Episode 502: Building High-Performing Sales Teams: Leadership, Trust, and Collaboration

Brynne Tillman: Welcome back to Making Sales Social. I am Brynne Tillman, and I’m really looking forward to our guest today. Jason Band is an operations executive with a track record of translating high-level strategic ambition into measurable business outcomes across global organizations in tech, media, healthcare, and consulting. Jason’s approach is people-first, but relentlessly results-oriented. He builds high-functioning leadership teams, designs operating models that align behavior to strategy, and creates governance frameworks that drive accountability without slowing momentum. In rapidly scaling environments, Jason focuses on building the operational machinery that allows strategy to execute consistently, sustainably, and at scale. Jason, welcome to the program.

Jason Band: Great to be here, thanks for having me.

Brynne Tillman: Well, I’m really excited to have you on today. When we were speaking the first time that we met, and I was really learning about the things that you do to help businesses scale, I thought, even though our audience is primarily sales and sales leadership, what you bring to the table is so powerful. Because when it comes down to it, sales is such a big part of that scaling, so I’m really excited to have this conversation. But before we jump into your genius, we ask all of our guests the same first question, which is, what does making sales social mean to you?

Jason Band: Sure! You know, for me, I think social is at the center of everything. I have a very people-first approach to things, and I think sales is the same way. Sales is about relationships, and emotional connections drive people’s interest in anything. If you’re not emphasizing that social element of how you sell, then you’re just selling them a widget as opposed to something that will improve, change, or help their life. That is ultimately how you connect people and get them to say, “I need this,” instead of, “Oh, that’s a nice-to-have, maybe I’ll get it someday.”

Brynne Tillman: I love that. That’s great. I think that is important when you are selling something to truly believe in the impact that you’re making in the world, so I think that’s great. I’m really curious, because high-performing teams is what every company I work with says is their goal. So what separates a high-performing team from an average one?

Jason Band: Sure, well, I think the first thing to think about is what does it truly mean to be a high-performance team? I think there’s a lot of misconceptions around that because most companies, when they talk about high performance, are really talking about accomplishments and outcomes. But the reality is that accomplishments and outcomes are a byproduct of a high-performing team. They are not the end-all, be-all of what you’re trying to create, and so you need to think in a slightly different term. If you’re just looking at the outcomes, you’re looking at a quarter-by-quarter view of near-term wins, and that isn’t representative of the quality of your team; that’s representative of how you did that quarter. A simple example from the sales space is, “Hey, Brynne increased the win rate for her team in Q2.” Wonderful, that’s good news and a positive thing. Does that mean you have a high-performance team? Maybe it does, maybe it doesn’t. If that win rate goes down in Q3, do you no longer have a high-performance team as a result of that? I would argue that looking at one metric and saying that outcome suggests the success of the team isn’t really what it means to be high-performing. That just means you turned in a good performance during a period of time. For me, the real indicator of what it means to be a high-performance team is: does the team produce more together than they would as individuals? Simply put, is 1 plus 1 greater than 2? If you’re a high performer and I’m a high performer, but the two of us in separate groups would produce the same thing as together, we’re not really any more high performing. Whereas if you have a skill set I don’t have, and vice versa, and together we make each other better and coach each other on developing those skills, that’s where you create real high-performance teams. It’s that synergy and collaboration that brings them together and allows them to be more than just individual contributors. A term I like to use a lot when talking about leading and growing teams is being a “force multiplier,” meaning your contribution doesn’t just reflect your individual work; it also helps other people on the team as well. That could be other top performers, or it could be the weak link on the team. It’s all about having a culture where everyone recognizes that growing the skill sets of everyone and supporting the other people on the team enables all of you to get further faster.

Brynne Tillman: I really love that, and I just want to go one deeper on this. Often when I’m working with sales leaders, they have the job description of what their next rep should look like, and it is the same job description over and over and over again. In that case, you’re hiring for a specific list of skills, and you’re not getting the diversity that you’re talking about. What would you recommend when a sales leader is hiring or growing their team to make sure they’re getting those balanced skills, versus focusing on the same couple over and over again?

Jason Band: Well, I think there’s a couple of things there. There’s looking for diversity of skills, but there’s also understanding hard skills versus soft skills, and what important soft skills are going to drive team cohesion, collaboration, and leadership. It depends on the roles you’re looking for, but on a sales team, you may want someone who is great at closing, someone who is really good at building pipeline and lead generation, and someone who project manages all of our pursuits. There are different skills based on understanding the ecosystem of how you actually drive business and close deals. You have to ask: do I have all of the activities that need to be accomplished, and do I have somebody who can do them all? If you recognize a part of your team or an activity that is weak, then you target a job description that is more focused on over-indexing on that piece where you need help, support, and expertise. But the other piece of it is looking at those soft skills that separate high performers from high potential. High potential is something to really focus on because you want to have a team that develops a rhythm and a supportive atmosphere. That enables everyone on the team to feel secure, and that security encourages them to push outside their comfort zone to grow professionally. That growth connects people to a shared purpose, which then builds loyalty and camaraderie. Personalities matter as much as skills. If you focus exclusively on just skills, you end up in a scenario where a person may be great at one thing, but they’re toxic and hurting the rest of the team. Bringing people together and creating that cohesive, collaborative atmosphere is the separator of a high-performance team versus a high-performance individual who may not actually be beneficial to your team in the long run, even if they are in the short term.

Brynne Tillman: Yeah, that reminds me of The Challenger Sale and the “Lone Wolf,” right? They may be successful on their own, but they bring the team down. I think that’s really interesting. What I’m hearing is that culture is a big part of building this team, and everything I’m hearing is that 2026 is the year of trust. That’s the word of the year, right? Are we creating a team that can trust each other, that has each other’s backs, and has a sense of loyalty? How do you establish that trust quickly inside of an organization?

Jason Band: Especially today, I think part of why 2026 is the year of trust is because of social media, AI, and so much shifting about what and who you can trust from an information standpoint and a people standpoint. Ultimately, trust is the foundation of being able to create a collaborative atmosphere. Everyone wants psychological safety. It has become a big buzzword, but what that really means is you want to know your boss has your back. If you feel trust in your team and trust in your leadership, you’re going to be more willing to take personal risks to grow. I don’t mean risk in the sense of going for a crazy deal that could bankrupt the company. I mean it more in the sense of getting out of your comfort zone, saying, “I’m going to learn this new skill because I know that if I stumble, it’s going to be okay.” To use an incredibly simplistic analogy: my son is seven years old and learning to ride a bike without training wheels. If he trusts me when I’m holding his bike and say, “You’re not going to fall,” he knows he’s not going to fall. Then he can focus on his balance and pedaling—all the things that, as an adult, you take for granted, but are a lot to focus on when you’re first learning. If his main focus was “don’t fall, don’t fall,” then he’s not focusing on anything else, and he’s not really going to learn. It’s the same with a professional experience. If your primary concern is, “They’re going to fire me if I mess up,” or “I’m going to get yelled at,” then you’re being ruled by fear. Fear is a very toxic way to drive a culture. I’ve been at those companies and worked for bosses that do that, and it’s painful. You don’t want to take risks there; you want to just do what you need to do to not get fired. The way you focus on building trust from a leadership standpoint starts with genuinely engaging with your team. Genuinely engaging means more than just, “Hey, how was your weekend?”—though having a relationship that goes beyond purely work is important in building camaraderie. It means really engaging with them to want to know their opinions, get honest feedback, and lead with empathy. You want to understand their point of view and learn from it, which doesn’t mean you have to agree with everyone or follow their point of view, but you have to want feedback. In my experience, the best bosses I’ve had and the best teams I’ve been on have all been teams where the leader wants honest feedback. That’s the way I approach it with my teams. I set an expectation as soon as I hire people that when you show up to a meeting, I expect you to have a point of view and be willing to share it. When they do, I put real effort into understanding their point of view, why they’re saying it, and taking what I can to help further the discussion, and I encourage everyone else on the team to do the same thing. That’s how you get real collaboration. I’ve also been in situations where the boss says, “I think we should do X, what does everyone think?” This sounds like asking for honest feedback, but what they really want is to hear, “You’re a great boss, that’s a smart move.” If you try to say, “Well, what about X, Y, or Z?” they suddenly shut you down. That sends a message to everyone: “I don’t want a collaborative environment. I want yes-men, and I want you to follow my orders.” When you do that, you kill people’s motivation because people don’t want to just execute. When you’re talking about very junior people, they might be in a position where they just want you to tell them what to do. But past a certain level, if you’re talking about a senior sales team, and their point of view and life experience isn’t a factor in driving how you implement and execute, they’re going to feel like, “What was the point of me being here? You can get a robot to do this. I’m an individual, I want to be respected, and I want to have autonomy.”

Brynne Tillman: Yeah, so I think that’s great. What I’m hearing you say is you really need a strong leader to have that high-performing team. You could have all the talent in the world, but if the leader isn’t showing up in a way that’s meaningful to that team, they’re not going to work to their capabilities.

Jason Band: At least in my opinion, yes. I have seen this happen many times. I’ve been on teams with incredible talent and passionate people, but the boss overrides every decision, and eventually, people get frustrated and stop trying. You can look to sports for easy examples. If you’re a basketball fan, the 2012 Lakers had one of the most stacked lineups in the history of basketball, but they had bad chemistry, bad culture, a bad coach, and they didn’t make it past the first round of the playoffs. On the other side of that coin, pretty much everyone has heard of “The Miracle on Ice,” the 1980 U.S. Olympic hockey team. Especially with the Olympics going on now, where the U.S. just won gold again against Canada, there are multiple movies about that team. They were not the best players or incredible talents, and they were actually far outclassed by their counterparts. But they really cared about a shared mission, they were in it together, they trusted and believed in each other, they were a family, and they had an amazing leader who created the culture that allowed that historic upset to happen. It can go both ways. Good leaders can really motivate, set the tone, and bring non-collaborative people into an environment where they learn to be collaborative, or at least limit their negative feedback because they see it doesn’t feel comfortable in that environment. On the flip side, bad leaders can just suck all the oxygen out of the room.

Brynne Tillman: Oh, yeah, and I’ve been around them, for sure.

Jason Band: We all have. We’ve all had bad bosses and good bosses. Unfortunately, in corporate America these days, the management skills that make for great bosses aren’t necessarily the things getting promoted most often. It’s much more outcome-oriented and self-preservation oriented. It’s like, “Well, I get things done,” or “I’m the good politician that takes credit for the people around me.” Those people climb high and fast, but that’s not a high-performing team.

Brynne Tillman: In hiring for these high-performance teams, we talked a little bit about diversity and skill. But these sales leaders, particularly, are hiring and looking for skill, thought leadership in the industry, and domain excellence. What is the balance in what they should be looking for? Is there a recipe?

Jason Band: I would say there’s a bit of a yes and a no to it. I don’t know that there’s an exact recipe, but there certainly are things to look out for versus what to avoid. If you look at research, there’s a clear answer that diversity is valuable. There are studies from McKinsey showing that diversified teams outperform uniform teams by 35%. Inclusive teams make 87% better decisions twice as fast. But ultimately, those facts don’t really tell you what to look for in a diverse team or what it means to have one. Diversity purely from a skill standpoint is somewhat missing the point. You brought up domain expertise. Absolutely, as a salesperson trying to sell something, if you don’t understand the industry you’re selling into, it’s really hard to customize your pitch to what they want. It’s hard for them to feel like, “How can this person give me the answers if they don’t even know my business?” I would argue some of that is required for all of your sales people to be good at what they do. But you also need to think in terms of what skills you want in different roles on your team, because not everyone is your closer or the person who shows up for the pitch. There are pursuit managers pulling things together. You may have great people driving leads, but if you have bad pursuit managers, they’re not going to win you a deal—though they sure can make a deal fall apart. Having those supporting people feel like their support matters, and that they are appreciated and valued, really motivates them to do their job well and learn other skills. When you’re thinking about where that recipe for success comes from, it comes more from understanding and leveraging the individual strengths of who you have, and recognizing key strengths you need to add into the mix, rather than just a preset. I’ll give you another analogy. If you want to make a pot of Italian-style tomato sauce, you’re going to put your standard ingredients in and let it cook. Over time, you’re going to taste it and say, “Does this need more salt, more oregano, more this or that?” You modify based on what you feel is missing. That’s the real recipe. It’s this mix between the standard pieces you know you need, and the fine-tuning you do over time based on how the team is working and whether things are working well. If you’re closing more deals, that’s great. If you generated a much more robust pipeline than last year, that’s good. But if you have high attrition in a part of the team, what do you need to do to address that? How do you fill the gaps that arise over time? That’s a huge part of where leadership comes in: understanding what’s missing and being able to fill those gaps, and not just thinking, “Well, people are miserable, but they’re closing a lot of deals and working 80-hour weeks, so I’m not going to do anything because you shouldn’t fix what’s not broken.” But it is broken, because that team working 80 hours a week is going to burn out, people are going to quit, and ultimately, you’re going to have a ticking time bomb on your hands.

Brynne Tillman: That makes so much sense. Now we have this team, and I heard you say earlier there’s a difference between high performance and high potential. Talk to me a little bit about how you identify and break down the two. Who is a high performer versus a high potential, and what do we do with that?

Jason Band: Performance and potential are not the same thing. Performance is really about what you have done in the past, whereas potential is about looking forward. For most people, performance is a quarter-by-quarter retrospective view of, “What have you done for me lately?” As a salesperson, I’m sure that resonates with you because it’s the question asked of every salesperson in history. You could have closed Coca-Cola last year, won the big award, got your trip to Cancun for being number one, and everyone is saying, “Brynne’s killing it.” Then you have a slow year, and what happens? Something goes wrong, and it doesn’t matter. The difference is that potential is more about looking forward, while performance tends to be retrospective. If you focus more on potential, you’re not over-indexing on just current ability. It’s more of, “Where can they go? How can they grow to be a leader on my team or get really great at something new?” When you think about potential and that forward-looking view, the three big markers are ability, engagement, and aspiration. Ability is pretty straightforward; it’s skills. This person is articulate, a smooth talker, great at a cocktail party, very bubbly, and connects with everyone. Or, on my side of the world, it’s a brilliant technical engineer or architect—hard skills. Engagement is about whether they are genuinely able to engage with people, learn, collaborate, and influence. Engagement isn’t just asking, “Hey, do you want to buy this?” It’s creating those emotional connections. Can I engage you at an emotional level to drive an outcome, whether that be influencing you to buy something, coaching you to be better at a skill, or helping you take a risk and have more confidence? Aspiration is the third one, and it is easy to misunderstand. Aspiration is really about having a growth mindset and shouldn’t be confused with career aspiration in the sense of wanting to be CEO. A lot of people think if you don’t want to be the master of the universe, then you don’t have aspiration or aren’t aspiring towards something great. That’s not really true. We’re not all meant to be CEOs, and plenty of people don’t want to be. I’m a perfect example of that. My aspiration is COO-type roles, not CEO. I don’t want to be the CEO. When you think about what real aspiration is, it’s not the title you’re trying to achieve; it’s about aspiring to achieve mastery in something, or a desire to constantly learn and grow. Those are the people you can mold because they have high potential. The high performer who thinks, “I never have anything to learn, I’m the best at everything, and I’m never going to change” has a very finite longevity at your company. They’ve hit their glass ceiling. Whereas somebody who always wants to learn and grow is going to be able to adapt and change over time. That salesperson who sold in the print media space 20 years ago could now sell digital because they wanted to learn. The one who didn’t ended up failing. I’ve seen it on the sales side. One of the companies I worked at was a data and marketing company that started in the print and direct mail space. We hired a sales lead who was a phenomenal guy at building and growing sales teams. He was super nice, smart, and a pleasure to be around. He was a huge success when they were in the print space. But as the market evolved and went into technology, he didn’t want to learn. He kept doing what he was doing, and the team crumbled because he didn’t understand that in this new world, the sales cycle is different. You’re no longer talking to CMOs; now you’re talking to CTOs and CIOs. His points of contact changed, the pitch changed, the cost and everything about what he was selling changed underneath his feet, and he never adapted. You really need to think in terms of whether people are going to be adaptable and look at what’s happening tomorrow, rather than just settling on what they are currently good at.

Brynne Tillman: We’re seeing that with AI in sales. There are so many sales leaders that are putting their heads in the sand and saying, “I hope this AI thing goes away, I really don’t want to use it.” But they have to.

Jason Band: And it’s not going to go away. None of this stuff goes away. Are you familiar with the Gartner hype cycle? Right now, we’re in the hype stage of AI, and we’re rapidly approaching the trough of disillusionment where people are going to say, “I’ve spent all this money, and it’s not working the way it was pitched.” In my opinion, AI is not just going to replace people. It is more about amplifying the productivity of people and altering what activities they do, not eliminating them. But there is so much complexity to having good data, using it correctly, prompting correctly, and using RAG datasets to augment the hallucination factors. You need to learn how to use it to accelerate what you’re doing, rather than trying to ignore it until it disappears, because it’s not going to disappear.

Brynne Tillman: When I started in sales many eons ago, we did not have cell phones, websites, the internet, or email. We were literally cold calling from the Yellow Pages and knocking on doors. I remember when I got email in 1992, sitting in my manager’s office saying, “How do you expect me to have time to figure this email thing out when I’m so busy?” Obviously, I adapted and figured it out. Back then, it was actually called CC Mail, it wasn’t even email initially. To me, it’s like saying, “How am I going to get emailed?” Email did not replace people, but it made our jobs easier and faster. That is what AI is built to do. Jason, thank you so much. Is there a question I should have asked you that I didn’t?

Jason Band: The one thing we didn’t get a chance to talk about was: when it comes to high-potential employees, what are the key signals to look for in an interview to spot them? We can quickly do a little of that. First, when you’re talking to people, look at whether they ask “why” or just “how.” “Why” shows they are really thinking and want to understand the context, whereas “how” is just asking for something to execute mindlessly. Second, do they take initiative beyond their job description? Are they looking to do more and grow? If they only work in their little scope of remit and don’t care what happens around them, it shows they’re not super collaborative, not particularly interested in understanding what the rest of the team is doing, and aren’t showing initiative to grow. Third, do they build relationships outside of their immediate team? Are they always trying to build relationships and look for more people to connect with? You never know when you need something from another group. I’ve been that guy at a bunch of organizations where everyone comes to me when they don’t know how to get something done, because I’ve done favors for every single person in a position of usefulness. When I need a favor, I reach out, and they take care of it for me. I remember one time in particular when I was working on a big migration—an entity move from an acquired company—and we needed to get a bunch of stuff done through HR. The global COO at the time was screaming at HR, asking why it couldn’t get done and saying she needed it yesterday, but HR insisted there was a process. The COO was pulling her hair out, and I said, “Hold on a second, let me make a call to the head of HR Ops.” He was about four levels down but was the person who literally had his fingers on the keyboard. I asked him if he could get it done today because of the huge financial impact otherwise, and he just took care of it. The COO didn’t understand how it got done when the head of HR had said no. It was because the head of HR was so far removed from the work that she only knew there was a queue, but I knew the person who managed the queue and could put us at the front of it. Those relationships always matter.

Brynne Tillman: I love that.

Jason Band: Oh, go ahead.

Jason Band: The last piece, which you brought up earlier regarding high performers who are challenging, is what I call the “brilliant jerk trap.” There are people who are high output with low relational intelligence, and they can be toxic to a team. Those people sometimes are the worst because they sound good on paper and have shiny accomplishments, but they kill the morale of everyone around them. Half the time, they are not as good as they seem because they just take credit for other people’s work, claim ownership of stuff, or throw people under the bus. The person who seems too good to be true more often than not probably is.

Brynne Tillman: That’s great advice. That’s a really good place to bring this in for a landing because you brought some really fabulous insights. I know these are the things you do inside of organizations, and the impact you make is outstanding. I’m looking forward to seeing your future. How can people get ahold of you?

Jason Band: They can reach out to me on LinkedIn or via email. I can provide an email address for you.

Brynne Tillman: Yep, we can put that in the show notes. Jason Band, right? I really appreciate you investing your time with me today. You brought some insights that will have a real impact on the teams and leadership listening. To all of our listeners, when you’re out and about, don’t forget to make your sales social.

Jason Band: Thank you so much; I really appreciated being on. It was great talking to you, and I hope everyone finds this useful.

Brynne Tillman: I’m sure they will.

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