What happens when a bartender-turned-restaurant-owner discovers a passion for experiential marketing and becomes the CEO of one of the top exhibit houses in the country? You get Michael McMahon.
In this episode, Michael opens up to host, Jane Gentry, about his winding path to leadership, how he cultivated his leadership voice over decades, and what it really means to “get out of the way” as a CEO. Jane and Michael go deep on practical tools for empowering executive teams, navigating change, and leading with intentionality and authenticity.
If you’ve ever felt like the bottleneck in your business, this candid, reflective conversation will challenge and inspire you to lead differently.
About Michael McMahon, President & CEO at Hill & Partners
Michael McMahon is the President and CEO of Hill & Partners, an award-winning experiential design firm with 30 years of success in the B2B tradeshow and event industry. With teams in Boston, Las Vegas, and Orlando—and a strong network of legacy partners—Hill & Partners delivers immersive brand experiences across the U.S. and internationally. The firm was founded in 1995 with a people-first philosophy, evolving beyond transactional production to become a collaborative, end-to-end engagement partner for both emerging and established brands.
Michael’s passion for face-to-face engagement began in the restaurant industry and evolved through hands-on experience in architectural model building and tradeshow management. That early exposure sparked a decades-long career in experiential marketing, where he continues to be energized by the work and the people it connects. He is also an active member of the Experiential Designers and Producers Association (EDPA), having served on both its board and executive committee.
Transcript of the episode, lightly cleaned up.
Michael McMahon: There is no path that is laid out for you. There are just lots of paths that you could choose. And then sometimes the path that you’re least skilled to do might execute better because you know you’ve got to be on your game. Realized is I was that person who was advising from a place of knowing in an area that was entirely new. If you get in the way of everything that you want, if you start to realize that, then you go, wow, that’s the thing I’m in control of. I’m the slowest learner in this place. Taking me 30 years to get here. I’d like to see you guys get there in two, three, five years.
Jane Gentry: Intentional in the way that you need and you have to realize that every move you make has a material impact on a person or family.
Michael McMahon: Is greater than the sum of its parts, people specifically. All I have is my experience and my intention to do the next thing. If athletes at the top of their game have a half a dozen coaches, know, nutrition, then why would you not think that would be an advantageous thing to do?
Jane Gentry: You can’t love person for their potential, you have to love them where are now.
Michael McMahon: Yes, I wish I was introduced to the idea of a rabbi, a mentor, a coach.
Jane Gentry: Welcome to CEOs Unscripted, the podcast where real talk drives real growth and delivers real results for mid-market leaders like you. I’m your host, Jane Gentry, and each week we’re pulling back the curtain on the unfiltered stories of CEOs, founders, and executives who face the highs and lows and everything in between. After 20 years of consulting in enterprise, and then experiencing firsthand the reality of being a CEO in a mid-sized company, I discovered why they say it’s loneliest at the top. For most mid-market CEOs, there’s no handbook. You learn through trial and error or by reaching outside your organization for help. That’s exactly why I created CEOs Unscripted, a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Each episode offers an unfiltered, behind the scenes look at the wins, the losses, and the playbooks shared by CEOs and founders who’ve been where you are. No fluff, no jargon, just unscripted, honest conversations about what it takes to lead, grow, and scale in today’s business landscape. If you’re ready for candid conversations, real world insights, and lessons from leaders who’ve walked the path, you’re in the right place. So grab a seat at the table because it’s time to get real. This is CEOs Unscripted. Welcome to CEOs Unscripted. Today I have Michael McMahon with Hill and Partners out of Boston. Hi Michael. So good. Michael runs and I should run, that sounds so low tech. Michael is the CEO of an exhibit house. Tell everybody what an exhibit house does,
Michael McMahon: Hi, how are you today? So, an exhibit house is an organization that works with brand companies to bring them to the market. We’re really in the B2B space. So, if you imagine a B2B brand has to move about the country, move about the world and connect with their customers, our organization designs, builds, maintains and manages properties for those companies. In a way that allows them to stick to their high value activity while we move about the planet.
Jane Gentry: Love it. Okay, so here’s how we start here. I want to hear your backstory and I tell everybody every time we record this, I don’t want to know what I can see on LinkedIn. Give us the good stuff.
Michael McMahon: Right. Yeah, so I guess it’s both interesting and not interesting. I’m essentially, I went to school in Massachusetts, grade school, graduated, went off to be an engineer. And this was in the very early 80s because people said it was the job you should be attempting to master. I had a math aptitude. I was interested in being sort of a champion of my own life, so very excited about that. Found out pretty quickly that I maybe didn’t have the education or the credential-seeking chops that most people have. So two years into my college experience, I actually dropped out, completed a two-year associate degree in business, and immersed myself in the restaurant industry. My intention when I was in the restaurant industry was to own a restaurant. I don’t come from a family that has restaurants. It just seemed like an interesting goal. You know, I can cook, but I love the idea of all kinds of kinds of people working together. Looking back, it’s easy for me to shape it now because I’ve lived my life at the time. I was just pursuing what interests me. So I got a job for a company called TGI Fridays, sort of an old franchise. At that time, they were scratch kind of a scratch cook kitchen.
Jane Gentry: Still exists though.
Michael McMahon: Yeah, no, I think they have a commissary and I think it’s gone a little Cisco personally, but that’s just my opinion. I got on a corporate training team for them in the southeast down in the Carolinas. So I had the opportunity to open a few restaurants with them and sort of experience that professional training atmosphere where there were a lot of materials, a lot of communication and also human support to learn things. Again, credentialism has never been a real interest of mine. So mastering something to get a ribbon never really drove me. It was the people and the experience that I liked the most. I went through their system and basically learned just about every position in the company without being a manager and also not waiting tables. For some reason, I didn’t want to wait tables.
Jane Gentry: Mm-hmm.
Michael McMahon: Completed my period of time at Friday’s after three or four years, I was a head bartender in the eighties when drinking was a big business, happy hours, that sort of stuff. And without really knowing, I had really honed my, my bonding and rapport skills. I think they were relatively natural, but I loved engaging with people in a, an informal environment. And because I’m not a person who can really construct myself to show up in different ways in different places, I just took that with me everywhere I went. In other words, I treated every engagement of just as just me and another person. Two customers at TGI Fridays, one was in the food business, one was in the beer business. We decided to open a restaurant. So in, I think it was 1985, we opened up a restaurant called Fifth Street Cafe and Gallery. Local artwork, two-story old brick building. And we went on that partnership venture for about 24 months before I left. I learned an awful lot there too. So in that journey, I learned the difference between having and doing because I was around people who had felt they arrived. In restaurant ownership. And I still was a person who wanted to do the work. Right. Wanted, you know, so I saw every day as an opportunity to fail or an opportunity to succeed. Never really, I never really got to a point where I felt like I arrived. That never feeling like it’s good enough has driven my entire life. And it’s not a feeling of being less than it’s just being very aware that each day you’re earning the day. In that process, I realized the partnership wasn’t the right thing. I went on to be a GM of another restaurant for a private owner. Learned a few more things. A couple of years later, I decided to sort of blow it all up. And I returned to Massachusetts. And in that process, I got a job with an old friend working in the trade show event space as a show manager. In the show management role, it was mostly at cities and in venues where we flew in, we walked around, we herded cats, but it was in this professional brand space. It spectacular. So in the trade show and event management role, what I learned is that the same sort of challenge that I got in the restaurant business, which is you sort of took inventory at the end of the day, right? And then you fix the things you did wrong. You modified the needs for the next day based on what you learned. And then you, then you did it again. In the trade show and event space, it’s the same thing, but the time period’s longer, right? So the project is a period of time versus a day. And in that process, I found that I love that I got all of the different phases of managing something that was much, much, much larger. And I sort of fell in love with it. I loved all of the stress to have, you know, the idea of a product manager, a marketing manager, a VP, a salesperson showing up in San Francisco and walking into this exhibit, which is this mini architecture in the middle of the floor, that’s the intention is to be a clear representation of their brand. And then they all have to vie for their own success in their role in this place that’s, you know, essentially temporary. To watch the different stresses, to understand and sort of see the music that’s played, you know, the music of people all trying to get what they need. It was just easy for me. It was easy for me to see the forest. The challenge for me was how do I deal with all these trees? Right. And So I did that for years. And then there was a of a turning point in that situation. I kind of had to move on from a family. It was a family company. They gave me an opportunity to look for another job because they were selling. So it was a liquidity event for them. And I walked into a local company up here in Massachusetts to just see if I could get on that fabrication side. And I walked in the building, actually met my future partner. She interviewed me. This is very, you can edit this out, but very timely and interesting thing at the time she said, you know why we like you? And I said, why? And she said, because you can’t have a baby. The reason why she was very high performing salesperson, she had three really amazing women on her team and they all had just gone through their first pregnancy. And, and she, you know, Susan was quite an achiever. So, that put a dent in things. Right.
Jane Gentry: Mm-hmm.
Michael McMahon: Yeah, so I remember just telling her, you know, in a perfect world, you can’t really say that, but I get it. Took a tour of that building and all the people that I admire in life, all kinds of kinds existed in that company. And I saw the possibility of being able to work with all of them from someone who works on the loading dock to designers, model builders, the accounting people were accounting people, but there were like 15 of them. Yeah. I left, went home and talked to my wife and said, you know, I don’t know if I’m going to get hired, but I’ll work in that building within 30 days. So I’d met enough people in the building that I would have just walked back in there and said, you know, where do I start? And that was really the beginning of all this. So, you know, it’s a long story to the beginning of an entirely new chapter. 33 years old. The time I was 31 at 33. Susan asked me to go into business with her outside of that environment. She was 12 years my senior, a little bit of a midlife crisis, I would say. She saw big business coming into this space and roll-ups and that sort of stuff. And she kind of wanted to be her own entity, finding a way. So we went into business together and… She was for all intents and purposes. We used to call this, I was her work husband, she was my work wife.
Jane Gentry: And I’m your husband.
Michael McMahon: Yeah. And in 1995, we hung a shingle and I think she thought I was going to be, you I had an equity position. It was very, very small. It was a percentage of nothing, right? Cause we just opened a company. I think she saw me as someone would have an equity position, but she really saw me as a doer. I flew all over the world. Did all those things. Gradually overnight, we found out that I was more interested in the business and she was really interested in getting business. She was just a wonderful salesperson. She could turn it on, turn it off, common ground. Was just really, it took me a while to realize how amazing she was. And then after about eight or nine years, A couple years in a row, I tried to orchestrate an opportunity for her to either make a decision where she wanted to be, 12 years my senior, or I was going to have to go do this again. And the reason why I’m sharing this is I had a plan in my life. The plan was lead or get out of the way. I had no problem leading. Was my high school’s, the most unlikely high school class president.
Jane Gentry: Boop
Michael McMahon: I was captain of the soccer team. Was all those things, but not in the same way that achievers are. A lot of people that want to be in that role, it was pushed upon me. I was told, and I think it was because I really liked, I could engage with all kinds of kinds of people.
Jane Gentry: That’s how I ended up the Jerry Foreman. I didn’t think so, because I didn’t vie for that. I was just sitting in my chair quietly, I think, I thought.
Michael McMahon: Well, actually, know, see, I’m sort of comfortable with the person you are just from a distance, you know, from the bleachers is first and foremost, you actually intellectually, you know how important eye contact is. But I think also naturally or either maybe you’ve learned it, but you’re also very natural at it. So I can imagine you going in the room and then there’d be a bunch of people who feel as though they matter when you’re looking at them. Right. I think I have the capacity to do that, but it’s more I have to have the engagement. I have to be interested. I have to ask questions.
Jane Gentry: Yeah. Mm hmm. So your partner left and here we are.
Michael McMahon: Yeah, so in 2000, I made her an offer in 05. Basically, it was an interesting thing. I think why I think this is interesting for business people is there is no path that is laid out for you. There are just lots of paths that you could choose. And then sometimes the path that you’re least skilled to do, you might execute better because you know you’ve got to be on your game, if that makes sense. So for me, for me, the acquiring this business is I have, you know, I two little kids. I have no money. All I have is my experience and my intention to do the next thing. And here I am with someone who is ready to end this chapter. Right. She’s done. And she kept on wanting me to tell her what I wanted to do. And I was like, no, this is it. This is how it works. You’re the principal. I’m the minority shareholder.
Jane Gentry: Mm.
Michael McMahon: You need to tell me what you’d like to do and then I get to sign up for it or not. And she had a very difficult time with that. Because, I, in my CEO forum nowadays, I see my peers going, you know, I just wish someone would, I just wish someone would say this, or I just wish someone would take the reins. And the thing is you’ve got to invite them to take the reins and you’ve got to say that, you know, I think you have to look at another human being and say, there’s no right or wrong. Let’s just play with this. What happened is she really couldn’t come up with something. So I’m there like, do you want to live in an island? Do you want to be a remote business owner? Would you like, you know, if she had said she wanted to be a remote business owner, Jane, I would have said yes. And I would have built what I’ve built and someone else would have owned it.
Jane Gentry: Being.
Michael McMahon: And so I’m so grateful that she was like, all of a sudden, I can be out of here by December. And it was like June.
Jane Gentry: I love what you said like there is no path. I’ve said to people that work with me in the past, part of our strategy is to look for the doors that God opens and then try to have the courage to walk through the door. And that seems like a very, that seems to lack a lot of intellectual rigor.
Michael McMahon: Yeah
Jane Gentry: But it has worked out.
Michael McMahon: Yeah, would say, know, it’s tough because I’m, you know, I’m 62 years old and I believe I have things to say, right? But then in this world of everybody saying things, you start to say, these my words or someone else’s? Right? So, and there’s no, there’s really no place to just be echoing the thoughts and ideas and words of others unless you can attribute them to them, in my opinion. I have a horrible memory. So it’s very hard for me to say, like, if you said something brilliant to me, you know, I’d really have to work to say that if I share this with someone else, I got to make sure I give Jane credit and I don’t even trust my brain to do that. Right.
Jane Gentry: I it would come out exactly the same because I think I read a lot, I talk to a lot of people. And honestly, I don’t think I’ve had an original thought ever, Michael, but I think it’s these ideas that come from all of the places that I insert myself and my brain exists, right? And then they all mush around and kind of are curated in a way that when they come out, they’re not exactly the same. They also have my experience filtered through them and my point of view.
Michael McMahon: Right, well, you just said part B of that. So thinking that on one hand, and then speaker came to one of our events a few years back. He wrote a book called The Creative Curve. I don’t know if you were at that event, but he had researched the creative process and he came to the conclusion that creative people, just artists, creative business people, consume in excess of five hours of information a day in the area of interest that they’re attracted to. So for someone like me, it is, it’s business, it’s business people, it’s leadership. And then what he concluded was that becomes the raw material from which you create your next thing. So that’s what you just articulated is, yeah.
Jane Gentry: I think that’s what I do for a living is to carry the amazing ideas of other people into a way that is relevant to a particular client. That’s really how I see my role.
Michael McMahon: Yeah. Yeah, and I’m playing around with that internally. You my intention now is to maintain a relatively flat organization, but the executive team that, you know, is directly, I’d like to say, sit around the table with me because they do. But in a hierarchy of things, I am owner, CEO, and president, is how do I share with them, you know, how I see the world and situations and engagements? And then invite them to speak it back to me in language that suits them. And then ultimately, what we’d like to do is have a shared way we communicate about our mission and vision and what we believe in. But it needs to be true and genuine. It really needs to be We have authenticity as a core competency here. I’m sorry, core value. And it’s be true to yourself and genuine. And I really think that is like speak the words as if they’re yours.
Jane Gentry: Yeah. So one of the things I hear from CEOs and I experienced it, by the way, you might have that intention, but when you are in the room, no matter how, how much you want to get this input from people and this feedback, the fact that you are sitting in the room with that authority and that title makes it difficult for people to really be authentic in that moment? How do you how do you encourage people to do that? Or how do you get around that?
Michael McMahon: Well, my father always used to say, got to do the time. I think this is the tough thing of business. I love small business because I think it’s centered on being human and human beings. Think as what we produce or contribute in the marketplace becomes a thing that, you know, people work in systems on that thing. You have to build in layers, you have to build in tools and systems to manage it to some level of predictability, right? And in that process, we try to do this efficient leadership, this thing where there’s lots of clarity and you cull things down and there’s punishment and reward. And when I say punishment and reward, Punishment could be disappointment. There’s lots of different things. I don’t know if I have the brain power to do that in larger and more robust organizations. But how I do it here is I do the time. Like I spend with my greatest loyalty used to be to every human being in my company to the same level of attention. Now my loyalty is to these five people that run this organization that will literally be the energy that creates the next best work that this organization does. I’m trying to, my intention is to connect with them as a business leader, as a person who’s pursuing this work. And you just have to do a lot of time there because each person is accepting, risking or attempting their version of leadership, you know, this hybrid leadership management thing. And you kind of have to meet them where they are. And what I’ve learned is, I can’t set the clock on that in any type of time frame, time frame that I’m used to. I’m if you and I talk about something today that we’re going to do, I’m looking for action to be taken.
Jane Gentry: Yeah.
Michael McMahon: Did you write it down? What are you doing tomorrow? Most people are rolling it into their month. You know, I mean, it’s incredible. I have to, you my feeling is I have to respect the process people, the steady relation people. A lot of people that are in my role, we are just we are our greatest asset and our biggest challenge when you systematize an organization, right?
Jane Gentry: Tell me where, because I’ve just had this experience with somebody, tell me where you think you’re the biggest challenge as you systematize an organization.
Michael McMahon: I’m a very passionate person. I can do a lot of things pretty well. I can do a ton of things marginally. You know, I mean, really, and I, and, you know, there’s a book, the ADHD entrepreneur, I was never diagnosed, but there’s a whole family of brain, you know, people in my head. I haven’t named them, you know, but, you know, it’s not a personality thing. But if we’re talking about accountability, I can be that person. If we’re talking about risk, I can be that person. If we want to just try something and there’s not much to stand on, hey, let’s give it a shot. So if we want to have structure, let’s talk about the structure. Let’s talk about when it goes well, when it goes bad. Are you here? Say, who’s the hammer? You know what mean? Like, and I don’t care if your hammer is covered with pink fur or if it’s a yabble. I just need to know what is the consequence that you put forth if you’re asking for something. So my greatest asset is I’m willing to talk about all of those things, all of those possibilities. Where it becomes the biggest problem is people like structure, process, timing. People want to know what does success look like for me in this world?
Jane Gentry: Okay.
Michael McMahon: And in leadership and management, that hybrid thing, you’re managing people, but you also have to give them space. The outcome isn’t usually constructed from a number of steps. Or maybe the steps are there, but the level of achievement isn’t that, it’s not like this. It’s a little ontological. Know, I remember there’s a trophy out in our lobby, Jane, and it’s a Falcon trophy. It’s something we sort of award people for excellence here. And it’s not on a timeframe. Sometimes it can go six months and there’s no Falcon award. But on the coin that’s attached to it, it says, conceive, believe, achieve, which is the mantra I lived my life by until… I decided you need to take the pattern out of that. It’s like, you can go right to achievement and the rest will take care of itself. You know what mean? If the achievements up here, like if I walked in a room and I wanted to meet you, the linear person is going to go, well, I’ll see who she talks to. Then I’ll ask them a little bit about her, you know, and I’ll orchestrate my way to meet this person. No.
Jane Gentry: Woohoo.
Michael McMahon: I’d like to meet this person. I want to be respectful. I’ll look for my spot. And then whatever happens. It could be like, you know, I don’t talk to people that are over six feet tall or whatever, whatever rules someone has.
Jane Gentry: Yeah, yeah. So when you, you know, I said, you know, I’ve been having this conversation with a client that’s in a growth phase. And I said, you know, first off, we’ve got to get to the root problems of what’s causing the pain right now. Let’s not put band-aids on symptoms. But part of it is as you grow, a lot of times the CEO becomes what I call the decision bottleneck.
Michael McMahon: Yeah.
Jane Gentry: Right? You have to be involved in way too many things. And so what I heard you say a moment ago is you are empowering those five people that are basically running your company to lead. How do you get yourself out of the way to improve what I call time to decision, right? Make your own decisions. We miss opportunities.
Michael McMahon: Yeah, it’s a great question. All right, so I built a couple of tools around this. So when I’m talking to people, so I 100 % agree with you is if you get in the way of everything that you want, then if you start to realize that, then you go, wow, that’s the thing I’m in control of. And I’ve tried this. The first phase of this was probably around, you know, we come out of COVID, I want to build the organization, but I don’t want to go back to doing all like start over. So I’m gonna build, we’re gonna build the organization and really put this void between me and the work we do and work to have these people who aspire to fill it. And then the unfortunate thing is I found out that all of my effort to give them that space was actually conditional. You I thought it was sort of unconditional. You know, these people, I admire them, they are capable, but no, condition, you know what mean? So the space was there. What I realized is I was that person who was advising from a place of knowing in an area that was entirely new. It isn’t me making those decisions. So you start to have to go, well, I started to learn, this took me like 16, 17 months to say that it’s on you guys while my total body energy was no, it isn’t. You know, so It’s on you so I come in and then I would be in a point of frustration is almost as if they disappointed me. Like why aren’t you doing it this way? Does that make sense?
Jane Gentry: Yeah. So let me ask you, because you’re a self-reflective person, so I think you’ll be honest with this hard question. Yeah. I have a client who, he brought in a CEO, a president to run his company. So he had one guy for your five guys, right? Right. And the relationship just broke recently. And so was talking to the president and I said, can I tell you that this is something I see more often than I would like, which is a leader, a CEO brings in somebody to run and I’m making air quotes here, the company, right? You’re accountable to the budget. You’re accountable to the outcomes and the strategy. And yet these CEOs have what I call they are grenade launchers. Okay. So I say to them, so what happens is the CEO is still out in the world, right? Because he’s driving the he or she is driving the vision of the company, but they have shiny object syndrome. So they see this new thing and they go, Hey, we have to do this. And they want that grenade right into the budget right into the strategy. And yet that president is still accountable to the outcome. How do you avoid that?
Michael McMahon: Well, first and foremost, I think you need to have a set of words and phrases that you both agree on their meaning. Because what I do, so I talk about tossing grenades. We have brand clients who throw grenades over the fence all the time and completely disrupt some very clear communication that they’ve sent our way. They’ve sort of… That’s the nice thing about being in a B2B space is your clients are teaching you all the time. And then if you don’t like what you’re seeing, I think a leader in his own organization says, well, we shouldn’t do that. Like we shouldn’t do that to our own people or our partners. In other words, if it doesn’t feel good to us, it can’t possibly feel good if we do. And yet so many companies adopt behavior that isn’t effective. Um, what I do now, so it was months and months and months. What I do more often than not, I say, I actually stop and say, how do I, how am I occurring right now? Is this occurring as am I occurring as frustrated, angry, bossy? And most of the time they work for you. So they’re going to be kind. Um, but at least I’m suggesting that they have an opportunity and then I’ll say this heightened energy is not anger.
Jane Gentry: Right? Right.
Michael McMahon: It’s not frustration. It’s heightened energy because that’s how I am when I get excited. I’m excited. So then I ask them, I can do that from this position back here, if you’d like. We play around with it. Now I’ve known these people all for a decade, right? So at least a decade. So I do that. And I use the words you and you guys as a team and this stuff that you’re working to build, this future that you guys are working on, I don’t use I, I just don’t use it. And if I use it and I hear myself, I’m like, that’s by the way, that’s my ego talking. So if you guys say I much just know, that’s a big part of how we get where we want to go, but it doesn’t have to lead the way, right? Yeah. So I’m, I know this is sounds really fuzzy, But this kind of stuff is personal. When you’re making million-dollar decisions as a team, and you’re pursuing things, and they affect people’s livelihood, and we activate a lot of teams, I believe it’s very important to see how we are showing up in a room. And I’m the first person to say that I’m the slowest learner in this space. It’s taken me 30 years to get here. I’d like to see you guys get there in two, three, five years. How do we do that?
Jane Gentry: Yep. I like the intentionality of that. I think I’ve said this on the podcast before, which is I had a boss at one point who I thought did not pay attention to the impact that he had on people’s lives. And I called him out on it. And he said, Jane, all I can do is be myself. And I said, no, nothing. That’s not good enough. You have to be intentional in the way that you lead.
Michael McMahon: Yeah.
Jane Gentry: And you have to realize that every move you make has a material impact on a person or a family affiliated with this company. And I thought that was just kind of the laziest form of leadership I had ever heard. That’s not to say don’t be authentic. I do want you to be yourself. I just don’t want you to be the laziest version of yourself.
Michael McMahon: I so agree. Can, at any given moment, we can be the next best version of us and we either can look at our surroundings and look for the cues or by the way, you could be entrepreneurial in that and say that, you if I were to look in the mirror, maybe I should comb my hair. You know I mean? I mean, you know, there’s that’s, cause some people I think they get, actually this is being taught to a lot of young people and what we’re moving away from it is, to be true to yourself and genuine or authentic is some picture you have of one version of yourself and you think it’s unique. I would say if you had to go out and look for it elsewhere, it’s not unique. You’re joining some club, right? But that true to yourself and genuine is like, what is my heart telling me? And I know I’m speaking to you, so it’d be like there’s a power greater than us, right? It’s not intellectual, right? I mean, you can intellectualize it. So, know, what is this saying? And am I true to myself and genuine? And that’s really difficult in the workplace. You know, I can’t imagine organizations where they inherit senior members of their team. And I’m sure you work with a lot of those. There’s the risk management there when someone’s in a career is they need like, you know, they need opposition research on everybody that joins the team. And then there’s some way they’re handling them.
Jane Gentry: Because…
Michael McMahon: Righteously, the world has told them that’s what they have to do. It’s why I would never excel in those positions in a large organization because I don’t like to be handled. So therefore, I don’t like to handle people.
Jane Gentry: That’s why we have a relatively new AI powered platform that we’ve invested in to do what I say, increase time to diagnosis. So it doesn’t take three months to figure out where we need to be working in a client organization. But two of the pieces of that are what we call an identity assessment, a corporate identity assessment. Do all the people see the organization’s identity the same way? You see immediately where there’s misalignment. And because decisions are going to get bottlenecked again, because people don’t see the way we make decisions the same way. And the second one is a change assessment. Where specifically in the organization are, and I mean down to the name of the person, Where are we going to see resistance to change? And I think that helps with some of those things that you’re talking about, right? You know, the best strategy on earth. But if your leadership team is not aligned around how we make decisions against that strategy, and some of those people are really resistant to change, it doesn’t matter the brilliance of your strategy will never get executed on.
Michael McMahon: Yes. So true, so true. I believe, you know, I’m a little bit of a SEAL Team Six kind of guy and I never served our country. But the idea that there’s only so many people that you can have in your finite tribe that you can move and inspire and also see and react to. I 100 % believe what you’re saying. And I’ve also had that challenge.
Jane Gentry: Yeah.
Michael McMahon: So ego again, I used to think that if I shared my personal mission and vision around working with other people that I literally could be the answer to any human being who comes through the door, help them be successful. I honestly believe that I could create successful people. Give me your tired, your weak, your angry or whatever. So I loved helping people. Liked, know, I’d pave this road. I’d send them off on the trail in this place, you know. My intentions were true and genuine for me, but incredibly misguided.
Jane Gentry: Think about what you said earlier, and I think I’ve said this to you in other conversations. You can’t love a person for their potential. You have to love them where they are now. Right? Yes. Yes. You are like seeing the potential of people and seeing them in their future selves that they may or may not even want to live.
Michael McMahon: Yeah, now, yes. And now I’m in this role where I’m in the, this is the wonderful thing about actually living into this sort of CEO role. So I’m CEO and president, but I really have a collective presidency in five VPs and I get to play in that room. But the CEO role is, you know, mission vision, where are we going? Sort of resources, that sort of things and, and really bouncing back and forth. But I say, I always use the term from the bleachers. So I’ll walk up to anybody and I’ll go, from the bleachers, this is what this looks like. And what I believe it’s the message is saying is, I know I’m over here. I know I don’t know all the circumstances, but this is what I see. And a lot of times now I’m airing more on their behavior and their engagement as leaders versus me suggesting that, you know. From the bleachers this graphic designer looks like they’re taking advantage of you. You know, I don’t do that. I’ll say from the bleachers, it looks like when I look at you and your team, it’s very clear who you advocate for. I can see the touches, I can see the energy. Is there anybody that you don’t advocate for? You know, and then I use the term, go…
Jane Gentry: Right.
Michael McMahon: Should we do the NFL draft, which is should we sit in a room and place your team in a hierarchy and then let’s talk about those bottom two. Are they, and we use the term, you know, the fives and sixes in life, you know, can we make them a seven or an eight? Like with our effort and energy, it’s all what you’re talking about. It’s this, you can only have so many projects. You also can’t have,
Jane Gentry: Yeah.
Michael McMahon: A team of aces unless you’re prepared to herd them, right? Because in my opinion.
Jane Gentry: No, I agree with that. And I’m trying to remember what I’ve read recently that supports that with some data. It’s too many. I said I said to you in our earlier conversation, a lot of chiefs, not a lot of Indians. Right. And the tribe needs chiefs and Indians both. Yeah. Yeah.
Michael McMahon: Right. Well, having you found with, you know, with high achievers, I think high achievers will be successful anywhere they go. So, you know, giving them ultimatums is to me is not a way to modify any behavior that may not be in line with where we’re going. So I do a lot of with people with achievers, I go like, I need you to communicate what you see and what you’re trying, what you’re wanting to accomplish. And then, and then I can work with how they communicate that. And then I can say from the bleachers, that’s not how it’s occurring at all. You know, if, you know, from me, and then I go like, I’m just a guy and we all know I’m not just a guy, but I try to use language so that I can crack through the, you know, the, that outer shell, that knowing shell. And maybe have people make slight course corrections. And then I also like to highlight their talents. I go, know you’re a very talented person, but this is a skill set that I think you have that I admire. You know what mean? If someone has the ability to perseverate over an email and then generate words that move, like move people, if I can find that, the written word for other people, I just go like, how long did it take you to get here?
Jane Gentry: Now, think that’s an important role. And when we talk about inspirational leadership, and I know you’ve seen me talk about that and talk about how important affirmation is to people and that almost everybody I’ve ever met who’s been successful has had a person in their past who saw something in them they didn’t see in themselves and encourage that attribute or whatever, whatever that is. And I think that’s critical. And I hate that we have been talking for 45 minutes and didn’t get to a bunch of stuff we wanted to talk to. But what I usually do here is do a little rapid fire. Are you up for it? Sure. Okay. So what one thing Michael, did you learn early in your career that impacted your success?
Michael McMahon: The whole is greater than the sum of its parts, people specifically.
Jane Gentry: HOSTY Okay, how does that manifest?
Michael McMahon: I learned that if I could get people on the same page to do something, I would find myself like joyously reflecting on a period of time. And I would say to those people, do you realize that if any one of us took this on, like we’re still grinding at it? Like we’re so far from being done. I just think the… The idea of a well-motivated team heading in the same direction, it’s why everything is tribal here. Everything is a discussion. We call it the thing that leads to the thing.
Jane Gentry: I agree and that’s why we look for that misalignment, right? That’s the thing that all screwed that up. What one thing do you help young people learn in business?
Michael McMahon: Well, I said my father used to say, you got to do the time. I’m a big proponent of if you’ve earned it in life, communicate that to me. If you’ve earned it in life and everything, then so go your path. But I believe young people, they need to collide with other people that have different ideas, different thoughts, different processes. I think the real learning comes in between those times when people are either teaching or being taught. In that, you know, it’s the dark matter of, you know, life. And, you know, it’s that space no one sees. It’s why like collision and engagement, we’re in the experience, you know, an experiential economy. So I would like more young people to do the time in an office, in an environment where they’re colliding with people, a little less efficiency and purpose. Sometimes can really allow an individual to make strides.
Jane Gentry: I love it. They say the best time to plant a tree is 20 years ago. The next best time is now. Is there anything you wish you have done 20 years ago that you do now?
Michael McMahon: I wish I was, so this is what I wish, and it’s interesting because of the role that you play. I wish I was introduced to the idea of a rabbi, a mentor, a coach. Yeah, well, my dad used to say, my dad used to say everybody needs a rabbi and you know, we’re Catholic. You know, someone who is an advocate, an advocate for where you are,
Jane Gentry: I’m a rabbi.
Michael McMahon: And is open to sort of letting you imagine where you could go. And then with an occasional, a little occasional judgment here and there, like, you know, bring you in. Because once I started getting coaching and or feedback loop training, my CEO forum, so much amazing occurred in my life. So much abundance came. So That would be another young people thing. If athletes at the top of their game have a half a dozen coaches, nutrition, then why would you not think that would be an advantageous thing to do, is to have people in your life who are helping you reflect on your progress and maybe helping you see and achieve some of your goals.
Jane Gentry: About it like a guy, Seth Mikowski, who’s a mindset coach for professional athletes. And your CEO forum is your mindset, right? And it’s not because people are judging you in particularly, but they’re asking you questions and they’re forcing you to reflect. Yeah. What you reading right now? Or who are you following? I know you’re doing that.
Michael McMahon: Yeah, yeah. No, yeah, I go in and out. Maxwell has a brand new revision to his leadership book that is, so I read that 25 years ago. I’m reading it now. It’s actually giving me some insight on how I might be able to find my team, find themselves in a leadership matrix, because he’s got like 20 different leadership. I’ll say identities or skill sets. Really instead of working on leadership, someone can go like, wow, I’m a natural leader in these categories or these spaces. Boy, but I really would be better if I worked on this sort of leadership. So I love the way that book is structured right now. I wish I knew the title to tell you. It’s this 25th anniversary. It’s like 30 or 40 % new stuff. And it’s one of those things, leadership stories plus Well, actual stories of business owners or entities or brands. I love that kind of stuff.
Jane Gentry: Anything else?
Michael McMahon: No, I wouldn’t say there’s, you know, this is where I am now. I would have to, if I had known, I would pull up, I take a picture of every book I read and I have little, you know, snippets. I call them jewels that come from those books. And if I get a lot of jewels from them, I share it. You know, I don’t share the jewels. Just say, know, maybe you should read this book. But nothing else at the moment.
Jane Gentry: What do when you’re stuck, Michael?
Michael McMahon: Well, I learned by hearing myself talk, I’m one of those people, it can be painful. So when I’m stuck, I actually voice it. And then I learned way back, way back when I was a personal power Tony Robbins guy, and know, that was a significant… Yeah, you have, there you go. Well, I learned a little jewel from him and I use this when I’m stuck is ask your brain…
Jane Gentry: In the fire walk. Yeah.
Michael McMahon: Good questions. I use the term good. In other words, I would never say why am I stuck? Because it’ll tell me. I do a little more like, so how long is this going to take to find the next thing? You know, I’ll say something like, you know, what do I have to do? What do I have to do to take action? I’ll ask myself questions and then my head will go right towards it. The solutions are unique to each person. Does that make sense? So for me to work on something, sometimes I just have to get my head out of it. That means I have to go to lunch with someone and not even talk about that subject.
Jane Gentry: Yeah, I’ve been prompting AI on some of that stuff. Own personal AI, but I’ve been playing around a lot in AI for the year to see what would be beneficial to my clients. And so I’ve been asking AI some of those things. And it’s so fascinating. Is there anything that I didn’t ask you about that you wish I had?
Michael McMahon: That’d be great. No, but this is sort of respond to what comes around me. This concept of AI, one of the things that I’m very excited about and I’d rather have someone show me an example, but I’ve heard in lot of circles the concept of an AI colleague, in other words, creating an AI persona so that you could essentially be exploring an idea, but you could communicate that idea to an AI what they come at you from. What?
Jane Gentry: With a terrible you make your own AI buddy.
Michael McMahon: Yeah. Yeah. And there’s a possibility to me, I think there’s a possibility. If I was starting my business today, I could be an AI, I could build an AI buddy that is a well-trained CPA financial person turned business person that has started X amount of companies under a certain gross revenue, build that thing and then cue that for questions. And then over here, I could have another AI colleague that I’ve built and imagine that. You could do that at a fraction.
Jane Gentry: That’s so cool. Yeah, that’s so cool. Yeah. Thank you so much, Michael. I’m happy to with you. And I look forward to sharing this with people. And I hope you come back someday.
Michael McMahon: TELL US YOUR- All right. Been a pleasure. And I love this idea.
Jane Gentry: Thank you. And this is CEOs Unscripted. See you next time.
Michael McMahon: You
Jane Gentry is a strategic operating model advisor and former CEO of two PE-backed companies who helps mid-market CEOs redesign their companies when revenue grows faster than the business was built to run.
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CEOs Unscripted
Where Real Talk Drives Real Growth And Delivers Real Results For Mid-market Leaders.
Welcome to CEOs Unscripted, the podcast where real talk drives real growth and delivers real results for mid-market leaders. Each episode offers an unfiltered, behind-the-scenes look at the wins, the losses, and the playbooks shared by CEOs, founders, and executives. Grab a seat and join us for unscripted, honest conversations about what it takes to lead, grow, and scale in today’s business landscape.


