Donald Thompson: You and I are very similar. Not obviously you’ve run some billion dollar organizations, um, but it’s still similar from what I’m seeing in that.

Right. You have to know what your lane is. Right. And I enjoy the chaos. I enjoy bringing, uh, an organization from really. A set of Lego parts, right. And building something that has a brand and some marquee clients, but when it’s time for some of the structures scale mechanics, right. There’s a lot of other folks that can do some things better than I, when you look at your leadership journey and things that you’ve learned, I have in my notes, mark Twain.

And so I’ve been waiting for, you know, the, the weeks that we’ve had this on schedule. Tell me a little bit where mark Twain and some of that philosophy fits in. 

Matt Sheehan:  You gave me a bit of a hint of some of the questions that might be coming. So I started to prepare and what hit me pretty quickly was the letter that mark Twain wrote a friend, if you’ve ever heard this.

And he wrote a very long letter. And at the end of the letter, he said, I would have written you a shorter letter. But I didn’t have the time. And I heard that years ago. And I think we, we, a lot of us have heard it. You’re not in your head. So I know you’ve heard it before. And it does say to me that simplicity takes a lot of effort in a lot of time.

So when you said leadership lessons, I laughed first by the way, weeks ago. And I said, this is one podcast, man. I don’t think I could do that. So I started to listen to mark Twain again and trim this down a little bit. So I can go through a bit of my truncated list if that works, but that’s my tar mark Twain is always on my shoulder saying take time, get it simple.

Um, the question about leadership is a broad one to me. And when I think about leadership, I break it into three segments, personal leadership, systematic leadership, and then strategic leadership. Personal leadership is, you know, how do we lead close in? Right. How do I lead myself? How do I run my own personal life, my family, um, and maybe even those direct reports in a business setting, systematic leadership is when you are called to lead broader than just a small team, you have to start thinking about how your voice can translate, how you can lead systematically across multiple.

Folks or teams or geographies that’s different than one-on-one leadership. And then lastly, we can lead our people really well. We still have to make good decisions and that’s strategic leadership. How do we make decisions? Is that framework makes sense?

Donald Thompson:  It does. It does. 

Matt Sheehan: Can I dive in? 

Donald Thompson: Yeah, please do. 

Matt Sheehan: All right. So on the personal side, Yeah, mark Twain would probably not be too thrilled with me cause I have too many bills, but I’m going to crunch this down for you. 

Donald Thompson: So we got plenty of tape and time before you start. Like I’m all about free consulting. You can talk as much as you want. 

Matt Sheehan: Uh, love it. I love it. Cool. All right. So, um, I’ll give some bullet points under each, right.

And then feel free to, you know, we can, we can dig in. One is my dad, uh, carried so many lessons with him. He said, Maddie, you know, that’s what we do in Boston. He said, you don’t need a C on your Jersey to be a captain. That’s a lightning rod. I mean, to give me as a seven-year-old back then the, the right, the ability, the willingness, the welcome mat to go lead.

Even if I wasn’t the top. Ooh, that’s real power. That’s real power. So for me, I try to share that with others. As in I despise hierarchy. Uh, now you need some hierarchy to keep order in businesses, but in general, I want everybody to bring that. And usually it’s not, the guys  on the board table who have the best ideas and you have to, you have to give everybody that, that, that view.

So that’s one, uh, C in New Jersey. I firmly believe you have to know your track. And this is another tip. My dad gave me, it’s basically know yourself so well. Know, how you impact your environment. And that requires a lot of reflection, a lot of self-awareness. So I have, you know, my leadership tenants that I’ve worked dearly hard to understand and operate on and self-awareness is a key and I need to push myself more and others to really think about themselves.

It feels selfish at times. There’s no way to lead others. If you, if you can’t lead yourself, you know, don’t mistake leadership for authority. I see this all the time. I and I, and it’s, it’s, it’s, it’s unfortunate. I did it early in my career a few times. I thought it was just, oh, they gave me the stamp and the badge.

And now I can, it’s not like that true leadership. And I’ve made my mistakes along this path to learn that it is about serving others and the great leaders get there because the folks on their team did great. We need to serve them and help them. And then the boomerang happens when they produce and they perform in there.

Excited and engaged all of a sudden you perform because your team’s performing.

Donald Thompson:  I want to jump in there. It took me a lot of years. So you got the first time I was in the big cheer and leading a company, I was leading afraid. And because I was afraid I was harsh on every detail. I was a little bit too aggressive because I didn’t really know my place or my, my style.

And as I’m insured and reason that comment resonated. I started to simplify things and said, wait a minute, if I help each one of these 100 employees in my own way, be 20, 30% better. How strong can we be? And so the moment I took my eyes off what I was going to do that day, versus what we need to do and get done that day, I was able to retain more folks.

I was able to recruit better and that change was innate. And so I very much, you know, have a lot of lessons as, as hard as you do, but it’s hard because as you move up the ladder in business and ranks, it is about your individual contribution. Right? My sales quota, right? My report. My big deal that I won, but to really succeed as a long-term leader, it’s gotta be how we perform.

And that was a big switch for me. 

Matt Sheehan: Yeah, that’s right. That’s great. Next one is leadership is personal. Hey, this all the time, it’s not personal. It is personal. It is personal. Um, specifically when you, you know, somebody might not fit and you have to have those really hard moments. And unfortunately I’ve had to do it to some really great sweet people.

Um, it is personal and, and I’ve been on the other side of that too. And, um, it’s not fun to see or hear it’s so, yeah, it’s just business. It’s not business. So let  take care of people along the entire journey. However long that is, uh, I’ll give you two more in this personal leadership side. Uh, Howard Bihar, the second in command at Starbucks.

I’ve got to talk with him a few times in the last, uh, six months. And, um, he’s written two books. One is the magic cup and he says there, uh, and I’ll quote him. It’s not the, climate’s the character. And it is brilliant because as I think back on my career, and I think about my career moving forward, I think about my kids and the stamp they’ll make on the world.

It is truly not about the resume. That’s not what lets me sleep well at night. It’s a boat, the character, and I’ve made mistakes along the road. Surely early on when I was, I was running and gotten a little too fast. I wasn’t taking care of those around me. Um, but I’ve certainly come to know and Howard just hit it so well that when I look back, it is my wake.

Um, I want that to be that I left good character at behind me that I treated people well, along the way. And it’s true. That’s what I think about a lot. And, and the mistakes I made character mistakes early. Those are the ones that really bother me. It’s not the tactical strategic decision it’s that’s the  stuff we’ll get over.

It’s the character stuff that is, um, S sticks with me. And then, and then lastly, and I’ll pause is there’s a big difference between stress and pressure. Pressure is when you work with your folks on the process, how did you get there? But if you really want an innovative company, mistakes have to be allowed.

And stress is that constant hammering on the results. Now I’m a very results driven person, very much all for myself. I’m a very, I’m a goal setter, but I do realize in an organization when you’re bringing the collective together, you have to put some through the magnifying glass on the way we got there.

That’s pressure versus stress.

Donald Thompson:  It does. And it’s also table stakes for leaders now in how we must lead. And we go into the future because the next generation can deal with and appreciate pressure, but not leaders and managers that create constant stress, they’ll move on that’s right, right. And you have to earn the right to create that kind of pressure as well.

And then in that goes back to one of your other tenants and building that trust and I’ll tell a quick story. It was really interesting. We’re in the offices of one of, one of our firms that I work with. And there was a deliverable, someone had it. And I said, Hey, you know, let’s just say, it’s Julie. Hey, Julie, it’s great to see you.

She’s like, I’m only kind of great to see you. And I was like, whoa, what does that mean? She’s as well, it’s Friday. And I gave you a commitment and this project’s just not ready for me to show you something. And I said, well, tell me, tell me what’s wrong. Couple XYZ. Just didn’t come out the right way that I feel good about it.

I said, well, I’ll tell you what. Why don’t you send me an email where we’re at, reset my expectation and I’ll manage the other piece, but you just deliver something you’re proud of. And I got it. And then she just await dropped out. Right. And she was like, thank you so much. And our job as leaders is to manage the stress.

The pressure’s already there. She didn’t want to deliver something that wasn’t high quality that’s already good. What she was experiencing was stress. Something that could be taken care of, of what that negative impact could be. Right. And our teams are, have the pressure to deliver quality. As leaders, we have to help manage that stress.

Matt Sheehan: It’s great, great perspective. And yet we have to keep that in balance because we also have folks we try to answer to and results matter. And so, um, it’s, uh, it’s, that’s such an interesting dichotomy is we as a system, as a team, as a collective, we have to produce, um, but you gotta give yourself some room as.

As the team to miss a few times and individually, if anybody expects perfection, it just, it doesn’t, it doesn’t exist. And so, uh, yeah, I love that comment. And what a, what a tough balance for this. 

Donald Thompson: One of the things that has helped me because I’ve made so many mistakes in my journey. I’m not as judgmental anymore. And to your point experienced my standards, aren’t lower, but I’m not judgemental. So I want to know the why I want to know to your point where we got here and why we need to fix, how do we make it better the next time? So we’re not here again, but people don’t want to feel that judgment. Right. But they’re okay with needing to rise to a standard.

Matt Sheehan: Oh, right. And they will step up and step up and do that. 

Certainly when you have their back and you show them that one time they will, there’ll be there late on a Friday night. They’ll be there early Saturday morning and getting it done because people are mostly self-driven and 

Donald Thompson: oh, and here’s the one thing. And this is like, uh, young folks that are people that are into video games and different things. They have the term cheat codes. Right. And what I’ve tried to teach my teams. Is that you want to create deliverables for your clients on Monday afternoons, you don’t set deliverables on Friday. You set them on Monday afternoons.

And the reason is because in your final debriefs on that Friday, if you’re not ready, you have the entire weekend. And then you have Monday morning. To address that Monday afternoon delivery. And so in what I’ve been in service businesses, I try to teach our teams. Don’t set deadlines for Friday. Friday’s a hard stop, but Monday afternoon you can do your Friday morning check-ins and most things you’re going to deliver.

You can have a much better solution answer game plan with 72 hours over the weekend. It doesn’t mean you’re not going to be inconvenienced over the weekend. Things are going to be hard, but to the client, They never knew you missed. And it was a project management, just little secret that I forget to really continue to convey, but it’s all about when you set the expectation and for a client, there’s really no material difference unless you are landing an airplane.

Right. Do you mean like if you’re in an airplane, there’s a difference between Friday. And Monday, but in most businesses, there’s not a material difference between Friday delivery or Monday, but those two days in between to clean up, if something didn’t go quite right. Is usually huge. 

Matt Sheehan: Um, I’m taking notes over here, man. That was good. That’s it? So that’s brilliant. I love 

that. 

Donald Thompson: Right. But anyway, I hijacked that. 

Matt Sheehan: No, no, no, no joke. I love it. 

Donald Thompson: Thank you for saying that, man. That’s so funny. 

That’s great. 

So you were on systemic systematically and you were flowing. 

Matt Sheehan: Yeah. Yeah. So if we manage ourselves well and our, our close in teams, where all then when we start to grow as leaders, it becomes systematic. It becomes broader than that. And I do believe there are, um, different requirements.

This is not just great one-on-ones anymore. This is about how to 50 people in a warehouse. Hear that message. It’s very different. Right? And so a couple thoughts on systematically. Um, I think fit is really important. We all look at resumes and we look at backgrounds and all that. What I’ve come to find is that I mentioned this before I look for drive and humility almost in any role.

I do believe in diversity, but I do believe there has to be some common characteristics that, that get all of us on the same page for me. And I do think businesses are an extension of that, that drive and humility are the key. So I mentioned that before folks who just have that sense of awareness, uh, reflection and drive to go be better than they are today.

You give that to me all the time. We’re going to, we’re going to be in good shape. So fit. I look for fit a lot and that’s systemically, right? Bad news never gets better with age. So I have this, this thing all the time, because I am an optimist. Uh, people get a little weirded out when they walk in. It’s the first time time, and they say, oh, I have good and bad news.

I said, bring the bad and we’ll get to the good. And they said, but I thought the way you give feedback is yeah. Feedback. You give some good and then you get to the, uh, you, you get to the, the tough stuff. When it’s news about an organization or something like that, you have to go with the red first and, um, you can have one bad thing can cause can wipe away 10 good stuff.

And so as an organization, I think it’s really important that you create an environment and we’ve done a decent job of this in the past. I can always get better. That is, is not blowing up on mistakes. Um, giving some room for that and give people the room to say, I made a mistake. Here’s what happened.

Here’s my idea to fix it and move on. And if you can do that systematically, nothing will get brushed under the rug. And that’s really important. Next one is a debate than hold hands. I see, great examples of this. And then I see it, uh, falling apart where you’re in a meeting and this could happen in a team, in a room.

It happens, you know, a leadership teams all the time where you have a really healthy debate and then folks walk out of the room. And I’ve seen folks say, well, I don’t really agree that will crater culture it’ll create a culture of a team of an organization. And so what I’ve always tried to do, and I’ve learned this from other great leaders that I’ve worked for.

Certainly my buddy, Greg Kaplan, who started Redbox, he was all about, we can have fierce debates, but when that door opens, we’re holding hands on the way out. And so that’s super, super important. I mentioned before, uh, uh, purpose and values driven businesses. I don’t think I have to go into that. More of it’s really an important one.

Uh, we talked about culture. I do think in all this innovation and all the tech and all that culture is the, it’s the hardest thing to copy. And it’s been written about a lot in the last 10 years, and I’m happy for that because a decade ago it was all about the tactical stuff. The stuff you can measure, the development time that stops per day, whatever your business is.

For me, the, the thing is so hard to copy is the way people interact, the way you make decisions, the way you gel, the way you handle mistakes. And that’s all in my mind, culture. And that I think is hard to do, but when you get it right, it’s the most powerful thing there is in any business, in any industry.

You know, I’ll say, I’ll say one more is I do believe organizations need what I call connective tissue. So I’m a big one-on-one person. So when my direct reports, I am almost robotic is what, whether it’s Friday or, but now all my deadlines are going to get pushed to Monday. So that’s my change. Um, I really believe one-on-ones yeah.

Or important to get a cadence because businesses are like organisms. They have a floats that that’s the boat with oars, and you’ve got to get the whole flow going. But that one-on-one is the connective tissue because CEO is, can send out emails all the time. And I know, people delete them sometimes, or often it, it, because they’re busy and they have their world to manage.

And so how do you build that connective tissue within an organization? One of the ways is things like all hands meetings, you know, every month, every three months, whatever your cycle is, get everybody together. Given technology today, you can, it’s much easier to do, but then it comes down to making sure managers actually meet and talk to their employees very frequently.

And when you do that, then all of a sudden, the ladder starts to build from the CEO to the leadership team. They’re meeting weekly, and then they’re meeting with their direct reports and then the folks in the warehouse, actually are hearing the message frequently that connective tissue is super important, but it is, it takes, it requires discipline 

Donald Thompson: and it’s easy to get busy, right?

From an executive perspective, right? Thinking about things that impact you individually and not the things that impact the money. And that is that communication. And I was talking a lesson that I’ve relearned, you know, it was, I tried to build companies like you do that. Our employees and team members have a lot of autonomy.

Right. And I was asking, one of my leaders is, look, I’ve said, people can organize their schedule. They can, if they have too many priorities, let’s check, let’s talk about it. And it was really, you know, a VP of vis development at TDM. She said, Don, it’s not that people aren’t hearing what you’re saying, but most organizations don’t truly operate like that. Most people are coming from environments where things are dictated to them. That means you have to continue to share this new model, demonstrate this new model and we will get it, but it’s not going to happen, like you think overnight, because we have to unlearn, right. That relationship between trust and leadership, where it’s not been done well in certain organizations.

And that was such great feedback, right? Because it gave me clarity that I have more work to do. Right. I can’t say it once, twice. I’ve got to say it probably 20, 30, a zillion times. I have to model it, understand that, but that it will sink. And, and getting that perspective from one of the leaders in my organization was helpful to me.

Right. Cause I was like, why? I said it twice, like right. If you need a little bit different in your schedule, if you have too much XYZ, it’s like, nah, once you get the 50 we’ll, we’ll get it. And then we have to live it. 

Matt Sheehan: Oh,  repetition is key. And I’ve seen people to your point, come into open organizations like that and be very uncomfortable because it was, it was very command from the top.

And in some environments that may work, you may need that in some environments. So not all companies are created equal as, as you know, but, um, in this world, certainly in the services world and tech, I think you have to have that openness and, um, and, and people will get there, but maybe more than 50 times.

Donald Thompson: Yeah, that’s right. So I could literally, without exaggerating, talk to you for hours, but you’re running a business. What haven’t I asked you about? That you’d like to share. 

Matt Sheehan: It’s been a, it’s been brought in, in a great conversation, um, sharing with like-minded folks about that. And so, you know, for me, I just, I love the role that business has in my case members’ lives.

Right. So that we can create that peace of mind. But it’s also a responsibility as a citizen that I believe businesses have. And that’s not a political statement in any way, shape or form. I love the responsibility that organizations have and the impact that they can on, on the world. And I’ve said for a long time, Uh, the world will continue to have issues and we’ve had issues for, for a long, long time.

And oftentimes the rate of those issues grow faster than, uh, non-profits can keep, keep up. Now I’m a big fan of nonprofits. I sit on, I guide one today, but I think we need entrepreneurs to step in and create what I say sustainable solutions. And so I guess my last thought would be just celebrate the business folks out there who are trying to start something hard.

Who, uh, because I’ve been, as you have in that Fox hole before, keep at it, keep working hard. And there are some issues that we need to solve as entrepreneurs. And when you can make money at solving an issue, ironically, that sustainability, when you don’t have to go back to the well every year and raise more money.

Uh, that to me is, is hard to do. And I know some great nonprofit folks, but just hats off to obviously the nonprofit folks, but to the entrepreneurs out there, just keep at it. And it’s hard. But when you get there, it’s, I’m not sure there’s much more rewarding. That is awesome.