Episode 629
Bill Gallagher argues that overworking is not a badge of honor but a sign you have not built and empowered a real team. He opens with a story of a CEO who micromanaged through a company sale, insisting on controlling every detail despite knowing the damage it caused. The transition took longer, leadership churned, and both new and departing employees suffered because the CEO could not let go.
Gallagher identifies five reasons leaders work too hard: lack of trust and perfectionism, fear of failure, ego and hero syndrome, habit from the founder years, and being too busy to delegate. Each keeps you stuck in crisis mode. The hero syndrome is particularly insidious because it requires problems to solve, so your ego becomes invested in keeping things chaotic.
The path forward starts with understanding which reason drives you, then inventing a new why that makes delegation essential. If your mission, team, or legacy matters enough, you will retrain yourself to step back. Gallagher emphasizes that this mindset work sits at the center of his coaching, alongside the mechanics of strategy and execution.
Key takeaways
- Overworking signals you have not built a team capable of operating without constant supervision.
- Most leaders work too hard for one of five reasons: lack of trust, fear of failure, ego, habit, or being too busy to delegate.
- The hero syndrome requires crises to thrive, so unchecked ego keeps you manufacturing problems to solve.
- You can create a new why rooted in mission or legacy that makes stepping back and delegating essential.
- Shifting from doing to leading requires addressing your mindset and behaviors, not just improving processes.
In this episode
- 00:00A CEO who could not stop micromanaging
- 02:54Five reasons leaders work too hard
- 04:47Ego and the hero syndrome
- 06:59Overworking is a sign you have not built a team
- 08:22Inventing a new why to change your behavior
Read the full transcript
A CEO who could not stop micromanaging
00:00Bill Gallagher: Have you ever had a week when you're completely slammed, but somehow nothing actually moved? Is this one of those weeks? That's not really a time problem. It's a busyness habit problem. My new book, Busy Is Broken, Do Less, Scale More, is all about growing by doing less, not more. Read or listen to a sample chapter over at busyisbroken.com. That's busyisbroken.com. It's also on Amazon and other booksellers.
00:25Bill Gallagher: The biggest reason you work too hard? The biggest reason you work too hard is you don't trust anyone else to do it. Look, let me tell you a story, and I'll tell you some of the other reasons that people work too hard, people like you and me. So I was coaching a new CEO of a healthcare business who was all up in everybody's business. The company was in the middle of a sale. The founding CEO was exiting. There wasn't a lot of years of lead up to this transition. We hadn't developed a whole succession plan. And now I needed to help coach the company through the transition and deal with all that. But the new CEO was so worried about the old and the new team and everyone getting together well and their role as the new CEO that they were micromanaging everyone in process, including me as the coach, telling me how to do my job. I saw them getting in everyone's business all over the place. And behind the scenes, people were complaining to me, and the CEO acknowledged to me, yeah, I'm kind of micromanaging it. I've got to make sure this thing goes right.
01:34Bill Gallagher: They acknowledged to me that they were doing it. They didn't really acknowledge the cost. I think they were clueless about the cost. But they said, I'm doing this because—and then they had a reason, right? Because it's got to go right, because I have to make sure, because my butt's on the line, because it's got to go, because it matters, right? There's a lot of money. There's my career, everything else. And then they went ahead and did it anyway, knowing that it wasn't the best idea, but being willing to trade off that whole thing. Well, look what happened is that the whole transition took a lot longer. There was a significant impact on the churn of the leadership and people in the team. New people that should have worked out didn't work out. Old people couldn't wait to get out the door. There was a whole lot of issues with that. Now the transition eventually went, but there was a real impact to the business, the business performance, the financial results, and the cohesion of the team, time lost, money lost because of that CEO's micromanaging.
02:39Bill Gallagher: They just couldn't let go, and they were unwilling to look at the cost of what they were doing. Now we had a lot of people in this business, and there was a lot of money tied up. This is a major company that had grown from a handful of people once upon a time to a big company. Now there's a big exit and a lot of money riding on a successful transition, except we've got a leader who's doing it the way they're doing it because they're terrified that the people aren't going to get it right and something's going to go wrong. They ultimately don't trust the other people involved, including me, the coach, right, telling me how to do an opening exercise or how to run a timer, any number of things that I have done for many, many years, like basic level kinds of things, right? So a fundamental root core thing. And it probably wasn't the first time this person had done things. I think in any time of pressure over their life, and in fact I learned as I peeled back in conversation, they had done this since a very early age when they got on a project with fellow students at a young age in class and the others weren't picking up the thing. They just did everybody's job for everyone else. And they did very well in school and in their career with that, except there's a cost, right? We'll get to that as well in a future episode, but let's talk about the reasons first.
Five reasons leaders work too hard
04:02Bill Gallagher: It could be that you do that for that reason. That's probably the biggest reason. But trust and perfectionism, this thought that only I can do it, only I can do this, can get this right. And you might have a combination of these things. The second one that we hear a lot of is fear of failure, right? I'm not sure how this is going to go. I can't afford for this to fail. I've got to work really, really hard, and I'm just afraid something's going wrong. And it could be there are real consequences. Like, there's a lot of money on the line. There's your career. It could be, depending on how it is, your house, your family, your relationship. Like, there's things hanging on your success or so you think in the business, and you're just not at all confident of the whole thing.
Ego and the hero syndrome
04:47Bill Gallagher: Another one could be your ego. So this is the hero syndrome, right? So the third big reason is you just are a big old ego that's unchecked and lacking a lot of self-awareness, and you're going to save the day. And look, it's intoxicating to be the hero. And there are many times when those of us who started companies loved it. I love to be the hero. I love to do. But a hero requires a victim. A hero requires a crisis, right? For a hero to thrive and to show up and to be a hero, they need problems to go deal with. Our ego is deeply invested in that, and so that could be at play.
05:23Bill Gallagher: Another one is kind of habit. Like, it's a founder syndrome. And it wasn't the case of the CEO that I was talking about in the story, but it could be that you started the company this way. I have another company that I'm coaching actually right now. Founders started working in a particular way. Now the company's growing and going through rounds of funding, and it's time to change their leadership and approach. It's time for them to bring more direction and mentorship and coaching to the team and less doing and less involvement in every little thing. But they have a habit. This is the founder syndrome, right? A lot of past-based behaviors that they haven't snapped out of yet. Maybe they've never done it. Maybe they've never had to work a large distributed team where they didn't have direct control in things. And that's all they know to do. They haven't developed that muscle yet.
06:18Bill Gallagher: And then the last one, at least our top five, is they're just too busy to delegate, right? So I'm really busy right now. I'll work on delegating later after this crisis, after this project, after the thing. And pretty much, like, after this week things are going to get easier is the kind of thing we tell ourselves from now until we die or retire. So, like, after this week things will settle down, right? That's like a thing that you find yourself saying. And at some point you wake up and, I don't know, maybe in your forties and you're like, oh, I've been saying that for a while, haven't I? Maybe that, like, dealing with one crisis after another, one major project, one crunch, one whatever is kind of just how life is. Like, we're always kind of—you do get a vacation every now and then. Get a breather. You get a good night's sleep every now and then. But a lot of times, a lot of what we got is kind of that, right? So let's think about the reasons that you and I do it. I can say that at one point or another I've done all five of these. So I don't think that, like, doing them—now you might have one more than another that you will do.
Overworking is a sign you have not built a team
07:32Bill Gallagher: Definitely, the ego hero syndrome is the kind of thing that I've done plenty of times. I've had fear of failure more than once. I've been in a habit, like being a founder, just having my hands all up in the business, and I'm just used to it. And so I just jump in without even thinking. I've been so busy sometimes that I haven't handed off. That one, I do a little bit less. The trust and perfectionism, a little bit less for me. So what is it for you? What do you think it is? I can think of different CEOs that have this plank, and then not just CEOs, but other leaders in the companies, whether they be a small entrepreneurial company or a fairly large mid-stage company. I can see these going on all the time with the different leaders that I've worked with.
08:19Bill Gallagher: Now, here's the deal. Overworking, working too hard, it isn't a badge of honor. It's a sign that you haven't really built and empowered your team. So this is a useful thing to remember here. Your overwork, your micromanaging isn't a badge of honor. It's a sign you haven't built a real team. So think about why you do what you do, and that is maybe the opening to begin to shifting it, to getting out of this mode, to moving beyond to something else. But first, let's look at why you do what you do. And then maybe you could invent a new why. You could make up a why that empowers you in some way to shift your behavior.
Inventing a new why to change your behavior
09:03Bill Gallagher: Look, I'm not micromanaging. I'm not overworking today. I'm going home early. I'm working on my tennis game. I'm going sailing. I'm going surfing. I'm going to take a run. I'm going to play with my kids because I'm building a great team, because I'm building a company that lasts, right? So what is the why that you would have that would shift it? Your work, your product, your service, your marketplace, the problem you solve in the world is so important that you've got to retrain yourself from this habitual way of dealing with crises and problems and challenges. You've got to retrain yourself because your new why is so important. The mission, the purpose, the team, the legacy of the business is that much more important.
09:46Bill Gallagher: In my coaching all the time, this is a key thing that we focus on aside from the basics of Scaling Up, right? Developing a great strategy and dialing in the execution, getting the team right, and optimizing the cash and all that stuff, the strategy and the planning work that we do. Through all that is you as the leader and your behaviors. How do we shift your mindset so that if you've got one of these whys for working too hard, for micromanaging, let's have you create and invent a new why that has new behaviors naturally show up. So what is a why that makes shifting your behavior so important? The mission, the purpose, the company, the reason for the company's being, that's the kind of thing. So we want to help you build a stronger team so that you scale with ease, so you can grow your business without sacrificing your life. That's the kind of thing we really care about here. I hope this has been helpful. I hope it gives you something to think about. I'll be back. I'll talk to you more about some of the ways that we do it, how we shift this more. Let's start with the why, and let's come up with a new why to create a new set of behaviors. We'll talk to you again soon. Keep scaling.
10:57Bill Gallagher: Thanks for listening today. One last thing. If anything in this episode hit home, my book digs into it further. Busy Is Broken: Do Less. Scale More. It's all about how to stop drowning in work and build a business and a team that scales without you. Available right now with content samples at busyisbroken.com. Go grab it. Be less busy.
Bill Gallagher coaches CEOs and leadership teams on the Scaling Up framework. If something in this episode landed close to home, the free 20-question diagnostic is a good place to start.
