"True leadership isn't just about making decisions. It's about being authentic, serving your team, and building real connections.”
In this episode of Executive Evolution, host Craig Anderson sits down with Matt Tait, CEO of Decimal, to have a conversation about the transformative power of authentic leadership.
Matt shares how transparency and authenticity have steered him through challenging times, including scaling a company and navigating the uncertainties of the pandemic. He
also jumps into the importance of leading with core values, managing both up and down within your organization, and the necessity of self-care for sustainable leadership while opening up about his reliance on family support, executive coaching, and peer groups.
After You Listen:
- Get your copy of The Great CEO Within by Matt Mochary
- Get your copy of I'm Proud of You: Life Lessons from My Friend Fred Rogers
- Connect with Matt on LinkedIn
- Follow Matt’s podcast, After the First Million
- Check out Decimal
- Connect with Craig on LinkedIn
- Check out Craig’s monthly free training on holding difficult conversations
Key Takeaways:
- Position your office to engage with your team. Align furniture for eye contact and spontaneous conversations to build relationships
- Embrace transparency. Openly share challenges and plans to gain trust and validate your team’s feelings
- Stay healthy for better leadership. Prioritize daily workouts, even if it means waking up early for "me" time
Things to listen for:
- [02:05] Lightning round with Matt
- [19:34] Advice Matt would give to his younger self
- [21:23] Craig's takeaways
Transcript:
As I looked out the window, I saw the reflection of somebody walking past my door looking at me in the office. And I realized I can't see anyone in here. Welcome to Executive Evolution. I have over 25 years of leadership experience in corporate America. I learned a lot of lessons the hard way and I created this podcast so that you won't have to. Started a new role leading a division of a business and moved into the office, not really thinking much of anything about how the office was laid out or where the desk was placed. But the reality was my computer was facing the window and my door was back over my left shoulder about 20ft away. Well, I was new. People didn't know much about me and they were curious. So they were all looking in the office, hoping to make eye contact to start a conversation. But my office was completely lined in the wrong way for me to even engage with my employees. That night I stayed late, repositioned all the office furniture so that as people came by my office, I could actually start to get to know the team and get to know the employees and really start to build the relationships you need to lead a team effectively. In today's episode of executive Evolution, I meet with Matt Tate, the CEO of Decimal, and he has a great story of his Executive Evolution, of how his first leadership role really taught him some key lessons, and then he has expanded on those to really build a team that has scaled tremendously since he started it in January of 2000.
Craig Anderson [00:01:32]:
And we really get into a discussion about the importance of leadership, authenticity and connection. So let's move right into this week's episode. Matt, welcome to the Executive Evolution podcast. I'm so glad you could join me today.
Matt Tait [00:01:50]:
Craig, thanks for having me. I really appreciate it.
Craig Anderson [00:01:52]:
Oh, yeah, absolutely. As a fellow podcast host, you know how much fun these can be and how much you can learn as we go through the progress. Right?
Matt Tait [00:02:00]:
I love having the stories and just having good, deep, kind of authentic conversations.
Craig Anderson [00:02:05]:
So yeah, let's see how we do today. As I don't start with deep, authentic questions, I'll jump right in for our episode today with the lightning round. Are you ready to go fast?
Matt Tait [00:02:16]:
I'm ready.
Craig Anderson [00:02:17]:
All right, question number one. What is the best leadership book you have ever read?
Matt Tait [00:02:22]:
I have two that are tied, so I like to cheat to win on these. One is the great CEO within by Matt Mochary. I've never read a more tactically helpful book as a CEO, and that book, the great CEO within, is very helpful for that. The second one is I'm proud of you. Life lessons from my friend Fred Rogers by Tim Madigan. I have found that to be an amazing book about how to treat people, how to be, and. And how to say things that aren't normal to say.
Craig Anderson [00:02:50]:
Oh, that's fantastic. I think I was a kid watching Fred Rogers when it was original stuff, and I just always remember the lessons, so that's really good. Good. All right, next up, who is your leadership crush?
Matt Tait [00:03:02]:
Oh, this was an easy one. I have always been a massive Teddy Roosevelt fan. I have found that what he has or what he overcame, his authenticity of who he was, and just a I don't give a shit mentality, along with just an endless and a boundless energy I thought were amazing. At one point, the guy was literally shot, and he kept doing things. And I think Teddy Roosevelt, for all that he was able to accomplish and kind of the leader that he was, was pretty amazing.
Craig Anderson [00:03:33]:
Yeah, I have read a couple of his biographies, and then. Did you ever read letters to his children?
Matt Tait [00:03:38]:
Oh, yeah.
Craig Anderson [00:03:40]:
So good. What an amazing man. I know. Oh, I could go on. He's just. He really is my favorite president of all time.
Matt Tait [00:03:47]:
You look at just the span of what he was able to accomplish from being sick as a kid and, like, just building himself up into a really. Just strong and vital person and then leading through a pretty crazy time. I've always thought he was somebody worth aspiring toward.
Craig Anderson [00:04:07]:
Yes. All right. You are the first person to mention him, but I so appreciate that call out, because he is a great one. Okay, last one. Given what we've learned so far, in ten words or less, how do you define leadership?
Matt Tait [00:04:20]:
To me, leadership is being willing to be authentic, stand on true values, and empower and serve.
Craig Anderson [00:04:31]:
People love it.
Matt Tait [00:04:33]:
I think that was less than ten.
Craig Anderson [00:04:34]:
It was ten ish. We don't stand too much on ceremony. We try and get it close, but that authenticity is something that seems to me has been more recent in, like, the last ten to 15 years. We really didn't hear that people wanted the leader to stand up and rah rah and chat and tell everybody everything was great, even when it wasn't. How has that pivot affected your leadership style towards more authenticity as you've grown your businesses?
Matt Tait [00:04:58]:
For me, I haven't always been that way. And I learned the hard way how important it was for the people I was leading, and for me to just do that, and the final straw was, leading through a pandemic is a trauma we will all be recovering from for a very long time. And the reality of that time and there are other times that are equally as bad. In all of our individual lives, we're people, and it's okay to be a person, and your team identifies with that aspect of things, and they sense when you're just full of shit. To me, I think if you truly want to help people and truly want to lead, being who you are is the best way to do that every single time. And putting on a face is hard to do, and you never feel good doing it. You may pretend like you do, but you never actually do.
Craig Anderson [00:05:55]:
Yeah. The thing I always found was, if I'm up there trying to get the sunshine pump going for the team, but my last business I had before I went off and launched this was a call center business. If I'm telling them everything's great, but the phone's not ringing, they know it's not great, and so it undermines any authority or credibility I have as a leader on anything else I might want to talk to them about. So just talking about the challenges, being truthful, and then saying, here's what we're trying to do, helps align people along behind you.
Matt Tait [00:06:23]:
I think they have the same feelings when that phone's not ringing. They're scared, and you're scared. And telling them that you're scared but you have a plan validates their feeling and validates their trust in you.
Craig Anderson [00:06:36]:
Yep.
Matt Tait [00:06:37]:
If you just say, I have a plan and things are great, then you've missed a big piece of that validation and trust, and it'll make it harder the more times you have to do that.
Craig Anderson [00:06:46]:
100% agree. Excellent. On the podcast, we always like to talk about your leadership journey. So, you said you're kind of a recovering attorney, you some serial entrepreneur. They have created a lot of businesses, but what I'd love for you to do is take yourself back to that first real leadership role that you had. What was that role for you?
Matt Tait [00:07:08]:
For me, I started my career out as an attorney, and I joke now I'm a recovering attorney. It's a lifelong affliction, but I had gone from that to the tech space. I thought it'd be really exciting to be in tech. And after a few years of helping do new things in a really amazing tech company here in town, I had the opportunity to combine my careers with a company called Case Pacer, and it was leading sales for and building sales for a legal software, and then also leading sales for a services sidecar business. That was my first leadership experience, and it was building a team from the ground up. It was being in somebody else's company. It was really developing sales processes. It was doing all of those things while also having twins.
Matt Tait [00:07:58]:
So I like chaos apparently, because that was just a bunch of chaos all at once. It was a very valuable experience. I think, like all of us, every job we have, every person we work for, for just like our parents were raising our kids, you learn good things to do and things that you'll do different, and that was a good place to learn both sides of that coin.
Craig Anderson [00:08:22]:
Yeah. And when you look back at that, stepping into that leadership role, what surprised you the most that you didn't see coming about being a leader?
Matt Tait [00:08:32]:
I was just having this conversation with one of the leaders at my current company, Decimal, and I told her that when you step into a director level or a head of role, you are truly serving and managing up and down. You have to manage the people that work for you, and you have to manage your boss and the expectations of the roles above you. And I don't think I'd fully conceptualize that in leadership that you have to manage up and you have to manage down. I'd always understood that my job as a leader was to make the lives of the people on my team easier. Like, that's always, that service mentality has always been there, but also trying to do the same for my boss and that would make me successful was something that I had to learn.
Craig Anderson [00:09:19]:
Yeah. And so as you progress through that, what were some of the tough lessons within that? What brought you, hey, I really do need to be managing up in this current kind of middle manager role or middle leader role. Where was the precipitating event that you said, oh, man, I need to put some more effort into this.
Matt Tait [00:09:34]:
Our boss at the time, really, we had a lot of travel that needed to happen to events and conferences and all of that stuff. And our boss at the time really loved to go to every single one. And there was a time, because I had just had twins, where I was like, I'm not traveling for two to three months. I didn't take a paternity. I think I was back to work a week and a half after having them. But I did kind of a flex schedule for a few months. And as I was sitting there, I'd hear a lot of people saying that our boss was never around. Like, we didn't see him.
Matt Tait [00:10:05]:
But today I run a remote company. There is a value of presence. There is a value of being seen. There is a value of just being there that is really important. And that's something that I really learned heavily of. It's not just do what I say, but it's do what I do, like lead by example. And that example you have to be present for now. I think in today's world, we've learned how to intentionally do that in a remote environment.
Matt Tait [00:10:33]:
So presence and the definition of presence has changed. But I think being present as a leader was something that I learned in a very big way, the importance of in that role.
Craig Anderson [00:10:44]:
Yeah. Teams are looking for somebody to set the tone. Right. The leader sets the tone of the organization. And if they don't see them, or as we talked earlier, if they're not coming across authentication, I remember a company I worked for, the CEO, kind of, we built the space, and you couldn't even see him from the hallway. His office was back and cornered and tucked. People don't see you. They don't believe in you.
Craig Anderson [00:11:04]:
They don't even know what you stand for. And it's so important to get out among the team, and it's hard because you have to be intentional about it. Right?
Matt Tait [00:11:12]:
Oh, 100%. We launched Decimal out of an accounting firm here in Indianapolis, ended up buying it from them a few months later. But at that firm, I was brought in as a kind of director level, a higher level person. They gave me a nice big office, and I hired two people to help me launch what is now Decimal. And they gave them cubicles on the other side of the building, and without telling anybody, because I'm kind of a ask permission or forgiveness rather than permission type. Anyway, overnight, one night, I moved all of these desks and extra tables into my office, and I said, we're all working in here, period. They tried to talk me out of it. I was ordered not to do it, and I said, no, this company, this starting point, will be in my office.
Matt Tait [00:11:54]:
Feel free to give that cubicle to somebody else. But these people are all going to work in here with me, and that's how we're doing it, because at that point, particularly at the birthplace of a company, that presence and that togetherness is really important.
Craig Anderson [00:12:08]:
Oh, man, that's great. And that makes a great transition, because now you are the CEO of Decimal. You launched this company going into the pandemic four years ago. How has your leadership style evolved from that early leadership role to now? We've talked about some of those things, but what is your leadership style now?
Matt Tait [00:12:29]:
Number one, I'm very clear about what my values, what the values of the company are, and I lead with that first. We have a whole slack channel at Decimal. That is all about getting kudos and props to people. And in that you label a company value, what value did they display that help them earn that promise, that values? First mentality is where I start from. Number two is I am exceptionally transparent and authentic in who I am. It's taken me a long time as a person to get comfortable in who I am in my own leadership style. And it's evolving and it's changing, but I'm okay talking that through. I've also learned the value of being vulnerable in front of people.
Matt Tait [00:13:11]:
I would say as a child of the eighties, that's not something I grew up doing or was very comfortable with. Still probably not very comfortable with. But I forced myself to be uncomfortable in public. And I found that in leading a company that's grown as fast as we have, it's trickled down into a pretty awesome culture. And I've also found that during the pandemic, we had some big tragedies that hit a small company that then grew into a much bigger company at Decimal in a very short period of time. And me being authentic and vulnerable, stitched the company together in a way that could have destroyed it before it even had a chance to really get started. That type of values, first, authenticity. It's just who I am, and I'm comfortable being uncomfortable with it.
Craig Anderson [00:14:01]:
One thing, though, when you're doing that right, and I kudos to that, because I do think that's important for leaders today, but that's putting a lot of energy out of you into everybody else. That's kind of really giving everybody that support. But at the same time, you as the leader are dealing with a lot. Right? All those people are depending on you. How did you hold it together? What were the things that calmed you and kept you from freaking out during a really intense period of time?
Matt Tait [00:14:30]:
I have an amazing boss. Some people may say she's my wife and she really helps center me. She's awesome. She's a great sounding board. She gives me somebody that I can talk to. I'm an amazing co founder, jacob. Now I have an amazing coo, michael, that I'm willing to share most of the burdens with. And in addition to that, there are certain things that I do selfishly for me.
Matt Tait [00:14:54]:
And I have found that being selfish in certain aspects of my life is some of the most unselfish things I can do for my team. So there are three things that I really focus on for me. Number one is my health and my body and my overall being in shape for 2 hours every morning, hour and a half, I work out before my kids and my employees are awake. It's the only time during the day that I have to meet. The minute any of them wake up, somebody is asking for something and that's cool. And so I do that. Number two is having a coach. As soon as we raised money, as soon as we really started to grow.
Matt Tait [00:15:29]:
I interviewed somewhere around 30 to 40 CEO coaches until I found my CEO coach. And he is an amazing man and he's super smart and he's been doing this since literally the year I was born, 1983. And he's been a really big help for me, finding a CEO group, a group of peers that I can talk about some of the things that I don't necessarily want to talk about with even my co founder or my coo or even my wife that are just like, I'm scared. I'm worried. I'm dealing with this. I don't know what this is. I'm bad, I'm happy. Like some of those joys you want to temper in front of people, too.
Matt Tait [00:16:05]:
Having all three of those things, so personally focusing on me, having a coach and then having a peer group have all really helped center me and give me the outlet, because I think where a lot of leaders fail is they think their team is there to serve them. I look at it as I'm there to serve my team. That involves me being a sin eater, me pouring out a lot every day, oftentimes in a million different contexts. But to have a couple of things on a daily, weekly and monthly basis that are selfish to filling my cup allows me to do that better.
Craig Anderson [00:16:38]:
No, and that's great, because unless you sit in the chair running the organization, you don't really know. Everyone kind of thinks, well, I could do that. Right? How hard can it be? You've got all these people to do stuff for you. And that may or may not be true, but the reality is everything comes down to you. You can have a great board and a great leadership team, but at the end of the day, you're the person that everybody's looking to make the thing work. And that's a lot of pressure.
Matt Tait [00:17:04]:
It is.
Craig Anderson [00:17:05]:
So by giving yourself those breaks, by giving yourself kind of self care, by coming to a community of coaches and then having somebody you can really bounce stuff off on, that's really taken some of that stress load off so that you can actually continue to pour back into the team.
Matt Tait [00:17:19]:
And look, the other part of it, too is I'm lucky enough to take vacations. And part of it is I've got young kids and so in balanced schedules, they get a week off way more times a year than I ever did. And I have found that every quarter, I reach a near burnout stage where I've just given too much. And being able to unplug and spend time focused on me and our family. And I think I average around 200 messages, emails, or slacks a day. To not have to focus on that is very helpful.
Craig Anderson [00:17:51]:
Yeah, absolutely. Now, you talked earlier about what you learned in that early leadership role, about managing up. But what other lessons from that early leadership role have really made you the leader you are today as you've evolved.
Matt Tait [00:18:04]:
As a reaction to how things were? That is one of the things that's really locked in being a values first leader. And at Decimal number, one value we have is do the right thing. And number two is be transparent or default to transparency. And those are two values that I learned at that first leadership role that I just said, you know what? Even if it's to my own detriment or the detriment of our company, we will do the right thing every single time, and we will be transparent. We are more transparent than any other company, probably sometimes to our detriment about what's going on, what we're doing, where we are, how things are going, even how I'm feeling. And I didn't want to keep things bottled up. I didn't want to hide things. What I really have found is, when you keep secrets, your team knows it, and they will add a narrative if you don't.
Matt Tait [00:18:56]:
They will also add their own narrative if you do. But you have a chance to direct it if you start that conversation. And you build trust by being the beginning chapter of that book. And you will always be fighting an uphill battle if you are trying to react to the narratives that other people create.
Craig Anderson [00:19:17]:
Love it. No, you're right. And people will fill in anything. Right? They'll sit in the corners. You'll hear the whispers.
Matt Tait [00:19:23]:
They rarely do it by giving you the benefit of the doubt, too.
Craig Anderson [00:19:27]:
Yeah. Presumed positive intent, when times are hard, are usually not where people lean into.
Matt Tait [00:19:32]:
Oh, good lord, no.
Craig Anderson [00:19:34]:
So, that's what you've pulled forward to wrap this up. What I want to do is give you a chance to jump into a time machine. You're an eighties kid. You probably lean to the DeLorean. But I don't want to presume, but if you were to jump into a time machine and go back to young Matt in that first leadership role, what's the one piece of advice you'd give him that would help him sleep through the night. Be more effective, whatever you'd like him to be.
Matt Tait [00:19:58]:
It's okay not knowing what you're doing. It's okay figuring it out. And it's okay asking for help. What I have found, and I've been really lucky in my career to be around a lot of amazing people, some tangentially, some directly, and people want to help you. And there's nobody that starts as a CEO that knows what they're doing. None of us have any freaking clue how to handle everything that comes our way, sometimes on a daily basis. And in my first leadership role, in my first role as a CEO, I tried to hide from that. And so to me, just knowing it's okay to not know what you're doing, I wish I would have been comfortable hearing that at the time.
Matt Tait [00:20:39]:
I'm sure somebody probably told me that, but I wasn't comfortable hearing it.
Craig Anderson [00:20:44]:
Great. Well, Matt, if people want to follow you, learn more about what you've got going on at Decimal. Where are the best places for them to do that?
Matt Tait [00:20:51]:
Just connect with me on LinkedIn. Just Matt Tate on LinkedIn. If you want to learn more about leadership and hear some pretty amazing stories from other leaders who have built businesses through that messy middle of scaling, we do have a podcast after the first million.
Craig Anderson [00:21:07]:
Great. We'll drop links to all those in the show notes so people can find you there. Matt, thanks so much for coming on and sharing the story of your Executive Evolution today.
Matt Tait [00:21:16]:
Craig, thanks for having me. I always appreciate these conversations.
Craig Anderson [00:21:23]:
As always on Executive Evolution, I like to leave you with the key takeaways in the areas of confidence, competence and calm. And there are some great examples to draw from in Matt's story. In the area of competence, he talked about being a values first leader, and those two values he talked about were do the right thing and be transparent. When you have clear strategies and visions and ways that you run the business and things like do the right thing and be transparent, it gives you confidence because that drives your decision. You're not weighing every tough decision against some vast unknown metric. The guidepost of how you run your business are so crucial in the area of competence. He talked about how he was being successful as a leader but needed more support and more insights. So he surrounded himself with both a CEO peer group and an executive coach.
Craig Anderson [00:22:16]:
And that helped to build his own competence by helping him to learn new things, by getting advice from others who maybe experienced those things before, those very things that he's probably experienced for the first time and didn't know how to handle. So an executive coach or peer group can really start to help you build your leadership competence and in the area of calm. What I really appreciated is he has both sounding boards in his spouse and on his team that help him to kind of work out and work through issues and are sounding boards for him. And that ability to get that out of his system allows him to stay calm. So those are the key takeaways this week. As always, thank you for listening to the executive Evolution podcast. And remember, you can go from being an accidental leader to the greatest of all time leadership. All it takes is developing your confidence, competence and confidence.
Craig Anderson [00:23:09]:
See you next time on Executive Evolution.