In this excerpt from the Scaling Up Business Podcast, veteran business coach Bill Gallagher introduces the "four sins" that repeatedly block CEOs and leaders from successfully scaling their companies, despite having solid strategy, execution frameworks, and metrics in place. Drawing on two decades of coaching experience and case studies from his book Busy Is Broken, Gallagher defines each sin, illustrates it with anonymized stories, and explains the tangible consequences: 1. Failure to Delegate – CEOs retain decision‑making and execution, preventing ownership transfer and delaying exits (e.g., "Thomas" who took seven years to sell his company). 2. Micromanagement – Even after delegating, leaders stay overly involved in day‑to‑day tasks, stifling team autonomy and causing turnover (e.g., "Lee" at a national healthcare firm). 3. Perfectionism – Leaders chase endless improvement, constantly adding frameworks (OKRs, Radical Candor, etc.) and never shipping, leading to overwhelm, staff churn, and even personal fallout (e.g., "Eddie" whose company and marriage collapsed). 4. Strategic Myopia – Leaders focus inward, neglecting external market realities and over‑expanding strategic focus, which can erode value dramatically (e.g., "Rocky" whose $2 billion company fell to $200 million). Gallagher challenges listeners to identify which sin they most embody, seek feedback from peers or coaches, and commit to change over the next two weeks. He also teases the next episode featuring Michelle Crepolani and promotes his book and website for deeper diagnostics.
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After nearly 2 decades of coaching in one form or another, 13 years of coaching full-time, touching, working with thousands of leaders around the world, in depth with hundreds of leaders, I noticed 4 behaviors that really get in the way of scaling. We do all the work in scaling. We get the strategy right. We build up the teams. We lay in great execution frameworks and structures. We set priorities and we make plans and we have dashboards and metrics and we do all these kinds of things, have great meeting rhythms, and we optimize the cash practices and the business model for the business. And then somehow we still have issues. And I think the thing that we miss out a lot that isn't there so much that I love to talking about are these 4 behaviors that I think get in the way. I want to talk to you about these. I call them sins, the 4 sins. So hey, before we get into all that, my name is Bill Gallagher. This is the Scaling Up Business Podcast. The show comes to you every week. This series of conversations is drawn from my book, Busy Is Broken. You can get Busy Is Broken wherever you buy your books, Amazon, etc. So go order a copy right now and read the whole thing for yourself, all the stories, all the diagnostics, that kind of thing. This is a little snippet from it about the 4 sins. And I'll give you some of the examples and stuff from the book to get you started with it, give you something to think about right now. So all that and more. And like, subscribe this so you get it next week and so on the next one. But what are the 4 sins? So the 4 sins are pretty simple. I'm going to give you some examples of each of them. But first sin is failure to delegate. Delegation is the first sin. You don't actually delegate. The second sin Micromanagement. Micromanagement is I have people I've delegated, but I'm still up in your business. The third sin is perfectionism. Perfectionism is I just keep— maybe you're off working on it, but every time it comes back, I noodle on it. I add a little another thing. I never let anything ship, either my work or your work, And that gets in the way. The last sin is strategic myopia. Like, I'm too inwardly focused on the business. I'm not looking out in the world. So that's the 4th of the 4 sins. And, you know, there's other things we do, but these are the 4 biggest things that I see again and again. So what do I mean by each of these? Let me paint a picture of each of them. The first one, and these stories are actually all in the book throughout. There's a chapter in particular In particular on the 4 sins and then some deeper case studies on each of these things. But first one up is a guy, I'll call him Thomas, the sort of more cautionary tales. I use anonymous names for them, fictionalized names for people, and I distort the facts a little bit so that we don't embarrass or make people uncomfortable talking about their sins. So Thomas sets up this great company. It's a beautiful company, great in the world, lots of potential value. But Thomas's failure to delegate spanned decades and it kept him from selling the company when he wanted to retire. So when Thomas wanted to tighten up things and then go to sell the company, instead of taking a year or two, it took more than 7 years. And this at an age where, you know, it would have been really great. Thomas was now much older, approaching 70 years old when I first met him, and wasn't able to exit that company for some time because he had failed to delegate. He had lots of people. So, you know, we can have lots of whos around our business and not have given things away to them. We have helpers. We're surrounded by helpers who work on things, but they are not owners of things. So failure to delegate. And it doesn't matter how many people you have. It's the way that you handle the tasks, functions, processes of the business. And another business very much like this that I worked with in Northern California, Yeah. I've seen a lot of companies where the founder delegated to one person and he brought in the replacement person for him, but he set them up much like he had and put them in a structure like he had. And until they made a change, they had the same problem that he had. So he brought in a replacement for himself, and then that person struggled because they were surrounded by people. I'm not talking about a small— I mean, it's a small business, I suppose, in the grand scheme of things, but 75 people. Thomas also had a fair number of people between the office, the warehouse, the manufacturing. There's a lot of people in that business. This other business I'm talking about in Northern California is 75 people. The founder replaced himself with someone and they're surrounded by lots of helpers. But the replacement, the COO who comes in behind the founder is also deluged, overwhelmed, like can't deal with anything, can't think, is stressed out, is exhausted because people just keep bringing them things because they haven't delegated the decision, the execution of things, they're still involved. They have people doing things, but all of the thinking and ownership of things comes back to them. So that's delegation. Micromanagement is more like Lee in the book. So I come in, Lee's actually a successor also to a founder. Founder didn't like to meddle in things. Founder was also a bit of a micromanager and then hired a micromanager like them. So Lee comes in to take over from the founder And this nationwide healthcare company, and it's already a pretty big company. They come in to have me help them get better at hiring people because they need to hire, they say, 400 people a month. But 400 people a month would be a staggering amount of turnover in a bit like a 4,000-person business. And they had just taken for granted that's the way things were in their industry. But as I started to work at just the first level of who owns what, I realized that yes, there was delegation. There were people, but there was enough cross-ownership, and the founder and now the replacement CEO had their hands in everything. I mean, to the point we even like I'm running an offsite, and Lee's telling me how to do the warm-up exercise and changing it on the fly because Lee can't let anything go. Lee's involved in everything. That habit had probably started in middle school. I think. From what I gleaned from it, about 8th grade. And Lee probably was the one who could get the project done. So didn't work well with the other teammates, letting them do things on a school project. Had to be the one who filled in and did all the parts for everyone. And probably it was nice for a student to do that, but it didn't set up well for running a national company, right? So perfectionism gets in the way. Now, In the case of Lee, people were stifled, suppressed, especially the new executives who came in from other professional backgrounds. They were like frustrated and thwarted and suppressed and upset about the situation. So old and new both started to churn out. The turnover was very difficult and became a real issue in the company. So The company didn't go out of business. The company existed, but the amount of money wasted and the turnover in staff was enormous until Lee settled down and stopped micromanaging quite as much. So micromanagement is you've delegated and you haven't given things away. Perfectionism is the case of Eddie. So Eddie, another West Coast company, a tech business. We coached also enough people that there was plenty of people to give things away to. We did delegate and Eddie wasn't in. Eddie's form of, I suppose it's extended micromanagement, was perfectionism. Eddie would read a new book, a new story, a new framework, and he'd be like, okay, now we're doing OKRs. Okay, now we're doing Radical Candor. Okay, I changed up all these. We want to go a little further than we did with the one-page, with the job scorecard. Turned the job scorecard into an 8-page job scorecard, not a 1-page job scorecard. People were like, what do I even do? How many KPIs can I possibly have? Like all these things, all these lists, all these skills and qualities, like it's beyond. It was so overwhelming to them. The same thing true around OKRs versus priorities versus rocks versus we're going to use this software platform, that software platform, and like on and on and on. We're going to do radical candor. Which is just an excuse for talking too long in their case or dumping on people. It just went on and on. So, the overwhelm of perfectionism got in the way. So, it wasn't just like, let's do OKRs and run with that, or let's do rocks and run, or let's do priorities, or let's have the job scorecard or the whatever. It was always, always, always, always changing. Right. I have more than a couple CEOs like Eddie. In Eddie's case, both his marriage failed and the company failed. The company went out of business, was sold off for parts. Eddie's marriage failed, became a weekend dad. I don't wish that for anybody. That is an example of perfectionism, right? Not shipping things. I see this again and again in quite a few companies. The CEO, the restless CEO who keeps reading another book and bringing in another and another and another and another. Settle down. All of our books and things like that, they say a lot of the same things. You need just a couple of them, right? Not a jillion of them, right? Find the one or two and master that. Stick with that. The last one is strategic myopia. So this is one of the more painful ones. I open with the story of Rocky fairly early in the book. Rocky came in as the replacement from the founders in a tech company. that went to over $2 billion. But Rocky decided they were going to be in all kinds of things everywhere, and he outsourced their strategy to a big-name firm, spent a lot of money to develop a 100-page strategic plan that opened too many fronts. In this case, in their case, it was 4 instead of just 1 where they had risen to $2 billion value. Now they're going to be in 4 things because, oh, they've got 1,000 people now and a $2 billion valuation. But they're talking about competing with many billion-dollar companies now, global behemoths, and they started to stumble. And then Rocky got so involved in all kinds of things, customer issues and things like that, but essentially internal, he forgets what they're doing. He loses the plot on the strategy. It's too divided. He's too divided. He tries to be Superman, and the company goes from a $2 billion value to selling off in parts for less than $200 million. Definitely the most painful of those stories. So failure to delegate, delegate but then micromanage, perfectionism, not letting anything get out the door without endless changes and mired in forever, like perfectionism, failing to ship things, and then becoming too involved in the operation of the business, you're not looking at the big picture. That really is the 4 sins. My challenge for you over the next couple of weeks is, which of the sins are you doing? And very often we do more than one of them, but which one do you do the most? What do you lead with? What gets you in trouble first? And then how do you compound it? I'd just like you to notice it for the next little bit. We've talked in the past about the 5 engines, why we do what we do. Spend this next 2 weeks thinking about what you do. In addition to looking in the mirror and your personal reflection, Ask your 4 mates for clues or a buddy if you have like an accountability buddy. Ask your coach if you work with a coach. Talk to some of the people on your team. Give them permission to be honest with you. Ask them, which of these sins am I guilty of? Where do I need to like level up? So that's my challenge for you for the next little bit. In the next episode of this series in a couple weeks out, I'll talk to you and tell you the story about Michelle Crepolani. Michelle Crepolani is somebody that some of you probably know from EO down in San Diego area and has a really heartwarming, heartbreaking story about leading a business one way and then having a transformation in a different stage of life. So that's all coming up next week. In the meantime, go find the book Busiest Broken wherever you buy your business books. Amazon or wherever, and go to busyisbroken.com. Claim your reward for being part of the preorder crew. And until then, keep scaling. Busy Is Broken, busyisbroken.com. Go look for that. We'll talk to you next time. Keep scaling. Have a great couple of weeks.
