In “Focus on Impact, Not Money,” Todd Siegler shares candid lessons from a career spanning nearly every C-suite role—CFO, COO, CAO, CDO, General Counsel, and eventually CEO of his own company. A Princeton and Tulane Law graduate, Todd reflects on the differences in executive roles across organizations, the dynamics of C-suite interactions, and how managing direct reports effectively builds trust and results. His message is clear: the best leaders aim to create impact, not just chase titles or compensation. For aspiring executives, his story is both an insider’s view of the C-suite and a roadmap for building meaningful leadership.

For the full interview: https://ocns.co/coo-cfo-todd-siegler-focus-on-impact-not-money/

10 Min Clip Transcript

Michael Mitchel: [00:00:00] Hello, this is Michael Mitchell. I launched the podcast Exploring Talent in 2019. In 2021. I renamed it CXO Conversations. Hope you enjoy this episode and will subscribe to CXO conversations. For more great interviews, visit oc national search.com or your favorite podcast platform and subscribe. Enjoy. All right.

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Today we’re in the ballpark district of Denver and joined us on Exploring talent is Todd Siegler. Todd graduated from Princeton University in Tulane Law School. Talk about a well-rounded CXO. He has been A-C-F-O-C-O-O, chief Administrative Officer, chief Development Officer, general Counsel, and save the CEO title for his own company.

We’ll discuss matters around the personal journey of holding these different positions, differences in the roles from a personal and organizational perspective, C-level board interaction and management of VP and SVP direct reports. Welcome to the conversation Todd. Please, uh, share an interesting fact about yourself to our listeners.

And what you are doing today. Well, first of all, 

Todd Siegler: Michael, thank you for inviting me today. Uh, and thank you for the kind introduction. An interesting fact about me that you [00:03:00] don’t know. Um, I was a very bad English teacher in China for a year. And so after I graduated from college, uh, many years ago in 1988, uh, I spent a year in China, uh, teaching English and then, uh, left about.

30 days after the tenement square massacre in 1989. So, really, wow. Uh, a crazy experience. Um, has nothing to do with what I’m doing now in terms of what I’m doing today. We’re doing two things. One is we’ve established a legal advisory and business advisory firm where we are helping companies with financings, m and a transactions restructuring, uh, and outsource general counsel work.

The second thing we’re doing is developing interesting products around commercial contracting. And so our first product at Knock on Wood, we are hopeful to launch over the next quarter, is around auto negotiating non-disclosure [00:04:00] agreements and m and a transactions. It is something that causes a lot of friction in m and a transactions.

Uh, NDAs have the same 12 provisions across all NDAs. And we’re trying to optimize that process. And one that my partner and I, uh, understand deeply. 

Michael Mitchel: I wonder how many, how many people start their career thinking this is gonna be my linear progression, uh, where I’m gonna get and how I’m gonna get there, versus how many people take advantage of opportunities.

And is that intentional or accidental, or does that happen more often than I think people realize? It is a great 

Todd Siegler: question. I, I think it’s accidentally intentional. And so I’m gonna combine the two I. I think if you go and you find opportunities where you can have a significant impact in whatever role you play, I don’t care if you come in on the finance side, legal side, business side, and you can prove that you can do a good job.

Um, and drive the business forward. Opportunities will present themselves. 

Michael Mitchel: I, [00:05:00] I know in my, I, I know in my case specifically, I think this is true, most recruiters, no one grows up wanting be a recruiter. Um, and I started my career at unit Parcel service in the back of a truck throwing boxes. And yes, they do throw the boxes, people, um, I moved into sales and they had a strike.

Being management, I had to drive. And then when the start goes over, I would found myself in the back of the truck again. And I did the math quick. I’m not getting out until my replacement comes in. And I wrote a memo with my wife of 22 years now and where to go to find people. And I got transferred the next day and I’ve been recruiting and never planned on it.

It just, it just happened. And it’s a, I think this happens so many more times than people realize. 

Todd Siegler: And I agree with you and I think that’s why when people ask me, gosh, should I take this job or that job? I try to focus people on. Where will you get the right experience? Where will you have a role that gives you a meaningful act impact in the business?

And maybe third, let’s focus on how much you’re gonna make because we can all make money. But if I [00:06:00] get great experience, if I have a, a huge impact, I’m gonna get more and more responsibility and get to grow in my career. And so, so I, I think you’re right on. It’s, it, it happens as you build that credibility as you.

Uh, are able to deliver results at a company, you’re gonna have a higher likelihood. You get more and more responsibility with folks that know you versus, look at my resume, come hire me. 

Michael Mitchel: And you, you mentioned making a, a job choice based on money. There’s two things. One, I read a statistic years ago where money is the sixth reason why people make a change.

Um, but my, my advice to people based on my own experiences, never, ever make a decision based on money. It’s always a short term. Mistake decision, but I wanna kind of, moving on, I wanna pivot over to, I really am curious about this role. What is a chief admin officer, a chief administrative officer? 

Todd Siegler: And, and so in, in my, uh, experience, uh, when I became [00:07:00] a chief administrative officer, I, I handled the, the following functions.

And so the HR admin function, real estate, legal, um, it, it’s really all of those things in and around. The admin real estate legal function. Um, and then unfortunately I also got the CFO title at the same time, and so I ended up running the finance side as well. But I think typically that chief administrative officers handling your HR real estate facilities and the legal function.

Michael Mitchel: How does the, how would you say the role impacts the company on both a technical and strategic level? 

Todd Siegler: Again, I think it depends on the company. In, in the company that I did this role for, I had a CEO that really respected the HR function, uh, as well as the legal function. And so you’ve got to have an outsized impact.

Uh, in that role. I think if you’re at a business that does not necessarily respect those two roles, um, it’s harder to have that [00:08:00] impact. And typically those companies don’t have a chief administrative officer. They’ll have a VP of HR and a legal counsel and not have them on the executive team. And so I, I think as you think of roles where you’re going to have a, an impact in a business.

I think it gets, it’s important where that role fits in the organization, and I think it tells you a lot about the importance of that role depending on where it fits. 

Michael Mitchel: So would a company who has a, a chief admin officer also have A-C-H-R-O, or would it be more of a VP of HR who reports to the the CIO?

It’d be the latter. How many hours of how many hours a day did you work? 

Todd Siegler: Uh, that was a, a company, uh, called Market Force. Um, where I got, I joined there, uh, after Verio and I was, uh, the first hire after the three founders. And so all of our hires were uphill from there. Um, but it was, uh, yeah, you, you did, you played a lot of different roles and worked a lot of hours, but.

If you’re excited about what you’re doing, it, it, it’s fun. 

Michael Mitchel: [00:09:00] What did you say? What did you take away from that experience? 

Todd Siegler: You know, that was a, uh, I, I spent nine years there and so I got, I got to wear lots and lots of different hats, and so I came on board initially to run the corporate development function, and so we were a consolidation play in the mystery shopping space.

So what does that mean? Our investment thesis was that we could buy 5, 6, 7 companies in a space called Mystery Shopping. And that’s where you send independent contractors into a retail location to do an audit. So they go in anonymously and they basically fill out a survey of 30 questions, um, about an operational audit.

And we looked at the industry and said, gosh, this is a massive market. Right when you think about mystery shopping and audits and customer sat and customer experience broadly, and our thesis was we’d go in and buy these companies, add technology and scale the business. And so initially I came on to do that.

Uh, [00:10:00] they found out I was a lawyer. So the next day I got the general counsel title. Uh, and then over time I got more and more responsibility where ended up being the chief administrative officer, ran the corporate development function, integrations, legal and finance. And for folks that get to know me, I also ran the technology team for two years, which will make many people laugh.

Uh, but yes, I got to wear lots of different hats. And that to me is what is, that’s exciting. ’cause, you know, from, from a career path for me, getting those experiences or, or of the priority to me. And, and those are things that stay with you through your career, how much you make, uh, where you work. All that changes over time, but it’s those experiences that become the foundation to allow you to grow and do more things.

Michael Mitchel: Speaking of experiences, you’ve been involved in more than one multibillion dollar with a. Transaction events. 

Todd Siegler: So, so as part of my career, I, I’ve been blessed to, uh, to make lots of money for [00:11:00] other people. And so I’ve been involved in $2 billion plus transactions. Uh, that, you know, knock on wood, were great outcomes.

Unfortunately, those were my first two in-house roles, and so I assume that’s what happened with every opportunity. Uh, I have since learned that’s not the case. 

Michael Mitchel: So is it like the movies where it’s, you know, one o’clock, two o’clock in the morning and the deadline is that at 4:00 AM and everyone’s, they’re kind of wallowing their own filth with piece of boxes and, you know, high drama.

Todd Siegler: Yeah. So, yeah, so transactions, I, I think, uh. It’s interesting, I, I’ve been involved in a hundred plus m and a transactions, maybe more. Um, and each of them is a little bit different and, and almost irrespective of size, it’s the same issues. Uh, what I tell people is the bigger transactions, I don’t feel badly calling my CEO and waking ’em up at two in the morning to say, Hey, we’ve got an issue.

Um, and resolving it. If it’s a $5 million transaction, it, it’s maybe a little bit less stress. 

Michael Mitchel: [00:12:00] So what’s, um, what’s a war story from one of them? You know, you tell, you tell to appear over a drink that’s like, you’re not gonna believe this. 

Todd Siegler: Yeah. So one of those larger transactions, which I, I won’t name, uh, we did have to do that.

And I had to call my CEO in, in Dallas at probably midnight, one o’clock in the morning and try to explain to him that he had a legal issue in the transaction. And he said to me, well, Todd, you’re my lawyer. And I said, well. Gosh, technically I’m the company’s lawyer. And so that was a, a hard conversation and we had to hire personal counsel for, uh, my CEO, who by the way, is one of my biggest mentors.

He’s been phenomenal for me. Um, but that was just a, it was a funny conversation with me having to tell him, no, I’m actually not your lawyer. I’m the company’s lawyer. Uh, but it all worked out fine. We solved all the problems. Everybody did well. Uh, 

Michael Mitchel: you know, I mean, going back to your alphabet soup of titles, um, how did the different roles happen?

Some of ’em were at the same [00:13:00] time. Some of ’em were be, you know, what was behind that? And just tell me, I know we, we kinda hit on it earlier, but, right. You know, please feel free to expand. 

Todd Siegler: I think a lot of what I’ve been lucky with is finding roles where you come into a company doing a role that you are, are, are, are very good at, right?

So if, if you come in and say, I am an expert at X, right? I may come in as your general counsel and then folks see you, your ability to do more than just that role and you get more and more responsibility. Uh, you fortunately or unfortunately end up with more and more roles. And, and for someone like me, I like having those different roles.

Um, but it is interesting as people ask you, gosh, Todd, what are you? Uh, oftentimes I just fall back on, I’m a lawyer ’cause it’s easier to describe, but I’ve been blessed to have lots of different roles and lots of different experiences, which allows me to sit with clients or sit with companies and say, tell me what your problem is [00:14:00] and let me see how I can help.

And you can wear those different hats. To go help solve interesting problems, which is at the end of the day, what I like doing. 

Michael Mitchel: Going back to your ca CAO, uh, time, because I find that role very fascinating. Clearly. How did, how does that role prep someone for being a COO or a CEO? 

Todd Siegler: You know, I, I, I think it, it, it helps, uh, I would say as I think of that CEO role or COO role, it, it’s funny, I have a.

An odd definition for C-O-O-I-I, I like to tell people the COO is all the things that the CEO doesn’t want to do. 

Michael Mitchel: They make the trains run on time. 

Todd Siegler: Exactly. And so you get to do the things that your CEO says, gosh, that’s just not in my, you know, in, in my, in my lane and, and what I want to do. And so I, I, I think that that COO role and how the CAO role helps you.

I think depending on how strategic that CAAO role is, you get exposure to lots [00:15:00] of different aspects of the business, which is what you want for that CEO role or COO role. You want to be comfortable managing a sales team and understanding how to manage a pipeline and managing, uh, quote to cash, all those types of things.

You want to be comfortable in the finance arena, you want to be comfortable in the admin function. And this doesn’t necessarily mean, gosh, I gotta be an expert in every single one of these, but I need to be smart enough to understand how to drive those organizations, how to set the right objectives, uh, how to get people to be successful.

And, and I think at the end of the day, as you think about building successful teams, the key for me is tell people what you expect. And then celebrate when they’re successful. Like, like I look at it and say, as you get older, you realize if your team is wildly successful, you look great. Right? So, so the idea of hire a people, hire folks that are smarter than you, which in my [00:16:00] case is pretty easy, right?

And then let those people do a great job if you have to micromanage all the great people you hire. Either you’re not hiring the right people or you’re not managing ’em the right way. And, and so I, I think that’s the, the other part that I think is really important as you think about building teams. 

Michael Mitchel: Yeah.

What I was at a, a conversation with a, a panel of CHROs. It was a free flowing discussion and I was really surprised to hear one of them say, I do not know what my CEO expects of me. Yeah. And that, that floored me. ’cause I thought, well, you’re at, you’re at the pinnacle of your career, some would say. And when you’re at that level, you’re supposed to know it all.

But clearly that’s not always the 

Todd Siegler: case. And I think that’s a function of both that CHRO and the CEO. Right? So, so I think it, it’s a two way street, right? So I look at it and say, you want people on your team that yearn for accountability. That, that want to be accountable, that want to be [00:17:00] successful, that want to grow their careers, and that’s your job as an executive.

I wanna bring good people on. I want to grow them. I want to be out in front of anytime they want. You know, any, anytime they get a raise or they get a promotion, I want to be out in front of it. If my, if my employees have to come to me and ask me for that promotion, or ask me for that raise, I missed it.

Right, and, and so I, I think it gets to the same point, which is if you’re the CEO of an organization, each of the folks on your team that are direct reports to you should understand, here are the overall objectives for the objectives for the business. Here’s where you fit in, here’s where you have an impact, and here’s what I expect.

And guess what, then if you get the right people on the team, they will run through walls. They will have a sense of urgency, and they’ll get it done. If we come to work every Monday and say, gosh, what am I gonna do today? You’re, you’re not building the right structure. 

Michael Mitchel: I don’t think. You’ve been both A CFO and CLO.

Which role do you feel has the most immediate impact [00:18:00] on the organization? 

Todd Siegler: And I keep saying this to you and I apologize. It depends. Right. So I, I look at it and say some organizations only have that CFO who ends up being an operational CFO and does a lot of the stuff that the CEO doesn’t wanna do.

Sounds a lot like a COO, uh, and sometimes you have a COO that may even manage the finance team, right? So, so they end up being similar roles in, in organizations. I think both can have a massive impact. Um, and it just depends on the organization. It depends on your CEO. Um. So, so that, that’s a hard one to answer.

Does it depend on the 

Michael Mitchel: culture of the company if it’s mid-size or enterprise? 

Todd Siegler: Yeah. Typically the, the smaller company won’t have A-C-E-O-C-O-O and CFO. It’s just too many C-level folks, right? You’ll have a CEO and a CFO and that CFO will probably take that operations role as well. Um, as you get bigger, you see a little bit more.

Uh, specialization, right? Where that CFO will [00:19:00] have the controller function, the fp and a function may have an admin function, may have a legal function, and your COO may be more sales and operations, uh, focused. So, so I think it just depends on the size of the company. Um, and I think what you’ll see as you think about your career is folks will come up through that finance.

Lane and shift over into the finance slash coo. You see that quite a bit. Um, and then you’ll see folks come in from the operation side, go into that president or COO role. 

Michael Mitchel: I know you’re gonna say it depends, but I’m gonna ask anyway. Which has the greatest strategic influence? 

Todd Siegler: Yeah. You got me again, I, I gotta think of another word besides it.

It depends, you know, I, I, I think maybe the, the, the way that I would answer this is as you look at new opportunities. Uh, to me it’s all about the team, right? And so I, I, I’m less, and you’ll see it in my, in my background, I’m less fussed by what you call me. I’m more [00:20:00] concerned about what role and what impact I can have.

And so finding that right team, finding a team that we all know what we’re good at, but I also respect my HR person giving my head of sales advice. Maybe if it, even if it’s on sales, I don’t care. But I want to have that respect, that mutual respect, uh, among my team. We’re, we’re all in this together. We’re all trying to make the business better.

And it doesn’t feel like, Hey, I’m telling you you’re doing a bad job ’cause I want your job. No, no, no. I want the company to be better. And I’m not just telling you, Hey, I think we should do it a different way. I’m giving you some suggestions on how we might go do that. Um, so, so I think a lot of it gets back to team, always right?

I always tell people. Give me an awesome team and a mediocre idea and we’ll crush it. 

Michael Mitchel: You, you mentioned that you’re not big on titles, and I just had coffee with the executive today and this person was looking at a couple of opportunities and the title of Head of Blank [00:21:00] came up and I said, I know it’s an emerging company, but you may wanna have a C title on that.

Not so much from an ego perspective, but because it sends a message to the organization. That what your responsibility and what your authority is. But if someone’s going after that CT title, just from Eagle perspective, and that’s just the recipe for disaster. 

Todd Siegler: Uh, and I agree with you and I, I, I think unfortunately we live in a world as we transition from job to job where I look at your title and I say, gosh, you’ve done that before.

Come do that for me. Right? And so when you get into this head of X versus CFO, I’m a head of finance versus A CFO, why? It begs the question. Um, but at the end of the day, I, I still rely on, if I do a phenomenal job and I go in and I’m the expert in finance at that company in six months or 12 months or 18 months, as we grow, they’re gonna tell me, Todd, you need to be the CFO, right?

Or they’re gonna tell me, Hey, you need to be the see this, if it’s the [00:22:00] right experience and the right company. Work hard, and then the role will come, and if it doesn’t go 

Michael Mitchel: find something else. Aside from personal career accomplishments, why should someone want to become A-A-C-O-O? Why should you want, 

Todd Siegler: um, you know, I, I think as you look at a COO role, it’s really that number two role at an organization and for me.

It’s, it’s that ability to have an outsized impact at a company. And, and so I think as you progress in a company, you get to have a bigger impact. And, and what do I mean by that? I mean, you get to mentor and grow people. You get to make decisions that have a ma you know, massive impact on the business. You get to, you know, affect strategy in the business.

And, and so I, I think. You know, as I look at elevating within an organization, it’s not just about, gosh, Todd, you got to be a C, whatever. It’s the impact you have, not only on the business, but on people and [00:23:00] growing people. And then, you know, my, my favorite, and I’ll tell you a story. My, one of my favorite stories is, uh, when I was at Market Force, I had a guy that worked for me that managed all of our integrations.

And did a phenomenal job. He did such a good job that we eventually promoted him to COO, so he became my peer. And I looked at that and I said, that’s one of my fondest memories, one of my biggest accomplishments. And so that’s the kind of stuff that I think’s really exciting as you go into a business and grow it.

And at the end of the day. If you can promote all your people where they don’t need you, awesome. I’ll go find something else to do. 

Michael Mitchel: I think you hit on something. I think that’s a sign of a very strong leader, um, when someone can help promote someone to become U of A peer or above them. Yeah. I have a client that one of his sellers actually became his boss over the years, and I’ve always respected him for that.

’cause that’s, that’s not an easy thing for someone to do. Well from a, a [00:24:00] management perspective and a, and a ego pride perspective. 

Todd Siegler: Yeah. And I, I think when ego and gosh, how do I look in this transaction gets involved, I think you make bad decisions. And, and I look at it and say, you know, my role oftentimes at a company is to build scale, build process and build people so the company doesn’t need me, which sounds, what are you talking about?

But at the end of the day, that’s my job and I’ll go either figure out a new role at that company. Or I’ll go do something else, but, but have the confidence because you went to those different roles to get the right experience. That at the end of the day, if you’re willing to work hard, you can get stuff done and you’re somewhat intelligent, you’re gonna find a job.

And so that’s been my philosophy in life and so 

Michael Mitchel: far, so good. One of my favorite questions to ask, um, prospective candidates, regardless of the role or level. Is their existing role or their previous role is what’s [00:25:00] your legacy? And so, which is a great question. Yeah. Because I think that that’s really goes, goes right.

What you’re saying is you shouldn’t, I don’t think you should be in it for yourself. It’s what, what can you contribute to the organization, to the team? 

Todd Siegler: I, I, I think you’re absolutely right and, and I look at it and say. I get the reality that we all have to make enough money to pay our bills, support our family, support our lifestyle.

I got it. But at the end of the day, I think the bigger impact that you have is the legacy you have, right? So is that, you know, folks you used to work with 15 years ago that come back to you and say, Todd, hey, this, my experience with you was awesome and now I’m the CEO of X. Those were awesome calls to get.

Like I love those versus, Hey, how much money did you make when you sold that company for x billion dollars? In my case, nothing. But it’s irrelevant. But, but those are the things that I, that I think are important. But again, we’re all different in what motivates us, but that’s, that’s what motivates [00:26:00] 

Michael Mitchel: if someone is a newly minted vp, regardless of the industry or.

Sector, whatever. What should they be doing today or for their career to prepare themselves to become A-C-O-O-A-C-E-O at a c-level? That’s a pretty broad question. I know. 

Todd Siegler: I, I think it’s a couple things. I I think it’s continue to stretch yourself, continue to find yourself in roles with responsibility where you feel a little bit uncomfortable in your seat.

And, and, and another words, a couple words of wisdom is we’re all uncomfortable in our seats. Right. We all feel like we’re posing right as we do these different roles. And, and my advice would be continue to strive to do new things, different things. Don’t get into a comfort zone where you come to work, you can do it with your eyes closed and it doesn’t stretch you.

Um, those are the ways I think that you get more and more responsibility. I think those are the ways that you get to elevate within an organization. And at the end of the day, that’s what makes you more [00:27:00] valuable and more marketable in the next role that you take. 

Michael Mitchel: What, um, what aspect of being at the C-level surprised you?

Todd Siegler: Gosh, what surprised me? 

Michael Mitchel: Um, 

Todd Siegler: you know, I, I think the, it’s the impact that you have, which has been a pleasant surprise. I think sometimes, and again, this gets to be team dynamics as you’ve been at lots and lots of different companies. You know, sometimes you’re surprised by the politics and the team dynamics.

Even at the C level. You, you often look and say, gosh, why are you worried about that? Um, you see a lot of egos in the room sometimes that you scratch your head on. Um, but I think that’s at any level. Um, but it’s, I I would also say what surprises me is you may have the same title at two different companies, and it’s two very different jobs.

Um, which is exciting, but it, it, as you look at new opportunities, A CFO at company A and a CFO at company B [00:28:00] may be very, very different. And as you go apply for those jobs, or think about taking those jobs, ask the questions, what does it, what does it mean to be the CFO? What decisions do you get to make?

What role do you get to have? Um, so I, I think the titles being the same and the jobs being different has been a bit of a surprise. Um, but also the impact you get to have. In a positive way. 

Michael Mitchel: You really started to hit on this earlier, but I want to kind of expand a little bit. What part of being at the C level did you find most rewarding?

I, I know you’re gonna talk about the new experiences and the challenges, but, uh, expand if you would. 

Todd Siegler: Yeah, and I, I think there’s also another affliction I have, which is I like to mentor. I’m a, I’m a really bad youth coach, and so I have, uh, coached girls basketball. I got to do that for, gosh, eight years.

Um, I love to mentor people and so that’s been one of the more rewarding things that, that I get to do is seeing people grow. Um, seeing your teams do well. Um. [00:29:00] That’s probably the more, most rewarding part for me. I mean, I think all the stuff we talked about earlier about the positive impact and the significant impact you can have on the company, um, is important.

But really the mentoring’s been, it’s been fun. 

Michael Mitchel: How do you manage your direct reports, VPs, EVPs, SVPs, and how did you bring the best out of them? 

Todd Siegler: And, and so a lot of that for me, and we’ve, we’ve hit this a lot, is, is setting objectives, um, making sure folks understand expectations. Having discipline around one-on-ones.

I know that sounds really silly, but, but having a 30 minute one-on-one, and I look at that as that is a meeting for my direct report to come to me. And it’s their meeting. And the first part of that meeting will be, you know, how are we doing on the three or four objectives that we’ve got, but the rest of it’s for them and keep the meeting.

Oftentimes we get really, really busy and we say, gosh, I [00:30:00] don’t need to meet with those folks. Um, and so, so that’s part of it. I think, you know, we talked about this earlier, hire great people, hire a players, whatever you call it, and let them do their job. I think we’re, where people get confused is they feel like they’ve gotta micromanage their great people.

Tell folks what we need to get done and then have the confidence they can get it done. And when they have an issue, they’re confident to come to you. And when they do a great job, give them the give, give ’em the kudos. Like I, I look at it and this will sound silly, and I say, guys, when you guys do a great job, it’s all you.

When we mess up, come to me. Right? It’s on me. And that gives them that comfort to say, gosh, I’m gonna go try new things. I wanna run through walls because, you know, my manager is sitting right beside me. Like I, I think another thing that’s really important is if I expect you to stay late on a Friday or work over the weekend, I wanna be sitting [00:31:00] beside you, right?

I want to be eating the cold pizza with you. If I tell you, hey. Hey, you know, John, you gotta be here at four o’clock on Friday and work the whole weekend. I’ll see you on Monday. That doesn’t work. And so I think it, it’s, it’s that lead by example, you know, give your team the leeway to be successful and then give ’em the credit for doing a good job.

Michael Mitchel: So let’s talk about board experience. Um, what are the differences between a board that’s doing well and not doing well from your, your perspective? 

Todd Siegler: Yeah. I, I think from a board perspective. It, it comes to the ceo. I really think it’s the CEO’s responsibility to find the right cadence and the right way to manage a board.

And what I’ve found to be the most effective is step one, is how do I get the right mix of management team folks, if I’ve got investors of investor folks, and then most importantly outside industry directors. And so I wanna get the right [00:32:00] mix. I wanna have the right size. I don’t need 72 board members, and I don’t want one.

Right, but find that right size. Is it five, is it seven? What’s the right number? And then I wanna manage that board. And so what does that mean? I want to have one-on-one calls every month. One hour. I want to have a set agenda for my board calls, and I want to have a pre-meeting with all my board members.

So when I get to the board meeting, they understand the overview, I know the questions they want to ask, and then we can focus on the meaty problem or issue we want to hit with the board. And when you watch a well run board meeting where you’ve got the right agenda, the right me board members, you know the questions and you know how it’s gonna flow, it works great.

If we walk into that board meeting, we say, gosh, we got a board meeting. What do y’all wanna talk about? It doesn’t work well. And so I think it’s that organization around it. It’s engaging your board members ’cause they want you to be successful, especially the investors. Um. If you manage it the right way, I think they can be really powerful.

Michael Mitchel: I also imagine at the board [00:33:00] level, these are people who are very successful in their field. Mm-hmm. There’s a lot of ego going on, and so how do you, how do you work with that? How do you manage that? Or 

Todd Siegler: do they manage you? It’s tough and I, and I think part of it is the one-on-one calls, right? Part of it is that CEO building the relationship with the board members where they can vent to the CEO versus vent in a board meeting.

Um, and it’s picking the right board members. Yeah, 

Michael Mitchel: but not all of ’em are like that. I know that there are board members out there that are very soft spoken and they’re there because they want to contribute as well. So I don’t want everyone to walk away with a feeling that board members are, all of the board members are like that.

Are boards a blessing, a curse, or both? It 

Todd Siegler: depends, and I keep saying that, you know what I, I, I think it, it’s important and it’s incumbent upon that founder, CEO, that executive team. And it goes to the, the team you end up hiring. It’s, I want my board to be effective for me. Right? A [00:34:00] lot of these folks that sit on boards can be hugely impactful to a business if you use ’em the right way.

And I, and I just think it’s, it’s, it’s use those, ’cause you’re right, there are lots of big egos on boards, um, and you see it, right? It’s this master of the universe. I know it all. Um, and, and I think as you build relationships with your board and they realize, gosh, I really understand the business. I really understand what these guys are trying to accomplish.

You get a little bit less of that. Does it all go away? Of course not. 

Michael Mitchel: So we’ve, we’ve gotten your, your perspective on board as a CXO, but now as a service provider, what’s your perspective? 

Todd Siegler: You know, it, it’s been interesting and so depending on the companies that I work with, I will have. Everything from no role to helping run the board meeting.

And so it, it’s across the board. Um, what do I prefer? I prefer being on the team and running the helping run the meeting. But as a service provider, it just depends on how people want to engage with me. And it, and it goes back to [00:35:00] my original thesis on how I approach clients is, listen, what is the problem you need me to solve?

Where do you need me to have an impact? And so that’ll drive how much impact I get to have on, on board meetings. 

Michael Mitchel: When you made a strategic decision for a direction of the organization that didn’t have the outcome that you had attended, what was your initial thought and what was your takeaway? So 

Todd Siegler: I, I look at business and say, the most important thing you can do is do the very best you can do to understand the facts, but make a decision.

I, I often call it analysis paralysis. I never have perfect information, but make the decision and then always recognize that even when I make that decision, if it’s the wrong one, we’ll figure out how to fix it. But don’t be afraid to make a mistake. Make the decision and move the business forward. And, and I think you want to, you know, my advice to folks is 

Michael Mitchel: learn from your mistakes.

That’s exactly where I wanted to go [00:36:00] next. ’cause I really suspect there are those out there who think they can’t make a mistake if they wanna become a CXO. You’re telling them, embrace that mistake. That’s the only way you get better. If someone says, I’ve never made a mistake. When you’re lying, you’re not trying hard enough and you’re missing out on a learning experience.

Couldn’t agree more. It’s kinda like going 

Todd Siegler: scan. If you never fall, you’re not trying hard enough. So I’m always trying, and I agree with you. I think it’s, if you find yourself in a culture. At a business where everybody that makes a mistake gets lambasted and ridiculed and doesn’t, it’s, it’s, it’s, it’s not a culture where I can push the envelope and it’s okay to make mistakes.

My advice is go find something else to do. 

Michael Mitchel: How did all the previous experiences and duties of the mini c roles you’ve had come together for your own firm? 

Todd Siegler: I think it’s helped us engage with clients in a number of disparate ways. And so I, I, I often joke with my wife, I’m like, I, gosh, I wish I’d done this earlier in my career.

And her point to me is [00:37:00] nobody would’ve listened to you. But as you get that experience and you get that permission, um, to do lots of different things and so that’s what’s been really fun and interesting for me. 

Michael Mitchel: If you could give career advice to 25-year-old Todd, what would it be? 

Todd Siegler: That is a great question.

There’s so many things I would tell him. You know, I think it is continue to push for those opportunities that deliver tremendous experiences for you. Don’t get enamored with, oh my gosh, these guys wanna pay me. What? ’cause every time you take that kind of job, it ends up not being the right job. And so, you know, continue to stay true to yourself.

Continue to put yourself in a position where if something doesn’t feel like it fits within your moral compass, you can say no. And you’re not, you know, you’re not forced to do it. And you know, another life lesson that I would tell that 25-year-old Todd [00:38:00] is live below your means. Always give yourself that flexibility to say, you know what, this isn’t the right spot.

Michael Mitchel: I can’t emphasize that enough. I got a call from an executive, uh, the other week who unexpectedly got ripped out of an organization. And he told me that he has to have a job in three months or he can’t make his rent. And his base was 3 75. And I was just like, there’s no reason on the planet you should be in that situation.

Todd Siegler: So I dressed up for 

Michael Mitchel: you. 

Todd Siegler: So I’m putting on a collar shirt today, but I agree with you. What’s the point? And I’ve got buddies that are making a million, 2 million bucks a year saying, gosh, Todd, I can’t make ends meet. You look at ’em and say, I, I don’t get it. And so it’s easy to spend up to your salary, uh, and everybody tells you not to, but it’s easy to do.

But it gets to, you know, prioritizing what’s important. And I don’t care if it’s in the work environment where you say these five [00:39:00] things are important. On a personal level, what’s important? If you have kids with what your kids you feel like is important for them, focus on what’s 

Michael Mitchel: important. ’cause if you get behind the curve ball like that, you’re not working for yourself, you’re working for the system.

Todd Siegler: That’s right. And then you don’t have that ability to say, gosh, I don’t feel right doing this. Like, like I grew up in Houston and I look at the Enron story. 

Michael Mitchel: So what was the best, worst job you’ve ever had, and what influence did it have on your career? 

Todd Siegler: Worst job. Best. Worst 

Michael Mitchel: job. 

Todd Siegler: Well, let me tell you the worst job, and I’ll tell you my best, worst job.

I’d say the worst job I had was I worked on a ranch after my junior year in college. I thought I’d get to ride horses and I thought it would be awesome. I would wake up every morning at five 30, get in line. I was the last guy in line and my job was to put up fencing, was to clean out grain silos. It was 110 degrees in the middle of Texas and it made me continue to study hard and want to get a good job.

So that was probably my worst job, but had a big influence on me in terms of best, [00:40:00] worst job. It, it’s an interesting question. So I, I look at. My experience is, and I say I actually look at all my jobs as having lots of good and maybe some bad. Um, but it’s like the question on, Hey, do you like that CEO? And I look at it and I’m like, I actually liked a ton about the CEO, but there were certain things I didn’t like.

And so I continue to go back to no job’s. Perfect. Right? If you’re afflicted with working too hard, which is a challenge for me, you’re gonna work hard everywhere. So you can’t complain about that. It. They’re good and bad in every job, and I think you learn from everyone. And maybe there’s been a job or two where I’ve stayed a little too long, and maybe that’s a good lesson to learn.

If you’re not learning anymore and you’re just staying there ’cause you think you’re gonna make a bunch of money, that’s not right, that’s not the right reasons to say. 

Michael Mitchel: So we’re kind of wrapping this up. Do you have any book or podcast recommendations? 

Todd Siegler: You know, that is a, that’s another one. Um, you know, I love all the Malcolm Gladwell books.

Uh, I can’t read enough of those and the Freakonomics books I love. [00:41:00] You know, one that I, I really continue to read over and over ends up being the Lean Startup. It’s just a really interesting approach to building businesses, and you and I talked about this and we’ve talked about it a bunch before, which is it’s that customer driven development, sitting down with customers and saying, this is a problem we think you have, and how we wanna solve it.

Taking the time to listen and understand what the customer is trying to solve and, and how your product solves that problem. Um, it’s just been interesting to me. 

Michael Mitchel: Yeah. If someone wanted to get in touch with you, what’s the best way to do it and is it okay, first 

Todd Siegler: of all? Okay. Uh, and secondly, LinkedIn’s probably the easiest.

And so if you go to LinkedIn and type my name in, it’s TODD. My last name is Sigler, S-I-E-G-L-E-R. I am happy to connect with folks and see if I can be 

Michael Mitchel: helpful. Well, Todd, I really appreciate your time and it’s been a, a very engaging conversation, at least for me. Um, hopefully, uh, folks found it as [00:42:00] well. Um, thank you for your time.

Thanks for being exploring talent. Thank you for including me. This has been a ton of fun. 

Todd Siegler: Thank you. 

Michael Mitchel: So my personal takeaways from this conversation was, when looking at opportunity, think about ways that I can learn from the experience. And embrace, embrace these new experiences and really just have more than one mentor.

Don’t go for a boilerplate, uh, template and model. Just go with the work works for myself, and that’s why I’ve got so many mentors. I’m not gonna tell you what you should take away from this interview. For each person is unique in their passions, career goals, and experiences. I do hope you learned something and enjoyed the conversation.

Please give us five stars, iTunes, and share your comments. That’s the only way we can improve and ask the questions that you want to hear. I’d like to thank Jolan Crossland, an award-winning banjo and bluegrass artist. Jalan HA is from the Bighorn Mountain to Wyoming, and he graciously provided his music for exploring talent.

When I think of talent, Jalan always comes to mind First, please visit jalan crossland.com. I’d like to thank Angie [00:43:00] for all of her research during her 16 plus years at my firm, OC Executive Search, and for her work on this podcast. I always give credit where credit is due. Exploring talent’s name came from Angie.

Thanks for my pod producer, Joseph or without this podcast would not be possible. And of course, Corey, my pod engineer. Please follow us on LinkedIn under Exploring Talent. My LinkedIn is Michael Mitchell with one L and our Twitter handle is talent explored. Share our show and please drop me a note.

Thanks for joining.