your salespeople like winners.
Here’s a perfect example of how competitive salespeople are and how much they like winning. My last team became obsessed with bocce golf. My two AEs who won are pictured below with a giant bocce golf trophy. I don’t even know where they got that trophy by the way.
Salespeople will compete at anything.
People act how you treat them. Treat your team like winners. But if you treat your team like they’re losers, don’t be surprised when they play like it.
When leaders doubt their team’s commitment, micromanage every move, or create environments where people feel like they’re constantly being judged rather than supported, performance tanks.
Instead: get genuinely excited for them. Make it fun. Make it matter. And support the hell out of them along the way.
3. Vanity Metrics as Fun Fuel
I love vanity metrics. I think they get a bad rep.
Let me be clear, when I say “vanity metrics”, I’m being a bit tongue-in-cheek. These aren’t the meaningless activity metrics most sales leaders obsess over. I’m talking about setting bold, audacious targets around your core metrics that seem almost ridiculous when you set them. Like “Let’s smash the all-time record for Disco Calls in a month” or “Let’s sell 12x the revenue this December compared to last December.” Yes, I’ve done that.
They break limiting beliefs on what’s possible and make it feel inevitable.
I also love tattoo bets.
My Together Sales Team had a tattoo bet where we’d get the company logo when we hit $100M ARR. One of my SDRs loved this idea so much that the next week he got our logo on his own… and we were not close to $100M at that time.
I won, or lost, a tattoo bet… depending on how you think about it for inking the largest deal in company history. I sold all 40,000 employees at Warner Brothers and ended up with a bull tattoo.
Here’s why I love vanity metrics:
- They give the Sales Team a clear, narrow goal to lock in on from your core metrics
- They break limiting beliefs about what’s possible and set a new standard
- They energize the Sales Team (and if you do it right, the whole company)
- They turn the mundane into an impassioned pursuit
- They give people something fun to chase and conquer together
That’s where the magic happens. People bond through adversity. They unify around accomplishing what seemed impossible just weeks or months earlier.
The key: Base them on metrics that actually matter. Don’t set vanity metrics around the number of cold calls or emails sent. Set them around Closed Won Revenue, Qualified Discovery Calls, or other metrics from your core four.
And when the team smashes it? It teaches them how to win. What winning takes. What winning feels like. It builds belief. And belief is contagious.
4. Master the Four Metrics
Most sales leaders track way too many metrics. They hammer their teams about the number of cold calls made, emails sent, $ of pipeline generated, and conversion rates. So many conversion rates.
The problem? Their teams have no idea what’s really important.
Even worse? Most sales leaders don’t even understand these stats. I went to grad school for economics. I understand stats. And I can confidently tell you that the endless stream of metrics most sales leaders track isn’t helpful. Nor is their phony analysis of them. They don’t understand trends. They’re usually just telling stories that hopefully fit the data but aren’t actually correct.
When teams see these dashboards and hear about these metrics, they get wildly confused because salespeople generally aren’t great with math either. The result: people don’t know what matters, what counts, what they should be tracking, or what’s actually going on.
This one is controversial. My approach is to stay laser-focused on just four metrics.
… and if you can attach a tattoo bet them? Even better.
Only Four Metrics Matter
- Closed Won Revenue ($)
- Discounted Forecast ($)
- Retention Metric: GDR or NRR
- Top of Funnel Metric: # of Sat and Qualified Discovery/Demo Calls
It’s not complicated. Very simple. Very clear.
Communicating the Metrics
I make sure that the Sales Team understands and knows how we’re performing as a team and individually. At my Weekly Team Kickoff meeting, I share very simple slides that include the following monthly and quarterly metrics:
- % of Closed Won Target Achieved (team)
- Closed Won Leaderboard (individual)
- Discounted Forecast (team and individual)
- # of Qualified Discovery/Demo Calls (team and individual)
Radical honesty is crucial. If we’re crushing it, I celebrate that and get excited. If we’re behind, I tell the team that too, no sugarcoating. Too many sales leaders lie to their teams about performance and spin stories that just aren’t true.
I used to make the mistake of being too hard on the team when we were behind target. It was demoralizing and counterproductive. Now I’ve learned the balance: give them the truth with ownership and accountability. “Here’s where we’re at. We’re behind our target and I’m concerned. Here’s how we pick things up…”. The key is honest assessment paired with clear action, not doom and gloom.
Metrics are important. Just be laser focused on the ones that matter. If your salespeople can’t read the scoreboard or don’t know how points are tallied or you’re lying to them about what the score actually is… how are you supposed to win?
People always, always know where we stand.
5. Employee-Driven Development
Most employees treat their careers like something that happens to them, not something they control. They wait for managers to tell them what their goals should be, when they can be promoted, what roles exist, and basically every crucial career milestone. And most managers are happy to accept this responsibility.
Why do people do this?
First, it’s how most companies are structured. Traditional corporate hierarchies train people to wait for permission. Annual or semiannual reviews, promotion committees, rigid career ladders create an entire system that is designed around managers controlling employee progression. Employees learn to play by these rules.
Second, limiting beliefs run deep. Employees carry limiting beliefs that act like invisible barriers, holding them back in ways they often don’t even realize. They think:
- “I haven’t been trained for that role.”
- “What if I pursue my dream and fail?”
- “Maybe someone else will get it instead.”
- “What if the position isn’t even available when I’m ready?”
Third, it’s safer to wait than to lead yourself. Taking ownership of your career means taking responsibility for the results. If you dream big and fall short, if you take risks that don’t pay off, it’s entirely on you. Most people would rather have someone else make the decisions so they don’t have to face the pain of failing at something they really wanted.
I flip this completely: I empower employees to guide their own development.
The Promotion Framework
Most companies create promotion systems where people feel like they have little control over the outcome. Whether it’s real or perceived, employees believe there are too many variables – politics, timing, budget constraints, who your boss likes, and subjective performance criteria. When the path feels that uncertain, most people don’t pour themselves into pursuing it.
On my teams, promotions are simple:
- Crush your target*
- Be a great teammate
The only asterisk is consistency. It’s amazing how many salespeople will hit you up for a promotion after one great month or quarter.
It’s up to you. It’s not up to me. People often think managers give promotions. I’ve never given anyone a promotion. Promotions are earned. This creates accountability and ownership over career paths and performance. It’s exciting and motivating. When the path is that simple, people go harder. Simplicity creates focus and focus drives performance.
I don’t create roles. You do. This level of autonomy and control can be incredible. My employees can progress way faster than they could otherwise.
Last year I could tell my employees were waiting for me to tell them what their progression path would be. So I delivered a presentation to expand their thinking beyond traditional progression models and help them understand that they owned their progression, not me. I wanted them to have loftier aspirations for themselves.
I believed in them and I want them to believe in themselves too.
The message was simple: Your next role exists if you want it to. Your pay cheque is what you make it. Dream big. Pour yourself into whatever you do.
Below are a few slides from the presentation that I delivered to my Sales Team at the start of Q4. They were so fired up about their careers. Talking about ambitious goals, their dream roles, and taking massive action to make it happen. The energy was contagious and our results proved it. That quarter, my team SMASHED countless company, team, and individual revenue records. This fired-up energy was exactly what several team members needed to earn the promotions they’d been chasing all year.
When you give people control over their destiny, performance skyrockets.
Quarterly Personal OKRs
So now that people are dreaming big about their goals, how do they actually accomplish it?
I love the OKR format. It becomes their roadmap for personal growth. Every team member creates their own quarterly OKRs. They come up with their objective and they define their key results. They determine what success looks like for themselves.
They might ask me to review their OKRs or they’ll ask for input, but it’s to make sure they have a tight plan, not to tell them what to do. They own this completely.
We publish our OKRs for everyone on the Sales Team to see. I also share my own OKRs with the team so they can see what I’m working on and striving for.
Here’s an example of what personal OKRs look like:
We also included an Activities section where people define the specific daily and weekly actions they’ll take to achieve their key results. They own creating this execution plan. It ensures their ambitious objectives have a clear roadmap for how they’ll actually get there.
This approach completely changed my leadership style and ties directly back to my ‘Belief Over Pressure’ philosophy. Before we started creating individual OKRs, I was pushing people toward goals I thought they should have. I had my own agenda for their development and kept hitting resistance because I was imposing my vision of who they should become.
Now I no longer have an agenda beyond helping them achieve their own goals. Which I love doing. Their resistance disappeared. It’s so much more motivating for me to help someone pursue their chosen path than to try convincing them to want what I think they should. This shift made me a much better leader.
When people set their own ambitious goals and create their own roadmap to get there, extraordinary things happen. They don’t just meet expectations, they shatter them. Because they’re not working toward someone else’s vision of success, they’re building the career they actually want.
The shift is incredible. People go from asking ‘What should I do?’ to boldly stating ‘Here’s what I’m going to accomplish.’ They become self-motivated, proactive, and relentless in pursuing what they want. This kind of drive is impossible to manufacture but easy to unleash when people control their own path.
6. High Care, High Expectations
Employee-driven development might sound like less work for a leader. It’s actually the opposite. Empowering people to drive their own growth requires massive investment from leadership. It’s the bridge between saying ‘you control your destiny’ and actually helping them build the capabilities to succeed.
This connects directly to everything we’ve covered so far. For example, telling people they own their careers and transparency around promotions will do little if you leave them to figure it out alone and don’t actively support their development. If you do that, you’re setting them up to fail.
Development-focused leadership communicates that you really believe in people and care about them.
My leadership approach is “High Care, High Expectations”. I provide a highly supportive growth environment where I invest heavily in each person while also holding incredibly high standards. I expect a lot from my employees, and they know they can expect a lot from me.
Working on my teams is great if you want to be a high performer. But it sucks if you want to be stagnant or average. One of my former team members captured this perfectly:
“Thomas changed the trajectory of my career. I learned sales from Thomas. He (also) taught me how to lead: how to inspire, coach, and actually manage a sales team. A lot of people talk about mindset, Thomas actually lives it. You see it in how he coaches, how he leads, and how he shows up. If you bring Thomas into your orbit, expect to be pushed, challenged, and fully supported (his coaching sometimes even doubles as therapy). You’ll come out the other side better and with a lot more money.”
That’s exactly the dynamic on my teams, simultaneous challenge through belief accompanied by support that accelerates growth. My investment in development colours everything: how I communicate daily, the development programming I create, and the time I dedicate to individual growth.
Coaching as Your Primary Tool
Many sales leaders undermine development and performance by leaping in too quickly to solve problems. They’re so eager to fix, solve, and offer solutions when their team shares challenges. However, their first instinct should be a curious mindset rather than playing the rescuer.
They default to telling their team what to do in day-to-day situations and then periodically schedule training sessions to teach new processes. That’s the extent of learning and development for most Sales Teams. This approach also kills engagement and limits growth. The exact opposite of what you need for a winning culture.
The better approach: Build a development culture where the majority of your interactions are coaching.
High expectations means I ask my people the hard questions that help them think through challenges themselves, rather than just telling them what to do. This is what a curious mindset looks like in practice.
If I had to tell my team what to do all the time, it would actually show that I have very low expectations for them. Jumping in to “help” inadvertently leads to one-upping yourself. You raise your status and lower theirs, whether you mean to or not. Coaching flips this dynamic. Instead of positioning yourself as the problem-solver, you position them as capable of finding their own solutions.
When leading people, there’s a time to tell, train, and coach. It’s essential to know the difference and when to use each for maximum effectiveness.
Telling vs Training vs Coaching
What is Telling? One-way communication where you deliver information, decisions, or instructions without seeking input.
- Example: “You need to update that proposal by end of day”
- Example: “That objection handling approach isn’t working. You should stop using it.”
- Example: “All deals over $50k need legal review.”
This is most effective for urgent situations, compliance requirements, or when onboarding someone who needs clear direction.
What is Training? Structured knowledge transfer where you teach new processes, tools, or strategies to individuals or groups.
- Example: “Here’s how our new CRM workflow functions.”
- Example: “Let me walk through the updated pricing structure.”
- Example: “Here’s each step of our Discovery Call playbook.”
Training works when everyone on the Sales Team requires the same information or when implementing new company-wide systems.
What is Coaching? Two-way dialogue where you ask questions that help people think through challenges and develop their own solutions.
- Example: Instead of “Make 50 more calls” → “I’ve noticed that your call activity is down. What’s getting in the way?”
- Example: Instead of “Follow up with that prospect tomorrow” → “What’s your read on where things stand with this prospect?”
- Example: Instead of “You sound nervous on calls” → “How did you feel about your Demo Calls this week?”
Coaching works when you want to develop long-term capability, when people need to own the solution, or when the challenge requires individual problem-solving rather than standard procedures.
Why Coaching Works
Leaders avoid coaching because they think building long-term capability comes at the cost of short-term performance pains. The opposite is actually true. Coaching drives stronger immediate performance because you solve the right problems with people invested in implementing solutions. It also radically shifts your team’s culture.
Coaching prevents you from becoming the bottleneck. In my early days of sales leadership, I became a huge bottleneck because I had built a system where everyone needed to come to me for answers. I couldn’t even go on vacation. I mistakenly thought that meant I was really important. What it actually meant was that I had created a dependency cycle instead of developing my team’s problem-solving capabilities. I was overwhelmed and my team was under-developed.
I changed my approach to coaching first. My people and my company needed it to grow. Scaling is the name of the game in tech. And it requires building capabilities throughout the team, not concentrating decision-making in one person. Now I actively look for areas where I can empower and elevate my team to remove me. The vacation test is a good one. If I can’t go on vacation, then I’ve created a bad system. When I go on vacation now, if issues arise (and they do) my people learn to solve problems rather than waiting for me to return with solutions.
Your assumptions are usually wrong. After 10 years of sales leadership with exceptional results across multiple startups, it would be easy to assume I know what’s blocking my people or what needs to be done to close a specific deal. But experience has taught me the opposite. My assumptions are often incomplete or flat-out wrong.
Like Discovery Calls, I’m often wrong when I make assumptions about prospects. So I take a listen first approach and ask lots of questions. The same applies to my team. When I jump straight to solutions I consistently miss key pieces of information that change everything about the real problem.
Coaching requires the same curious mindset and toolset that great discovery does. Instead of assuming I know what’s blocking someone, I ask what’s getting in their way. When they ask for deal support, I don’t jump to solutions. I guide them through their own analysis and let them tell me how I can support them, then we explore solutions together.
This approach consistently reveals that the surface issue is seldom the real issue. Often, much like with our prospects, people don’t express the challenge explicitly because they actually aren’t sure what it is. With coaching questions you can uncover it. But if you jump straight to telling based on what you think you see, you can solve the wrong problem entirely.
This happened recently when I was working with a Head of Sales on implementing coaching into his management style. He wanted to see coaching in action, so he asked if I would temporarily coach his AEs while he shadowed to help him develop his own approach.
We were in a session with one of his AEs who had just come off his best month ever. It was also the best month for an individual seller in the company’s 10+ year history. He was on fire with so much energy. However, he had some concerns too because the previous year he’d had his strongest quarter ever followed by an abrupt performance drop. So our recent sessions had focused on consistency and maintaining momentum.
As we kicked off our coaching session, I was disheartened to see that he’d left two of the three sections completely blank in his coaching doc. And in the week prior, he had filled out less than usual. I immediately assumed that his record-breaking month was clouding his coachability and eroding the effort level that got him there. This is a very common problem for sellers.
My assumption would have been accurate for many sellers but it didn’t quite fit here. He still had his usual coachable mindset and was showing strong engagement. Normally, I don’t proceed with the session if the coaching doc isn’t completed in advance. But I was curious what was happening here, so I set aside my assumption and let the session unfold naturally without asking about the incomplete doc.
Midway through the session, he told me how helpful our recent team DiSC workshop had been. The structure and clarity were huge unlocks for him. I asked him about other areas where he’d love more frameworks. As we explored this, he revealed something unexpected: structure was both an unlock and a blocker for him.
When I asked for an example, he explained that the structured coaching session and doc were great but now he was feeling blocked by it. He had actually added more structure to my standard template than I typically use. He explained that his challenges earlier in the year had been relatively easy to categorize. But as he unlocked new performance levels, his challenges were much more complex and he wasn’t sure how to articulate them. As a result, the structured format was actually preventing him from expressing what he needed help with.
After the session, I told the Head of Sales, “My assumption about why the doc wasn’t filled out was completely wrong.” He replied, “I actually get chills when that happens.” We both assumed the AE was becoming complacent and were wrong. He was actually still highly coachable but the real issue was that he was struggling to articulate increasingly sophisticated challenges.
If I hadn’t stayed curious, we wouldn’t have even done the session at all. Instead, we solved a performance blocker in one conversation. This shows exactly how coaching can have immediate impact. There are countless examples where curiosity saved me from jumping to tactics and leading us down the wrong path. And it was the difference between winning the deal rather than losing it.
People resist imposed solutions. When you’re given a solution without being asked for your input you naturally feel less ownership over it. People implement solutions they create or co-create themselves more effectively than imposed solutions. When someone thinks through a problem and arrives at their own answer, they have higher conviction and follow-through.
This is why telling doesn’t work even when you’re right. You can have the perfect solution but you’ll meet resistance and/or undermine enthusiasm if it feels like you’re forcing it on them. They might go through the motions but they’ll lack the commitment that comes from discovering the solution themselves. As a leader, the solution becomes yours to enforce rather than theirs to execute.
The coaching process transforms solutions from external impositions into internal discoveries. People usually don’t resist the insights they generate themselves. They own them, refine them, and follow through because it feels like their idea rather than your directive.
If you have a coaching first approach, when you do need to tell people what to do they tend to be much more receptive. Your directive carries weight because it’s rare. They listen more carefully and resist less because telling isn’t your standard operating mode. Whereas, a tell first approach generally leads to a build up of resistance and silent dissent.
Even if your assumptions and solutions are correct, imposing it without buy-in often leads to poorer execution. Coaching leads to solving the right problem, with stronger context and input, and people who are invested in implementing it.
Why Leaders Don’t Coach
Many leaders struggle with the leap from telling and training to coaching. It’s usually done with the good intentions of just trying to help and to ‘add value’ as a leader.
But there are deeper reasons leaders avoid coaching:
They feel like they have to know the answers. Many leaders believe that not having the answers, or being perceived as not having them, will make them look incompetent. This is particularly true in sales where your team expects you to be exceptional at selling yourself.
I once asked my VP of Marketing what it was like managing the Design team without a design background herself. She seemed confused by the question because of course she didn’t need design expertise to manage designers. But sales is different. If a VP of Sales doesn’t know how to sell, their team won’t follow them anywhere. This creates pressure to always have the right answer instead of asking the right questions.
The urgency in sales environments interrupts coaching. There’s constant pressure with deals moving, end of quarter approaching, and increasing targets to hit. Coaching requires patience that feels incompatible with the pace. I know when I’m stressed, swamped with back to back calls, and locked in smashing our target it’s easy for me to forget to coach and default to quick directives.
Even leaders who understand coaching’s value struggle with this. I deeply believe in coaching but still sometimes default to telling and training because it feels expedient to just give the answer. When you know the solution, or think you do, asking questions feels like wasting time. Why make someone think through what you already know?
It feels good to be the expert. Beyond external pressures, there are internal rewards that can come with telling and training. It feeds the ego and makes leaders feel smart, needed, and in control. We’re wired to have a strong preference for clarity and certainty, which makes telling and training feel better than the open-ended ambiguity that coaching requires.
Some leaders also unconsciously enjoy the dependency this creates. It validates their importance. Coaching, by contrast, requires sitting with uncertainty and trusting others to find solutions. This can feel uncomfortable and risky for leaders who are used to being the problem-solver. It also requires setting aside the ego that says you’re the only one with the answers.
Shifting from telling and training to coaching transforms your team culture. Instead of creating dependency, you’re building capability. Instead of compliance, you’re creating ownership. Your people learn to solve problems rather than wait for solutions.
How to Implement Coaching
Coaching isn’t a separate activity you schedule. It’s a mindset shift that changes how you respond to every interaction. Making this shift takes time and practice as you break the old ingrained telling habits. It will likely feel unnatural initially but the results justify the discomfort.
This section shows practical ways to implement coaching into your daily life as a sales leader.
One-on-Ones
Most leaders run weekly one-on-ones with a pre-set agenda that dominates the meeting. They come with a laundry list of items to cover and questions to ask (and they’re not coaching questions). It’s leader driven and dominated resulting in the employee’s topics being crowded out. It doesn’t provide the space to uncover what’s actually on the employee’s mind.
I flip this completely. My 1:1s are employee-driven, not manager-driven.
I don’t know what’s most pressing to an employee until they tell me. My 1:1s start with 3 coaching questions every week starting with “What’s going well?”. The dialogue flows from there. These questions allow them to open up about career development, wins and losses, personal challenges affecting their work, and the other important items on their mind.
As a note, we don’t discuss the strategy or tactics on deals here as we have other meetings in the week where we can do this. Without clear boundaries, it’s very easy for one-on-ones to become deep dives.
As the employee drives the conversation, I ask questions that help them fully uncover and identify the issue, explore gaps, and solutions.
Below is an example of a real (anonymized) one-on-one slide that demonstrates how these three questions work in practice:
Download a blank version of my 1:1 template to use with your own team.
Weekly Coaching Session
The “coaching” that most sales leaders do is actually better characterized as call reviews with the goal of developing skills with telling and training as the delivery method. This is done either one-on-one or in larger group settings. The manager typically selects which call to review and provides feedback. This approach is well-intentioned. And was my approach years ago too.
What I learned is that the traditional approach has significant limitations. It’s manager-driven rather than employee-driven, it may not address the salesperson’s most pressing development needs, and it can create defensive or nervous environments where people struggle to absorb feedback effectively.
The approach I’ve moved to is real coaching that is employee-driven.
Why Small Group Coaching?
There are a few key reasons why I prefer small group coaching over 1:1:
- Shared Experiences: People realize their improvement areas aren’t unique, reducing isolation, and increasing openness
- Collaborative Ideas: Solutions build off each other as team members contribute different perspectives
- Scalability: More efficient for leaders while maintaining personalized attention
Group Coaching Format
- Hour-long weekly session
- Maximum 3 people plus me
- Everyone in the group has the same role (e.g. AEs, AMs, BDRs)
- Adapt to meet people where they’re at. Some variations include:
- General vs. Themed: Sometimes completely open-ended, other times focused on specific themes (e.g. discovery) based on what the group wants to work on.
- Structure:
- Question-focused sessions: Full hour dedicated to the three coaching questions with no call review.
- Hybrid format: 30 minutes of coaching questions, then one person shares a call of their choosing from the past week.
The Skill-Mindset-Behavior Question Framework
The coaching doc focuses on categorizing reflections to the questions under skill, mindset, and behavior. Most sales leaders and salespeople solely focus on identifying and improving skills gaps. Whereas I believe that sales performance is a result of skill, mindset, and behavior. And that skill is actually the least important of the three.
For example, if someone on my team is struggling with setting upfront contracts, it’s rarely because they don’t know how to set them (skill issue). It’s usually a mindset challenge, often driven by disruptive emotions like fear of rejection or worrying about being too pushy with prospects.
This framework helps to strengthen the salesperson’s self-reflection and to dig deeper into the root causes of their successes, development opportunities, and blockers.
Download a blank version of my group coaching template to facilitate sessions with your own team.
The Hybrid Approach
With the hybrid approach, for the call review portion, each member of the group leaves feedback on the call in our coaching doc prior to the session. I’ve learned that the feedback should focus exclusively on positive reinforcement. In the past, I found that constructive criticism from peers and I can feel heavy and very negative, almost like a roasting session.
With high performers, this positive-only approach works because they usually know their development areas and are already very critical of themselves. And with this format, they tend to bring up collaborative questions themselves asking things like, “What do you guys do in this situation?” or “How would you handle this?”
Additionally, the call reviewers tend to learn more and have more takeaways to implement from their peer’s call when they’re focused on positive reinforcement rather than critiquing. When you’re looking for what someone did well, you’re actively identifying techniques and approaches you can adopt, rather than just spotting problems.
Weekly Development Programming
Beyond weekly 1:1s and group coaching sessions, I create systematic team development through structured weekly programming. This approach ensures consistent growth opportunities while building team culture and shared learning.
Here’s a glimpse at what this looks like in practice:
Ice Breaker Mondays
- What is it? A different person runs a creative, fun, team-building exercise each week. It’s amazing how much effort people put into these!
- Why do we do it? Because it’s fun! And a great way to build connection in our remote-first working environment. It also gives people a chance to run a team meeting.
Sales Team Kickoff (Tuesday)
- What is it? We review our four core metrics (closed won, discounted forecast, qualified demos sits, and team performance), celebrate wins, and provide strategic updates for the week ahead.
- Why do we do it? Creates transparency and alignment on both results and strategy. Everyone sees how we’re tracking against targets and knows the key priorities for the week. The public recognition of wins is energizing while the data-driven approach keeps everyone focused on what matters most.
O&R Wednesdays
- What is it? People submit challenging objections from the week and we work through rebuttals as a group.
- Why do we do it? Transforms individual challenges into collective learning opportunities. When someone shares a difficult objection they faced, the entire team benefits from problem-solving together. This builds confidence, furthers development, and reduces the isolation that can come with sales challenges.
Thinking Thursdays
- What is it? We read a chapter from a book, one of my articles, or watch a TED Talk and then we discuss what we learned, how we can implement it, and resistance we had to the material.
- Why do we do it? Creates a culture of continuous learning while encouraging critical thinking. We engage with the material, question it, figure out how it applies, and how it fits with our other frameworks. Discussing resistance is crucial. It surfaces real concerns and prevents silent dissent. Silent dissent leads to execution and adoption issues. Whereas when people can voice their concerns openly, we can address them together and increase the likelihood of successful adoption.
Fridays
- What is it? We have smaller role-specific team meetings (e.g. the BDR team).
- Why do we do it? Allows for targeted development on things specific to each role. Friday gives people focused time to work on the unique situations they face with peers and their manager who understand those specific contexts.
The Compound Effect
This consistent investment in development creates a compounding effect. When you systematically combine employee-driven 1:1s, small group coaching, and daily Sales Team learning experiences, people start believing in themselves more and adopting self-development habits. They begin reading sales books independently, asking for extra coaching sessions, peer coaching each other, and actively seeking growth opportunities.
This deep level of care gets people to aspire to be their best. The growth mindset becomes self-sustaining when people feel genuinely cared for and invested in.
7. Create Motivating Compensation Plans
Too many Sales Teams have compensation models that don’t make sense and don’t motivate. Salespeople on these teams have no idea how to win, what they win, or if they won.
Variable compensation can be a HUGE motivator in sales. But if your salespeople don’t understand it, then you’re missing a significant motivation lever. And part of building a winning sales team culture is not just winning together, it’s about winning individually too.
I first started my sales career managing 3rd party sales teams all across the United States. I had the privilege of working with and learning from some of the best sales professionals and leaders in the world. I got to hop around and see the best and worst practices from these teams.
The pattern was clear: lower-performing teams had salespeople burdened by complicated variable compensation models they couldn’t understand. It killed motivation. Meanwhile, high-performing teams had simple, clear comp plans that were easy to understand.
This ties directly back to my core themes of simplicity, control, and transparency. Salespeople perform best when they control their outcomes and aren’t distracted by complexity. This applies to career development and compensation.
My Sales Compensation Model Principles
1. Achievable
- Good: OTE is the expectation for my teams. If they’re not hitting it, then something is wrong.
- Bad: OTE is aspirational at way too many companies.
2. Simple and Known
- Good: follows the structure of “if the salesperson does X then they get Y.”
- Example: When an Account Executive closes a deal, they get 10% commission on the contract value.
- Bad: follows a structure like “if the salesperson does A, B, and C then they get Y and get Z if S happens.”
3. Salesperson is Paid for What They Can Control
- Good: A BDR is paid for a Discovery Call that they set that sits and is qualified. Achieving this is fully in the BDR’s control.
- Bad: A BDR is paid for a Discovery Call if the Account Executive closes the deal. Achieving this is only partially in the BDR’s control but ultimately their pay is contingent on the competency of the AE.
4. X is Paid as Close to Completion of Y as Possible
- Good: Paying variable compensation biweekly or monthly
- Bad: Paying variable compensation at the end of the quarter… or end of the year (yes, I’ve seen this!)
5. Same Role, Same Comp Plan
- Good: everyone on the team in the same role (e.g. BDR) has the exact same OTE, base salary, and variable compensation plans.
- Example: All BDRs have a $60k base + $40k on-target variable. All Enterprise AEs have a $150k base + $150k on-target variable.
- Bad: different people in the same role have different OTEs, base salaries, or variable compensation plans.
Love When Your Salespeople Make Money
One of the most toxic things I see companies do is change compensation plans when salespeople start making “too much” money. I’ve heard countless stories from salespeople who crushed their targets, only to have their comp plan changed because leadership didn’t like the big payouts.
This is backwards thinking that destroys trust and motivation. I love when my salespeople make money. When someone on my team has a huge quarter, that’s cause for celebration, not panic. Your best performers generating massive commissions means they’re driving significant revenue for the company.
The moment you change someone’s comp plan because they’re “making too much,” you send a clear message: “We don’t actually want you to succeed.” Trust evaporates. Sellers lose their desire to pour themselves into their work. And employee churn skyrockets.
As a salesperson, you have to trust that the company you’re working for will honour their commitments. Variable compensation inherently puts salespeople in a vulnerable position because they’re essentially betting their livelihood on the company keeping its word. They’re betting on leadership not moving the goalposts when they succeed.
When that trust is broken, it’s nearly impossible to rebuild. I’ve never changed comp plans because people are outperforming their OTE. Never. That’s punishment for success.
This is how much I love when my salespeople win. Last year, my top performing AEs had such big Q4s that they asked if they could schedule time with me for investing advice. That was one of my proudest moments.
Pay Transparency
Transparency is a key theme that runs throughout my sales culture and this applies to compensation as well. I take a bit of an unorthodox approach by sharing the OTE for every role and level within the sales org with everyone on the team. I typically share this in a team meeting or document that everyone can access – complete transparency means everyone has the same information.
This means BDRs can see exactly what the AE compensation structure looks like, AEs know what management roles pay, and AEs and AMs can see if they’re paid the same. I even share my own compensation structure.
People absolutely love this approach. The energy shift when you implement full pay transparency is incredible. Here’s why it works:
It’s motivating. When a BDR can see exactly what they’ll earn as an AE, it’s not some mysterious carrot dangling in the distance. They know the financial reward waiting for them when they get promoted. It makes their goals tangible and exciting.
It builds trust. Nothing destroys team culture faster than people wondering if they’re being unfairly compensated. When everything is transparent, there’s no room for suspicion, resentment, or the weird dynamics that happen when colleagues think someone is getting a better deal.
It reinforces fairness. When people can see that everyone in the same role has the same comp structure, it eliminates any sense that compensation is political or based on who’s better at negotiating. It’s pure meritocracy where if you perform at this level, you get this compensation.
I implement this on my teams even though it’s never been company policy. The impact of this has actually been bigger than I expected. People feel respected, trusted, and motivated. When compensation is simple, fair, and transparent, it becomes a culture driver instead of a culture killer.
Performance explodes when sales comp is simple, fair, and tied to controllable outcomes. When your team understands the rules and trusts they won’t change, they stop holding back and start going all in.
Sales Team Culture Drives Performance
People ask me how I break revenue records so fast.
It’s not luck. It’s not magic. It’s about creating systems and a culture that make any salesperson with the right mindset and behaviour exceptional.
A culture of belief over pressure. Where everyone wins together. That empowers people to control their own destiny.
The principles in this article aren’t theory, they’re the exact playbook I’ve used to smash records at all of my companies as soon as I’ve arrived. And you can do this too. When you combine team unity with individual empowerment, simplicity with transparency, and belief with accountability, extraordinary things happen.
If you’re building or rebuilding a Sales Team, don’t leave culture to chance. You have everything you need to build this culture starting today. Build belief in your people, create systems they can control, and watch them accomplish what seemed impossible.
Because when your Sales Team truly believes they can win, and you give them the tools to do it, success becomes inevitable.
You must be logged in to post a comment.