Episode 641
Bill argues that most leaders can't step away from their businesses not because they lack systems, but because they haven't changed how they lead. He shares how he prepared to take a month-long family trip to Italy by systematically training his team to solve problems without him. The key wasn't just dashboards and meetings—it was stopping himself from being the answer to every question.
Starting nine months before the trip, Bill began asking his team a simple question every time they brought him a problem: what will you do when I'm gone? He forced himself to step back and let them practice making decisions. The result was a team that ran the company beautifully during a critical growth phase while he was completely offline for a month.
Bill challenges listeners to create their own compelling reason to leave—not as an escape, but as a gift to their team. He warns that leaders who love being the hero surround themselves with people who need saving. Building a business that runs without you requires methodical preparation and a willingness to pass the baton instead of throwing it.
Key takeaways
- When your team brings you a problem, ask them what they would do if you weren't there instead of giving them the answer.
- Book a trip or commitment far enough in advance that you have time to train your team, but close enough that it forces you to actually let go.
- If you always need to be the hero, you will always surround yourself with people who need saving.
- Systems like dashboards and meetings are necessary but not sufficient—you also have to change how you operate as a leader.
- Give your team nine to ten months of practice making decisions without you before stepping away for an extended period.
In this episode
- 00:00Can your business survive a month without you
- 02:36Systems alone won't make you nonessential
- 04:29Training the team by asking what they'll do when you're gone
- 06:52Creating a compelling deadline forces real change
- 08:10A month in Italy while the team ran everything
- 09:32Stop being the hero your team has to rely on
Read the full transcript
Can your business survive a month without you
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.
00:28Bill Gallagher: What would happen if you stepped away from the business for a month or more? How about let's build a business that can run without you? Let's turn you into an owner, a founder and an owner, but not the hardest worker in the business. Right?
00:46Bill Gallagher: Some years ago, I hit a point in the business where, and life, where I realized with my wife that we were planning to take summers off or even whole years off, and yet we were now right in the middle of a really significant business crisis. We had decided before we even had kids that between the age of like 10 and 14, kids are really aware of a lot. There's strong impressions made in that time, and they don't yet hate you. Right? They're not in the middle of their teen years where they don't want anything to do with you and your plans or your life or like that. So we said at that point we were gonna take some real time off, and now it was time to do that, except it wasn't convenient. Right? It didn't fit. I wasn't able at that point. I hadn't sold the business. We still had a business. It required me to be there. If I went away for a week, I was on phone calls and reading emails and doing all kinds of things. I couldn't really get away, and yet here it was. So the business is where the business is at, and it's inconvenient that my kids are at that age, and many of us faced with that kind of a situation would simply sacrifice that. We'd say, well, it didn't happen right now. We'll do it later. Except later maybe doesn't ever really come.
02:06Bill Gallagher: So here we are at that thing. We said, okay, great, we're gonna get away, and I need to start preparing for this. So there are things involved in preparing to be nonessential to the business, be able to step away for a month or a summer or a year, that you would do. You would put in a great meeting cadence. You would be operating on annual and quarterly plans. So every person would have some connected set of priorities that tied to the company as a whole. You would put those kinds of things in. Right? You'd have great planning. You'd have consistent meetings where you looked at the plans and worked together well as a team. You'd have dashboards, scorecards, metrics, things like that, a whole set of those simple kinds of things so that the business ran itself without you doing it. But you'd also have to deal with you. I put those things in place back in 2001, roughly. 2002, 2001, I started learning them. I'd actually learned part of them even years before and had some of them in place, but I really had most of that stuff in place by 2002 in the business. So now it's 2009, and we look a year ahead and we're like, it's time to take time away except I can't do it. So how is it that I have all these things in place, and I still can't take time away? How is that? Well, that is that I still am me. I still operate as a leader and hold the team in a particular way.
Systems alone won't make you nonessential
03:31Bill Gallagher: So not only do we wanna put in the structures to the company, the execution structures of planning, regular planning that all ties together, dashboards and scorecards to keep visibility to our progress in the plan but aren't so overwhelming that we can actually use them, and a meeting cadence where we look back on those. Those are the three big things. We wanna hone our process. We wanna have the right people on the team. There's a lot of other things that you would do to be able to create a business you could step away from, but those are the big things. And then there's us. There's me. The way I operated is I solved everybody's problems. I was involved in every big decision, and that kept a lid on the results, the capacity of the business, and suppressed the team. Their fullest power, their creativity, their innovation, their ownership, their self-expression. You want more ownership out of your team? Maybe let go a little bit. Maybe pass the baton. Maybe empower them. So now I have to deal with this because we said we're gonna get away. We said we're gonna go away. So we plan to go away for the summer. I started in the fall of the prior year. I started telling the team, hey, next summer, we're gonna be gone. We're gonna take a family trip. I don't know where yet, but when I'm gone, what are you gonna do? And now as they brought problems to me on the daily, as they brought a new challenge or whatever, I said, hey, I'm gonna be away. How are you gonna handle this when I'm gone? What will you do if I'm not here? How's it gonna go? Each problem they came to me with, I said, wait a minute. Next summer when this happens, what would you do in that situation? And I kept pushing back, and I created reminders for myself to alter the way I acted as a leader, to step back, to pull away from the way I led the company and the team.
Training the team by asking what they'll do when you're gone
05:19Bill Gallagher: So it took a lot of practice. Right? Because I had a whole lifetime, like you do probably, of answering and solving people's problems, telling people what to do, that kind of thing. That's what leaders in companies, founders, entrepreneurs do on the regular. We tell people what to do. We solve problems. We intervene. Right? Except I wanted to go away on my trip and not intervene. Well, as the year approached, I don't know, somewhere around the spring of the next year, we started to create a more clear plan. We were gonna go to Italy. And we didn't have the exact time set up, but when the kids got out of school, we were leaving for Italy. We started to map out our plans. And now it got even more real. I started saying to the team, how will you handle this when I'm in Italy with the family? Right? I didn't wanna be on intervention calls and customer calls and answering email and solving things and running scenarios and budgets. I just wanted to be informed that things were okay and enjoy my time. So I kept that training thing going. Now it's getting more real though. We have an actual date. We're starting to have an itinerary. We have a destination. I'm really going to Italy. Right? For real. And that kind of compelling thing made all the difference in the world. Now here's the thing for you. Where could you go? What could you create that would not only be massively fun and great for you, your life, your family, your relationship, like whatever, but would also actually be a gift to your team, would give your team a chance to level up?
Creating a compelling deadline forces real change
06:52Bill Gallagher: I don't think you should do it tomorrow. You probably wanna put it out. I spent about nine or ten months working on this with my team, leveling up my leadership and helping them to level up in the process so they had the confidence and the permission to apply their natural intelligence. They had the experience to go for it. Right? They already had a lot of those things, but I needed to step back to start to train them up, to give them permission, to empower them, to teach them to trust themselves, to think clearly, and not to screw it up. Right? You don't wanna just throw the baton at someone. You wanna pass the baton. You wanna have some planning coordination.
07:30Bill Gallagher: You want them to be able to take it and run with it. So that's going to take a little bit of work. I think creating something compelling, an exit, is a powerful thing to do. It realigns your life. I have a new one for myself this year. I'm going away to a writing retreat to work on a book I've been thinking about for a long time and working on and ruminating and fomenting and like that. So now I'm going away. I booked it. I've paid for it. I know where I'm going. I know when I'm going. Now I have to start to deal with and put my team and my life organized around that so that I get the maximum benefit from that and the minimal impact.
A month in Italy while the team ran everything
08:10Bill Gallagher: Well, in 2010 with an 11 and a 13 year old, we took off. We went to Italy. We only ended up going for a month. It wasn't like a whole year. It wasn't even a whole summer. It was a month. But a month for a North American CEO, owner, founder is a big deal. Right? It's not like some European or other countries where they're well organized around long trips away. We can barely get away for a week or two in the United States.
08:37Bill Gallagher: So for us, that for me, that was a huge deal. We went away for a whole month. We went sailing. We went driving around. We saw sights. We went to dinner. We saw famous people. We just had an amazing time and a magical time in the kids' lives. 11 and 13. Right? My kids are now grown. I have a grandchild. Like, it's a whole different, that time is gone, but they and I, we all remember that today. So as a family, remember that we have that, and my team leveled up in the process. Right? And that's the key thing. On my trip, I got regular emails, pictures or summaries of the Daily Huddles of the weekly meetings. I got little briefings, and I didn't intervene on it. No customer interventions, no major problems or that kind of thing. Maybe a small question or two, but really everything was taken care of. The team ran beautifully in a time of very significant growth for the company, and it made all the difference in the world.
Stop being the hero your team has to rely on
09:32Bill Gallagher: Again and again, I see this makes a real difference. It'd make a big difference for you to take on something that would begin to shift it. Create a crisis for yourself. Right? The word crisis isn't necessarily a bad thing. Crisis is a turning point. Right? Create a personal made crisis. Right? So you don't have to be the hero all the time. Remember, to be a hero requires that you need someone who needs saving. To be a hero requires a victim. If you love being a hero all the time, you're creating a situation where you are surrounded by a team who always needs saving. You don't want that kind of team. You want a team full of powerful, confident people who operate well together, and that's a shift that's worth talking about. So we'll talk about that again in the next, in one of the next recordings.
10:19Bill Gallagher: But if you'd create some reason to pull back and to start to empower the team to level up, that would make a real difference for you and for your business. I hope that's helpful. I hope you come up with something. I hope you have a great trip wherever you end up going or whatever you end up doing, that it's a fantastic experience and it helps you level up your life. Do it methodically. Don't do it overnight. Do it thoughtfully. Don't screw up your company. Keep scaling. We'll talk to you again next time.
10:48Bill 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.
