Green Flags when Interviewing Executives with Todd Sullivan

Intro: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with Todd Sullivan. Todd is a multi- time founder with lots of successful exits under his belt, leading him to found his current company, which is called Exitwise. Good to see you, Todd.

Todd Sullivan: Matt, thank you for having me. I'm excited to be here.

Matt Blumberg: Yeah. So my first question to you is what's Exitwise? Tell us a little bit more about it. It does sound like a business that everyone who listens to this podcast or watches it on YouTube should know about.

Todd Sullivan: I would love that to be true. Yeah. Exitwise, it comes from my experience building and selling companies. We're really a platform for business owners who are interested in selling their businesses to learn first about M& A and the M& A process, but then to build the best M& A team in the world, very industry specific team in the world to help maximize their outcome.

Matt Blumberg: Okay. It's great business. Very needed, I know that. So my question to you today is about interviewing. So you've hired lots of executive teams over the years. What are you looking for when you interview candidates for senior executive role? Top one, top two.

Todd Sullivan: Yeah. Boy, it's a great question and I think I've learned to do this over time. Whether I'm good at it or not, I think our current executive team is by far the best I've ever, ever had. So number one, I hire people that I can really trust. And so that's a big word, really difficult. How do you figure out how you trust somebody? And so I have the benefit of 52 years of experience, right? My work life, maybe it's 32 years, so I know a lot of people now, right? And you can see their track record and you can ask friends if they know somebody that maybe you don't know well enough. But I spend a lot of time with those people. I actually write personal letters during that process because this isn't going to be a weak process if it's somebody on the executive team, I treat them like a partner, right? Somebody that is going to be in the trenches with you in really important moments. I get to know their families. I think having an understanding of... They understand your family, you understand their family, it gives a pretty good perspective of who they are and where they're going, where they've been. And I think lastly, the best thing I can do is hire people that I actually know. So I've been fortunate enough on our team to really know for a long period of time having worked with these people, kind of similar to you and your co- founders, right? You've known these people and so that trust is there. I know that's a hard one, Matt, to figure out.

Matt Blumberg: No. Really, it's such an important one because I always say the most important thing in leading a company is creating a healthy dynamic on the executive team. And when you have that, things go well and when you don't, it's a disaster. But the foundation of a healthy executive team is trust. So interviewing for trust or hiring on the basis of trust is really important, but it's really hard to do if you don't know people because trust is something that tends to be built up over a long period of time. It does involve getting to know people personally as humans and sharing vulnerabilities and getting some of that back. And doing that from a cold start can definitely take a while. And some of the techniques you talked about are really interesting. How much of it comes down... If you're talking about someone you don't know, how much of it comes down to just being in the process with them for a long time? Or can you accelerate it? Like if you have a hire that you've got to make, can you spend 24 hours with someone inside of three weeks and get it, or does it just have to be over three months or six months of kind of getting to know them longitudinally?

Todd Sullivan: I don't think I have a great answer for it, but the people that I will hire more quickly, they come from the networks of the people that I know and trust, right? So I absolutely have to spend time with them. They have to have certain criteria, right? At Exitwise, you have to have built and sold a business. And then the second part of that is having empathy for your fellow founders. Because this is a really difficult process that you're going to go through, and I need to know that you're going to be there in a very empathetic way and handle the crazy that happens in that 11: 00 PM call that you're going to get when somebody's freaking out about this lack of translating emotion to finance. So I'm looking for very specific personalities. If they're going to get hired quick, they have to come highly recommended for people that already work here, that have been through that process with me. But even then, I think it's really interesting to write that personal letter of what life is about, what this business is about to you, and what you're really looking for is what comes back. Because-

Matt Blumberg: Clearly it's not about what you said- inaudible

Todd Sullivan: No, no. You're waiting for what comes back. And I think I've made a lot of mistakes in previous situations, so I do not have the magic here, but so far this has worked incredibly well because it leads to incredible amount of transparency. And some might... If they were sitting here going, " Wait, you share everything?" We're small enough team today where everybody knows what we're trying to accomplish and why and how we're going to do it. And I think that's critical, particularly as first hires. Sorry, I'm not giving more on future hires, but that's where we are.

Matt Blumberg: It is a great technique and a great piece of advice, and one of the reasons I ask this question regularly on this show is to sort of build the pattern up over time. And I haven't heard this particular technique yet, but I really like it. Thank you for taking the time to share that.

Todd Sullivan: Oh, absolutely.