E177 | Why Successful Founders Hit a Growth Ceiling: Executive Coaching Insights from David Heaps

Your biggest strength may be the very thing keeping your company small. That is the idea behind this conversation between Don Williams and David Heaps, an executive coach who works with founders, CEOs and business owners across the United States. David, a former COO and the founder of Leadering, says every successful leader carries at least one habit they cannot change alone. His coaching starts there, with the leader before the team.

David also shares how months of silent isolation in the Amazon jungle shaped the way he coaches executives today. The two men explore why founders become the bottleneck in their own business, why so many avoid accountability, follow-up and tough conversations, and how hidden beliefs quietly steer leadership decisions. Don adds his own tools, including Shoshin (beginner’s mind), considering the opposite, and the case for hiring an outside coach early.

If you lead a startup, run a growing company or want to build better leadership skills, this episode gives you a fresh way to look at your own habits. It suits founders, CEOs, COOs, senior executives, HR leaders and aspiring entrepreneurs. Listeners can also book David’s complimentary Inner Architecture Audit, a 90 minute session, at leadering.com/PES. Press play on the Proven Entrepreneur Show and see what your own leadership has been hiding.

For information on how to work with Don visit us at https://donwilliamsglobal.com
You can also reach out to Don Williams at https://provenentrepreneurshow.com

Watch the episode here

Why Successful Founders Hit a Growth Ceiling: Executive Coaching Insights from David Heaps

Hey, Don Williams here with today’s episode of the Proven Entrepreneur Show. I got a great new friend, person with an unbelievably unique life experience. That is part of the reason he’s a phenomenal entrepreneur. David Heaps with Leadering. Welcome to the show.

Thank you, Don. I really appreciate being here.

Man, thrilled to have you. So the name of your company is leadering. Okay.

Mm-hmm.

And we’ll kind of get how you got there, but but for now, tell us what you do, who you serve, why you do it.

Yeah. So I’m an executive coach. I’ve had a practice called leadering for about eleven years now. And I serve executives, mainly owners, founders, CEOs, with companies that usually have about twenty five to two hundred and fifty employees. And I’ve found through the years of doing this that though they are quite powerful in their lives in many ways, they can overcome almost anything.

As is evidenced by the fact that they have these amazing companies that they’re running. But underneath that, I’ve noticed that each of them has at least one thing that they can’t make themselves do or stop doing. And it’s impacting them, it’s impacting their company, it’s impacting the people that depend on them. And they don’t quite know what to do about it if they’re even aware of it. So I help them find it, I help them understand it, and I help them end it.

Every successful founder has at least one thing they can't make themselves do or stop doing, and it affects their company and the people who depend on them. Share on X

Love that. And and and I think I think it’s just human. No matter how successful we look on the outside, there’s something on the inside that that we’re worried, fretting, avoiding, you know. it’s it’s never kind of all one way or the other. So love that you

Yeah.

do that.

I’m gonna jump into the I when I first met you, you t you t shared this thing with me and I was like, Holy smokes. Okay. You spent more than ten thousand hours in silent isolation in the Amazon jungle.

What did you learn about human beings in silence that you could have never learned in the boardroom?

Well, I didn’t go down to the jungle. Well, first of all, let me say that I did not do that in one long stretch. I did it in, you know, three to six month stretches over about four years. And what I learned was all about me and where my choices were coming from. and was understanding that the choices that I normally saw as being available to me were quite r restrictive.

And so I learned about me and I I wasn’t really thinking about other people too much, especially the the the first time I went down there. I was just learning about what was going on with me. And then when I got out and I started my practice and started working with people, and I started applying some of these mm, I don’t want to say concepts ’cause they’re not, but when I started introducing this learning into my coaching

I started seeing that this is everywhere and we’re all basically the same, but we just have different things at the bottom that are informing our our choices and shaping our lives.

I love that. And so I’ve always, you know, I do some work in my practice on leadership. And it it’s interesting to me how many founders, CEOs come to me and they’re like, what can I do to these people to where I’ll be a better leader? And and of course the answer

Yeah.

is always like, I I don’t know of anything you can you can do to them. the the eternal struggle in leadership is not leading others. It’s like can I

Can I lead me? Would I follow me? And and and and and if I can make progress there, the rest of it will kind of naturally, you know, fall into place. but but

The eternal struggle in leadership is not leading others. It is asking whether you can lead yourself and whether you would follow yourself. Progress there makes the rest fall into place. Share on X

Well, what

what you just said there was if you look behind me, it says leadering. That’s a it’s a created word, but that’s essentially what that’s all about is you you you’re gonna have a very rough time trying to lead other people before you’ve taken any time to lead yourself, which I I don’t wanna make that sound like it’s a one and done, it’s an ongoing project. But if you’re not focused on yourself first, then that comes with what it comes with. Yeah.

You'll have a very rough time leading other people before you've taken time to lead yourself, and leading yourself is an ongoing project, not a one-time fix. Share on X

Yeah, yeah.

I you know, I always start out with, well, well let’s you know, let’s talk about what a leader is. One, a leader is somebody going somewhere. Okay. If if you’re just standing still, I I I don’t think you fit the definition of the word. And two, as you’re going somewhere, you should be able to stop.

Do a 180, look behind you, and there should be at least one person of their own volition

Yeah.

following you. And if there’s nobody following you, again, I don’t think you fit the definition of leader. And the and the other counterintuitive thing I share is this. I’m like, I totally disagree with the term good leaders and bad leaders. I

Mm mm mm mm.

I think leaders are good. And people that are

not doing well. They’re not leading. And so and so there’s a conflict there. They may be in a position of leadership,

Sure. Yeah.

but they’re not actually leading. So okay, we could riff on this forever. Let me let I I should get back to work here, David. Okay, so yeah, yeah. You keep me on track. I I have a little ADHD pingon.

Please do, please do. Okay, okay.

So you worked and worked with successful founders and CEOs.

What’s something you’ve observed that highly successful leaders think looks like a strength, but maybe is really a weakness?

Looks like a strength, but yeah, I think I’m just I just had a client just drop in and pop in my mind. Sorry, I just snapped.

That’s good.

this is pr this this person that I’m thinking of is somebody that we would consider a rainmaker. I mean, when they walk into a room, it’s very clear. They’ve walked into the room, everything shifts, all the attention goes to that person. This person knows the business better than anybody.

And they have a tendency to take over everything. So, you know, they have a bunch of employees and people that report to them, but they don’t easily, their decisions don’t easily survive contact with this individual. So he has for a long time he’s thought he’s been doing real really well by following up behind his people and maybe touching up and doing this or that that will make it a little better.

or making sure that every decision is funneled through him to get his approval. And of course that just causes the business to stay constricted, not able to grow, and it weakens the people that he’s trying to develop.

A founder who funnels every decision through himself and follows behind his team to touch things up keeps the business constricted and weakens the people he is trying to develop. Share on X

Yeah, I man, I can see that. It’s so common with entrepreneurs, you know, so you know, sometimes you have to share with them, hey, the the bottleneck is at the top of the bottle. You’re the bottleneck dude. Or

Yeah, yeah, yeah.

do that, you know, many times it’s female. What do you think’s the most dangerous untruth successful entrepreneurs can believe about themselves?

The most dangerous untruth.

Yeah. I’m it’s a polite way of saying lie, the most dangerous lie that successful entrepreneurs believe about themselves as

Hmm.

leaders.

I you know, I would apply this to anybody, not just leaders, but when I hear somebody say something like they’ve done the work.

It’s that. Because that implies that it’s behind you and you’re finished. And that tells me right away what I’m dealing with. Somebody who thinks they’re over the finish line. Yeah.

When someone says they've done the work, it implies the work is behind them and they're finished. It tells me right away they think they're over the finish line. Share on X

Yeah.

Yeah. Yeah. I you know, it’s funny how that finish line keeps moving as you move through lives. You know, I can see the horizon. I I start going to the horizon, but as I get to the horizon, the horizon has moved away. And and and and as well it should. So sometimes

I think you begin coaching conversations by asking what are you avoiding?

Mm-hmm.

And so I’m gonna turn your question back to you if I can. What do you think most successful entrepreneurs are avoiding?

Yeah, that’s a great one. And that’s honestly where I start with most of the people that I work with. And most of them are avoiding, well, it’s really funny to say this because they they are in a position of leadership. They are running companies, but they are avoiding the things that come with leadership. And I would say that the the top of that list.

It’s so strange, but so many of them are avoiding simple things like following up and holding people to a standard. I know that’s

Mm.

it seems like that would be something that most of them would be good at. I find the opposite. I find that most of them are really, really bad at that. And there’s a very, very good reason. Well, there are many good reasons why that’s the case for them. I also find that they carry quite a bit of embarrassment and shame over the fact that they’re not able to do this thing that

They they imagine everybody else does without effort, and it’s not true. I would say that’s the that’s the top of it.

Many founders avoid following up and holding people to a standard, and they carry embarrassment and shame because they assume everyone else does it effortlessly, which isn't true. Share on X

Yeah, I I I totally agree. I think entrepreneurs, it’s one of the reasons, you know, the EOS and scaling up and bloom and all those they’re basically accountability programs where they help leaders hold people accountable because I think the average entrepreneurial leader that they know they should, but they just avoid the tough conversations.

Yes.

You know, they’ll get better.

Well, they probably won’t get better. You know, they’ll

Hmm.

they’ll get worse. If you’re lucky, they’ll stay at the same performance. But you know, what’s that quote? The obstacle is the way. If if

Mm, mm, mm, mm.

you’re avoiding it, that’s probably the the green light, go down this lane, tackle this first.

I agree with you completely. And it’s not so simple from inside the system that’s producing this problem. It’s, you know, which is why we have coaches and other people that reflect back to us different things. it but it’s a it’s a very challenging thing for for most leaders. And so this is the place we start. This is the this is the entry point. And there’s not one reason why

somebody’s averse to for example, I’m thinking of somebody right now who has an aversion to being an authority figure. And he I mean, this has survived

15 years of of of leadership. And so when we pulled this apart and we got underneath this and we found out where you know what was underneath this, it takes us back because I I I use these frustrations, I use these avoidances, I use these problems that are here right now in the present that are affecting what are you are are are not doing. Excuse me.

And what we found under this particular person that I’m thinking of is his relationship with his dad. He had a really tough dad. I mean he was loving and you know, he wasn’t abused in any any sense that we might think of it, but he was really tough to deal with and he was really hard on him. And no matter what he did, he just couldn’t please this guy, could never quite get his approval. And so what happened is he didn’t ever want his employees

To view him as he viewed his father. So he has this of aversion. So so let me back up. What he’s afraid of is essentially what leadership or confrontation threatens to turn him into, which is his father. And he and he’s

Yeah.

not aware of this at all. So we all have these beliefs obviously way down beneath, you know, all the other areas of our psyche. But the important part is that there’s pot protection that we’re not aware of that that forms around these beliefs.

shows up in our mind as a as a voice that says, Do this, don’t do that, don’t show this, make sure you never do that and it seems like a a reasonable thing to say in a in a in a normal moment and over the course of a life, it’s what shapes it shapes your leadership, your company, your relationships, everything.

Yeah, yeah, I I totally get that. And and let me say this on the you know, on the coaching piece. you know, you’re a coach, I’m a coach, there’s a lot of great coaches out there, okay, but I’m always in awe of someone who says, I’m gonna get an expert, I’m gonna get a third party, I’m gonna get a fresh set of eyes to help me with this. And I hired my first coach probably fifteen years ago.

And I worked with her for two years. Okay. Love her to death. moved, went to a different coach. I know people who have multiple, they have a they have a an executive coach, they have a a trainer, they have a this, they have a that. And I I would just tell the audience, if it’s not your superpower, get somebody who it is their superpower.

Make it easy. In the long run, it’ll be far less expensive than going through 10, 20, 30, 40 years of junk. Okay. And and then the second thing that resonated with me was this. I think almost all children, of which we all are children, we may be maybe older like me, but I’m still a I’m still somebody’s child. And and I think we we grow up in ha in whatever type of household we grow up.

And there are certain things that our parent or parents demonstrate the way they live their life that we’re like, hey, I’m gonna do a lot of that. Okay. Hopefully there’s hopefully that that’s universal for everybody. On the other hand, even from a a great positive childhood, there’s some things you look at that you say, I’m not doing any of that. Okay. And and that I think that’s just human nature. I’m gonna emulate this and I’m going to avoid all that.

And and it all seems normal in our minds because that’s what we saw, that’s what we lived. However, the beauty about a coach is you get a little perspective and a little breadth and a little width and a little air, okay, to maybe see things differently. And then the other thing that I really help think helps is if you approach coaching with kind of that Shoshin mindset, you know, coming with a beginner’s mind, though I may be a master in

this particular

Mm-hmm.

discipline, I’m going to act like it’s all new to me and I’m gonna learn from this person. And

Mm.

actually that’s not a bad way to live, much less would be with a coach, but just live learn everything you can.

Agreed.

Okay, what point have you noticed? Is there a point? Is there a commonality point where the very thing that makes an entrepreneur successful?

Turns in it turns into what’s holding them back.

Almost always.

Yeah.

Almost always. Because that thing casts two shadows and you can’t cut one out.

The trait that made an entrepreneur successful almost always becomes what holds them back, because every strength casts two shadows and you can't cut one out. Share on X

I love that. I’m stealing that. Cast two shadows. Yeah.

Yeah, yeah.

I’m definitely well, I’ll ask you. Can I borrow that? Okay, thank

It’s it’s yours.

you so much. Yeah, because there’s you know, the you know, there’s Myers Briggs and the Berkman and Disc and Clifton Strength. You there’s a zillion of those assessments.

Sure.

And one of my favorites is the VA and ratio on 20 character strengths. Well, my top character strength.

is judgment. And that’s really that’s a good one to have. Okay.

Sure.

But you know, the yin and the yang of it is that while I’m blessed with typically good judgment.

judgmental you know because because there’s two sides to the coin and so I think it’s very common that maybe what for a while is is a accelerant for entrepreneurial excess at some point you cross the halfway the coin flips and and maybe it’s a challenge holding holding you back for further growth.

Sure. I most of the entrepreneurs that are the the executives that I work with, excuse me, they’re they’re not even aware that their entire life is a pretty intense campaign to disprove something very deep that they have come to believe about themselves. And it’s usually I find having something to do with powerlessness. They have a a a deep knowing that that that

they are powerless because they had some situation when they were young where they weren’t able to do anything about it. So so their reaction to that is to find themselves at the top of one organization, leading people, making money, all the things that makes one powerful. And they notice at some point in that journey that that powerlessness and those fears and that limited decision making that we were talking about earlier followed them right into it.

And if not in the form that one would imagine, but it sort of lends itself to what we were talking about earlier about being that that friction point or that bottleneck in your company. There is some point where you actually have to allow the people that that you’ve brought in around you, hopefully smarter than you, to actually exercise being smarter than you. So that’s the the two shadow thing. It got you to where you are, it’s the reason you have a company, and now it threatens to keep it smaller. Actually

some in some cases even lose your company.

A founder's strength got them where they are and is the reason they have a company, but it can now keep that company smaller or even cost them the company. Share on X

Yeah, I I I so agree. And and that was so good. When we go to editing, I’m gonna ask Karen to double the volume on that segment so

that people really pay attention to that.

Yeah.

Because folks, that was like solid gold right there. okay, we’re we’re into the fourth turn. I can see the checkered flag.

Ha.

here’s here’s I think my last question.

What’s something about leadership you believed as a CEO?

that you now believe was wrong.

Well, first of all, I was never a CEO. I was a C O O. So I’ll just make that correction.

C O O I sorry. I E E I E I O. I was close.

Something that I believed, my gosh. I yeah, that’s a pretty easy one. When I was in the height of my my powers and you know, I was deep in the corporate world.

I believed I was dealing with all of the options that were available and I thought I saw all of them available to me. And now sitting where I am now, knowing what I do now, having done the work that I’ve done now and helped, you know, many, many people look at themselves, I understand that at that time the range of options that were normally visible to me were just absolutely tiny.

At the height of my corporate career I believed I was weighing every available option, but the range of options I could actually see was tiny. Share on X

And you know when you bump into the edge of those because you get angry or you get upset or you avoid or you are annoyed or all the different things you can become. So I think that’s the top one for me.

I love that. I I know for most of my career, you know, I thought I was the smartest guy in the room. And

Mm-hmm.

and in a lot of rooms I was, which

Mm.

which just furthered that belief. Okay.

Mm-hmm.

Not in every room, but in a lot of rooms I was. And as I’ve finally begun maturing, you know, one day I hope I’m gonna be all grown up.

You know, I’ve come to realize I don’t know much. You know, I know a couple things. And and everything else is kind of open, it’s kind of open season.

Mm.

And, you know, a couple years ago I I learned this. I don’t know where I learned it. It’s not my concept, but I learned the concept of considering the opposite. So whatever your default reaction is to a stimulus, just take a half a second and think, I wonder if the exact

opposite could be true.

Mm-hmm.

And the scary, kind of scary thing about it is when you do that, about half the time you say, yeah, it it actually could be. And

Mm-hmm.

and so that, you know, helps with perspective.

Whatever your default reaction to a situation, pause for half a second and ask whether the exact opposite could be true. About half the time, it could. Share on X

Mm.

David, I I don’t do this very often, but I reserve the right to recall the witness and to call you back for a second episode in the future. And so

If if a founder, an exec, a CEO, an entrepreneur out there would like to reach out to you and leadering, what is the best way to do that?

David (20:22)
Yeah, probably my website and I’ve also created a a landing page for your viewers. So if they just go to leadering.com forward slash PES, proven entrepreneurshow. Yeah.

Yeah.

yeah, there’s a landing page there. And I I wanna say too that there is an offer there to sign up for something I call an inner architecture audit. It’s a 90 minute session.

And if you bring in with you your biggest problem, constraint, whatever that is, by the time that ninety minutes is over, you will go away with a very detailed map of what’s underneath it, why it’s showing up, how it’s impacting your your business and more importantly what you can what you can do about it. But you will understand very well what’s going on by the time you leave.

Amazing. How generous. Thank you very much. So let me repeat that. Leadring.com slash P is in proven. E an entrepreneur S is in show. P E

Yes.

S. And that’s a landing page built specifically for us. We’re grateful. Thank you so much. And

Mm-hmm. Yeah, absolutely.

and there’s a and there’s a complimentary offer there. And so take advantage. David, thank you so much. It’s been my pleasure to have you on the show today.

Absolute pleasure. Thank you so much, Don.

You bet. Hey, that’s today’s episode of the Proven Entrepreneur Show. Tune in next time. See you then. Bye now.