Episode 657
When a capable leader suddenly loses confidence and decides to quit, the problem often isn't incompetence. It's that they've gone private about a failure and let it define them. Bill Gallagher shares the story of Alex, a CEO who went from confident and engaged to stuck and ready to walk away after losing a major deal. The breakdown didn't start with the loss itself but with keeping it secret and letting shame replace honest communication.
Bill walked Alex through three questions that reversed the spiral in minutes. First, take stock of what's actually hard and broken, then notice what's still easy and working. Second, identify what's missing, especially in yourself. Third, ask what's now possible in the face of all of it, not by faking positivity but by restoring what's absent. For Alex, honesty and commitment were missing. When he told his team he felt stuck and needed help but wasn't quitting, everything shifted. Within four weeks the company was back on track.
Bill has used this same framework in his own leadership crises. When things broke down in a company he led in the early 2000s, he admitted to his team that he had no plan but would fight to the end. The honesty and commitment rallied them, and they produced a breakthrough over the next year. The way out of being stuck isn't powering through or pretending. It's getting present to the facts, naming what's missing, and declaring what's possible from that ground.
Key takeaways
- When you feel stuck or like a failure, the first step is to take full stock of what's hard and broken, then deliberately notice what's still easy and working.
- Look at what's missing in yourself, not just in circumstances, and focus on qualities like honesty, collaboration, or commitment that you've withdrawn.
- Ask what's now possible in the face of everything good and bad, not by faking positivity but by restoring what's absent, often starting with honest communication.
- Admitting to your team that you're stuck and need help, while reaffirming your commitment, can rally support and open new possibilities faster than pretending everything is fine.
In this episode
- 00:00When a confident CEO suddenly wants to quit
- 03:45The deal that went bad and the silence that followed
- 05:32Take stock of what's hard and what's working
- 07:38Identify what's missing in yourself
- 08:53Discover what's possible without faking it
- 10:38Honesty and commitment turned the team around
Read the full transcript
When a confident CEO suddenly wants to quit
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.
00:29Bill Gallagher: When everything breaks down all at once, or when you get stuck, I've got three questions that'll get you unstuck, that'll get you back, that'll help you start to set things right again. So maybe everything's broken down at once, maybe a little bit's broken down. I'm going to help you with that in what has worked for me and the people that I've coached over the years. Three simple questions that'll help you start to get back on a path of workability and power and all of that.
00:56Bill Gallagher: Hey, everybody. My name is Bill Gallagher. I'm the Scaling Coach and host of the Scaling Up Business Podcast. Our show comes to you every week, and we share some ideas, some tips, some stories. We bring guests, that kind of thing, to help you grow your business and do it without suffering, without sacrificing the things that really matter to you. So you'll find all our shows and more wherever you're getting this right now. Like, subscribe, turn on your notifications, or go to scalingcoach.com. At scalingcoach.com is our website, and it's where you can sign up for our workshops and find out about coaching, things like that. So this here, wherever you go. Alright.
01:39Bill Gallagher: So I guess I could start off. I'll tell you about a client that I coached years ago. He's a representative of many. I'll call him Alex just to keep him anonymous in this case. But Alex, in one bad week, went from confident and in action to completely stuck and pretending. So I'd been coaching Alex for a while. He was the new CEO of a company, and I'd been brought in by the board to work with him, and he was great. He took it on and embraced the coaching fully. And we had great sessions. And then one week, everything went off. And when I met with Alex the next time, he just seemed off, and he was kind of going through the motions. And I said, hey, what's going on with you? This is not the normal Alex. And he stopped, he's like, yeah. He's like, I don't know. I think that maybe I'm the wrong person for this job, for this company, for this role, and I think I need to move on.
02:45Bill Gallagher: And I was like, wow. That is really different than the person I've been talking to for a few months. And he's like, yeah. I just—it finally came to me. I'm the wrong person. And I'm like, wow. This is, for me, it felt really new. For him, it was like, finally came to me. It's been cooking there. Right? I'm like, okay. Pause. I got it. Maybe you are. Maybe it's time to move on. But let's dig into this a little bit. Let's look at it. So what happened? And it took him a minute because he's just, like, full of how I'm going to go, how I'm going to end this thing, how I'm going to exit this company. He's way down that road. And he hadn't really noticed when and where it changed, but it changed because a couple weeks earlier, everything was fine when I talked to him. He was, like, in action and had ideas and plans and passion. And now I'm talking to a guy who's, like, stuck, broken, and feeling like a failure, and he's ready to move on.
The deal that went bad and the silence that followed
03:47Bill Gallagher: So Alex paused. He's like, okay. Well, I guess it kind of started shifting for me when I was doing this thing. So he went to pitch a big account. He really needed this thing. He'd been counting on it. He'd been working on this big account, this big deal. Right? He wasn't the primary salesperson, but he certainly worked on key things as the CEO for the company. This is a big deal, and it went badly. And, at least for the moment, he lost that opportunity. And then he didn't tell anyone. He got private about it. He kept it to himself. He felt like a failure. He didn't know what was off. And his whole demeanor, his outlook started to shift from that moment. He didn't see that until I asked, till he started thinking about it. So he started to take stock of the situation. He started to think about that, and then he started to shift down and get totally off.
04:44Bill Gallagher: So I said, wow, look at all that. And so he started to notice that he had shifted there and that things were off. Now that started to give him some presence, some peace, some ability to look at things more. And in a matter of, I don't know, a few minutes, it wasn't that long of a conversation. He started to take stock of all the things that were good and all the things that were bad and started to think about what's missing in the company and in himself right now. And then we started to look at, so what was possible in the face of everything that's good and bad? And that's when Alex saw a whole thing for himself. So let me hold the resolution for a second, and let's pull out what happened there.
05:31Bill Gallagher: So the first thing is to fully take stock of the situation. So we know we begin with the hard and broken things. Right? So what's hard, what's broken, what's not working? So all the bad stuff. Bad stuff. Hard, broken, not easy, like that. Missing, failed, et cetera. Take stock of that stuff. Okay. Good. Now what's easy and working? I'd love to start there, but you might not be able to. Wherever you start, like, if you start with the bad stuff because you're stuck, that's fine. Now, let's go over to and take a little effort to notice what's actually easy and working. You will notice some things. Right? You will notice a variety of things that if you take a minute, even if you're feeling pretty dark, depressed, sad, stuck, frustrated, however you're feeling, you'll start to notice some things that are easy, that are working. It's not completely hopeless. Right?
Take stock of what's hard and what's working
06:32Bill Gallagher: You can also go personally and not just the business problem, that realm, but you can also just look at the environment around you. Like, when the world seems crazy, sometimes it helps me to notice the sun, the trees, the wind, things like that. Right? So let's take stock of and expand a little bit what's easy and working. Now that we have the good and the bad, that's the first thing, the circumstances, the particulars. Now let's look at what's missing. So what was missing for Alex in that time? Right? What's missing for you? Would be, like, confidence, positivity, honesty. What was missing for him right now? So we start to think about what's missing there and things like that, like positivity, a plan, good expectations, openness, creativity, collaboration, honesty. We got a list of things that are missing right now.
Identify what's missing in yourself
07:38Bill Gallagher: That's the second thing. What's missing right from this picture? And that's like a deficit. It's very related to the hard or broken. And the most useful thing to think about what's missing is to take a look in the mirror. There'll be circumstances that are missing. Right? But as much as you can, look at what's missing with you, with the one in the mirror. Right? So Alex did the same, and he saw those kinds of things. Right now, what is possible in the face of everything that's good or bad? Not, like, let's power over things and pretend something and do a power pose and psych ourself up and, like, be positive when we're not positive. Look. If you're sad, if you're a little hopeless, if you're a little depressed—
08:23Bill Gallagher: Fine. Be that way for now. So that's not possible. It's not possible to pretend or fake something. You might—some people would talk about that. I don't think that's very helpful, and it takes a lot more effort. I'm talking about what's possible in the face of everything good and bad that's there right now that you hadn't considered. And we do that by looking at the things that are missing.
Discover what's possible without faking it
08:53Bill Gallagher: When you look at what's missing there, like Alex looked at honesty, creativity, those are missing. And even having failed at something and being sad about it and feeling like a failure, he could be honest. Right? Who could he be honest with? Well, he could be honest with himself. He could be honest with his spouse. He could be honest with his team. And that would be interesting. That would be liberating. He could say to his team, I screwed up something. I've been really depressed. I've been moping around and keeping it private, and I feel like I'm not being very creative or collaborative.
09:38Bill Gallagher: So honesty is like one of the first things. It's often a useful missing thing when we want to get unstuck, when we've got to restart. But honesty is often a quick thing to look for that's missing that is possible. So he just was honest about how he's feeling in the failure. He didn't necessarily have to be honest about, oh, I'm thinking about quitting or whatever. It was sufficient to tell the team, I've been feeling really depressed and like a failure. That's plenty sufficient to open up something. It's plenty sufficient to say, I notice I'm not very collaborative. I notice I'm not very creative. Right? And I'm feeling stuck. Like, that alone made all kinds of things. That was possible for Alex, being honest in the face of it.
10:27Bill Gallagher: Now, it was also possible for him to allow creativity, for him to allow collaboration. So honesty and collaboration were possible. And another thing was also possible that Alex saw—you might see something too—and that was committing to something. So his commitment was missing. Right? He was holding back his commitment, thinking about quitting. And so he could actually say, I'm feeling bad. I feel like a failure. I'm not being very collaborative or creative right now, but I want you to know that I'm not going to quit, that I'm here, and I need your help.
Honesty and commitment turned the team around
11:11Bill Gallagher: Right? So I did that once when things were really, really bleak in a past company I led, and admitted to people I was stuck and I didn't have a plan. But I left them with my stand, my commitment, my honesty, and it turned out to be one of the most powerful, brilliant, passionate moments. The team rallied. We produced an extraordinary breakthrough over the next twelve months. Well, the same thing happened for Alex. He went to his team. He told them, Listen, something went bad. I'm stuck. I've been keeping it private. I'm going to be honest with you, and I don't really have a good idea, and I'm not being very collaborative right now. But I'm coming to you now because I'm not quitting. You can count on me to find a way through this. I need your help. Right? Powerful.
11:55Bill Gallagher: Things shifted very rapidly. Within the next four weeks, things were back on track. I can't remember if they got that deal back or it was just something else, but it all turned around within four weeks. It's been some years since the Alex story, but it really stands out for me in memory, as did my own. Like, the thing that I did with the company where I came and I confessed—that was in the mid, early 2000s—and we totally turned around. And now it took a few more months to turn it around, but we had a big crisis. And I left people with my honesty, my communication, my collaboration, my stand, my commitment to fight to the bitter end. People loved that. They came on board.
12:39Bill Gallagher: So when you get stuck, when everything breaks down, the way out is three questions. So the first is to kind of take in what's easy and working, what's hard and broken, the what's so. Take in the facts. Right? Then look at what's missing, and now consider what's possible. Not faking it or powering through it, but what's possible from the missing, from the things that are missing that would actually light you up, that would start to open up something for you. I hope that formula works for you. It worked for Alex. It worked for me. It worked for many, many people I've coached over the years. If you're feeling stuck, when things break down, these are the three questions that will help you start to get back on a powerful stance, turning things around, and making a real difference.
13:21Bill Gallagher: I'm Bill Gallagher, Scaling Coach, and I hope it's helpful for you. If you want more of that kind of thing, go to scalingcoach.com, find out about our coaching, our workshops, things like that. But otherwise, like, subscribe, share this with somebody else that you think it'll help. And until next time, keep scaling.
13:45Bill 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.
