Ep 18 - The Role of the Sales Leader: Winning Through Your People

September 22, 2026 • 00:16:24
Ep 18 - The Role of the Sales Leader: Winning Through Your People
Think Big. Win Bigger.
Ep 18 - The Role of the Sales Leader: Winning Through Your People

Sep 22 2026 | 00:16:24

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Hosted By

Dennis Deal Sorenson

Show Notes

Why doesn't the process-driven sales system execute itself?  

Dennis Sorenson draws on lessons from a barbershop and a restaurant floor to show sales leaders what it actually means to point, arm, and monitor their teams — and why culture must be taught, not just defined. "A great system requires great leadership," he explains, arguing that hands-in, hands-on engagement — not oversight from a distance — is what turns a framework into real, repeatable performance. 

Sorenson unpacks two real relationships — with Fletch, "The Proper Barber," and Tyler, a restaurant manager he calls "the hospitality leader" — to illustrate engaged leadership in practice. Referencing Mike Weinberg's Sales Management Simplified, he breaks down the discipline of pointing, arming, and monitoring a team, and draws a sharp line between micromanagement and genuine investment in people. "Great leaders do not lead from a distance," he says, closing with a challenge: connect ambition, strategy, and execution back to leadership itself, because the system does not execute on its own. 

In This Episode: 

(00:00) Recap: the four Ps and three disciplines of process-driven sales 

(01:14) Great leadership is what makes the whole system work 

(02:21) Meeting Fletch, "The Proper Barber" 

(06:30) Tyler, the hospitality leader 

(08:42) Mike Weinberg's framework: point, arm, and monitor the team 

(12:12) Hands-on leadership versus micromanagement 

(14:51) Closing: look for leadership lessons everywhere 

Share with a sales leader or seller who's ready to build something that lasts. Subscribe to hear all future episodes![Text Wrapping Break]About the Show 

Think Big. Win Bigger is hosted by Dennis Sorenson, CEO of Cove Group, a strategic partner for companies seeking to optimize sales performance and achieve sustainable growth. With deep expertise in enterprise sales and fractional CRO leadership, Dennis specializes in addressing challenges at the point of friction—where inefficiencies, misalignment, or resistance occur within the sales process. 

The podcast is built on Process-Driven Sales and the three pillars of Ambition, Strategy, and Execution. Each episode breaks down the systems and operating rhythms that drive predictable performance, giving leaders and sellers practical insights they can use immediately. This is for professionals who are ready to stop improvising, start operating with intention, and build repeatable success over time. 

Resources: 

Produced by Castos Productions[Text Wrapping Break] 

Process-Driven Sales Substack: https://processdrivensales.substack.com/  

Dennis Sorenson LinkedIn 

Cove Group 

Horizons West 

Chapters

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Episode Transcript

[00:00:00] Hands in and hands on Leadership is not micromanagement. There is a very important distinction between being a micromanager and someone who is hands on and hands in micromanagement says, I'm watching because I don't trust you. Great leadership, Hands on. Hands in leadership says, I am engaged because I am invested in your success. That distinction matters. I'm Dennis Sorensen and this is the Think Big, Win Bigger podcast. This is the podcast for sales leaders and salespeople who know they're capable of more and are looking for a system that is predictable, repeatable, scalable and forecastable for growth. It's not theories, it's not motivational speeches. It's an ambitious way to operate your business. [00:00:48] Over the last several episodes, we've spent a lot of time working through the process driven sales system. We've Talked about the four Ps of Planning, Preparation, practice, and play. [00:00:59] We've also talked about the three disciplines that make that four piece system work. And those disciplines are the discipline of ambition, which is seeing the real potential of our accounts or our sales territories. And then strategy, which is then developing the plan for how we're going to pursue that real potential that we identified in ambition. And then the discipline of execution, which is where we leverage our go system or goals, objectives, strategies and tactics to make sure that we are focused on day to day, week to week, a plan that actually executes against the strategy that we've identified to achieve the ambition that we know is there. That real potential that's there. In this episode, I want to step slightly aside into what I might consider the method level of the three different layers of system, method and motion that we talk about. [00:01:51] And it's not because what I want to talk about today is really different from the system because the method and the motion and the system must all work together. They must all be integrated to truly have a process driven sales system. [00:02:07] Today. What I want to talk about, I think is critical to making the entire system stack work. Great system requires great leadership and great sales leadership requires leaders who are engaged in the business who are actively helping their salespeople succeed. I was reminded of this recently in a place that has really not much or nothing to do with the way that we might traditionally think about sales. Throughout my career, I've developed a habit of looking for ways to learn. Looking to learn from things that I read or things that I watch, situations that I might find myself in and people that I meet. I'm always looking for nuggets, for golden nuggets that I can apply to, to sales and to sales leadership and in building and leading sales teams. Some of the best sales leadership lessons I have found don't come from sales organizations. Sometimes they come from simply paying attention to people who are doing exceptionally good work at what they do. A little over two years ago, I had the great opportunity to be introduced to a friend of mine, Fletch, who I will call and refer to in this episode as the Proper Barber. My first experience with Fletch was completely different from any other haircut experience I had had or experience going to the barber that I'd ever had. That first experience was the reason why I continued to return back to that barbershop. Over the past two years and over 24 visits and times in Fletcher's chair, I've had many hours to sit there and I've had many opportunities to listen and to watch Fletch and his team do what they do. Over those visits, I began to notice why the experience of the proper barber is different. On one of my recent Saturday morning visits, I got to see from the front row, from the barber chair that I was sitting in, how all of this got brought to life. I was, at the time, the only client in the shop. Fletch took advantage of the opportunity of having only me in the. In the shop at the time. And he had his team gather around the chair. And at that moment, he was not just working in the business, he was actively leading it. He was teaching his people. He was helping them understand how to best deliver the proper experience. [00:04:33] He had his hands in and his hands on the business. He was teaching his people and he taught discovery. I watched how he taught his people how to ask questions of their clients. And then he talked to them about how to listen when their clients responded and how to understand what the client was really saying and how to ask additional questions so that they knew that they understood. And he also taught them why this mattered and how that discovery effort becomes the foundation for the curated experience that Fletch and his team deliver. At the Proper Barber, he was teaching service. [00:05:15] He taught and instructed his team how to serve the clients that come into that shop, how to interact with them, different ways to take care of the client, how to create that proper first class experience. [00:05:28] He was teaching them their craft. He taught them new skills in cutting hair as he was cutting mine. He was helping them to build new muscle, to continually develop the technical skills that they needed to be better and better at their profession. In many ways, what I watched that particular Saturday morning was a repeat of things that I had seen several times over my 24 plus visits to that shop. I had watched Fletch interact with his people in many different situations. I had seen him give guidance when someone was talking to a client who was entering the shop, when someone was talking to a client on the phone during a client interaction or a haircut that was being given. And after a client left the shop, he was constantly coaching and helping his people to improve. The thing that really stands out to me is that when I'm sitting in Fletch's chair, his attention seems to be 100% on me. [00:06:26] Yet at the same time, he's observing, he's watching, he's listening, he knows what's happening around him. He's fully engaged in the business. [00:06:37] That's what hands in hands on leadership means to me. Everything Fletch taught that day, he found a way to ground into the proper experience, the proper culture. Discovery was connected back to the experience. [00:06:54] Service connected back to the experience. Technical skills connected back to the experience. Every client interaction connected back to the experience that created the proper culture. Culture is not something you simply define. Culture is something you teach, you model, you reinforce, and you coach. Watching Fletch that day reminded me of another friend of mine, Tyler. Tyler is one of the best managers I have ever watched run a business. [00:07:26] I would describe Tyler as the hospitality leader. He's the best restaurant manager I've ever seen. When I first met Tyler, I was struck by the way he did his job that night. In some ways, it was difficult to tell exactly who the manager was because of the way that his people did their jobs, and they did them extremely well. [00:07:49] And also by the way that Tyler interacted with them. And it made it clear to me that, and clear to them that he was there to help them succeed, to help them do their jobs, to help them take care of every customer in the restaurant. That night, I watched Tyler help his busboys clear tables and move tables and set tables. I watched him help his bartenders prep behind the bar. I watched him help his wait staff deliver food to the tables. And I saw him working the tables and interacting with all the customers in the restaurant. He was also at the front desk with the restaurant's greeters. And he moved through every aspect of the restaurant's operation that night, helping to take care of everyone who was seated and helping to take care of everyone who was waiting to be seated. He was everywhere, but he was not everywhere because he needed to control everything. [00:08:44] He was everywhere because he was helping his people. He was winning through his people. Tyler had his hands on and in the business. Both Fletch and Tyler are great examples to me of sales leadership. To me, they do not work in what we might first think of as kind of a traditional sales leadership role. But make no mistake, they are sales leaders. And the sales leadership principles are exactly the same as sales leaders. We must have our hands in and on the business. We must be engaged in the business. We must know what is happening. We must know what our people need from us and what our customers need from us. We must help our people improve and we must help them succeed. My good friend Mike Weinberg teaches in Sales Management Simplified that our job is to point the team, to give them direction, to help them understand where we're going, what matters, what good looks like, what our culture requires, and what the outcomes are that we're trying to create. He also teaches that we must arm our team. We must give our people what they need to succeed. We must teach them. We must invest our time in them. We must, we must coach them, and we must coach them in real time. We must be in the field with our people, watching them play. In order for us to be able to provide real time coaching and to see the areas that we need to coach, we must help them develop their skills. In our monthly team meetings, we must use those meetings to help build sales muscle. We must help our teams prepare. We must be involved in their preparation, in their preparation for their account plans and in the preparation for their customer meetings. We must be the ones who help them gain the tools and the resources and the knowledge and the confidence that they need to do their jobs well. And Mike also teaches that we must monitor then the execution. We have to stay engaged. We have to observe. We can't be locked away in our office looking at some CRM screen and thinking that we're able to see what's truly happening in the sales battle that's occurring. We must listen, we must understand what's happening, and we must coach. Like I said, in the moment and after every interaction, reinforce what's working and correct what needs to improve. We must help our individual sellers get better. Fletch does this. Tyler does this. I don't know if either one of them have read Sales Management Simplified and I don't know if either one of them would describe what they do as pointing their team, arming their team and monitoring their team, but they do it and they do it really, really well. Winning through your people is not a passive activity. It is one of the keys to both their success and ours. It's one of the things that is really key for us to understand that we must do in order to be able to win through our people. Mike also talks about being hero makers versus heroes ourselves. And in order to be hero makers, we have to invest the time in helping our people and we must build the skills in ourselves to be able to win through them. The key thing is that we don't leave it to chance and that we engage, that we teach, that we coach, that we help, we guide, we reinforce, we develop and we support. We must help our people win. I believe that it's very important for sales leaders to engage enough with our individual sellers that they understand something very clear. My manager is here to help me. My manager is here to help me succeed. My manager is here to help me win. The seller needs to understand that their manager is not simply there to inspect them. The manager is there not simply to find mistakes. The manager is not there to micromanage. The manager is there to help this exceller succeed, improve and perform at a higher level and to do the best job that they can and win. Hands in and hands on. Leadership is not micromanagement. There is a very important distinction between being a micromanager and someone who is hands on and hands in. Micromanagement says, I'm watching because I don't trust you. Great leadership. Hands on. Hands in leadership says, I am engaged because I am invested in your success. That distinction matters. Your people should want your involvement because they know your involvement makes them better. The very best sellers that I have ever worked with have been the ones who demand the most of my time because they know they will be able to gain something from that interaction. They'll find one nugget from the interaction that they have that they can take to make what they do better. They should know that when you put your hands into their business, you are here to help them succeed. Great sales leaders win through their people. The lesson I took from that Saturday morning and all of the Saturday mornings that I've spent with the proper barber and my many, many meals with Tyler at his restaurants. And that lesson is simple. Great leaders do not lead from a distance. They're present, they're observant, they're engaged, they teach, they coach, they help, they reinforce culture. They develop their people and they help their people execute. Great leaders win through their people. Connecting all of this back to the process driven sales system is very important. And this is why I wanted to step slightly into the method level today and talk about this. Because ultimately it's not outside of the overall system. The system doesn't execute itself. Plan, prepare, practice, play do not happen consistently by accident. Ambition does not get realized by itself. Strategy does not get developed by itself. Ghost plans don't get built and they don't get executed by themselves. [00:15:05] The sales leader has a critical role in bringing all of these things to life through their people. The leader must point the team, arm the team, monitor the battle, teach the team, coach the team, help the team reinforce and stay engaged. The system itself becomes real through the leader. There are leadership lessons everywhere if we're willing to look for them. Look around you. Pay attention to great operators. Pay attention to great managers. [00:15:34] Pay attention to people who consistently create exceptional customer experiences. [00:15:39] Ask yourself, what are they doing that I can apply to my own sales leadership? My experience with the proper barber and the hospitality leader taught me and reminded me of the value of leaders putting their hands in and hands on the business, coaching their team, developing their team and helping their people win. Winning through your people. I appreciate you joining for this episode and until next time, I just tell you, just win. [00:16:17] This episode is brought to you by Kastos Productions.

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