Mindset

The Best of Break the Ceiling – Charlie Gilkey

For the next three weeks, I'm going to re-release episodes that are the best cuts from three of my very favorite Break The Ceiling Episodes. This week, I'm revisiting my interview with Charlie Gilkey.

Susan Boles
March 9, 2021
12
 MIN
Podcast
The Best of Break the Ceiling – Charlie Gilkey

I’m working on some really cool updates for my course, Not Rocket Finance – releasing at the end of March! – so I’m going to take a very short break from releasing new episodes to give myself some breathing room to finish those updates.

For the next three weeks, I'm going to re-release episodes that are the best cuts from three of my very favorite Break The Ceiling Episodes.This week, I'm revisiting my interview with Charlie Gilkey.

Charlie helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the book Start Finishing (2019) and The Small Business Lifecycle (2012), and host of the Productive Flourishing podcast.

Charlie and I talk about how to get out of your own way and how to avoid roadblocks that you inevitably run up against.If you liked these cuts and you want to hear more from my conversation with Charlie, you can go listen to the full episode here.

Even though I'm not releasing new episodes for the next few weeks, I am still meeting with smart business owners like you at my Dollars + Decisions Round Table. At the last round table, we talked about capacity issues and we had a really great discussion around getting into Maintenance Mode in your business.

To register for the next Dollars + Decisions Round Table, go to scalespark.co/dollarsanddecisions.

Learn more about Charlie:

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Episode Transcript

Susan (00:04):

Hey there, Susan here. I am in the middle of working on some really cool updates for my course, Not Rocket Finance, that we'll be releasing at the end of March. So, I'm taking a short break from releasing new episodes here to give myself a little bit of breathing room to finish those updates. So this week and next week, I'm going to be releasing episodes that are the best cuts from some of my very favorite Break The Ceiling episodes. This week, I'm revisiting my interview with Charlie Gilkey. Charlie helps people start finishing the stuff that matters. He is the founder of Productive Flourishing and author of the books, Start Finishing and The Small Business Lifecycle. And, he's the host of the Productive Flourishing podcast. Charlie and I talk about how to get out of your own way, and how to avoid roadblocks that you inevitably run up against.

Susan (00:54):

So, you talked about creating the bottleneck and not trusting your team. And in your book, you also mentioned five ways that you see business owners stifle their own growth and I imagine that's one of them. Can you tell me a little bit more about how you see that founder's mojo, those unique things starting to really impact their growth?

Charlie (01:16):

Yeah. Well, the first two are very heavily interlinked and they're the bootstrapper mindset and the bootstrapper habit. I always separate mindset and practices because sometimes, well, those will often diverge, but the bootstrapper mindset is just like, if it needs to get done like I do it, right? I know how to do it so I'm going to do it. We project that tone to our teams as well. If something needs to get done, they're going to do it, but we get this very like it's all on me mindset that then leads to the habit that we don't even think about say, delegating. We don't even think about talking to a marketing strategist. We don't even think about some of those types of things because we are the solution for every problem we have in our business, because that's what it means to be a bootstrapper, it's all on you.

Charlie (02:06):

And those two put together leads to a situation to where the bootstrapper, the founder is like, "I see a problem. I'm going to fix it." They immediately start fixing it. Then we get frustrated because the people that we bring onto our team don't see the problem and they don't fix it. And so it reinforces this habit that if there's something wrong, I got to fix it until we end up in that loop. We go into the third way, we stifle business growth, which is, I call it the having to sort through the bucket of marbles. It's like any given challenge in the business, there's one or maybe three core issues in there that really does require the founder to figure it out. But those marbles are in a bucket of other smaller marbles. Like where did an invoice go or did someone respond to this email or did you make that phone call and why is the sauna not working today and just all the things.

Charlie (03:01):

So every time you go in there and just try to find that one thing, you touch all these other ones. And then because you have the bootstrapper mindset, you start getting in there and fixing them or wandering, and it's like owning a problem that's not yours. And the thing about it is, is okay, in this specific instance of you answering this specific email, you're upside down, but keep in mind that by not building this process, by not building this delegation and work way in your team, you're committing to answering those types of emails for the remainder of your business life. And it's not just that it's one email. It's not just that it's one call. It's not just that it's one thing. It's like, we're all buried under a heap, a 15 minute to do so. So the fourth thing you roll into is the insufficient trust.

Charlie (03:53):

And I have to be careful here because trust is a loaded word. It both means the moral trust, lie, cheating, stealing, that sort of thing. But it's also just trusting in the sense that if someone says they're going to do something that it's going to get done or that it's going to be done well enough. And so I want to place it more on their teammates ability, more so than their teammates character. If you got a character trust issue, that's a completely different issue than if you have a ability trust issue, and because a founder's mojo and, and hopefully I'm showing... If this particular discussion sounds very circular in the sense where it's like, because this happens, this happens and then this happens again and again, that's actually because I'm trying to describe what happens, it's not just that I'm talking in circles here.

Susan (04:39):

That's absolutely what happens is it always ends up circling back to some other issue.

Charlie (04:44):

Yeah. And so, because they've got the bootstrapper mindset, they're like, it's on me to do it so I'll do it and that creates the habit and then they're always touching everything so that they're always fixing something, basically their teammates around them don't learn how to do the things that they learn how to do, and they can't do it. And so it ends up creating this insufficient trust cycle because they won't even delegate or ask their teammates to do anything because they don't trust that it's going to get done. So what do they do? They do it themselves and get ever better, get ever stronger in their founder's mojo and leave their team ever further behind. Once you can work through some of those, to where you get out of this bootstrapper mindset and you get out of the habit, you figure out what your core work is as a founder and how to trust your team, that last snag that I've seen founders do.

Charlie (05:35):

And this is a very counterintuitive one for so many founders and small business owners. Once you get to the point to where your team is already doing stuff for you and the business is working and things like that, the thing that immediately comes up for so many of my founders is if I'm not involved in the day-to-day operations of the business, what will I do? What am I contributing to the business? I can't have all these people out there working, and I'm not, that just doesn't... And when I say it that way, to be honest, most of you listening, who are a small business owners, you're like, but this isn't that the dream Charlie? And I'm like, that's what we tell ourselves but in practice, what we do is end up getting in the business and creating crises, creating challenges, creating frictions, or destroying the business so that we will have something to do.

Susan (06:28):

That's so true. I see that a lot in, it was interesting. The last like professional position I had was as a CFO and I was turning over my work to my replacement when I left. And we were having a discussion about what do you do day to day? And really my role, I had a lot of direct reports. They all were doing their work, the style, I know you're prior military too. So I'm sure you get this. The best thing I learned from the military was how to delegate things and to delegate things. And we were talking about what do I do every day at work? And I was like, I really don't do anything. I sit in a couple of meetings, but my job is to make sure that the people who work for me have the tools and resources and support to do their job. And I get out of their way. That is literally how this happens. My day-to-day is not doing much except occasionally putting out a fire.

Charlie (07:30):

Yeah. I think people underestimate how much work it takes to get the hell out of the way.

Susan (07:35):

It's so hard.

Charlie (07:36):

It's so hard.

Susan (07:36):

Yeah. For me the switch that I had to make mentally was building space in my own brain for part of my job is mentorship. And part of my job is to develop my team and make sure that they have the skills to do what they need to do. So sometimes that is, they come into the office and like you said, that's giving them tools, asking questions so that they can learn the framework that you would learn to solve the problem. They can actually step through that themselves. And maybe you spend the first time walking them through the process and maybe you spend the second time walking them through the process, but once they've been through it a few times and they understand that they are empowered to solve that problem on their own. And now they know how to do that then it's less of an issue the next time, because they'll just start solving the problems themselves.

Susan (08:33):

And depending on the person, that process takes a little bit longer for some than others. But the switch I had to make was that that is a core part of my job as a founder or as a leader, is that my job, when you're talking about what do you do all day if you're not actually in the, sticking your fingers in the business, your job is to sit there and be a mentor and develop your team. And that was one of the ways that I managed to get my fingers out of the day to day or the temptation to get out of the day-to-day because I could tell myself I was still doing something.

Charlie (09:10):

Yeah, I'm still adding value to the company. See, but that's where I want to really hang out in this space a little bit if we may, Susan, because what that drive to contribute and to do something and to create value, I think fundamentally confuses how owners, how we should be thinking of ourselves as owners of a business. Regardless of whether you're an S-corp and how you do your pay or your wages versus dividends, but there's a part of the value that you create from doing the work in the business. In the earlier stages of your journey, a lot of your value comes from the work that you do in the business. The longer your business works, it's not the technical work, it's not the working in the business to use the well-worn Michael Gerber sort of things, it's how you work on the business.

Charlie (10:07):

But I would take it a little bit more, how you work on the business, through your team. And in a later life cycle, the healthier businesses, the best founders are the ones that are doing what seems like the least work. If your business can survive for two or three months without you, besides a random phone call here and there, because there's just an edge case, that is the value that you've created. That is the value that you created, not you button, seat, time, sitting in an office, pining away for something to do or pining for some way for someone to tell you good job or pining for your sense of contribution in the world because we got to remember, businesses should serve people, which by extension, businesses should serve their founders and owners. And unfortunately, Susan, you and I have both seen it, how much it's really a one way street that the founder and owner is serving the business, but not really getting their life back for it.

Susan (11:12):

If you liked these cuts and you want to hear more from my conversation with Charlie, you can go listen to the full episode. It's episode 34, and we will drop a link to it in the show notes. Now, even though I didn't release a new episode this week, I am still meeting with smart business owners, just like you at my dollars in decisions round table. The next one is happening Tuesday, March 16th, at 2:00 PM Eastern. At the last round table, we talked about capacity and figuring out how to increase it. And we had a great discussion around getting into maintenance mode in your business. So come join me for the next one. To register, go to scalespark.co/dollarsanddecisions. All one word, no spaces, or you can just click the link in the show notes. Hope to see you there. Break The Ceiling is produced by Yellow House Media. Our executive producer is Sean McMullin. Our production coordinator is Lou Blaser. This episode was edited by Marty Seifeldt with production assistance by Kristin Runvick.


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