Ep. #983 - Letting Your Leadership Team Lead

Matt DeCoursey 00:01
And we’re back! Back for another episode of Startup Hustle. Matt DeCoursey here to have another conversation I’m hoping helps your business grow. Did you start your own business? Are you managing one? Because if you did, or you’re thinking about it, you’re either a leader or getting ready to be. And I think one of the hardest things about being the leader is sometimes letting your leadership team that you’ve hired lead. As founders and entrepreneurs, we feel that our businesses and our projects are our babies. And sometimes, it’s hard to hand them over to others. We’re going to talk about that and more after I let you know that today’s episode of Startup Hustle is sponsored by Double. That’s a flexible assistant service for busy executives that matches you with an experienced assistant. And you only pay for the hours you need. You tell Double everything you’re looking for in an assistant, and they match you with an experienced, dedicated remote assistant. Double handles all the upfront, time-consuming items, such as interviewing, matching, onboarding, invoicing, and training. You can go to withdouble.com. There’s a link for that in the show notes. And you get 50% off your first month when you sign up and use the code HUSTLE22. Link in the show notes; HUSTLE22 when you sign up. So that’s done with Double.com. Use the code HUSTLE22 and unlock 50% off. I need an assistant, dude. You talk about leadership, and I’ve actually been working on that. I’m probably going to try Double. It’s the first episode of the new sponsorship. Now, we talked about leadership, and part of being able to be present for leadership is sometimes clearing yourself of other tasks. Maybe we’ll talk about that. I don’t know. With me today, I’ve got Will Robinson. Will is the CEO of a fintech in banking and AI documentation efficiency, Encapture. There’s a link for that in the show notes too. Do you know what’s even easier than trying to go type it into your browser? Just scroll down and click those links straight out of Dallas, Texas. Will, welcome to Startup Hustle.

Will Robinson 02:09
Hey, Matt, thanks for having me. Glad to be here.

Matt DeCoursey 02:11
Yeah, I’m looking forward to this topic. This is I like anything involving leadership or selling stuff, or if I get it really well, sales leadership. But where I’d really like to start our conversation today was with a little bit more about your backstory. Are you, Will Robinson, the real danger out? Do you get that?

Will Robinson 02:30
That’s right. That’s right, man, straight out of the 1950s. I knew I knew. I get it probably four to five times a week.

Matt DeCoursey 02:38
Yeah. Sorry. Sorry to tack on that. Yeah. It’s your aging. Well, from being from the 50s.

Will Robinson 02:45
Yes, thank you. Thank you. Well, it’s funny because I’m 35 years old. And, you know, for a while, there was just a certain generation that grew up watching the show, and I thought, You know what, when I hit my 30s, 40s, this is gonna die. No one gonna remember it. And then, of course, two years ago, Amazon made their biggest budget series ever, and it’s lost in space. And so there’s now a whole new generation of people saying, Hey, man, I saw this show. And it’s awesome. And there’s a character named Will Robinson, and have you ever heard of it? And I just kind of roll my eyes?

Matt DeCoursey 03:17
Well, I figured that I had to be part of your backstory.

Will Robinson 03:21
So I do ask my parents that all the time. I’m like, where did you guys think? And they were like, you know, William Robinson, that’s a pretty standard name. We didn’t really watch the show. And we just didn’t think anything about it. So you know, I’ve got three, I’ve got three boys now and young kids. And, like, as we’ve gone through the naming process, that has been a very, you know, explicit part of the conversation with my wife.

Matt DeCoursey 03:44
Well, glad we got to start with the birth part of your backstory. And now, let’s fast forward maybe more to like the professional or transformative process of leadership or just being the CEO at Encapture.

Will Robinson 03:59
Absolutely, yeah, it’s been a fun journey. And it’s kind of a non-traditional journey to getting here. I started my career in the finance world, I was an investment banker who moved to New York City right after college and worked for a big investment bank worked for a big private equity firm, and we invested in software companies, and that’s where I got exposed to, to the software industry and felt like, Man, this is a pretty cool space. And for the rest of my career, I feel like there’s going to be a lot of innovation and opportunity. And I’d always been an entrepreneur at heart and started a couple of businesses as even as a kid to pay for summer camps and stuff and pay for my first car and, and always have that calling to feel like hey, I want to go run a business. So left the finance world and moved back to Dallas. Dallas is home to me, and I worked for another tech company before joining Encapture here as CEO. So the first CEO gig I’ve been in about four years, and it’s been incredible. It’s been really challenging, and it’s been really rewarding. Mean. And, you know, it’s one of those things that I just feel blessed to be able to do it.

Matt DeCoursey 05:05
So leadership’s a tricky thing. I mean, just get right into the meat and potatoes here? Because I think, by the way, I think leaders often get straight to the point. You know, as mentioned, talking about letting your leadership team lead at the beginning of the episode, I mentioned that, and I’ve been guilty of this too because I think that, you know, founder and CEO are sometimes different, as my company Full Scale Unit FullScale.io if you want to learn more about what we do, as it’s grown, I mean, I had no choice but to like, so we had 100 employees after a year. And you get to the point where there’s this phrase, all you can do is all you can do. And I had accidentally made myself the conduit for too much stuff. So I’m still four and a half years later undoing a lot of that, but I mean, what are some of the early lessons you’ve learned?

Will Robinson 05:57
Yeah, you know, it was funny when I joined Encapture, so we have an interesting backstory. We had been around for 20 years, kind of a different business model, the different leadership team, you know, the original founder was running it when I started. And so when I came in, I came in with some new growth capital that bought him out. And really, we had a very different kind of hypothesis about where we wanted to take the company and how to grow company. And it was, it was one of those situations where for the first year and a half, I felt like I was the only person at the company. And I know this sounds dramatic, but it’s true. It’s how I felt. I was the only person in the company who really believed in and saw the vision of where we were trying to go as an organization. You know, I had, I had about 35 or so employees that had been with this company for a long time. And, again, getting them to pivot and think about the world very differently, not only what we do in our core business model, but the way that we treat our customers, the way we treat each other internally, was a complete reset. And, you know, that was really hard because, again, for that first year, year and a half, I felt like I was beating the drum. I was the one who had clarity about the vision and where we were trying to go. And I was trying to, I was trying to drag people along with me. And I got to this point where I was able to hire my first kind of new leader in the company, our head of sales, our Chief Revenue Officer, kind of a new guy coming in, he bought into the vision, and there was this immediate uplift of him being able to can’t carry, kind of carry that vision alongside me. And it just immediately lightens the load by like three acts, having someone else that can come in and do that. So I would say, you know, the transition has been for me in the first year and a half. It’s just me beating the drum, kind of leading from the front. And then, as I built out a new leadership team that’s coming in fresh, I’ve been able to really step back from that and allow them to carry the vision and the execution of the vision forward. And it’s been, it’s been hard, but it’s been really freeing as well.

Matt DeCoursey 07:54
So you know, inserting a leader is a tricky thing because a lot of times, leadership happens organically and in a team, and you know, I think that you see a lot of businesses do that. They’re like, here’s the manager. And, I mean, sometimes that person struggles for traction, and they struggle for credibility. You know, when it comes to getting into a role where I’ve been in this in the past, I’ve taken over some leadership roles. I think being the leader at a company that you started, as opposed to getting hired to be a leader at a company that’s already started. It can be a wildly different bang. I mean, I mean, I guarantee you a bunch of people that are listening to this, if not everybody has had a job or been involved somewhere where there was an appointed leader that was very ineffective. And you know, that’s one of the things I think the first thing is, is if you are you talk about, you know, letting your leadership team lead. I think it’s the founder’s job or whoever hires you to put you in that role is also if they want you to be effective, and you want to let those people lead, you have to license, you know, you have to say, hey, look, I need, I need you to buy in me, I need you as this team to buy in, this is why we’re doing this. And this is the point here, but you know, like being able to say I need your support, I want your support. Now on the leadership side. I think that one of the first things you need to do if you are in charge of a team is to try to do anything you can to build credibility. Just because they say you’re the leader doesn’t mean you’re the leader. So for me, I like to go if I’ll sit down and I’ll do everyone’s job with them. Maybe I and I might only be like 15 minutes or a little bit. But I want to gain a little bit of empathy for everybody on the team and see what they’re going through. And I think it’s really easy to just ask people like, what do you think we could do to improve here, make sure that you’re listening to the people that you’re that you know that you’re supposed to lead because I think if you lose, if you don’t, if you’re, if you’re seen as not listening, or caring, or not giving a shit about any five input, or you’re gonna struggle for credibility.

Will Robinson 10:22
People want to know that they can believe in you, right? I mean, the reader comes in and, and, you know, my goal is always to promote from within. But it’s always hard because sometimes you look at the folks you have, and they may be great contributors to your team. But you can’t bet that leadership role on that person, maybe just yet, or maybe never. But the big thing for me coming in was, you know, I need to show that you got to show you gotta have a lot of empathy, that you care, you really care about the people here and you care about their success, especially if you’re going through a lot of change, like we’ve like we were going through where we were, we were kind of thinking about everything differently, you know, me getting in and saying, Hey, I may not understand every single job at this company. But I care about you, as a person, I care about your professional development and your well being. And I’m going to lead from the front in the sense of, if you’re here, I’m here. And so there were some little things around just even physical presence, like being in the office, you know, this was also right before COVID hit. And so that ended a lot of kinds of workplace leadership dynamic. But being around being in the office being present, I think is important for leaders, especially early on, to be willing to roll up your sleeves. And, you know, I remember there were some of our initial sales meetings where we were trying to redo our sales playbook and our pitch deck, you know, I would, I’d work the weekends and work super late at night to get this stuff done. A because it had to get done. b I don’t think anyone else could do it the way I wanted it to be done, which again, early phase, not the way to lead long term. But you know, it just demonstrated, like, hey, wills here, he cares, he’s putting out you know, fourth 100% effort. And you know, we can get behind that. So it’s shifted, I get to be a little bit more behind the scenes now. And I’m a big believer in servant leadership, which we can talk about later. But it’s been fun to either grow up internally, some leaders or bring in some new leaders from the outside and let them have a lot of room to ride with their teams.

Matt DeCoursey 12:17
Your success is my success. And that’s the message that I try to convey when I’m talking to the people that work at my company, and you know, it kind of throws them for a loop because I tell them, I work for you. And they’re like, No, that isn’t the case, your name is actually signed on my paycheck. And I’m like, Yeah, but I work for you. Because it’s my job to help you be successful. If you’re successful, then I’m successful. And that’s that. You talked about servant leadership. And that’s the you know, I’ll let you talk about that for a second. I don’t, you know, at the same time, I, I don’t necessarily set myself up as a servant, either. But that said, it’s like, you know that I think that that’s a main a big part of getting people to get behind you is they, if they feel that what you’re doing is also okay, help everyone else get what they want. And we’ll figure out what that is, first, figure out what it is because you get what you’re looking at a whole group of people is like, just take 20 random people, they’re all going to be motivated by different things. And they’re all going to also have different personality styles and just like different drivers. And I think having a basic understanding, because here’s the thing, if you have people that aren’t necessarily motivated by money, giving them a financial incentive, or equity or anything like that isn’t necessarily effective. I’ve actually been on the shitty end of that. Yeah. Where I ended up basically giving away shares to people that didn’t even care about any of that.

Will Robinson 13:54
Yeah, you gotta find you got to find that. You have to find what motivates people. And sometimes it’s sometimes money. Sometimes it’s working on interesting things. Sometimes it’s feeling like they solve a real problem. Sometimes it’s being heard, you know, we’ve got folks here who do a really good job and kind of a more public forum, because they like to be heard, and that makes them feel good. And so finding kind of what makes everybody tick is key. And then, you know, to your point, Matt, it was the servant leadership thing, it’s almost inverting the org chart is the way I talk about it. It’s like instead of it being this pyramid, where I’m the top point, and you know, everyone kind of trickles down. For me, it’s like I’m at the bottom. And, you know, our individual contributors are really the folks that are interacting with our customers every single day. They’re building our product, they’re implementing our product, and they’re the ones who make the little decisions that have a huge impact on the overall trajectory of the company. And so, you know, my job is to empower it’s almost kind of this this waterfall effect that like if I can empower my leadership team, my head of sales had a seat as head of product, to feel like they have a lot of clarity and what our goals are as an as an organization, and then the autonomy to, you know, make the decisions they need. And they realize that I’m here truly in a support role for them. It allows them to shine. And then you know, conversely, they can do the same with their folks under them, and with their folks under them. So it creates this culture where you don’t have to have a lot of clarity from, you know, at the org perspective, like, where are we going as a company? What are the metrics that matter by team, and then you know, having the right people on staff who feel comfortable with that, with that level of autonomy to say in just so competence around, you know, supporting people around them saying, hey, look, I’m not going to think about myself. First, I’m gonna think about the people around me before I think about myself. So we have a couple of three core values here that we talked about a lot that, that, that really play into that. And we kind of have a kind of a workplace culture mentality, again, kind of another tagline. So we use certain phrases to really drill this in. And it’s been, I think it’s been pretty effective.

Matt DeCoursey 15:57
So servant leadership is defined as a leadership philosophy built on the belief that the most effective leaders strive to serve others, rather than accrue power or take control. You don’t work for me, you work with me, and me, and that’s a key thing is crazy, man. So I’ll go, you know, the majority of our employees are in the Philippines. And before COVID, they all came to the same office every day, and I would go over and visit and I would stop and talk to everyone. I mean, I do try to do their job a little bit and just try to get a grasp on what they were going through and what they were dealing with. And I would always collect feedback after my trips. And people would say to our management that, I can’t believe Matt came and talked to us, the CEO came and talked to us, and I’m sitting there thinking, Where have you worked? You know, like, it was scary for me. I’m like, Where have you worked, that the leadership didn’t come talk to you? And that’s that, like, that’s what I think you need to avoid. And that’s, you know, now, here, we are kind of sharing some leadership tips. And we’re, you know, still promising to talk about letting your leadership team lead. I mean, this is this is a, this is a, it’s okay, because I think we have to kind of set a foundation for some of that. And, you know, I want to get into talking a little bit more about that right after I remind you that today’s episode of Startup Hustle is brought to you by Double the experts and pairing founders with remote executive assistants that you can trust with Double that’s like the word with Double.com. There’s a link for that in the show notes, and you can use the code. Hustlers 22, it’s 50% off. Last time I checked, that’s half. That’s half. Yeah, I’m verifying that with you, you are you Encapture does machine learning for banks and lenders. So did does the algorithm show that I’m correct.

Will Robinson 17:55
I believe that 50% is half yes.

Matt DeCoursey 17:59
And that’s that, you know, I have a speech that I give that goes along with my book that tells me that the whole premise of doubt is that 100% of your own effort is all you can give. And there’s always someone that’s like, Yeah, but I give 110% I’m like, No, you don’t know, for this ethically, because you have to, like take your own efforts. And like divide it like, this is where my attention goes personally, professionally or physically. Yeah, there’s always one person. Yeah, but I give I give more than 100% No, you know, yeah, 100% of what you can do is all you can do now, I want to I want to visit the subject of so you talk about you’re stepping into a company that already existed, you mentioned that so here’s the thing is, is I think a lot of times founders or or boards, or whoever’s running the company, go, they just kind of drop a leader in. And then they’re kind of like a powerless entity that doesn’t really have the ability to do anything. And so, you know, that’s, that’s, that’s been a challenge for me. And my company grew quickly. I’ve had to have sales leaders, marketing leaders, operational leaders, recruitment leaders, all different kinds of leaders put in and for me, what I learned is, the best thing I can do is get real involved with them in the beginning, and then get the eff out of the way. Yeah, like, I mean, almost like, and this is gonna sound non supportive, but this is totally supportive. So I think the best thing you do with letting your leadership team lead is almost kind of disappear for a little bit.

Will Robinson 19:44
Yeah, I mean, it’s, you know, there’s different styles and to your point, Matt, there’s there are folks out there who, who rule with an iron fist, you know, CEOs, founders and or even you don’t you could be that the head of a division in your company, you know, You’ve got a team below you, and you kind of rule with an iron fist. And every, every decision big or small comes through you. And, you know, it’s very hard to scale a business that way. And it’s very hard to actually bring in people who are going to be molded to have multiplier effects in your company. Because the people who do well, in situations where you roll with an iron fist, are just kind of these Yes men that are not empowered to make decisions, they’re always going to defer to you, and it shuts off creativity in my mind. So, you know, for me, when I bring in new leaders or promote people internally, you know, the first thing I do is make sure we have really clear expectations about what the role is and what I’m expecting them to do. And, you know, I’m pretty, pretty honest about you know, opportunities, I think that they can improve things or, you know, I give them a brain dump of my of my views, but ultimately, it comes back to, hey, here’s what I’m expecting out of you in this role, this is what good is going to look like from a metric perspective or organizational success. Now, how you get there, I’m putting this on you. So you’re the one driving the ship, I’m really riding along as an advocate, as a resource, as a sounding board. And, you know, I want to foster this relationship where you can come, you know, like, if you can come to me with problems, issues, or questions, and I’m not going to necessarily tell you, but I’m going to brainstorm with you. So. So we spent a lot of time talking about that and doing that. And, you know, unfortunately, not every person out there works well, under that, that style. I’ve had leaders here who, who have promoted up internally who I really wanted to feel like we could have this loss, a fair relationship where I’ve set the metrics, and they kind of have the the ability to go make it happen, and they just haven’t, they’ve really struggled, they don’t know where to start, they don’t know how to prioritize. So it’s a hard thing to do. But once you get it, once you get it going, it just allows people to flourish. And I think it allows me to attract some really, really high quality leaders into my company, and even young folks that are maybe not leaders yet. But when they look at the leadership style of the company, and we say, hey, look, as we keep growing, you guys get to be leaders, they get excited about that environment.

Matt DeCoursey 22:15
So when you talk about setting expectations, one of them and I do that one of the expectations that you have to set, though, is that I am expecting you to fail in some regards. And know that that’s not the end of the world. What I want to see is growth from that. And I’d never be upset when someone fails. But I do get progressively upset when we do the same dumb failure over and over and over by the time you get to like the sixth really like repetitive, avoidable, lame error, I start to wonder, I’m like, Okay, are you paying attention? Do you care? And can you do this job? It’s so yeah, I mean, I do. But I do expect that failure in the beginning. And that and I think it’s important to if you want to empower your leadership team is to let them know that upfront, like, I’m not expecting you to be perfect. And then I am expecting you to be open and forthright with me though, because as my company’s gotten bigger, I find that one of the things that is sometimes challenging is getting the real story of what’s going on out on the floor. And, you know, it’s like, well, we didn’t want to tell you because we didn’t want you to be upset, okay? Well, I, that you’re, you’re forcing me into a spot where I have no idea you can’t solve. It’s difficult to solve a problem you don’t know exists.

Will Robinson 23:36
Yeah, that’s my biggest, that’s my biggest fear being in this seat is that I’m in this ivory tower, and I don’t know what’s going on. And you know, like that, again, it’s kind of a mind monster. But, you know, so we have the same here. It’s, it’s high expectations, high trust, high accountability. And those are, those are the ways that we work together and that we lead. And so high expectations are what we talked about, we want to be clear about what good looks like, we are going to strive to be better. You know, I mean, that’s just that, again, that’s a culture, that’s a decision I make. And that’s a decision we make as a company, we will strive to be better. So we set high expectations, we’re clear about those. But then the high trust thing comes in. So it’s, look, we’re not going to micromanage you and your job and your role. We’re not going to whether you’re an individual contributor or a leader, we’re going to, we’re going to trust that you’re going to make the right decisions for your team, and we’re going to support you in that. And then the high accountability pieces is something that I think a lot of companies either tiptoe around, or they just don’t really want to get in, or they interpret it as a very negative thing. For us accountability simply is, you know, what were the expectations? And where did we fall into those expectations? Do we meet them? Do we exceed them? Do we fall short and why? And so to your point that you have to create a very safe environment for this accountability thing to work well. You want people to be able to show up and say hey, I failed, or hey, I tried something because I thought it was a good idea and It didn’t work, and then allowing ourselves to not you know, the result of that is not me sitting here berating somebody for oh, you failed, you know, you didn’t do a good job. It’s like, no, that’s incredible that you tried, what did we learn? And what are we going to do differently going forward, so that we can meet those expectations that we’re trying to meet as an org. And so that accountability piece, it requires a lot of trust, it requires, you know, I think starting with me an environment that says, hey, look, if something bad’s going on, we, we actually want people to raise their hands. And we, you know, and we want them to do it in a way where it’s not just complaining, but it’s like, Hey, I see a problem over here, or this is not working. Here’s what I think we can do better. And, you know, it also requires folks who have enough, you know, self confidence to admit that they’re wrong. And there are people out there and I have struggled with this myself personally in the past, where you just want to be seen as the person who always does everything right. And that’s impossible. That’s just such a bad way to live your life that leads to so many problems. But if you can kind of get past that and say, Hey, we’re gonna make mistakes, we’ve seen a lot of really good growth as a company, a lot of innovation here. And people really flourish because they realize I’m not gonna get, I’m not gonna get fired, if something doesn’t go the way we want it to, as long as I’m willing to talk about it, and brainstorm on how we fix it.

Matt DeCoursey 26:17
Yeah, with that, when I’m talking to a leadership team, that one thing I want to see is responsibility. Now, when I say responsibility, that I think a lot of people, if you ask people that say define responsibility, they’ll say, well, getting my kids to school on time, or showing up to work on time, I don’t look at responsibility like that responsibility is, is owning the results, and outcome of your own efforts. And it’s really easy to spot because people that aren’t that can’t take responsibility. Alright, so here’s someone and they, and they walk in the door, and they’re like, I got a speeding ticket on the way here, I can’t believe that a police officer would give me that ticket for going 45 and a 25. How dare he. That is not taking responsibility. So part of that, if you see that, and your leadership team, if you build a culture of blame, you’re gonna have a nasty culture soon enough, because everyone’s gonna just start blaming each other. And there’s no real, there’s no real productive outcome there. So part of the responsibility thing, though, as you know, there’s, there’s this concept of Extreme Ownership, which is the idea that as a leader, there are no, there are no bad teams, there are only bad leaders. So I’ve seen this a lot with in leadership roles, and you talk about sometimes, as the leader’s leader, you need to be able to clarify that. And at some point, I do this at my own company, if something fails, like enough, all you’re gonna start hearing me say, Okay, well, at some point, this isn’t this is on us, at the top level, because we’re not finding a way to get this done, whether whatever that is, you have to have this level of responsibility. And I think if you start to hear the tone, the tonality of blame occurring around your organization and your conversations with all of it, then you know that I think that that’s a big, big, big red flag, and you’re not going to really end up letting anybody lead if they can’t, like I said, it’s there, you got to own the results, your outcome is some, would you rather have an employee that failed at something, say, You know what, I didn’t do a very good job here. And I know why. And I can do a better job next time. I don’t think we’re gonna get the same result. Or would you rather have some of it was this person’s fault, or this was the reason it didn’t occur. Bla, bla, bla, blame, blame, blame, blame, blame. I hear the first person take responsibility. I’m going to handle that completely differently than someone that’s just constantly blaming everyone and everything about themselves for the outcome.

Will Robinson 29:12
Yeah, it’s a huge thing. And you know, I think in companies too, another thing that you have to look for is, is there cross functional blame, right? Is the sales team blaming the product? Well, we didn’t hit our goal this quarter, because the product didn’t have the features we needed, or the product team said, Well, you know, I’m not getting good feedback from my implementation team. Because, you know, I want to set priorities and set a roadmap and add features that they need. I don’t feel like I’m getting good feedback. You know, that’s the stuff that can become really toxic. And that’s something where I, you know, I’m not going to take credit for this for us, but, but my leadership here has done a really good job of not diving into that I’m gonna blame. You know, I’m gonna blame another team. You know, they’ve said, look, I mean, we definitely call out challenges and issues, but we do that in a constructive, you know, for them to say, okay, how can we solve this and you know, the other thing too on this mat that I think swings the other way that we’re having to deal with right now, if you are in an Extreme Ownership type environment, there are times where me as the the top leader, I do have to make the call that there are some things, if we’re failing, there’s some things that just simply are out of our control, that maybe have contributed to the failure. And so we don’t need to go back and blow up everything that we’re doing, but just recognize it for what it is, and like a good example right now, you know, with with the, you know, with economic uncertainty and rising inflation and interest rates going up, it’s just getting a lot harder for our sales team to close certain deals, and we’re selling into banks and lenders and, and, you know, they’re, they’re fairly, they’re a fairly conservative bunch, and, you know, to start with, and, and so they’re a bit fearful and say, Well, I don’t know, if I want to make a decision on buying your platform now, or maybe wait a couple quarters. And, you know, we had a really good productive conversation this week around some of the stuff that there’s definitely some things we can do differently, but some of the stuff is the environment in which we’re operating. And, you know, we need to, we need to let that place, we need to let that have its place. So we don’t unnecessarily beat ourselves up. So there’s this real fine balance. And I think, to your point, that most organizations are still trying to get to that, that Extreme Ownership or that high accountability type environment. But once you’re there, you do need to make sure that people aren’t, you know, not being too hard on themselves to where they start making bad decisions as a company.

Matt DeCoursey 31:30
Yeah, and like I said, the whole purpose of the responsibility is that, you know, someone’s got to take ownership of stuff, otherwise, it just starts just, I don’t know, it, that kind of stuff definitely flows downhill. And it can be, it can be really toxic. You know, when you talk about now, now, back to the idea of, you know, letting your leadership team lead I, I once again, want to point out to those of you listening, if you founded a company, it is your baby, and and look that I hear I hear some real red flags. I hear him a lot. So, you know, we talked about like, with Double, with Double.com. And with assistants and stuff like that, I think that so much of not letting your leadership team lead starts with a founder’s inability to begin to delegate simple things. And you hear things like, well, it’s easier for me to just do it myself. Okay, well, that’s, that’s a really great way to guarantee that you’ll always be the person to do it. And then those things pile up, and those things pile up and those things pile up, and then you end up being a blocker. And you know, the end I, what’s something when you think about something like, what are some red flags that a founder could say, or something you’ve experienced? I don’t want to ask you to throw anyone under the bus here. But, you know, there’s, there’s, I mean, you know, like the inability to turn up to begin to delegate simple things. And the idea that you’re always the best person, you can always do it better. Hey, look, if you’re a founder, if your employees were all you, they wouldn’t work for you. So I think we talked about setting expectations, I think so much of it starts with what are my expectations, because, like here at my company, there’s, I mean, I don’t have a job. Other than that software developers is the only job where I’ll hire people that are pre trained to come in. But even then, like say, they came to work for Encapture. They don’t know your platform, they don’t know how you do stuff. They don’t know, you got to have some level that like, hey, this person’s got to get up to speed. And that’s one of the things I hear from a lot. Oh, it’s faster for me to just do it myself.

Will Robinson 33:54
Yeah, it’s dangerous, Matt.

Matt DeCoursey 33:57
I mean, if you make that pile big enough, it’ll bury Yeah. Yeah.

Will Robinson 34:01
And, you know, it really starts with as a founder, CEO, you got to be really clear with yourself, what are your goals for the business? Like, what do you really want in life? And you know, there’s kind of the cliche, that every foundry there wants to be rich, or they want to be keen. And, you know, it’s, it’s being clear with yourself, what do you really want out of this, because if you’re, you know, if you’re really focused on being the person in control all the time, you can run a great five, six-person company, you know, and that will work really well for you, but you will never grow you will never scale. And if you try, there will be all sorts of issues and so things that I’ll say this Matt things that I focus on, that I try to check myself on to make sure that I’m letting my people lead 1am I getting really clear expectations kind of on an annual basis or quarterly basis on what I’m expecting out of them or out of their group. That has to be written, it has to be communicated 20 different times, to little things I don’t I try not to, I try to check and see how often I’m speaking up in bigger company meetings. Specifically, if it’s like a sales team meeting, like a weekly sales forecast meeting or a weekly, you know, CS implementation meeting, our product roadmap meeting, I don’t, I’d rather be a listener, and an observer than really the voice leading. And so that’s something else that you can look for, you know, if you feel like you’re constantly inserting yourself, or redirecting the conversation over the leader that’s supposed to be leading the meeting, that’s a red flag. If you’re, and this is hard for me, I’m saying things that are hard for me, there are little things that will happen that are not the way you would do them. Whether it’s the way, maybe a specific term in a contract written or, or maybe a training, program cadence, or maybe the way that you someone’s trying to organize their team, their team structure, it’s maybe not the exact way you do it. But letting them own that, figure that out, and then just holding them accountable to the release to the results that you’re expecting, and letting them do that is something that I, I feel like I have to let go of a lot. So those are some top of mind things, at least for me, that I that I have struggled with in the past and I’ve tried to be intentional about is, the more that I can kind of fade into the background, from an X’s and O’s perspective, and let my folks lead really, you know, my responsibility here is to make sure that everybody that companies clear on the vision clear where we’re trying to go as a company, that, you know, the resources that we have are allocated properly, making sure that we have enough capital to achieve the goals we’re trying to achieve. And making sure my leadership team feels like they have my support. And then making their decisions. That’s kind of where I try to draw the line, you look at the decisions that the management team might want to make.

Matt DeCoursey 36:50
And I’m expanding on your thoughts here, so I’ve had situations I’ve looked at, okay, hey, this is the solution, we want to try. This is what we want to do, you know, so on and so forth. And I’m sitting here thinking, I’m like, I don’t think this is gonna work. But as the leaders later, sometimes you have to let people try their idea. Now look, maybe it will work, you might be wrong. Yeah, but Intel, if that’s the solution that your leadership team thinks is gonna work. You might, you might lose credibility and the inability to be the leaders later if you’re just shooting down everyone’s ideas, because they’re not yours. Now, I do that with salespeople, because, you know, like, we at Full Scale, we want a specific type of client, we get a new salesperson, and I’ll actually let them sign up the wrong client, occasionally, because I don’t want to just like, you know, I’m supposed to be approving every new client, we come in, and we’re not a big, we’re not a big batch operation, we want the right kind of people to work with not just people to work with. But if you have salespeople, and every time they bring a deal to the table, you just tear it up, not the right one now, the right one, not the right one, well, you’re gonna you’re you’re, they’re not going to stick around, or they’re not going to learn so sometimes, you know, it’s just like, I mean, it’s, it’s like having kids, man, it’s like, sometimes you gotta, you gotta let them, you gotta let them go make the mistake, and see how that works. Now, what I think is not a mistake, is checking out with Double.com and Startup Hustle, Startup Hustle listeners can go there, there’s a link in the show notes, they can use the code HUSTLE22 and unlock 50% off the first month, or you can just click the link in the show notes. It’ll take you there, HUSTLE22 Go check them out. I was looking at their website. And you know, I want to get back to the concept that if you want to be a leader, I’ve been working on this myself. So actually, I hired a mindfulness coach. And it was a new thing. I hadn’t done anything like that before. And it did. It’s done great. She’s done a great job helping me because the very first session was, okay, let’s talk about all the things that you’re doing or that sucking up your time or your thoughts that are preventing you from doing the things that are most valuable at your company. And that’s actually I came to the conclusion of wow, I mean, first off, it was a mind blowing thing to sit back and like get that list. I’m like, you’re like I’m like eight minutes into it and I’m like, holy shit. I am doing a lot of stuff that I don’t want to do. I shouldn’t do it and probably it isn’t the most valuable thing I could do. And it’s preventing me from doing other things like being a leader, finding more business and doing a lot of stuff. So for a lot I think for a lot of people that’s an assistant thing.

Will Robinson 40:00
I’ve got man, I’ve got a couple of different avenues for that. I’ve got a peer group of other software CEOs that I meet with regularly to talk through business stuff, and worked with a couple different coaches and mentors in the past to help bring clarity. And, you know, the thing to that has come out of a lot of that, which is interesting, Matt is, you know, to your point, a lot of help with structuring your day, one of the things that has been a recurring theme for me is having the right people at the company and on the team, and that’s kind of where a lot of this has come, you know, come back to if I’m trying to really, you know, we’ve been, we’ve been on this very aggressive growth path, and it’s been awesome, but it’s, it’s required, you know, me to, you know, bring in new folks let some old folks go and, and really be constantly tweaking the team that we have to do that. And the thing that typically holds us back are, you know, the wrong people in the wrong seats, kind of the, the, you know, the wrong people on the bus mentality. And that’s, that’s something that I think as a leader, you have to be very aware of is not, you know, you’ve got letting your leaders lead is critical, but also being able to kind of skip level, assess talent, and help your leaders see things that maybe they don’t see, because with their individual contributors, because they’re, you know, in it day in, day out. So we spent a lot of time in our company talking about, you know, talking about our people, and again, we’re 70 employees, so we’re not quite as big as you, Matt, but we’ve got 70 people, and in my one on ones every week with my leadership team, we can more or less kind of talk about every single but every single person at the company, and we don’t talk about every single person every week, but we kind of track how folks are doing and you know, where are they flourishing? Where are they struggling? And I have learned it’s been more beneficial to move more quickly on folks that are if they’re doing a good job, promote them up, give them more responsibility, and if they’re struggling, and it’s at a point where we’ve supported them as much as we can, and they’re just not going to make it to tracking everybody else down to you got to make a change. So that’s kind of the hard side, I think about being a founder or CEO is once you start growing and scaling your team. Besides letting your leaders lead, you have to be really vigilant about having high-quality folks on your team. If you’re trying to do big things, it’s a hard thing to do.

Matt DeCoursey 42:26
You know, it’s crazy, as the US government says that until you have more than 500 employees, you’re quite a small business, and I’m like whoever wrote that is a frickin idiot. They’ve never run. 10 is a lot. Yeah. 500. That’s wild. Yeah, that is literally the guideline.

Will Robinson 42:50
So, which is funny, because I mean, like, I just think about the problems that I face with 20, 30, 40, 50, 60, 70 employees.

Matt DeCoursey 42:57
But at 498, you’re such a small business. Yeah.

Will Robinson 43:01
You know, and it’s a small business of four. Yeah, yeah, it’s insane.

Matt DeCoursey 43:06
Well, here we are. And we have reached, we have reached our we are near our end here. And our discussion about letting your leadership team lead. I mean, what about today’s conversation stands out? Or what’s some of the best advice that we came up with today, in your opinion?

Will Robinson 43:25
Man, for me, it always comes back to you being clear as a CEO or founder, what you’re trying to do, what the company is trying to do, right? If you have a board or you have investors, they’re going to help, they’re going to help feed this, but I keep coming back to if your goal is to grow and to build a big company, which again, 200 people that’s a big company, I know that small business, but that’s a big company. You know, if you’re trying to really grow and build something great, you cannot do it yourself. You have to bring in strong leaders. And strong leaders are those who do not want you to micromanage them; they want to have the space and the resources, and the autonomy to go make stuff happen. That’s why they’re strong leaders in the first place. And so, figuring out for yourself, I think it requires some humility to understand what your strengths and weaknesses are. And really being intentional about stepping back and letting folks lead, I think, is what I’ve seen in my career has had the biggest impact.

Matt DeCoursey 44:24
Yeah, I’ve got an I got a couple of gems for once again, I want to thank the folks over at Double, and Double remote executive assistants can help you with everything from email to Calendar, organization expense reporting, database management, go-to with that’s the word with Double.com use the code hustle 20 to get 50% off just click that link in the show notes, and they’ve got plenty of people that can help you, so you know so much about this conversation has been about people that can help you. Let them help let people do their job like you know unless you want to do the job yourself forever. You got to eventually let someone know that you gotta either hire someone that already knows how to do it. Or you got to get someone in there that has the acumen and drive and understanding to get it done. And that’s not going to happen. If you’re standing there, letting people do it. Now part of letting people do it is accepting the fact that they’re not going to be perfect. You’re not, either. Trust me, you are not either. And that’s the big thing that comes with it. One thing I didn’t mention during the show that I think is important is when you are beginning, you talked about letting the leadership team lead. Well, in the precursor to them even becoming a leadership team. I, you know, I think one of the things that are important is I always ask people from hiring for leadership roles. I want to make sure that they are capable of having a tough conversation. And I think that’s something we didn’t get into. Because look, here’s the reality that not everyone’s going to succeed. And, and I think part of leadership is also having other people that can convey a tough message, you can say, say, you know, hey, well, you know, we’re not getting the results that we came here to get. And I’d like to hear your opinion on how, when, and why that might be the case and what we can do to find some solutions. I’ve come up with a few things as well. Now that look, that’s a polite way to have a tough conversation. That’s basically saying, Hey, dude, you’re not getting it done. I think you know that. I know that. Let’s figure this out. Now, if you’re not willing to have that conversation, a lot of people are scared that conversation terrifies people, like how many people in America have actually had to fire someone because it’s not a huge portion. And like, that’s, that’s a whole thing. So, you know, you know, we’re looking to do that. And I want to hear, I want to hear people that I’m putting in a leadership role. I want to hear how they’re going to handle that. Because I also don’t want someone that’s going to go in there, you know, and shoot first and then ask for names. Yeah, just meaning like there’s, you know, there’s a way to get in there and do that in a way that’s productive. I thought about myself 15 years ago, and I now have a different answer to that question. But I want to hear it from the leaders. And I want to make sure that it aligns, you know because there are people that want to lead with fear. And I just don’t keep like, Dude, I have like almost no churn at our company, like people rarely, if ever, quit their job at Full Scale. But that has a lot to do with why because we foot we’re a solution or solutions and results. Those are the things that drive what we do. So I think if you focus on that, and that’s the message you’re sending downstream to your leadership, say, hey, look, I don’t know what the solution is, but I’m counting on you to go figure that out. And we’ll catch up with you down the road.

Will Robinson 47:49
Awesome. Thanks, man. Appreciate it.