Bill Gallagher - Scaling Up Your Leadership (Part 1)

Facing the prospect of losing everything, Bill Gallagher found strength in vulnerability. When his business teetered on the brink of collapse, it wasn't a strategy that pulled him through—it was opening up about his fears. Bill shares how a heartfelt conversation with his wife helped to light the path to resilience, teaching him that vulnerability can be a powerful leadership tool. Join us as we unpack this transformative experience and explore how embracing our imperfect selves can create more genuine connections in leadership.

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Chapters

• 0:06 Vulnerability in Leadership
• 9:52 The Power of Self-Reflection in Leadership
• 18:06 True Self-Awareness in Leadership
• 24:53 Leadership Imperfection and Growth

Transcript

John Broer: 0:06

Good to have you joining us on this installment of The Bossh ole Chronicles and this is actually a two-parter because the amazing and wonderful Sara Best and I are welcoming Mr Bill Gallagher to The Bossh ole Transformation Nation. And let me tell you a little bit about Bill. I actually met Bill last year at PodFest, and PodFest was celebrating its 10th anniversary an amazing conference for experienced and aspiring podcasters and Bill's been doing this a long time. Bill has a podcast called "Scaling Up Business with Bill Gallagher, and make sure you go into the show notes because I'll put a link to not only his podcast but also our episode which published earlier this year, on May 29th. But beyond his podcasting, bill has extensive experience in business over 30 years of entrepreneurial and executive experience. He's really spent the last several years coaching and training others in leadership and performance, and what's really cool is Bill is drawing on his extensive experience leading four companies of his own, partnering and being an executive, and two others from startup through growing an organization to over half a billion dollars. What I really, really enjoy about Bill are his insights and very, very practical application of helping people be better in the workplace. He hails from the San Francisco Bay Area in California.

John Broer: 1:38

But today and next week, you, the wonderful members of the Bossh ole Transformation Nation, get to meet Bill Gallagher. Let's jump in. The Bossh ole Chronicles are brought to you by Real Good Ventures, a talent optimization firm helping organizations diagnose their most critical people and execution issues with world-class analytics. Make sure to check out all the resources in the show notes and be sure to follow us and share your feedback. Enjoy today's episode. Bill Gallagher, scaling coach extraordinaire, welcome to the Bossh ole Chronicles. Good to see you again. How you been?

Bill Gallagher: 2:25

Thank you. Really good. Glad to be here today. It's lovely where I am today and I'm glad to be home in the studio doing one of my favorite things.

John Broer: 2:33

Well, stuff you do really, really well. I will just tell our listeners that this opportunity came about. We were on your podcast, the Scaling Up Business podcast, which was great and thank you for having us there. But you recently posted I think it was a blog about vulnerability leaders being vulnerable and that just really caught my attention and I said Bill, we got to have you on the program. So Sara and I are so glad to have you here and just to let our listeners know you're here to share some stories, some very practical, real experiences and also some remedies and solutions.

Sara Best: 3:07

Bill, how do you define vulnerability?

Bill Gallagher: 3:10

Yeah, vulnerability and authenticity are collapsed, for people are often conflated and there's a lot authenticity feels like that's the more talked about thing thing everybody wants to do, like that's the more talked about thing thing everybody wants to do. But I think it's problematic because people confuse having opinions as, like, I'm going to speak my truth, you know, and, yeah, we don't need more opinions, but vulnerability is especially today we have a lot of people, a lot of opinions. Um, especially today we have a lot of people, a lot of opinions. Vulnerability is powerful because I share something that's not all put together right and that creates permission for everyone to be human, for everyone to have something that's not perfect and if you could be honest about that kind of thing, like things open up.

Bill Gallagher: 4:01

So, in the case of that blog post and I shared about a moment of my own leadership that, looking back on, it was maybe the most powerful moment that I can think of, the biggest monetary thing or whatever but I was struggling with a company that was on the verge of failure and the bank was trying to shut us down and trying to take my house and I was struggling alone and I was thinking I didn't have a solution and I was dealing with it privately. The only person who knew a little bit was my wife, but she certainly didn't know how I felt about it and I but I wasn't engaging my team and I didn't have an answer, and my whole career up to that point would be was about being smarter, like being smart and articulate. So I either find a way out or find a way out and talk my way out of a problem, right and and I think about, like those are still strengths that I have, I'm smart and I'm articulate, but they weren't enough. So I didn't have a way out. The bank was going to shut me down, going to take the my house. And I was just trying to figure out how to survive it. I was pretty sure, privately, that if the business failed and I lost my house, that my wife would leave me.

Bill Gallagher: 5:14

Wow, and I'd become a weekend, right, and that is the most terrifying thought to me. Of course, and I'm emotional about it today and almost every time I tell it, my kids are fully grown. Today it's a very distant past, but that's what was there for me. So, anyway, she put me at ease and she's like, look, I'm not going to divorce you over that .Like you could find yourself in some other reason that we would split up, but not for that at this time. And so that was like one way off, like my worst fear was now addressed by by speaking it to her.

Bill Gallagher: 5:51

So the first vulnerability was with her talking about what I was really afraid of, the um. And then she said you know, and you could start over, we could start over. There are many different ways. Here's a handful of them. We talked for a minute. She said and if, if you think that's what you want to do, then great, you know, I don't, I'm not going to fight over this thing, but what is the example or the lesson that you want to set for the kids?

Sara Best: 6:12

Wow, okay, that's powerful.

Bill Gallagher: 6:13

At this point right. Yeah, the kids at this point are like seven and five, you know like five and seven, or six and eight somewhere in there. And, so you know how much are they going to remember. But they are going to remember something's going to imprint, of that kind of thing and that, like I was just like I want to teach them to fight, to not give up, to like to do something, to shift something Right. I was really like really clear. She's like well, I guess you have some work to do then, so, shift something. Right, I was really like really clear and she's like well, I guess you have some work to do then.

Bill Gallagher: 6:48

So I went into the office. Um, I think it was that day or the next day, um, and I got the team. I said, guys, I, I have something to talk to you about. Um, we're in a spot like, uh, the bank wants to shut us down, you know. And so I laid it all out. I said I don't have a plan, and I understand now, given the situation we're in, if you need to leave, it's okay. Just please tell me, because I need to deal with that too, if you need to go to protect your family and your income and all that to stay. I could really use your help and I don't have an answer.

Bill Gallagher: 7:25

But I can promise you a couple things. One is I'll be really honest and open with you, like I won't or secrets around this or anything else. And the second one is I won't quit. I will fight to the end. To the police come lock, the sheriff locks the door. We're going to see this one through, right, and that was like Braveheart stuff, right. People were like, yeah, come on, we'll do this. Okay, we're with you. Everybody stayed and there was no one magic bullet. But together we pulled a bunch of levers and we figured it out and we doubled the revenue, profit and cash over the next year and we settled with the bank, got rid of them, wow, wow. That's really cool, right, and I was like on the verge of tears telling it. I mean, it was way more emotional in the moment and that kind of thing. But how is it that a leader with no plan who's crying in front of his team is more inspiring and powerful than having it all together and sounding like a big bully, right?

Sara Best: 8:25

Right, yeah, such a paradox, that's amazing.

Bill Gallagher: 8:28

So that's vulnerability, right? There's a personal story about me not being a client.

John Broer: 8:33

And a powerful one. Imagine that I don't know, I'm kind of thinking, Bill, after that meeting and you are just sort of overwhelmed with, I mean just feeling so blessed that I have these people that still want to be here. Um, yeah, because under the, if I were in the same position I mean if I were, if somebody shared that same information with me, you know, you'd really have to think twice about am I willing to put my faith in this process and this person and we're in this circumstance, and that's incredible. Go ahead, sorry.

Bill Gallagher: 9:06

The postscript. So we go through the year, we did the whole thing. We acknowledge people by the next year. A number of those people left. There were people there who stuck around for the challenge and that leadership, who didn't really want to be in our industry for that long, who just had been there at the moment. But they're like yeah, and the thing I think that's useful is great leadership and a big challenge will engage people who might otherwise not actually be that strong Like we had, you know, as a jewelry, fashion jewelry business. There were people who were like they didn't really care that they were there by happenstance and and I think it's it speaks, it just underscores how powerful that can be. Right.

John Broer: 9:51

Oh, yeah, well, Bill, thank. First of all, thank you for sharing that, um and and it is very enlightening. And you also mentioned the other end of that spectrum. When people get into leadership or they're in a management role, they think they have to have all the answers, they have to be tough, they can't show any vulnerability. You've got stories, stories about leaders that have just not had that self-awareness and fell victim to it. So take us through some of those that are really helpful for our listeners.

Bill Gallagher: 10:24

So I've now coached thousands of people around the world over the last 11 years and, like, really, I did part-time coaching before then. So you know, the stories span like 18 years of working with people to varying degrees, some several years and some for a couple days, right so, but I've. I have seen some remarkable things, some of which I'm like I'm guilty of I've done myself at times, but, but the wealth of perspective when you get outside and start to see other people doing things as well, and then you can look back and you can go oh yeah, I did that too, um, at some point. Right, right so I think so. The first one I think is is really to share is about the power of looking in the mirror, the importance of considering that your company is a ripple or a reflection, amplification of you and if you're not the ultimate leader, founder, your department is. Whatever we are. Our universe is reverberating, connected to who we are. So you could say that the business we have and who we are as a leader or the department we have, is like the front and the back of the hand the way you move, so goes with it your world, and that's like good news and bad news, and for me that mostly always occurs as like bad news. But so I'm coaching this guy who brings me in great company, health-related business, worldwide distribution for their products, great, positive, good, you know, in many uh respects. Also, you know, profitable, like a good run business in many regards. But he uh brings his team and starts working with me because, according to his words, private, the team is really passive, they're not really leaders and they're late on everything. Like nothing's on schedule, nothing, no, no promises are delivered on time. So that's great and their work they do is good and their goal is to be number one in the category worldwide and I love a big game.

Bill Gallagher: 12:32

So I start working with them and and we do some of the we do like, do an initial workshop and we start quarterly planning, we implement meetings and you know we're doing the kind of things that we do to help grow. And and then I hear on a phone call with one of the leaders that things are kind of unraveling, that there's a problem, that that whatever momentum we start is being undone. So I'm like, hmm, and I know that there is a meeting of the senior team the next day in a nearby town and I can arrange to cancel everything or reschedule things that I had on the next day and go there. So I arrange myself, I go down there and I get there a few minutes before. It's a little bit of a drive from where I am. I get there before the meeting and nobody else is early.

Bill Gallagher: 13:21

One other person shows up on time and then about 20 minutes later one of the very last people to arrive is the ceo and, uh, he's been traveling and he says some apology or whatever, but all the people sort of trickled in over those 20 minutes and and he arrives and he's got really, he's really well prepared and he's got pages of detailed notes of important, serious things that need attention in the company and he works through his agenda with people because he's glad to be back in the office. He's concerned about the state of different projects. He wants to, you know, interrupt him, head him off, and then he turns to me. Then he goes for like two hours. Now we're over time. He asked the team if they have anything other subjects they want and people defer. They're like no, we're good.

Bill Gallagher: 14:14

Are you everything, yeah.

Bill Gallagher: 14:16

And he turns to me. He says, do you have any coaching for us? And I said, well, there is, yes, uh, some things and we probably don't want to do it all at once, but for sure there's a design intent to the meetings, the way they run, the agendas, things like that. That probably deserves some further thought and study, because we want to bring up all the leaders and empower people and work the process, not just deal with the issues of the day. Right, so we want it for longer sustainable thing. So there's a fundamental structure to think about and some practices here, principles, and I said we can do a further debrief in your office adjoining the conference room. So he says, all right, everybody go look at the agendas. And then he says we'll go in the other room.

Bill Gallagher: 14:59

So we go in the other room and he says, so what do you got for me? And I said, okay, well, you remember why you brought me in. You said everybody was late and passive, like not really taking charge, and the good news, bad news is that it all starts with you and and you know it confirmed that. That's why he brought me in and that was his concern. I said look, you've taught people that being late is okay. You do it again and again. This meeting wasn't an exception. You're late all the time to things, so what right do you have to expect that anyone's going to be out of time with anything? You've taught them what you think about it and you just don't realize it. And then this business about you know being leaders and taking charge. You dominate the whole thing and the whole team with everything. There's no chance to step up or take an initiative or have that be heard. There's no room for that with you, right.

John Broer: 15:52

He's sucking the air out of the room.

Bill Gallagher: 15:53

Yeah, the good thing is you could work on this, like you could shift these things, and I promise the whole team will start to show up differently.

John Broer: 16:02

What was his reaction?

Bill Gallagher: 16:04

Yeah, I want to. That was our last conversation, are you serious? He ended our contract, all of our contracts, all of our work. People can get out of it anytime and that was the last time I spoke to him. He sent some other people to tell me we wouldn't be working together anymore.

Bill Gallagher: 16:22

And so look, it's not comfortable to look in the mirror. I can't tell you how many times I knew there was a problem in my wife or some coach had tell me Bill, this is all your fault. It'd be like F you man, it's their fault. I'm going to go fire somebody, and I do maybe fire somebody sometimes, but but the problem that ever allowed it, or the person that allowed it to happen, is me Right. So I deserve the company I have. I have the company I deserve.

Sara Best: 16:49

So well said. It stands to reason that you know this. This job is not for the faint of heart. The theme I keep bumping into recently, even with the vulnerability thing, is you know, I didn't really sign up for that and in reality, yeah, you did.

Sara Best: 17:05

Lencioni writes about that in "the Motive, his most recent book, or maybe it was before the Working Genius. But it's like, dude, do you understand that? This is a responsibility-centered role? It's not for status, it's not for anything other than that, and if it is for you, you're not the right man or woman for the job.

Bill Gallagher: 17:24

I had a new company that reached out to work with me just very recently and I started and I got like two days into working with them and we decided not to continue because they had a lot of like personal work to do and the three founders were not interested in being that direct in that. So we stopped it way earlier. But look, I can put all kinds of practices and work on your strategy and help you develop new practices for your people side of things and all that kind of stuff, and it won't make any difference in the world if you keep operating the way you operate All that kind of stuff. And it won't make any difference in the world if you keep operating the way you operate. If you don't level yourself up, then you'll just pull the organization down or it'll expel you.

Sara Best: 18:06

Well, and keeping in mind, the theme of that story was you know, look in the mirror.

Bill Gallagher: 18:11

What do you think it? Is Bill that makes it so excessively difficult for some people to do that we all have ways that we get comfortable looking and thinking about ourselves and being reminded of you know. So we all have a way that, like we get, like we make our peace with like, okay, this, literally this camera angle that I'm looking at myself I'm pretty good with, I like I look okay here, right, yeah, right, it's your good side, yeah, yeah.

Bill Gallagher: 18:40

Come from this side here here. It's your good side. Yeah, yeah, you come from this side here here. Uh, there's that camera on. Yeah, I really don't like the side angle. The jawline I'm not too happy with the receding hairline here. The thinning hair if I turn my head if you could see that like I'm not good with that, right, and everybody else sees that all the time I just go to brush my teeth or shave or, you know, do whatever I do. I look in the mirror this way all the time and I and my camera set up the. I've gotten comfortable with this and yet the world sees all sides of me, right?

Bill Gallagher: 19:12

Like and and you know this is about our, my physical appearance, metaphorically, and we all have that. But we have the same exact thing in every other domain our self-expression, our limits, our boundary, our rigidity, our opinions. Like all of it. People see all of it. And people see that we know, but we've tried to ignore, or hope has disappeared.

Sara Best: 19:39

Like the emperor with no clothes, Like yeah.

John Broer: 19:43

Well, Bill, we have an exercise we do. It's called front of t-shirt, back of t-shirt. I'll give full credit to Mike Zani. He's the CEO of Predictive Index. He's been on the podcast a couple of times. Yeah, and he talked about this, and the front of t-shirt is, and Sara describes it so much better. But the front of the t-shirt are the things that people that you know about yourself or that are more-

Sara Best: 20:06

Their strengths.

John Broer: 20:07

Their strengths. You know there are superpowers, but the stuff on the back or the camera angle from the back, the stuff that people say when we leave the room, yeah.

John Broer: 20:15

And you know like, for example, you want us to be on time, but you're always the one that's late. I mean, what kind of example are you saying? And you know, the thing about that too is Sara and I just recently, within the last year, had a sit down with a CEO and our relationship is fairly new, great organization, and they're going through some transition. But we sat down and said this change, this, this growth that you're about to experience, it's going to be most difficult for you because you've spent so many years in this particular setting and we are going to share with you some difficult things. Are you prepared to hear them? And I don't know, Sara, what would you say?

John Broer: 20:57

I think it was like oh, yeah, sure, yeah, but you'll know when I don't like it, and it's that's fair enough, but know that we're not going to know that, we're not going to lie to you just like you did, and so so far, we're still working with them, which is great, and he's, he's been, he's working at it, he really is. But this is a great example of somebody that will not hear it, and that's a shame. That is a shame.

Bill Gallagher: 21:17

And look on the surface, most people say, yeah, I'm good with that, I'm coachable. Right, on the surface we think we are, we answer honestly, but in reality there's a lot of times like don't go there, I'm not willing to be that vulnerable, I'm not willing to be that called out and we can get proud and postury about it. The guy you know like who are you? Like? I've grown this company to hundreds of millions and blah, blah, blah.

Bill Gallagher: 21:46

I'm like what have you done? And I'm like well, I did $500 million before I was 30, but okay, but that isn't even what makes me a good coach. My ability to coach is derived from my stand for you to be great and to achieve what you said you wanted, and my discipline or willingness to see you as bigger and better than you are currently showing up as yes, yeah, that's that's so profound and it's it's your willingness and your belief in someone that they can in fact take a hundred percent responsibility for the results they're getting.

Sara Best: 22:24

Yeah, the department that looks like them, the company that looks and feels and smells like them, you know their ultimate, you know gift is being able to take 100% responsibility. That's every one of us actually.

Bill Gallagher: 22:36

So I think that that most fundamental thing is look in the mirror. Look, we just had Marshall Goldsmith on our show, love him In the last couple of weeks and you know his core idea what got you here won't get you there. It's great the things that you have. They get you to a certain point and they're not enough to carry you for the rest of your life, for the rest of your growth, or they'll just hold you back. So you know, if you want to plateau at some point and sing about your good old days, you know that's a different game to play. But if you're really reaching and you want to keep growing something, then you want to also keep working on yourself as much as you are at work on your business that Travis Bradbury the guy who wrote Emotional Intelligence 2.0, did a lot of research and uncovered that the higher you go in an organization, the lower the emotional intelligence.

Sara Best: 23:28

And we could probably have a whole episode on why that is. But let's just agree that when people are promoted because they get results because of the actions they take, it's not that they don't want to develop their emotional intelligence, but at some point they stop getting feedback.

Bill Gallagher: 23:44

Yeah, very common you don't hear the truth.

Sara Best: 23:49

So I also think about if you really want to know what the impact is, you need to be asking people, because it is. Well we see many examples of very leading CEOs, some of the top business leaders in the world, who are profoundly flawed human beings.

Bill Gallagher: 24:09

So, it is possible to like have big results and produce big impact and still be a jerk.

Sara Best: 24:16

Yeah.

Bill Gallagher: 24:18

Right, it is. You know, Steve Jobs created an extraordinary company and inventions that change our society and that kind of thing, but he's never going to win dad of the year contest right. And we have a big multi-CEO these days running around the world making complete ass of himself and I think, in some cases, because of the quantity of money and the success and the power that you will, sometimes your excesses can get out of hand and you can actually regress in some ways for revolutionized transportation and the manufacturing but he was a bit of a Nazi.

Bill Gallagher: 24:55

You don't have to necessarily be a beautiful, human, godlike creature in order to. It's better. It's easier right, it's more sustainable, the organization is better for it, but it's not the only way to get it done yeah, it's, and sometimes it's very hard to attain, that's true, because they're still flawed.

John Broer: 25:15

I mean they're, you know they're, they're still human, absolutely, absolutely okay. So there's part one of our conversation with Bill Gallagher, the scaling coach and the host of the Scaling Up Business podcast. Make sure you check out all of the resources in the show notes and get to know Bill, and tune in next Tuesday for part two of this conversation, because it gets even better from here. We'll see you next week.