In this episode, Christina May sits down with Aaron Shapiro, the second-generation leader of Shapiro & Duncan, a 50-year-old family-owned mechanical contracting company, to talk about one of the hardest realities any business can face: unexpected succession. After the sudden loss of a key family leader, the company was forced to implement real-time succession planning, revealing gaps in communication, leadership development, and operational preparedness.
Together, they unpack what happened, what the company learned, and how they turned a crisis into an opportunity to build stronger systems, mentorship, and future leadership. From training pipelines and employee ownership to learning how to let people fail safely, this episode is a candid conversation about building businesses that can outlast the people who started them.
Christina May: So welcome to The Breakout Moment. So glad to have you here.
Aaron Shapiro: Glad to be here.
CM: Share your story about your company and a little bit about the succession planning, because I think that's something every owner, family — we even personally, right? It's like you don't really want to do your will, but you need to. And same thing with your company. So I'm really excited to dive into it with you today. So why don’t you talk a little bit about the company and growing up in the company?
AS: So Shapiro and Duncan, we're a family-owned mechanical contractor just in the DC area. So plumbing, heating, air conditioning for commercial buildings, hospitals, schools, data centers, government buildings.
CM: Data centers. That’s the new buzzword in there now, right? We didn't say that a year or so ago.
AS: Yeah. So my grandfather started it 50 years ago. This year, we're celebrating our 50th year, which we're very excited about. Grew up in it and now starting to become a leader in the company.
CM: That's amazing. You know, I share a really similar story with you. My grandfather was an electrical contractor and, you know, I got exposed to it. And I think that's why I got into business, because I grew up with him, you know, watching him. And, of course, there is a way I have to kind of explain it for everybody. If you remember, like Nick at Nite, you know, like the panels with the lights. There wasn't a computer, there wasn't a keyboard, like it was his old school.
You know, UL listing and all that, and learning that as a kid and kind of watching that. And I think that's kind of what bit me. I don't know if you have a similar memory or story.
AS: Yeah. I mean, my dad and uncle, growing up, they tried to find the most grimy, hardest thing they could do to get me to stay on the straight and narrow. So they had me installing grease interceptors in trash rooms and kitchens and in schools. And it kind of backfired because I fell in love with it and just enjoyed being with the people. The early mornings were tough, but you got used to it, right at the end of the summer when it's time to go back to school. You know, I got used to waking up early, but just being with the people and that camaraderie, that's what got me hooked.
CM: So I get that. So not the grease trap.
AS: Not the grease trap, yeah.
CM: Just to be clear, because that was a special love. For something like that, I feel like it has to be. So it was the people.
AS: Absolutely, yeah.
CM: And you were around people, obviously, that were older than you. So there’s a lot of mentorship, I'm sure, that happened there.
AS: Yeah. I mean, that's a big part of the culture of our company, is training and mentoring and, you know, pay it forward. There’s not enough people to do the work, so we have to train them and skill them up to take our jobs so we can then move up and become leaders.
CM: Absolutely. Thinking back to those formative years, was there maybe your grandfather, maybe not a family member, but was there a certain mentor, someone that really stood out to you in those years?
AS: Yeah. I mean, a lot. I feel like each position I had, there was probably a certain person that was the right fit there. I mean, my uncle who passed away, he was that one that kind of was consistent throughout the whole thing. But I would say each position had a very unique person. Sometimes a bad boss, as you learn the best of, “I'm not going to do it that way.” But other times, the good bosses, you're like, “How do I be more like that person?”
CM: That's amazing. Can you give me — like, I can give you a great example that happened to me. So very early in my career, I worked in publication, and I had a boss that was — I'm not going to say her name — but she was an interesting character. She didn't have a first name. She had three last names.
And all I could remember was just, if I ever move up into a position like this, I am not going to be like you. Just between the way that she spoke to people or the way that meetings were run, there were so many things I learned from that experience.
And I even think and reflect now, as I always tell employees here at Illumine8, that I want to make sure that some of the experiences that I had never happen here. And so if you're wondering why we have a policy about something a certain way, easy example would be: I worked in a company that was incredibly rigid, and I'm a caregiver. A lot of people are, and it's really hard to do life when you have a really, really rigid PTO policy.
And with that comes responsibility. But, you know, doctor's appointments and banks and stuff.
AS: They're not open.
CM: They're not open. And then, especially if you're a caregiver, you're taking care of an elderly person or you're taking care of a small child, how do you work around that? So that's become part of our culture here, flexible scheduling, things like that, just because life happens and, you know, the things that you can do, right?
AS: As a leader, set an example too of not only saying it's okay to leave early, but you have to do it sometimes yourself.
CM: I struggle with that. I struggle with that.
AS: Leave early, everyone's kind of looking around, but is it actually okay to take a day off? Is it actually okay?
CM: Yeah. So we have Summer Fridays here, and we cut off midday on Fridays from Memorial Day to Labor Day.
AS: Oh, that's great.
CM: Yeah. And we used to be slower, but we're not now in the summer. But it was just like, look, it's Friday afternoon. Nobody wants to be here. Including me. We do a lot of tracking of our hours, and whether someone's here or not, the work is not getting done productively Friday afternoon. You're almost doing everyone a service by letting them go.
AS: Yep. Regenerate and come back Monday morning ready to go. Yeah, yeah, yeah. I'd much rather have that.
CM: So you mentioned, as far as your mentors go, you mentioned your uncle. So talk to me a little bit about him. He kind of has a bit of a reputation and legend.
AS: Sheldon is definitely a legend, beloved by all of our employees, all of our clients, all the vendors. Definitely someone that is seen as one of the greats of the construction industry. So to have that as an uncle has been tremendous for me in my life.
But as far as succession, the saying of “what would happen if I got hit by a bus?” Like, how do you prepare for that? He passed away completely unexpectedly, and it forced us into that “what if” situation is real. For real.
CM: Yeah, yeah.
AS: So I would say a huge testament to him and his leadership is he did such a good job of delegating and hiring the right people that we are still in business, and we didn't miss a beat because of the way he led. He maybe didn't prepare the people under him for that to happen, but he let them be able to take the next step when that happens.
CM: Right. And, you know, talk a little bit — a lot of us, our families are part of the business formally or informally. I always tell people, if you have a spouse or partner and one of them's a business owner, God help you if the other one's not there. Better be really understanding. But those are our support networks.
In your case, you have other family members that are part of the business as well, right, that were going through this with you.
AS: Absolutely, yeah. So my dad was his brother and co-owner. We went through it together. Both my sisters are in it. Another uncle. So definitely a family business. Very family business.
I mean, there’s also a lot of employees that have been with the company longer than I've been alive. So I have a lot of uncles and aunts that are also in the family.
CM: I love the chosen family aspect, even in personal life. Being a chosen aunt is very cool, right?
AS: So we say we treat people better than family because if you get in a room with all of us and we're very honest interacting with each other, we don't want to treat our employees sometimes that way.
CM: Yeah, no. Treat them better than family. Yeah, yeah. I agree with that. I agree with that.
So they were going through this process with you. Obviously, this wasn't pre-planned. Now kind of sitting here, hindsight being 20/20.
AS: Right. You can look back and see what should have been done. Yeah. Right, exactly. It's given us opportunity to now — like my uncle is currently CEO and stepping away in a year — to do this the right way and start. You know, we took two employees, hired them as co-CEOs, and now we have a year to work underneath him and understand and start handing off those responsibilities, which I'm very grateful for, to be able to have that time.
CM: Yeah. Learn from what didn't go right the first time.
AS: Right. Learn from what didn't go right the first time.
CM: What were some of the things that didn't go right the first time?
AS: I don't know. I wouldn't say didn't go right, but just preparing things. Like communicating. When Sheldon passed away, there were some employees that weren't sure if the company was going to be around. So it's like, let's communicate and kind of have that reassurance to everyone that the company’s still alive and well and thriving.
And then other things like bank accounts and the urgent necessary things that just have to be done that you don't even think about, like signing paychecks. That's on the bank account. And when you have time to plan it, it's very easy to do. When you don't, everything's a panic and becomes very stressful.
CM: When you were going through this, who were the external experts, like the team that you needed to put together to kind of help guide you through this?
AS: Yeah, I guess it was definitely a team approach. Definitely the estate side, like lawyers. We brought in a company for succession planning events, so like, hey, what are the tools we need for me and my sisters and other individuals to grow those leadership skills?
CM: Accountant.
AS: Oh, accountant, yeah. Insurance. Absolutely. So there were a lot of things that never crossed my mind that we take for granted. Right?
Yeah. I think both sides of it really translate from the personal to the professional and who you are looking for for those things.
CM: So now that you guys have the gift of time, talk to me about what's happened since. So this kind of was a catalyst that pushed you guys to deal with succession planning kind of by fire. But let's talk about some of the results. What were some of the outputs?
AS: So our current CEO, Charlie, my uncle, now put a date on when he is planning on retiring. He's still going to be more of a mentor. He chose two individuals that he's going to be selling his shares to. So that's the first non-family members, which is very exciting. For me, it brought a new energy to the company, a new perspective.
CM: So employee-owned. You guys are moving to employee-owned.
AS: Yeah. Yeah. So I guess somewhat. It was two select individuals that have deserved it and worked their way up in the company. It’s been a very great experience. And like I said, new energy. My dad and uncle maybe are not as motivated for change. You know, they've kind of seen it. They're not inspired. You go to these two people with a good idea, they're like, “Let's get moving. How can we put a team together to make this happen?”
CM: That's amazing. That's amazing. So you guys have a formal mentorship program or training program?
AS: So on the field side, we have four individuals. They're training, and that's from the field side all the way up to CEO. Every position has a training plan. But especially on the field side, our apprenticeship program is very, very important to us. We're investing a lot of time and energy and money into individuals to get them trained up and move up in their career.
CM: And I think you made a really important point too, in that we talk about apprenticeships or training, on-the-job training, whether it's in the field or not in the field. There seems to be kind of a significant gap between what we're teaching and what we're actually doing in the field.
And I think there needs to be an approach to that, whether it's within your company or within your community, to really bridge that gap. You know, we're not Amazon, right? We don't have a whole huge team of people that's just dedicated to building out a university and pipeline for companies. We're smaller companies. We don't have those sorts of resources. But yet, at the same time, we still need a pipeline of trained people to come in.
AS: I mean, everyone wants an experienced person. Good luck right now finding an experienced HVAC tech or plumber or welder. But you can easily have one four years from now if you're willing to invest in them and train them. So it's having some vision of where you're going to be four years from now and hiring the people today.
One thing Sheldon always said was, “Why would I want to train all of these people just for them to leave and go somewhere else?” And his caveat to that was, “What if you don't train them and they stay?”
CM: That's a really great takeaway. I love that. I think for us, particularly whether in the trades or in any of these places, especially with the advent of AI — you want to talk about getting curmudgeonly and getting tired of change. I don't know about you, but I am like, come on, what's next? Yeah, this is getting a little old.
I mean, I love it and I embrace it, but at the same time it's like, oh, this is a good bit. But the rate of change that we're experiencing is having a direct effect on the hiring pipeline and the training pipeline of people coming into the company.
I don't have all the answers, for sure.
AS: No.
CM: But it's a tough nut to crack. It's a tough nut to crack. What other things came out of this? Obviously succession planning now is every — I'm sure not every role had a training plan before.
AS: That's relatively new. That's new.
CM: Right, right. What other impacts on the business?
AS: Yeah, I guess as far as the succession and training, one thing that is important is getting that person and letting go of responsibility, trusting the people below you and letting them take that risk and truly letting go. Letting people do their job and getting out of their way, which I think is a really hard thing for managers and leaders to do.
CM: And business owners.
AS: Yeah, you want to see everything. For someone to learn, you have to let them fail. And that's a hard thing to do because if you would have done it, you probably wouldn't have failed, or not to that level. So trust them, train them, and then just get out of their way.
CM: How do you deal with the failure side of it? I think that's the thing that's the hardest for experienced operators and owners because failure means the company fails. It's as if the company has to take a hit, right? And you have to let it happen.
AS: Yeah.
CM: And I believe it's so hard.
AS: I wish there was a better way, but I've tried to learn from other people's mistakes. It's just when you make a mistake, you never forget it. So it's just the best way to learn. We say, in 50 years, we've made a lot of mistakes, so we're starting to get good at this.
CM: Okay, over 50 years. And I always tell people, you're not hiring me because of anything other than all the mistakes I've ever made. You're not making them, so you get the benefit of every mistake I have ever made.
Creating a culture around “it's okay to fail” is also tough.
AS: Yeah. And the one thing we say is, “Bad news early is good news.”
CM: Okay.
AS: If you made a mistake, let us know. And we're not going to scold you for that. We're going to embrace that. And now you have a team to work together and fix your mistake. Where it starts to get out of hand is when you make a mistake and you hide it, and then it snowballs into something that no one can fix.
CM: And it's at the 11th and a half hour. And if you'd been proactive — I always tell people time is an option. If you tell me sooner, I have more options. If you wait to the very end, I am suddenly completely out of options and we're going to be in trouble, right? Like, please tell me in the beginning.
AS: So that's something as a leader too. When you get bad news, your blood is going to boil and your natural reaction is to get upset. But you have to think of that person and be like, “Thank you for telling me. Thank you for coming to me.” Because if you were to hear it from a client, that's a lot worse than if the person came to you with a mistake.
CM: Absolutely. Absolutely. Couldn't agree more with that.
Well, it was amazing to hear your story. I don't wish succession planning by fire on anyone, but I'm so glad that you guys were able to take Sheldon’s legacy and perpetuate it beyond the family into the company moving forward. So thank you so much for being here.
AS: Thanks for having me.