Episode 643
Most leaders struggle to delegate not because they lack capable people, but because unexamined fears from childhood still govern how they operate. Bill argues that recurring behaviors rooted in early experiences create a ceiling on what you and your team can achieve. He shares how nearly losing his business and home in 2001 paralyzed him until he voiced his deepest fear to his wife, which freed him to involve his team in solving the crisis together.
The pattern often begins between ages seven and thirteen. A student who learned they couldn't count on group project partners becomes a CEO who micromanages everything. Bill walks through how to identify these formative moments of anxiety or near failure, recognize the compensating behaviors you built around them, and understand that those same behaviors now limit your leadership. Once you see the pattern, you gain the freedom to try new ways of operating.
The belief that your team isn't good enough is usually a projection of your own fear of not being enough. Bill insists that most leaders are surrounded by capable people they don't yet appreciate because their lens is distorted by old fears. Personal growth must come before team growth. The invitation is to look in the mirror, confront what actually scares you, and evolve beyond the coping strategies that got you here but won't take you further.
Key takeaways
- Identify the formative experiences between ages seven and thirteen that created recurring fears and behaviors still shaping how you lead today.
- Voice your deepest fear out loud to someone you trust, because naming it strips away its power to govern your decisions in the background.
- Recognize that your inability to delegate often reflects your own fear of not being enough, projected onto your team as a belief that they aren't capable.
- Involve your team in solving real problems instead of protecting them from challenges, because people rise to meaningful work when given the chance.
- Level up yourself before trying to level up your team, because old coping patterns that helped you survive early on now create a ceiling on what's possible.
In this episode
- 00:00What's really keeping you from delegating
- 02:00When the bank came for my house
- 04:33Voicing the fear changed everything
- 06:39The CEO who couldn't count on anyone
- 08:54You're projecting your fear onto your team
Read the full transcript
What's really keeping you from delegating
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.
00:52Bill Gallagher: What's the real reason you can't let go? What do you suppose is the real reason that you struggle to let go, to let people do their job, to take a lighter hand on things? I bet you don't really know. I don't think most of us know. 50 Cent talks about it in his book and in his conversations about fear running the show. There's a kind of fear that each of us has. There are recurring fears and recurring behaviors, and the fear that's running the show probably started at a very young age. There's also extended versions of fears that we carry out into later parts of life. I think that a lot of these things start early. We have a fear. That fear is recurring for us. We develop behaviors in response to that fear's patterns, and we use those things to great result. Like, you got to a particular place. You achieved something in life. Here you are. You've accomplished something, and the fear is still underlying things, and that represents a lid. That keeps a lid on the way that you operate, the way your team operates, and the results that you get in your business.
When the bank came for my house
02:03Bill Gallagher: How do we figure it out? Well, I think when you figure it out, there's an opportunity to unleash something. I can tell you a personal story. I can tell you a client story. I got a couple examples of this. First of all, personally for me, I was running a business some years ago. And in the aftermath of the 2001 downturn, we found ourselves in a bit of a bind. I've talked about this many times. And my bank came to us and was going to shut us down. And they wanted me to close out our debt, our loans with the bank, and to take our banking business elsewhere because we no longer fit their profile. We were a little bit off on things. We hadn't missed payments, but we were in violation of the covenants. And anyway, so they wanted to shut us down. And there wasn't really a good opportunity at that time with the business results I had in that environment for me to refinance that debt. So it was going to mean the close of the business. And because I was personally guaranteed, it was going to mean they would take my house. And they were very clear about it with me. They said, listen, you have a lot of equity in your house. Just give us your house. Everything will be fine. You can go on with your life. And for them, losing the business, losing the house was pretty straightforward kind of a thing. It was just business to them. They knew that it was triggering for me, so they threw it out there hoping that I'd find a way either to give them the house or to settle the whole thing.
03:32Bill Gallagher: Well, I wasn't really clear about what my fear was. I was deathly afraid of the business failing, of losing the house. But mostly, more than any of that, I was afraid that that kind of an event would tear my marriage and my family apart, and I would become a weekend dad. Becoming a weekend dad, not having a whole family, keeping my family together, having my whole life come apart, that was deeply upsetting. Right now, I didn't think about that that much until I started talking about the fear. So for a long time, I tried to figure it out on my own. I was thinking, strategizing, imagining. I'm an ideas guy, so I'm looking for the way out. I'm trying to figure it out, and I feel like it's not so nice to say, but I feel like, oh, I'm smarter than anybody else on my team. And certainly around ideation and strategy, I should be better than all of them. Except I wasn't, and I didn't have a plan.
Voicing the fear changed everything
04:35Bill Gallagher: So in talking it out and sharing with my wife about the challenge and my fears about it, I finally said, I'm just afraid that if I screw this up, if this fails, you're going to leave me, and then I'll be a weekend dad. Right? And that, like, even surviving a divorce wasn't the worst thing. It was the idea of splitting my family apart. Right? That was the most terrifying thing. Well, having said that, she was able to say, I'm not going to leave you over that. We could have that happen. That's a very real possibility. And if that happens, we'll find a way to start over. Here's a variety of things we could do. Right? Whatever. So now my greatest fear is out there, and my ways of operating are now freed up. So instead of just having to be a particular way because I'm afraid of this happening and working so hard on it, I'm now kind of freed up. I have room to experiment with something that was going to cause the thing I worried about the most.
05:35Bill Gallagher: So what did I do? I decided I wanted to be the kind of leader. I wanted to teach the kids a lesson. So I went to my team, and I said, listen, here's the situation. The bank wants to shut us down, blah blah blah blah blah, on and on. And this is a pretty serious matter, and I understand if you need to go now, but I could use your help. And if you'd be willing and able to stick around, could we work on this together? And I made them a promise. I made them a promise that I wouldn't quit, that I would be honest and open with them. And that turned out to be pretty magical because people love a good challenge. Human beings love to take on something really significant. So they joined me in the fight, and together we actually found a way through. We navigated it. We worked it out. We doubled the profit, cash. We settled the debt. Like, it was amazing. It wasn't something that I figured out or they or any one of them. It was together we figured the whole thing out, and it didn't start until I confronted my fundamental fear and changed my behavior.
06:36Bill Gallagher: I had another client very recently, new CEO taking over a company, and taking the company through, like, post-acquisition transition of the founders out of the company and change. This person had developed fear and patterns that they couldn't count on anyone else. Right? And that started actually at a very early age, had always been the sort of kid or student that in the group project would fill in for everyone else because couldn't count on and couldn't work with other people. So they just learned to do the extra effort to go 10 times more than almost every other kid, and they carried that through in life. Now, as an adult, as a new CEO of a significant company after, and taking over from a successful founder, they were still trying to do that. Not counting on anyone else, micromanaging their way through everything, unable to let go. Well, it wasn't so good. It took a long time for this person, and it wasn't a profound shift. But as they started to see that this was a lifelong behavior, there was a little bit of opening.
The CEO who couldn't count on anyone
07:39Bill Gallagher: They finally started to shift when you start to notice the patterns and the earliest things. So think about what were the transformative experiences? What kind of student? What kind of kid were you? What order were you in the family? Where did you sit in class? Think about these early grade school experiences from, say, I don't know, maybe seven years old—you might even remember some earlier ones—through maybe 13. There's a lot of formative things and a lot of originating patterns. Think about moments of anxiety, of near failure, of overcoming adversity. Think about those things. What were those key lessons that were painful, difficult, embarrassing, shameful? What did you have there? And then what did you do to compensate from that? Those recurring versions of those fears and those behaviours are probably running around now. So that's, I think, the thing to think about, is look back to your life and start to notice the pattern. Once you notice the pattern, you actually have some freedom to begin to shift it up, to try some new ways of being. You're not limited by the pattern. You can say, oh, I did that pattern starting at a very early age, and now I have a chance to try some other patterns.
You're projecting your fear onto your team
08:54Bill Gallagher: The truth is you have lots of amazing people that work with you. You have great people on your team, probably in ways that you don't yet appreciate. You have great people who'd love to work for you. You have great vendors. You have great customers. We're surrounded by great, amazing people, and most of the time we're thinking about how they don't measure up, how they're not good enough, how we wish they'd take more initiative or be more like an owner mindset or any number of other things. We wish for all these things instead of appreciating what we do have. Instead of empowering them, we're running ourselves on fear—fear of screwing things up, of not being good enough ourselves—and then that gets transposed onto everybody else. And all we can see is how everybody else isn't good enough, because we, for ourselves, are that we aren't good enough, we have to work that much harder to be better and to somehow overcome something.
09:48Bill Gallagher: The truth is we're already pretty awesome. Like, you and I have amazing strengths. We have real weaknesses and shortcomings too. We have bad patterns, but a lot of the bad patterns that we have come out of these fears that start at a very early age, and we see ripples or versions of these throughout our whole life. And then we play them in ways that helped us to survive to get this way, but then end up limiting us in some ways that aren't actually so good. So it's really useful, right? If you want to level up your team, you want to start with the person in the mirror. Start leveling up you, the way that you operate. Be unburdened by that. Let's learn from what we did as a seven to 13-year-old and then evolve from that, not be limited to just playing out versions of that for the rest of our life, right, the latest version of that. So level up yourself. Figure out what you're afraid of and what your current behaviours are so that you can then move beyond them. Have some new kinds of challenges, some new successes and failures, develop some new fears maybe even. But don't be limited by those old ones, and don't be having them running in the background. Hope that's been helpful. We'll talk to you again next time. In the meantime, keep scaling.
11:03Bill 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.
