On this episode, Josh speaks with Dave McKeown, author of “Outfield Leadership“. They talk about some principals that make for good leadership.

Dave McKeown helps individuals, teams, and organizations achieve excellence by doing the ordinary things extraordinarily well.

He is the CEO of Outfield Leadership and author of The Self-Evolved Leader – Elevate Your Focus and Develop Your People in a World That Refuses to Slow Down.

He has a wealth of experience in connecting individual and team performance to improved business results with a particular focus on fast-growing, complex organizations.

In today’s episode you will learn about:

  • What is Self-Evolved Leadership?
  • What’s the problem with our current leadership models?
  • What do you mean by the cycle of mediocrity?
  • What is heroic leadership and why is it a problem?
  • What is the key mindset of the Self-Evolved Leader?


Narrator:        Welcome to Cracking the Cash Flow Code where you’ll learn what it takes to create enough cash to fill the four buckets of profit. You’ll learn what it takes to have enough cash for a great lifestyle, have enough cash for when emergency strikes, fully fund the growth program, and fund your retirement program. When you do this, you will have a sale‑ready company that will allow you to keep or sell your business. This allows you to do what you want with your business, when you want, in the way you want.

In Cracking the Cash Flow Code, we focus on the four areas of business that let you take your successful business and make it economically and personally sustainable. Your host, Josh Patrick, is going to help us through finding great thought leaders, as well as providing insights he’s learned through his 40 years of owning, running, planning, and thinking about what it takes to make a successful business sustainable and allow you to be free of cash flow worries.

Josh:                Hey, how are you today? This is Josh Patrick. And you’re at Cracking the Cash Flow Code. And today, my guest is Dave McKeown. And I hope I got that right. He’s the author of The Self‑Evolved Leader. And he’s got a business that’s called Outfield Leadership.

I always get this terrible pause before I actually introduce people. And I’m really sorry about that, Dave, but I have the memory of a gnat, it appears, these days.

Dave:               Not a problem, Josh. Great to be here with you.

Josh:                So, thanks for joining us. And we’ll bring Dave on. I mean, you just heard him say something [laughs].

Dave:               How are you?

Josh:                I’m well. How about yourself?

Dave:               I am doing just well. It’s a Monday. You know, new month, new week. All of those good things?

Josh:                So, Dave, let’s start off with answering my burning question which is what is a self‑evolved leader?

Dave:               The general crux of a self‑evolved leader is this. I believe that, in our organizations, we have somewhat ceded control of our growth and our development to the organization and we talk about leadership being a soft skill and all of that. And actually, becoming a more effective leader is your responsibility. It isn’t your organization’s responsibility. It’s your job. And taking ownership over your growth and your development sits with you. And so, at its core, a self‑evolved leader says there is value and there is quality in me becoming a better leader and, therefore, I’m going to work hard to make that happen. That’s really at its core.

And there’s a whole bunch of stuff about what that looks like, what it feels like, how do you get there. And I’m sure we’ll dive into all of that.

Josh:                So, I have a question about that. You have to want to be a leader, I would think, and you have to understand that you need to develop leadership skills. How do you get someone to understand that that’s reality?

Dave:               Your question is hugely important and one that I think we’ve been trying to crack for decades which is that most people end up in leadership positions just because they’ve been told that upwards is the best place to go. And so, you know, they get good at their job and, therefore, they get promoted as a result of it. And they don’t take the time to truly, really reconsider what it is that they’re taking on that, actually, being a leader is very different than doing the job that you initially were there to do.

And our organizations, in general, do a terrible job of this, right? We have a tendency to promote people that are good, functionally, at their job. So, a good salesperson becomes a sales manager. A good sales manager becomes a sales leader. But being a sales leader is not the same job as being a salesperson. And, actually, that’s where often failure lies because we mismatch those two things. And I think it’s like anything in life intention is the be all and end all.

So, saying to somebody, “Hey, you’ve got two routesyou can go down. You can either continue to get really awesome at what it is that you do from a functional level. And that’s great, and valid, and good, and we’ll support you and here’s a path for you to be successful on it. Or, do you want to make a journey towards leadership? In which case you have to forget almost everything that you already know about functionally doing your job and learn a whole bunch of other skills, and behaviors.” And just painting a picture of what those two things look like and the differences between them, I think, is a good starting point for that conversation.

Josh:                So, here’s the thing that I would like to go back to. I’m going to go back to the same question because that’s great if you’re an employee, and you’re working for a company, and you’re a salesperson being promoted to sales manager. And the owner should definitely be having that conversation with you. But if I’m the owner of the company, there’s nobody having a conversation with me, I’m going to have to discover myself.

Dave:               Right.

Josh:                So, again, I’m going to ask, the question is, how do you know that you need to develop leadership skills when you’re the owner of the company and nobody is around to tell you?

Dave:               It usually happens whenever you hit a cap in either the growth of your business or the complexity of it which then starts to bring issues and challenges for you. You can grow a business to a reasonable size without having any real leadership skills but, at some point, the balls are going to drop. And it’s usually at that point that founderowners start to say, “Okay, I can’t do this all by myself. I either need to build a leadership team that’s going to help me do it, or I need to change my approach to how I lead this organization.” And it’s usually that transition from being a very visceral leader – a lot of founder‑owners lead from the guts, and their ego, and it’s very much just founded on who they are as a person.

Usually, the ones that make a successful transition realize, “I’ve got to develop a better way, a more professional way – for lack of a better term, of viewing my business.” And actually, the funny thing is, the only reason that you would want to do that is (a) if you want to continue to grow and develop the business, you can have a successful founder‑owner lifestyle type business of a reasonable size without developing any leadership skills or attributes, really.

And, again, it goes back to intention, what do you want the business to be? Do you want to stay in a sort of a pseudo lifestyle business you don’t want to grow and develop? It’s probably quite dependent for its success on you, you can’t walk away from it, but you get to call all of the shots. That’s choice number one. Awesome. If you want to do that, that’s great. Do it.

But if you want to build a scalable business, then you’ve got to learn how to be a better leader. You’ve got to bring better leaders into it and make that choice number two. And I’ll finish on this, where a lot of founder‑owners get trapped is they see the routeof scalability and they’re like, “I want that.” And they pay lip services to some of the behavioral shifts that they need to make, but they’re so caught up in this sort of founderowner mentality that they can’t make the transition or they ultimately don’t want to. And, you know, at the end of the day, it’s about your intention – what type of business do you want, what you want your impact to be. I hope that answers your question.

Josh:                It answered it really well. And you also said something, right at the beginning there, which was the most important thing of all because that’s what happened to me. When the business breaks is when the owner‑manager decides they either have to change their behavior and fix the business or they have to take a big step back and re‑think about how they run their business.

Dave:               Yes, very much so.

Josh:                That was my experience. Our business had essentially broken and, up to that point, I was the world’s worst leader. I would blame or justify my way through life and nothing was ever my fault.

Dave:               Right.

Josh:                And I finally ended up– because our business was broken, I happened to go to a new age seminar, back in the early 80s, I sort of thought, I said, “Well, you know, maybe I should look in the mirror and start taking a little bit of responsibility for what goes on around here” which is exactly what I did. And you just did a magnificent job of explaining that when your business breaks, you’re going to have a choice, you get to go like, “Do I become a leader or do I just become a lifestyle business?”

And, by the way, I agree with you. There is absolutely nothing wrong with a lifestyle business. It is a really valid choice. It’s just you’re not going to be able to run the script of building a business, selling it, and having two tons of money you get to retire on. You’re going to have to use a different strategy. We happen to have those strategies but you’re going to have to use those strategies because that’s not the same trip that you hear in the Harvard Business School, or at Inc Magazine, or Entrepreneur Magazine. Nobody ever writes about the lifestyle business and how to successfully navigate through your lifetime with it but anyway that’s a different ballgame.

Dave:               I often, whenever I’m faced with a founder‑owner who’s going through that particular challenge, just say to them, “Look, you can either be king, or queen, or you can be rich.” And I think it’s to your point, like a lifestyle business, you’ll always be the monarch. You’ll always be in charge. But the wealth of building a scalable business and selling it for two, three, to four times the values is, like you said, that’s where the wealth comes off of it. And, again, just that what’s your intention? What do you really want to do? What do you want to get out of it? The worst is getting trapped in the middle where you think you want one but you’re not ready to make the behavioral shifts to get there.

Josh:                Yeah. You know, that’s absolutely true. So, what’s the problem with today’s current leadership?

Dave:               A whole bunch of things, not to sound too negative. I think that– let me just preface this by saying that I’ve spent the last 10 to 12 years working with senior leaders and leadership teams to help them make the transition to become more effective leaders. And I think what I’ve seen, over that time, is a lot of our models for effective leaders or leadership excellence are still founded on outdated ways of thinking. So, you know, stuff that came around in the ‘60s and ‘70s. And then, was popularized in the ‘80s and ‘90s. Just this notion of the leader as a hero, this notion that in order to be a good leader, you’ve got to be strong. You’ve got to lead from strength. You’ve got to be at the front. You’ve got to be the hero. You’ve got to be certain. You’ve got to know where we’re going and be sure around that.

You know a lot of our examples of models for leadership come from areas like sports, military, and movies which are all focused very heavily on this notion of the heroic leader. What that means and how that plays out on day‑to‑day, interactions with their team is usually this, the heroic leader gets their ego boost and believe that they bring value to their company by either saving the day, like literally just fixing problems or telling their team what to do. They’re the harbinger of all of the answers. They are the center of the universe.

What that does, however, is two things. One, it disempowers your team. They don’t grow and they don’t develop. They develop a sense of learned helplessness where if I’m constantly coming to you and saying, “Hey, Josh, I’ve got this problem. What do you want me to do about it?” and you save the day for me. At some point, I’m just going to stop thinking for myself. I’ll just come and say, “Hey, boss, here’s the problem. You know, you’ve saved the day every other time so go do it.” So. your team develops learned helplessness. And then, you become the bottleneck because everything lands at your door. You become frustrated. You become actually, at some point, burned out and you start looking at your team saying, “Why does nobody do anything around here? Why am I always the one that’s doing things?” Because you freakin’ do it, like it starts with you.

So, that notion of leading through acts of heroism, I think, comes through in real subtle ways. It doesn’t have to be big, overarching, jaw‑dropping acts but just little ways that say, “I’m the center of the universe here.” It comes from a reasonable place which is we’ve been rewarded, promoted, and assessed all our life on our ability to do stuff and know the answers. But, at some point, that becomes a liability to your organization. You become less valuable. In fact, you take away from the value because you’re disempowering your team and you’re becoming the bottleneck. So, for me, that’s where the foundation of ineffective leadership comes from. And if we can transform that, then we move towards more leadership excellence.

Josh:                You just reminded me of a couple of things. One is Joseph Campbell’s Hero’s Journey is that, you know, as leaders, we don’t want to be the hero. We think we want to be the hero, but we really don’t want to be the hero. We really want to be the guide. And once you understand– I mean, just go to see Star Wars and ask yourself this question, “Would you rather be Yoda or would you rather be Luke?” And in my mind, I would rather be Yoda. It’s a whole lot more fun. Now, if you’re Yoda, you don’t get all the credit. Luke gets all the credit, but you get all the wisdom.

And for me, being the guide is a great thing. I have this metaphor I call “leading from the back”. And I didn’t want to sit at the head of the table. I want to be at the back of the room so I can ask the really good questions. And that’s what a guide does. And if you’re a great leader, you’re a great guide. You’re not the hero ever, ever, ever.

Dave:               I agree with you wholeheartedly. And, actually, you want to build a team of heroes. Like, that’s what you want to do. You know, comically, if you think about it, everybody says they want to be Yoda, or they want to be Gandalf, or they want to be [inaudible 00:12:51] but, if you ran the movie, it’s like Yoda would literally be alongside Luke the entire time just, you know, jabbing and crossing people that came across his path. And that’s how it really plays out in our workplaces. We say we want to do it but we’re not.

And, ultimately, what it comes down to is you can’t build a scalable team, you can’t build a scalable organization, you can’t scale the impact that you have as a leader if you’re the hero. You just can’t. You get a nice ego boost. You’re wanted and you’re seen as being valuable but, ultimately, you can’t scale that. You can’t scale the impact.

And I think a lot of managers and leaders, when I get to this point in the conversation, would be saying, “What would I do–?” Like, I think, people have a genuine confusion. What would I do if I’m not saving the day? to which I say, “Anything that you want. Like, at that point, then you get to work yourself out of a job. Get to the point where your leadership is so good that your team looks at you and goes, “Hey, boss, your job is done. Thank you.” And then, you’ve got a new mountain to conquer, a new challenge to overcome. And what a way to grow your own legacy as a leader rather than being known as the person that literally just fights fires all day because you want to be the hero.”

Josh:                So, what you just are talking about is right on. And I have this idea that there’s a core skill that you need to learn to become a great leader. And the problem is most people try, and they fail, and they never want to try again. And that’s becoming what I call a delegating ninja. So, where does delegation fit in with your leadership model?

Dave:               So, I talk about five disciplines that any leader needs in order to move away from being a heroic leader towards being a self‑evolved leader. And delegation, effectively, is one of them. I call it facilitating team flow. I call them actually five disciplines because I’m fed up with the argument about whether leadership is a soft skill or not. So, I just say, “Let’s just not use the word skill. Let’s use the word discipline because discipline is hard to learn. It’s hard to master. It’s hard to get good at.” But discipline is a huge one.

And the reality is most leaders’ hesitancy to delegate starts with them and their own ego. It very seldom actually starts with the other person. What are the main excuses that we hear for people that don’t want to delegate? Number one, going to take me too much time. Number two, they’re not going to do it right, anyway. And number three, I’m going to have to fix it for them because they’re not going to do it right. All of those are founded more in the leader’s ego than they are in the person.

And when I’m having a conversation with somebody, I say, “If you’re telling me that you’re not delegating because you don’t believe your team can do this job, do it appropriately, or do it the way that you think that it needs to get done, if that’s really what you’re saying and that’s the honest truth, then why are they in that role? That’s a performance issue. Like, if you’re telling me that you’re not going to delegate to somebody because they can’t do it. Why are they working for you?” To which they go, “Well, look, they probably could do it.” And I go, “Okay, so what’s the real problem?”

What it actually comes down to is it’s a subjective call which is they won’t do it in the way that I would do it or they wouldn’t do it in a way that makes it feel like it’s mine, rather than they wouldn’t do it right. And so, my advice and guidance is always this, when you look at your to‑do list you should be able to cut that down between 50% and 60% through delegation. You should look at your to‑do list and honestly answer this question. For each item that’s on your to‑do list, is that something that truly only you can do that nobody else in your team could do without some advice, guidance, and coaching? If the answer is yes, okay, do it. If the answer is no, then you’ve got to spend the time because anytime that you spend upfront with somebody, delegating and showing them how to do your task, or project, or manage a relationship, will pay dividends on the back end. The time argument never holds weight. Show them how to do it once and they’ll do it for you 15 to 20 million times. So, get over yourself, get over your whole ego, try and delegate as much as you can off your plate in an appropriate way. And then, get out of the way and let people do it. Don’t micromanage them. Don’t hover over them. Give them the opportunity to come to you with challenges about it rather than just standing over their shoulder.

Josh:                Yeah, I agree 100% with what you’re just saying except for one thing. I don’t think it’s 40% or 50%. It’s about 80% of your activities should probably be delegated.

Dave:               The number is high, definitely.

Josh:                I tend to go with the 80/20 rule on almost everything and, when you look at your to‑do list, my bet is you’re going to find 80% of the things on that list can be done just fine by somebody else.

And, by the way, you don’t have to spend a whole lot of time documenting their jobs. The person doing the job can document it themselves as they’re doing it. You can just check the documentation to see if it’s right.

Dave:               Absolutely. Yeah, keep that light touch process.

And I also recommend and suggest that you’d be very specific about outcome, right? What do we need this outcome to be? But then flexible about the rest. Like, let them find out the way to get to where it is they want to go to unless, of course, the thing that you’re delegating is to follow a process, in which case, you have to follow it, obviously. But be flexible about how they get there and let them learn their lessons.

So many leaders, they’ll see somebody approach something in a way and go, “I tried it once that way. It’s not going to work so now is my time to intervene and tell that person that they shouldn’t do it because I’ve learned from that.” In this belief that we’re being helpful, it comes from a good place but the reality is you went through your own experience with your own skill set and in your own context that this person doesn’t have. And they will learn the lesson by letting them go do it.

Parenting’s no different. You know, let the kids fail. Use it as an opportunity for them to grow and develop.

Josh:                You know, that fits with one of my favorite mantras, “Fail fast. Fail cheap.”

So, we have a few minutes left, Dave, and I want to have this conversation because I always find it amusing, at least for me, which is “Are leaders made or leaders born?”

Dave:               Oh, made all the way through. 100%. I mean, I think that you have a small percentage that maybe have natural tendencies but everybody that wants to can be an effective leader so long as you set your intention to do it and you work through a process and you practice it.

I think that what we’ve done is, in calling leadership a soft skill, we’ve essentially said, “Well, it’s either going to happen by osmosis or it’s not.“ So, I’m eitherjust going to naturally get there or not.

Becoming a good leader is like learning how to play golf, or learning how to play tennis, or learning how to cook, or learning how to play the guitar. You can practice it day in day out and you can get better over time. So, I’m a huge believer that effective leaders are made and not born.

Josh:                Yeah, that’s my experience also.

And there are skills that you need to learn to become a great leader. So, you mentioned one which was delegation. What are the other four, real fast?

Dave:               Reclaiming your attention. So, getting good at what allows to interrupt you, I think. It used to be called time management, but I think it’s actually attention management now. I think it’s shifted.

You cannot be a great leader if–

Multitasking is not great leadership. Never was, never will be. You can’t be a good leader unless you really get a handle on what’s coming in and interrupting you every day. To get really good at reclaiming your attention, you facilitate team flow. You get that delegation going. You’ve got to support high performance which means being more coach like and less heroic like so that, when somebody has a challenge, you’re asking good questions to help them overcome those challenges and find their own solutions.

But you’ve got to be really good at having symbiotic conversations so, whether it’s giving feedback or behavioral adjustments, approaching somebody with empathy and vulnerability in a way that allows them to understand the options in front of them and to opt into one of those options.

And then, the final one is building shared accountability amongst your team, getting your team to be the accountability group rather than you, individually, holding people accountable so that people are excited to come in, share their goals, share their progress, and share with each other how they can support each other as they continue to grow and develop.

Josh:                Great.

Hey, Dave, we’re unfortunately– I can’t almost speak today– unfortunately, almost out of time.

And I’ve got your website up here. Is there something you would like people to do after they’ve listened to your great advice today?

Dave:               Yeah. Go to outfieldleadership.com, click on book, and you’ll be taken to a website that’ll allow you to download a free chapter. Well, actually, two chapters – the introduction and the first chapter of The Self‑Evolved Leader. Check it out. If you like it, feel free to buy it. Connect with me on LinkedIn. I’m there at David McKeown, would love to connect with anybody that’s there. That’s what I’d love for you to do.

Josh:                Okay.

Well, I have two things I’d like you to do. And I’ve always been told I should never ask people for two things but I am. And the first is if you would please go to, wherever you listen to this podcast, and give us an honest rating and a review. I would really, really appreciate it. You don’t know how much that helps people find the podcast. And I can tell you that folks who have listened keep telling me they really like it. So, I hope you do that.

And the second is, I’ve been getting pretty obsessed about what I call sale‑ready company. In fact, I have a book I just finished, called The Sale‑Ready Companyabout a family who is in the throes of doing a transition planning. I have a free e-book on what you need to do to get your company sale ready. And, by the way, sale ready does not mean you’re going to sell your company. It just means that it’s ready to be sold which means it’s more valuable for you while you own it and it’ll be more valuable for you if you ever decide to sell it. Easy to get. You just go to www.sustainablebusiness.co/saleready That’s .co and not .com. Again, that’s www.sustainablebusiness.co/saleready.

This is Josh Patrick. We’re with Dave McKeown. You’re at Cracking the Cash Flow Code. Thanks a lot for stopping by. I hope to see you back here really soon.

Narrator:        You’ve been listening to Cracking the Cash Flow Code where we ask the question, “What would it take for your business to still be around 100 years from now?”

If you’ve liked what you’ve heard and want more information, please contact Josh Patrick at 802-846-1264 extension 102, or visit us on our website at www.sustainablebusiness.co, or you can send Josh an email at jpatrick@stage2solution.com.

Thanks for listening and we hope to see you at Cracking the Cash Flow Code in the near future.

Topics: sustainable business podcast, Sustainable Business, key mindsets, good leadership, outfield leadership, cycle of mediocrity, self evolved leaders, dave mckeown

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