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Leaning Into Extreme Ownership in Leadership with Dennis McLaughlin

As leaders, we often strive to obtain the best information possible, but the reality is perfect information is a rarity.

In this episode, Dennis McLaughlin, Chief Financial Officer at Fortis, shares his experiences of moving forward without perfect information and how they have shaped him into a better leader. Along the way, Dennis sheds light on the value of extreme ownership, the importance of leading by example, and the challenges of transitioning from a peer to a manager.

Listen in for valuable insights and practical lessons on decision-making, accountability, and navigating the complexities of leading diverse teams.

After You Listen:

Key Takeaways:

  • Make decisions with the best information available, even if it’s not perfect
  • Leadership is about taking ownership, defining the mission, and leading by example
  • Your first leadership role may come without training, but embrace the challenge and learn how to navigate the transition from peer to boss

Things to listen for:

  • [01:55] Lightning round with Dennis
  • [06:34] Navigating the shift from peer to boss
  • [08:37] The value of a mentor’s insights and guidance
  • [11:14] Appreciating different communication styles
  • [17:11] Dennis’ advice for his younger self
  • [19:24] Craig’s takeaways

Dennis’s Transcript:

[00:00:00] Craig: As a leader, want the best information possible, but you will never have perfect information.

Welcome to Executive Evolution. I’m Craig Anderson. After spending 25 plus years in corporate America, I learned a lot of leadership lessons the hard way. I created this podcast so you don’t have to.

As leaders, we’d all like to have every bit of information so that we can accurately predict the future or the outcomes of decisions that we make, but it’s never that easy. As a leader, you may have a lot of information, some of it may contradict, it will rarely be perfect, but you have to make a decision nonetheless, In today’s episode of Executive Evolution, we’re gonna hear from Dennis McLaughlin, the Chief Financial Officer at Fortis. He had many times when he had to move forward without perfect information, and he’s gonna share with us what he did in those circumstances and how it helped him become a better leader.

So let’s go on to the story of Dennis’s executive Evolution.

[00:01:09] Craig: Dennis, welcome to the Executive Evolution Podcast. Glad to have you here.

[00:01:13] Dennis McLaughlin: for having me, Craig. you invited me.

[00:01:15] Craig: Oh yeah. No, think this will be a good interview. Looking forward to hearing about what you do. But before we dive in, why don’t you tell everybody a bit about what you do with Fortis today?

[00:01:25] Dennis McLaughlin: So I am the, chief Financial Officer at Fortis and Fortis, for those who don’t know, we’re a payments technology company. And our core mission is really to partner with software makers and ISVs to provide an integrated, seamless payments experience to their end customers. So they, provide all in kind of package offering. so that’s, our core mission.

[00:01:46] Craig: I don’t think I’ve had anybody on from that industry before, so it’ll be interesting to see what leadership is like in that context and from a C F O perspective. So, Let’s go ahead and jump straight into the lightning round. question number one what is your favorite leadership book?

[00:02:01] Dennis McLaughlin: My favorite leadership book is a book called Extreme Ownership by a guy named Jocko Wilnick. he’s a leader, the Navy SEAL teams, has gone on to have a number of, successful civilian ventures. Um, thing I love about this book is it takes experiences from the field in some cases in combat. are real experiences that he’s able to, distill down and create kind of no nonsense, you leadership lessons that really are applicable. You to, you even corporate life for a, finance guy,a lesson that, he, experienced over overseas in, combat and able to sort of apply it, the day-to-day life. that it lead here at Fortis.

[00:02:36] Craig: Yeah, it is an amazing book and how he threads those crisis issues he dealt with as a leader in the seals and then really even shows that same, maybe not level of danger, but the emotional impact you have in your day-to-day life as a leader around trying to be accountable and hold people accountable. I really love the way he threads it all together in that book.

[00:02:56] Dennis McLaughlin: Totally agree. One my favorites.

[00:02:58] Craig: Alright, Question number two in the lightning round.

Who is your leadership crush?

[00:03:03] Dennis McLaughlin: gonna be a spoiler off of my last answer. It’s, it is Jocko and,I follow him, on social media. I’ve read all of his books. Uh, listened to his podcast and, there’s no sort of veneer of political correctness and no, squishiness around, leadership, know, lessons that he, puts out there. I have found that I’ve been able to take a huge number of. lessons and things that he’s put out there into the world and,and applied it in my career, continue to do so.

I just really value his whole approach and his whole outlook on things. I would say hands down, that Jocko all the way.

[00:03:35] Craig: Yeah. Great. and do you find, as you’re going through your day, touching back in your head to some of those lessons that he has in the book as you’re having to make your day-to-day decisions?

[00:03:44] Dennis McLaughlin: Yeah. And so, I find that, I draw upon those lessons, almost daily, and borrow from the book. the cornerstone, lesson that I would probably say I use the most is really that sort of extreme ownership concept.

And that doesn’t necessarily mean that you have to take everything on your shoulders and everything’s, your responsibility, but it’s really just having the,courage to step into a situation and take ownership of it. and that means, getting the right people in place and enabling them to go forward and, tackle the mission that might be in front of you. It’s having the ownership to kind of step in when, know, everybody’s sitting around looking at the problem, gonna be the one that steps up and says, okay, is what we need to do to mobilize and, that’s just one of many, and, I use, you literally daily.

[00:04:24] Track 1: Yeah, people say there’s always that phrase that crap rolls downhill. But once you get into a leadership role, I think you find it actually goes against gravity and rolls uphill, and it all ultimately is up to you.

[00:04:36] Dennis McLaughlin: I’m glad you said that. I would tell you that, before I was in this chair, I used to look at the folks, the that sat in,C f O chair. ’cause I’ve been a finance guy for most

of my career. know, I used to look at that and go, oh, well, you know, they can just delegate everything down.

And as you said, like everything slides downhill. And,as I got into this chair, I learned within days that it’s nothing could be further from the truth. This is, only the, the that I’ve, I’ve in my career interms of being in this role, but certainly rewarding at the same time, but you don’t really know what to expect from this,level of role until you’re in the chair and. it’s nothing like what it is when you’re,actually in the seat and, and feeling the weight, the chair comes with.

[00:05:14] Track 1: Love it. so true. And we’ll come back to that point here in a bit. Last question, especially in light of what you’ve laid out so far, how would you define leadership in 10 words or less?

[00:05:25] Dennis McLaughlin: Okay, so define the mission. Enable the team lead with your actions.

[00:05:30] Track 1: I like that a lot. Yeah. it’s enabling the team, but really showing that you’re gonna do the right things too. that’s crucial. when I think of bad leaders, they especially do not do that last part.

[00:05:41] Dennis McLaughlin: lead by example. Is,a key cornerstone to, my kind of approach as a leader. when you get into the leadership position, you can’t lose sight of the fact that sometimes you still have to roll your sleeves up. You still have to, a part of the solution. that doesn’t mean necessarily you have to do everything, but, you are going to follow, who back up their words with actions. who sit in the chair and just kind of bark orders and,

tell people what to do and,really kind get a little too much pleasure just, being the boss. Those aren’t real leaders. Those are bosses to be a little bit cliche here, but, aren’t the people that people felt The people follow are the people who, have their actions lead with, their words.

[00:06:15] Track 1: No, you’re exactly right. And I can think of so many examples of people who didn’t do that, but expected the teams to work at a very different level in intensity than they do. And it’s not sustainable as a leader for sure. It is a manager, not a leader. All right. Well,let’s dive in.

Dennis, what was your very first leadership role?

[00:06:34] Dennis McLaughlin: So my first leadership role professionally was, uh, analyst at Capital One. they were a lot smaller of an organization back then. you know, at one point, pretty early on in my career, was promoted to senior analyst and given a small little team and, that came with no real training in terms of what it was like to be a manager or a, a leader. but all of a sudden I am, a kind of mid 20 something,kid as I always look at now, now I’m someone’s manager and I’m someone’s boss. And so that was, a role that I was thrust into and I had to figure out how to not only do my job, but also, lead this group of diverse folks that, were in analyst roles and there was a little bit of a peer now, from peer to boss situation. navigating those waters as well, which, which brought about, its own set of challenges.

[00:07:17] Track 1: Yeah. And that’s such a recurring theme is companies promote people and don’t teach them what to do once they’re in charge of a bunch of people. And you think back, kind you got that role, what was the reason they plucked you out of the analyst and dropped you into that manager role?

Craig – what was the reason behind it?

[00:07:34] Dennis McLaughlin: I think it was a case that a lot of companies continue to, know, use as a rule to this day. And I’m not sure why,I wish I could say Fortis was completely exempt from it, but we’re not. But it was the classic case of, you was good at my job. And so I think there’s this sort of mentality, sometimes unspoken, sometimes explicitly spoken that says, This person’s good at their job, so they must be good at leading other people doing that job and that’s a different skill set.

You being a good analyst and good with spreadsheets and numbers doesn’t necessarily always correlate with, with people. In fact, there’s some people who would say that those two qualities are inversely correlated.

But, Fortunately, I was able to sort of, know, largely using the golden Rule out of the gate to be using traits that I had seen in bosses that I didn’t like and saying, all right,well I’m not gonna do that. I think it was just really a case of,good at the thing I was hired to do and saying, you gonna make him manage a team of people doing that.

[00:08:25] Track 1: yeah, as you said, you followed the Golden Rule and, didn’t do the things you saw that were bad. But what did you do when you got into situations you didn’t know how to handle? where did you find your answers on some of tough leadership issues you ran into?

[00:08:37] Dennis McLaughlin: one of the things I did very early on, and is I sought out mentors. Capital One, and I I really, found a lot of value in that and,in some cases, they were people that I had gotten to know during my time there. in some cases these were people that I didn’t really even work, alongside, but I had sort seen them from afar. remember there was one individual who was the head of all of our Customer relations areas, many, many levels above me. know, we had interacted a couple times, but largely didn’t know who I was.

I was a very junior person, but just reached out and said, Hey, like,would love to spend some time with you and just, you know,once a month just so we could meet and pick your brain about things. And so, you I used that, as a resource to bounce things off of . Because it provided a,setting kind of outside of the boss, employee situation in a little bit more of a guard down ask like,how do you do this?

And how do you do that? And sometimes, especially when you’re younger, show weakness, you know,show that. I don’t know something. And if you’re in front of somebody that’s not necessarily your line manager, then I felt a little bit more comfortable kind of letting my guard down and saying, Hey, I don’t know how to handle this situation. Can you help me? And so leaning on a mentor type relationship has been a huge help, you

[00:09:41] Track 1: Yeah. And, and that’s such a theme I hear that, get put into these roles. They don’t get any training and you know, you also don’t wanna look stupid. You don’t want to tell people, oh man, I don’t know what to do. So kudos to you for finding that mentor. you think about that role, and looking back on it, how do you think you did?

[00:10:01] Dennis McLaughlin: I think I largely did okay. I said before, I borrowed things that I’d experienced from bosses that I didn’t like. And I let that guide me to say, well, how would I like to be treated?and, that helps to a certain extent. Um, say also though, it did teach me a lesson because, you the way that I like to be managed or communicated to isn’t the same as as everybody else.

And While the kind of dos and don’t help, create a wide framework, that I think helped, for the most part, folks that, that worked for me during that period of time, I can’t recall any of them that were unhappy. So I think, uh, largely went okay, and I continued to be promoted and,take on larger, larger you get exposed to, you different folks and different styles and you my communication style is different from other people. And so it’s a.a very interesting kind of learning experience numbers don’t have a personality and spreadsheets don’t have a personality, but people do.

And so,learning what, how to navigate those,was a big lesson. And, reality is the,more your career progresses, the,especially in a quantitative field like

little did I know at the time, you how much scales were gonna continue to tip where those skills would be just more and more important in my ability to do an awesome spreadsheet. Sort of starts to fade into the background a little bit.

[00:11:07] Track 1: Yeah. and if you think about like the one big lesson you learned from that role that carried forward, what would that have been?

[00:11:14] Dennis McLaughlin: my ability to tailor my style to piggyback off my previous point and,I will say that early on, of the things that I’ve gotten better with, with and maturity, or maybe it’s getting older, but, um,I was probably a little bit more stubborn in my younger days and a little bit more set in my ways in terms of,being very direct and, at times a little bit abrasive.

the hardest lesson that I needed to learn at the time was, and it was hard, particularly because I was young and just, hadn’t matured and sort of had enough experience.a big part of me may want to sit down with someone and go, okay, just, do it this way.

And it’s very simple and A, B, C, D, E, F go. not everybody responds to that. and

so being able to sort of not only understand it, but really appreciate that difference style and recognize that there are not only different styles, but there’s benefits to, those different styles and those different ways of communicating, terms of leading, you larger groups of people. As I said, like that lesson would just continue to come up. As the teams and the roles got bigger and bigger with time.

[00:12:11] Track 1: Okay. Well, let’s now fast forward, you’ve kind of hit a great level in a career of a finance person, C F O, now that you’re sitting in that chair, how does leadership look different when you’re pretty much at the top of the hierarchy?

[00:12:24] Dennis McLaughlin: being in this chair, having oversight over, you not just, finance, but also functions that I never thought I’d be managing. So,addition to finance, I have responsibility for risk management. But then the,third one, which has really been kind of biggest, of, of learning and development in this role is, hr.

So I’ve had oversight for hr,since shortly after I joined. The company. And so, a leader of a large department and,frankly in this chair, you’re,a leader of, of the overall company. And forces you to quickly evolve as a,leader and a person.

I still enjoy sitting down with a spreadsheet and knocking out a model and do it in data analysis. That’s fun for me. I know that sounds probably weird some folks out there listening to us as how somebody could find that fun, but I do. those aren’t the skills that are gonna make me successful in this role. The things that are gonna make me successful in this role is around ability to collaborate, bring teams together, find solutions, enable people to, find ways of doing things and,frankly, getting out of their way at times. it’s the softer skills. And,anybody listening to this that knows me well, may have a little bit of a chuckle to that. I’m sitting here talking about softer skills ’cause it’s not always been something that, that’s been my strong suit. but frankly, if had to weigh out, you know,that are gonna make me successful in this chair, it is more of those soft skill collaborative, bringing teams together and,and enabling them to go off and be successful.

Because the other,key that. A role this size quickly has taught me is, there’s so much that I’m responsible for that I can’t physically do myself. that was something that over the years I’ve learned more and more through delegation and the like, but the step function that, came with this particular role. it related to that particular skill was,significant. that took me outta my comfort zone. I feel like I’ve got it pretty well tuned in now. But,that’s a big key. And the another piece that I mentioned earlier that I’ll, I’ll reiterate here is,is something that I really strive for is,is really just leading by example. and I think that any leader that I’ve ever admired in my career, as well as just in life, are folks who I would point to and say that’s somebody who leads by example. So I try to exemplify that can take so many different forms, of the big ones that, that I see is, really staying connected with,teams.

Sometimes they’re my teams, sometimes they’re other teams, and just them know that, you know, when it comes down to it and we need to solve a problem, that I’m,more than willing to get in the trenches and,collaborate and, not sort of look at anything like, oh, well that’s not my job.me, if you’re part of a team and an organization,

nothing is not your job. we have a problem, we have to go take that hill. Then, we’re gonna go take the hill and we all need to sort of, lock arms and kind of go do it Everybody’s gonna have a role. And leading by example is kind of just another big one that’s important to me. And as I’ve continued in this role, it just becomes, much more important to my ability to be successful.

[00:14:57] Track 1: and I wonder, you know, when you look at the trajectory from being that numbers and data guy with models, and I know there’s always gray in numbers too, but data facts driven, and now you’re kind of at a higher level and there’s a lot more nuance, there’s a lot more interpretations and a lot more coming at you.

How do you manage the constant inflow of data and information, With just so much coming at you all the time and having to decide which,which hill are we gonna jump in? Which battles do I join? where do I spend my time? How do you kinda manage that from this higher level that you’re sitting at right now?

[00:15:27] Dennis McLaughlin: The way that I manage it is, there’s the acceptance that sometimes, in the face of a situation and you have imperfect information.

You’ve gotta be willing to make a call. and sometimes that call is my call to make. And sometimes that call is, necessarily me making that call, although I might be able to, sometimes it’s important to put my team in,a position where they can make the call and. The key thing that I have found as an important aspect I’ve had to become more and more comfortable with, and I feel like I’m in a good spot now.

And that is, even if there’s a call to be made and, and not quite the way that I would do it. my, in a position make the call that they see fit and,supporting them, even if it ends up being the wrong call. it was a thoughtful approach and, you was to the madness in terms of why they made the call and they weren’t,wasn’t just sorta careless whatever. it’s okay if it didn’t go that way.

We just, back up, we reassess and,go in a different direction. And Managing all the incoming is impossible to do by myself. And so putting the team in the position, as I mentioned, is the way that I manage it. And then, and when I need to make a call, even in the face of imperfect information, it’s having the comfort level to say, okay, this is a spot where I really have gotta drive to a precise answer.

And this is a spot where, you know what, I can use it, imperfect information and just do a little bit of a tummy rub and,then, you make a call and move.

[00:16:42] Track 1: that is one of the big challenges of leadership is you will almost never have perfect information. You will never have everything you need. Or think you need to make the decision. And sometimes you just have to make the best decision possible. it’s tough in any role, but especially in that world where you have this interesting balance in your role of you have the numbers side of the house and you have the HR side of the house, which are very different ways to look at things.

So it’s hard to get perfect information in any case. Here’s how we like to close the podcast, Dennis, you can jump into a time machine.

You can pick any time machine you want. If you want the DeLorean, you want an HG Wells time machine. Anyone you want, but jump in there. Go back to that Dennis at 25, 26. In that first manager role, is the one piece of information or advice you would give him that would help him be more effective in that leadership role?

[00:17:34] Dennis McLaughlin: first of all, I’m a DeLorean guy, so that’s the time machine that I would pick, in terms of,my vehicle of choice. But, the one that rises to the top for me is, and you don’t always have to have every single detail to be able to be an effective leader. used to be someone, especially when I was younger, is, you really strive to know every answer, every angle, backwards and forwards. I went into a presentation knowing, the numbers, you 15 layers deep and, there’s certainly value in that. But in terms of, my ability to be a leader, letting go of the compulsion that I had to sort of, you really understand and, and my arms around every single detail and every single knit and net is something that I would go back try to tell the younger me, know, hey, maybe there’s, there’s some areas here that you can kind of let go of that it’s not necessarily a requirement. For you to be able to lead. sometimes that’s challenging, you cause there is a part of me,that still likes gory detail. But,in terms of my ability to be a leader, either as a leader of a team, or a leader of a division, or now aC F O, uh, a company,I don’t have The time. it’s more importantly having the comfort level and being comfortable in this chair. not necessarily having perfect information as we talked about earlier. still the ability to lead,only my department, but also,as a whole.

[00:18:48] Track 1: I love it. That is such a good piece of information that I think a lot of leaders could benefit from. so Dennis, as we wrap up this story of your executive evolution today, we wanna just give you a chance, if people wanna follow you, get in touch with you, what are the best ways that people might be able to do that? you can find me on LinkedIn and the usual.Spots and then you can find Fortis, at fortis pay.com.

[00:19:10] Track 1: Awesome. Dennis, thank you for being on today. We’ll drop all those links in the show notes so people can find you, and we really appreciate you taking the time to be here today.

[00:19:18] Dennis McLaughlin: I enjoyed it, Craig. I appreciate you having me on.

I really appreciated Dennis sharing the story of his leadership journey with us today. It’s not always easy when you get promoted from within a group of equals to suddenly find yourself over that team, and it’s even harder as many companies don’t give you the training or the information you need, and as Dennis shared with us, you don’t always want to ask the questions of your boss.

You have to find other sources. That’s where a coach comes in as I do quite a bit of work with leaders in my practice or a mentor, which is something that Dennis pursued when he had questions. As always on the Executive Evolution Podcast, I like to frame our conversation in the three crucial leadership areas of confidence, competence, and calm.

And as I was just discussing, really found his confidence in those early leadership roles by finding a mentor. He took the initiative upon himself to reach out to people in his organization, to set up those meetings, to benefit from their insights, to help him develop as a leader, and that’s what built his confidence as he began that leadership journey.

In the area of competence, I really appreciated how Dennis discussed early in his leadership journey. He led the way he wanted to be led, and took those examples from when he felt well led. But then as his competence and experience grew, he realized that. Not everyone wanted to be led like he did, and he had to adjust his leadership style situationally the people that he was working with so they could optimize their performance.

And that’s a key piece of awareness for leaders to develop that everyone is not like them, and what made them successful won’t necessarily make others successful. And then what I really enjoyed was our discussion around imperfect information. Knowing that you’re never going to have perfect information is what can give you a sense of calm as you make decisions that aren’t always clear cut.

Very few decisions we face as leaders are black and white. There’s always nuance, and when you accept that your information won’t be perfect, but you have to make the best decision anyway. That will go a long way towards building a sense of calm, but more importantly, as Dennis talked about. When that decision wasn’t correct, you stop, you adjust, you move forward.

That’s really what that sense of leadership calm is all about.

[00:21:34] Craig: And as always, remember you can go from being an accidental leader to the greatest of all time leader. All it takes is developing your competence, confidence, and calm. We’ll see you next time in Executive Evolution.