Sessions with System & Soul

Reflection: Execution, Strategy… or Leadership? What Actually Moves the Needle

• Benj Miller, McKenzie Decker • Season 1 • Episode 15

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In this Reflections episode of Sessions with System & Soul, Benj Miller and McKenzie Decker unpack a question that challenges leaders in every stage of growth: is it strategy, execution, or something else entirely that drives real progress?

Pulling from candid conversations with CEOs and COOs, they explore why top performers do not always make great leaders, the hidden cost of relying too much on subject matter expertise, and how to navigate the long middle between today’s reality and your growth vision.

You will discover:

  • How leadership demands shift from startup to scale-up
  • Why “strategy vs. execution” is often the wrong debate
  • Signs your senior leaders are misaligned with their role
  • When to coach existing leaders versus hire fresh talent
  • A mindset shift that can break through leadership bottlenecks

Whether you are leading a tech startup in Austin, a manufacturing team in the Midwest, or a creative agency in Atlanta, this conversation will help you pinpoint what is truly moving the needle and what is quietly holding you back.

Sessions is hosted by Benj Miller and McKenzie Decker

The best businesses aren’t just built on strategy, they’re built on soul.

If delegation is something you’re wrestling with, the System & Soul network has more than 50 certified coaches across the country ready to help founders and teams delegate with clarity and confidence.

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McKenzie: [00:00:00] Hey, welcome back to Sessions with System and Soul. I'm Mackenzie. I'm here with Benj. We're glad you're joining us today. We have a special session. It's a reflection on some conversations that have been happening behind the scenes. We can't always bring you the conversation live, but there's a lot of really powerful stuff that happens in the world that we're in.

McKenzie: With the leaders that we encounter and lots of good stuff for you guys to take away and learn. There's a lot that happens behind the scenes that's good for every leader to know. And so that's what today's session is about. It's really about your leadership style. And I know Ben has had some really powerful conversations that he's gonna share with us just around when you need a certain type of leadership style in a certain stage.

McKenzie: Size of business. I know this is a tension we all deal with 'cause we all have a stage, we all have a style and we're always running into the next thing and trying to figure out how to manage it. So I'm gonna throw it over to Benj to walk us through this conversation. But before I do that, I just wanna thank Fist [00:01:00] Bumps.

McKenzie: Fist bumps is the company that helps us create this show. Creating great content is really hard. Getting it out there is even harder and making it great and better over time is the hardest thing, and fist bumps helps us to do all of that. So if you need someone to support you on the content marketing side of things.

McKenzie: To create your own podcast, to create your social media content, thought leadership they're the people you should reach out to. So get in touch with fist bumps. It's get fist bumps.com. Alright, Benj, let's do this. What you got? 

Benj: Yeah, so one of the things, knowing that we were having these sessions coming up and part of what we've been trying to do is get more of what happens behind the scenes into the conversations that we're having in the public.

Benj: And we can't always do that using names and real names than real faces. But we can do that by sharing some of the conversations we've had. So I've started to take notes of themes that I've. Been seeing these reflections episodes, and one of the things that has come up a few times over the last few weeks is basically the same [00:02:00] conversation in a few different contexts.

Benj: So I'll use an amalgamation of. The conversations into one person, but it looks like a conversation when a leaders frustrated with their report, their direct reports, and for a variety of reasons, they can execute well, but they fail to think about the big picture. They think about the big picture, but they can't execute on it.

Benj: They're great with their people. Their people love 'em, but they're all over the place and. I think it's helpful to think about this, not in terms of seasons of your business because the leadership we need below us and what I mean by below us is you've got you're a founder or maybe you're a founder with an operator, but that senior leadership team right below you has to look different for different seasons and stages of the business.

Benj: So when you're starting off, you're like most people who start in a season of I am a founder. I need horsepower to execute. [00:03:00] And so I'm gonna, I'm gonna use a little bit of a sports analogy through this. But like, when we start, we are the star player of the team. You're the founder. You can do a little bit of everything, most of everything better than everybody else.

Benj: You just need some people to go, get the uniforms and get the water and, plan the things so that you can show up and be the star. And that works for that season. You need that. That is the strength of the founder in that season. But that doesn't scale, right? So in our frustrations, we promote some people and now they're captains of their teams, right?

Benj: So we have, we still have a bunch of doers with some like player coaches in each one of the functions. That works for a while, and then you get to the scale where you need people that manage those people; they're not a player coach anymore. There's just too much, and now they're just a coach or should be just a coach.

Benj: Now we could go on a tangent here because most people don't [00:04:00] know actually how to coach a team, how to lead the team like that. Whatever. And then there's, then you get to the place where you're now leading functions of the team, and it's not just one layer of people, but you're leading the managers of people and you're leading the managers and managers of people.

Benj: And so this is where this conversation picked up. So we're not talking about the early stage, we're not really talking about that middle stage right now. Really. This is we're getting to that. Stage where you've got actual leadership leading the functions of the business and the amalgamation of my conversations started off in here's some questions like, how much of a subject expertise does the leader of that function have to be over every little thing within that function?

Benj: That's a big tension because we think that they need to be better than everybody in their team and smarter than everybody in their team to be able to lead them. 

McKenzie: Like they're technically skilled at the things they do . 

Benj: Yeah. And then the other conversation is like [00:05:00] one person was struggling with I've got this person who's greatest at strategy, but awful at the execution, the accountability, like actually getting things done on the other side.

Benj: I've got this person. This function that's great at getting things done, but that function actually needs more strategy and like thought leadership and forward thinking to what they're doing. But they don't have it. They just head down, get stuff done. They get stuff done great, but it's not gonna get us to where we need to go.

Benj: And so I paused the conversation. I said, Hey, heads up. This is a trick question before you answer it, but. What do you think is more important for that level of leadership in an organization? So what would you answer if I said strategy or execution at a senior leadership level of a company big enough where you're leading leaders or leading managers in an organization.

McKenzie: I think I'd say I'd say strategy. But it's a trick question, so I'm guessing wrong. [00:06:00] 

Benj: Yeah, it's do I say execution and that's a trap, or do I say strategy? That's a trap, and the answer is . 

McKenzie: I can explain my answer. Like you said, there's all these. It's like the people closest to the problems and the lower layers are the ones who need to be excellent in execution.

McKenzie: So I would think that the higher up you go, the better you need to be. Yeah. At strategy and expressing it. So that's why I'll do that. 

Benj: Yeah. And you're not wrong. And this is the tension and this is why if I said, okay, it's execution now, argue execution. You're like I can, as long as I'm in charge of this team getting their stuff done, and I can always bring in a consultant or a, somebody on my team is really good at strategy, do the strategy, and I'm there for the execution.

Benj: So it's really easy to argue either side of that.

McKenzie: Even what you described with the conversations you've had, you've described all these different situations where they've noticed gaps in the leaders on their teams, and they're all different gaps. It's the question is how do you feel?

McKenzie: All of [00:07:00] them, because everybody's got deficiencies in how they lead and do their work, so Yeah. Yeah. It's how do you solve for all of that when it's, you got a variety of needs there. So what is the answer? What's the real answer? 

Benj: Yeah so you're gonna be like, duh. But the real answer is you need leadership.

Benj: You don't? Yeah. Yes. The team has to have strategy and the team has to execute. And part of leading is being able to make sure that both of those are present on the team within the team. But what you need at that level is people that can lead people and. The example that I use and people overestimate my ability to operate a company.

Benj: I, I can do it for short amounts of time. It is not my strength, but I do believe that I could go into any business, in any team as a leader of the team, know nothing about the subject matter expertise of what they do. And improve the performance of that team. I truly believe that. I believe that about you too.

Benj: You could go into any [00:08:00] company, in any organization that's doing something that you've never heard of before and bring leadership and, we talk a lot about leadership and what is it? And 77% of it is who you are when you show up. And, but it's, it's leading people. And to lead people, you have to have conversations with people.

Benj: And part of leading people and having conversations with people is figuring out where is the strategic thinking within that team? Where are the people that are good at executing? Where are the people that are good at galvanizing and project managing? And pulling that out of the team and pulling the team together and actually making.

Benj: The team, a team, and not just a group of individuals. And I was surprised about how radical that idea was, that to stop thinking about subject matter expertise, stop thinking about strategy, and stop thinking about execution and start thinking about what does a leader look like at this level of an organization.

Benj: So I'm curious about you hearing about this conversation that I've had a few times. What comes up for you? 

McKenzie: My [00:09:00] one overarching thought with all this is and I'm curious how these people, if as you had these conversations, how they responded to that. Because in some ways, I think when we use words like leadership, it can be frustrating because it's so what does that mean?

McKenzie: And like, how do I go do that? Like how do I go apply that to the problem that I have? And maybe I'm being ultra concrete in asking that, but it's yeah, it's such an ethereal concept, it's so how do you, where do you start with that? How do you go in? Yeah. 

Benj: The reflections theme is a good theme because I think pausing to reflect and alright, so I just made a bold statement that I could go lead any team and increase performance, right?

Benj: Yeah. But if you stop and think who are the people that you've met along the way? Work or life that you're like, I bet if that person came in to lead that team, then it would improve. The team would improve. So you've got a theme that's struggling, but there's this person that if you brought them in, the team would improve.

Benj: [00:10:00] Start thinking about who those people are and like, okay, what is it? What is it about them? What is the, what are the intangibles? What are the tangibles that they bring? What is it about who they are when they show up, their character, their values? Then go look, okay, if I have this list that I've now created through reflection of personifying this person that can lead these things, then I can go maybe there is that person in my organization, or maybe I do know that person in a adjacent industry that I need to go recruit.

Benj: And you start thinking about how do I level up my leadership team with people that can really lead? 

McKenzie: Do you think that it can be taught to the people who are there? Like I'm thinking about the people that you described in those conversations, that it's like they have gaps, they're missing this, they're not like, do you

Benj: sometimes, there's, I'm in a season of life where I'm around youth sports right now, right?

Benj: All the time. You see the kids that are born to lead, that again, doesn't mean they're gonna have strategy and it doesn't mean they're gonna be [00:11:00] great at executing, but they have this presence about them that's naturally bent toward leading and people will follow them. So that's one answer. So you can keep your eye out for those people.

Benj: You can train them on making sure that they have the strategy and execution in the team. So that's one way to go about it. The other way is you say, okay, you've got somebody and they've, maybe they've got strategy or execution. In the case that we were talking about earlier, we've gotta teach them how to be more well-rounded, not as an individual, but as a team, and elevate these leadership aspects.

Benj: And a lot of times the leaders like here's why. The answer is sometimes the answer is sometimes because in the case that we were talking about earlier, both on the strategy side and the execution side, these people are so good, almost savant at the strategy and at the execution that you almost don't want to take the time.

Benj: To train them to be this other [00:12:00] thing called a leader. You want to leave them in their sweet spot because they're so freaking good at that, and it's almost better to let them be part of a team with a great leader where they can just sit in their sweet spot and flex that skill all the time.

Benj: Yeah. So the answer is it is possible, but it's not possible for everybody, and it's not always the right answer. 

McKenzie: There's a lot packed into what you're saying. I think that's why for me, I'm like, oh, this is a frustrating thing for everybody because

Benj: it's very frustrating. 

McKenzie: Yeah. And we were, I made a joke yesterday.

McKenzie: We were in, or earlier this week we were in a meeting and I'm like, but it's, this is real. And I keep thinking about it since I said it on Monday or whatever. Like I feel like I always start with frustration and then I find a healthier emotion and I think, but I'm trying to learn. Especially as I lead our team, that the frustration is almost like a, it's like a service light going on in a car.

McKenzie: It's Hey, it's [00:13:00] don't, I don't need to react outta frustration like that. That would be a whole nother episode. But like the frustration is like, Hey, there's something going on here that needs to be addressed. And now it's like, how do we address it? And what you've just presented is I think a couple of ways to think about that.

McKenzie: It's okay, is the frustration because. We are entering a new stage, like we're, we need to operate at a higher level. Is it that we have people on the team who are, missing aspects of the leadership that we need? And then what do we do about that? Do we do, can we elevate the person in the team?

McKenzie: Is there something about them that can be taught or coached up to play that role? Or, do we need to go find somebody who can really kinda, it sounds like the leader the leader is somebody who can really have the influence and the impact to bring out the best in everybody else.

Benj: Yeah. There's different frustrations at every stage. Every stage has its own [00:14:00] frustrations. Like when you're in that very first stage, you're like, you're overwhelmed because everything has to go through you until you figure out. How to not let it go. Everything go through you. Like just, there's everything.

Benj: My I forget where I got this, but somebody said, you can be king or you can be rich, but you can't be both. And what they meant by that is if you need to have your hand on every little button and person and direct everything. That's great. You can be king and everybody can do what you say and what you want, and you can be in charge and make every decision, but it's not scalable and you can't be rich.

Benj: To be rich. You need a bunch of other kings to work for you. If you wanna be really rich, you need kings who have a bunch of other kings that work for them. It's and there's no wrong answer. If you want to be king, you can be king, but you can't be, you're gonna always be frustrated if you're trying to be king and trying to scale into something that's bigger than just you 

McKenzie: and the other.

McKenzie: The other side to that, and [00:15:00] maybe this is a, I think people fall into two different categories with this. It's like the people who have a hard time elevating themselves because they wanna, they wanna do it all, be part of everything. And then you've got the people who wanna be king and wanna abdicate.

McKenzie: They're like, they wanna, they wanna sit high up. They don't wanna, they don't take the time to Yeah. Build the strategy and the execution. And so they're constantly like, why is this chaotic? And it's you've gotta you've gotta build, that's leadership too, right? Like the leadership in, for some people is stepping up and out into a place where other people can lead.

McKenzie: And I think leadership in other ways is training up. It's the same thing. It's just two sides of the same coin. It's like training up those people instead of abdicating and waiting for them to figure it out. Yeah, 

Benj: and in both the cases that we were talking, there is some training up that has to happen and there's some letting people go back down to their sweet spot and bringing in outside talent.[00:16:00] 

Benj: So that they can get to the next level where they want to get. So you can be king or you can be rich. I think is the theme. And there's frustrations, but I think, knowing is half the battle if you understand why you're having this frustration and you can't always jump out of it. Like I let a peer group of people in stage one and it's, I can give 'em all the answers of what it looks like to manage people instead of.

Benj: Be, the guy in the middle touching all the different things and all the people and telling 'em what to do. We could talk about delegation a bunch, right? And they're like, I have nobody to delegate to. I have nobody to lead these other people. And right now I can't afford it unless I want to go, raise money.

Benj: And that's not what I'm trying, that's not the game I'm trying to play. So the only way through that. Is what I call the long middle, right? It just feels like it's taking forever to get from this stage to this stage, but knowing that you're just in this stage, this is what the stage looks like, this is what the next stage looks like, and I'm working toward it even if it's not today.

Benj: And that's I [00:17:00] think the clarity and hope that people can carry with 'em, that'll help them even to realize, yep, I'm just in the long middle. 

McKenzie: Yeah, it sounds like if anyone, ending this episode and stepping out into the next step here I think if it raises awareness for anybody, it would be a great idea to take two hours and do what we call like a clarity break on all this.

McKenzie: Really think about the question of where are we and what would we need to do to get to the next stage? Spend some deep time reflecting on that. And then it sounds like this is in, it's a series of ongoing conversations with the people in your organization, so spending the time to really reflect and then go talk to the right people about it.

Benj: I'll give you one more example. As we were leaving of, I was in a session about two weeks ago, and the leadership team are all like. Super great people and super talented, but they have a lot of frustrations in in the actual business. So they're [00:18:00] executing well on what they do in the business, but actual, the actual business struggles.

Benj: And I just brought it to their awareness that hey, nobody in this room wakes up thinking about the business because they're a very project based business. So every, everybody in the room, one person wakes up dealing with fires every day, and everybody else is on these like big multi-year projects.

Benj: And I was like, until you have somebody in this room, in your leadership team that wakes up every day and heck, they could even if it was one day a week at this point for them. But ideally, every day thinking about the business, how do we build the business? How do we mature the business? And we start to take time doing that.

Benj: You're gonna be in this constant cycle because you're always gonna be doing the next projects and the next projects might get bigger and they might get more complex. And you're growing kind of the chaos within the [00:19:00] organization because nobody's tending to that as the organization grows. And so it was a little bit of a come to Jesus moment for them.

Benj: Because they're, they realized how much they're neglecting, building the actual business as they're, doing these big, enterprise projects out there. So it's another example of like just working on the business is the thing that can help create the platform to take you where you want to go.

McKenzie: Yeah. For everyone listening, this is your your next reflection. Go take a walk, go think about it. For yourself. You're at a stage some kind of stage. So what do you do? You need to get to the next one. Thanks Ben. It's good talking with you. It's good hearing what's going on with the leaders in our sphere and thank you guys for joining us today.

McKenzie: Once again, thanks to Fist Bump for helping us put this show on and bring this all together. We will see you next time for another episode of Sessions.

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Benj Miller

Host
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McKenzie Decker

Host