taylor desseyn

guidance counselor 2.0 · episode 179

locker room to board room w/ brian dougherty

oct 14, 2022 · 30 min · with brian dougherty · hosted by taylor desseyn

key takeaways

  • respect roles and expertise in your organization; don't micromanage by stepping outside your lane.
  • leaders take responsibility for failures so teams can play loose without fear and make better decisions.
  • when crunch hits, motivate by looking to teammates not authority; teams win fourth and one situations together.
  • break big projects into specific small targets rather than trying to hit everything at once.
  • cross-train across positions and departments early to understand how other roles work and become more valuable.

listen or watch

listen

spotify apple podcasts every app

about this episode

learn how football principles like staying in your lane, playing loose, and focusing on small details apply to building effective engineering teams and managing through crunch.

On today's show, I'm joined by Brian Dougherty. He was the CTO/COO at Jumpstart Health Investors when we recorded this, but he has since started a similar role for Snappt. Congrats, Brian! It was Brian's second time on the show and dive into the similarities between football and running a business. All you sports fans out there, get ready to ~ play ball ~ (I know that's baseball but still #sports)

Like what you hear? Connect with me-

Website: www.taylordesseyn.com

LinkedIn: Taylor Desseyn

Tweet me: @tdesseyn

Tik Tok: @tdesseyn

Pics of the life, wife, daughter & dog: @tdesseyn

full transcript

auto-generated from the audio, so expect a few typos. the audio is the source of truth.

Hello, hello. Thanks for listening to Guidance Counselor 2.0. Listen, I want to give you a quick rundown of what this podcast is and what you're about to get into as you listen to these episodes. We had Guidance Counselors in middle school. We had Guidance Counselors in high school, but we didn't really have Guidance Counselors in college and now as professionals, we don't really have anybody to turn to to ask a quick question to learn something about the job search or to navigate your career. So that is what I want this podcast to be for you. I want it to be a tool for you to navigate the job search and your career.

So that being said, I hope you enjoy this episode. And if you need to reach me, Taylor at vaco.com is how to get in touch with me old fashioned email social media at t s and t d e s s e y n. And finally, please rate and review this in the app store because I want this to be discoverable for others so they can navigate their careers. Hope you enjoy the episode. Brian, let's do a quick intro about yourself. Who are you? And then we'll just dive right into all the homework that you sent me. Yes, sure, man. So I'm Brian Dardi. I'm the chief operating officer slash chief technology officer at Jumpstart Health Investors.

I've worked in a variety of startups and large corporate enterprises, building tech teams, leading tech teams, for everything from product development, QA DevOps, support analytics, you name it. One of the things that's a little different about me, I didn't really come up in more of the traditional nerdy tech path. I was a football player in high school, was the MVP of my high school football team, played in college in a little D3 school, was the defensive MVP there. So there's a lot where I've formed how I lead and how I build teams based on my experiences playing football, which is kind of a different look from versus a lot different engineering managers.

So I thought it'd be interesting to come in and see like if there's any places, you know, can provide some insight into some of the things I learned in those experiences and how you can use those to build, you know, more effective engineering teams and be more effective in a business setting. 100%. 100%. So, all right, so I want to dive into, I want to go and dive into the first topic today. And again, I'm just going off this. This is completely like real time. I haven't really like, you know, I'm just he Brian sent me a list. I'm looking at it now. Tick tock for those of you watching.

Sorry, you're seeing my computer screen. All right. So Brian, I want to talk about the first thing. Trainers train coaches, coach players play. So I want to break that down. So what what a trainers train coaches coach. That's it. Yeah, that makes more trainers train coaches coach players play. Break that down and kind of how it would apply to obviously the business world? Yeah, and so like there's roles and responsibilities are important, right? And if you try to be everything and to everyone, you're not going to be effective, right? So there's many times where you got to, you know, respect your position and respect the expertise of those that are in that role for reason.

Even if sometimes you think you might know best, right? So you football field, there's many times where a player says, you know, they take a lick, their head hurts, right? And they want want to get back out there, their adrenaline is running well, they're in key pick and some ass, right? But the trainer says, you need to sit down, you know, we'll get you back in the quarter or next week. You got to step back, right? You know, you're not the trainer. You're going to do their job and let them be effective, right? Same thing with coaches, right? You might think that you see what the, what the offense is doing or what the other team is doing.

And you might not always agree with the play that the coach calls, right? But you've got to let the coach coach and then the coach also has to let the player play right like they can't go in and they completely micromanage and get so deep and make the players so neurotic that they can't play their game all right the coaches that they're actually be on the field playing so it's really about like understanding where you fit in into an organization and how you can all work to be effective but also more catching yourself when you're starting to get you know out of your lane in in an unhealthy way, right?

Where, you know, well, you might have more insight in a moment, potentially. You know, generally it can slow everything down and make everybody less effective. If you start, you know, trying to do somebody else's, somebody else's job where you might not have the knowledge, might not have the expertise, and it stops you from having that really, you know, sound cohesiveness as a team. Well, and I think also too, I mean, I think, you know, staying your lane, I think is maybe another thing. And that may seem, you know, a bad thing to say out loud, but talk about the importance of, from a coaches perspective, letting your team play loose.

And so I actually became fascinated with this concept of playing loose during COVID because I saw my teams, I mean, like, things were clenched. You know what I'm saying? Like, like people got nervous. Am I gonna get laid off? And I was like, listen, friends, you're good. Just go out and recruit. Go out and have fun, enjoy being at home, enjoy different changes scenery, enjoy intentional conversations with developers across the country, helping people, what's the importance of playing loose and then how as a leader can we instill that vibe with our team? Right, I mean, like one of the important things is easier a little bit in football.

Like no matter what anybody tells you, and tell you get to the point where you're in the NFL and your livelihood actually rides on it, that's why indeed it's refo, high school football. Okay, it's a game, right? You're playing it because it's fun, right? You know, not so we can make the NFL, not so, you know, we can get some crazy scholarship or something like that, right? So, you know, by treating it like a game and to your point playing loose, it just, it frees you up to actually, you know, not make so many mistakes, right? Because when you go in and start like making every play critical and there's another line in there, and over next play, right?

Like the only thing that matters is the current play, right? And if it doesn't matter what happened previously, whether it was great, right? You know, you put, you know, you did something amazing, you found some horrible bug in the code, saved the day, wonderful, right? That was great. That plays over next play, right? It doesn't matter. Just forgot to highlight your where clause and did a SQL statement and oh no, I just updated 83 million in rows in the database and took down production, right? Like, we've all been there, right? Like, it doesn't matter. Next play, right? You know, how do you respond to what's put in play the next way?

And if you go in and try to like get everybody playing from a place of fear, like you can't play scared, right? So if you put them in a spot where there's this feeling that if you make a mistake, you know, it's going to get pulled. You're going to get benched. The team's, you know, it's going to lose. You're going to lose, right? Like, whatever. like people just can't play appropriately, right? You gotta play back, let the game come to use some, and you know, cause that's where your creativity is, right? Otherwise you get so much tunnel vision, you end up tripping over your own two feet and getting hit by the issues.

Otherwise that, you know, you'd catch and see if you were just playing light on your feet and having a good time with it. Absolutely, absolutely. What do you think the biggest thing, and I don't know why I'm blurry right now, I gotta try to fix this as driving and saying, why, what, what would you tell the managers, like what's your biggest key to allow your team to play loose? That's a good question. I think it's making it clear that as a leader, you are going to take responsibility for anything that goes sound, right? You know, like a good leader, a good manager, the successes are always owned by the team and the failures are always owned by the manager and the leader, right?

So if you've got a coach or a manager or a leader that's leading in that fashion, it frees everybody up. Because everybody knows that all I'm really responsible for is listening, being coachable, right? And playing the best I can and not playing selfishly. And if everybody on your team functions that way, where they're playing, where they're working and playing for the guy next to them, right? And they're putting the time to follow procedures, I guess, would be the, you know, the core layering engineering, right? Like you're not going to be not like making changes to production directly or skipping code reviews or whatever, right? Like there's a lot of worries there, right?

As long as you're doing the right things, right, and trying your hardest, then, you know, you should be successful. And there's going to be times where you're not, right? Like, you're not going to win every game. But it's how you play it, how hard you play it. And, and the real leaders free up their team to think and play that way and insulate them from all the other crap, right, whether it be external stakeholders or other managers in the department that maybe don't run their teams that way or injections or like whatever, right? Like, I mean, all of that would be guarded by your engineering manager so that people can run and play effectively.

I love that. I love that. And oh my gosh, my camera is driving absolutely insane. So let me so you put in here fourth and one look over. So I'm kind of curious with that. So I was in the marching band. So basically I, so Brandon comes in, hold on, why do all of these conversations around leadership sound the same and often don't provide anything groundbreaking yet still come off as groundbreaking because people still won't do the things we've always been known they should do. It's a great, great question, right? I've often wondered the same thing. All of this seems so obvious, but you go into so many organizations is like, why don't you do this?

I think often from a place of fear, I mean, you can survive so much in ambiguity, especially in large corporations. When you say, this is on me, and really mean that, and really do it right, that can put you in the crosshairs. And a lot of people don't have the self-confidence and the self-validation to do that and genuinely put their team first. right? Like, it, you know, it takes a different mindset to look at it. And so many people are promoted quickly or brought in that really don't know what's going on. And, you know, the Peter principles in play that it's not as, and it's not always appreciated, right?

Like, if you're in a pathological culture of a corporation, you can get, you know, you can get sniped because of that, right? So, you got to find a corporation is the right culture to support it. And then And then the right person that goes and embraces and builds that culture on top of it to really run that way. And the company is to do that. It's awesome. Right? I mean, it's great. So I think going back to plain loose, I think having a culture where you're allowed to make mistakes and not just get yelled at or passive aggressive comments, I think it goes from the top.

And I think Brandon, I think what your question is and what your comment is is so true. But for me, it's one of these things where this stems from the top and I think there's a lot of people who, like if the upper leaders aren't being vulnerable in front of their teams and taking accountability and say, hey, I messed up, this was my fault, that's not going to trickle down. Like that, whoever's number one within your group or your division, your organization, company, like it needs to be set from the top. But if those leaders at the top are just, you know, cloaking daggers, kind of like just, you know, not really taking accountability, man, that just it trickles down tremendously.

The other piece there, the other piece there, Taylor and Brandon, that's really important, right? It's really easy. It's not really easy. I don't mean that, right? But it's more straightforward for an engineering manager to act like that and a leader to act like that, right? But the next step is building a culture within your team toward the entire team acts like that, okay? Because yeah, you can have a very supportive, nice, kind, has-your-back manager. That's wonderful. But you're usually going to be working on a larger team. And if there's to your point, microaggressions, chips, like if you're looking over your shoulder for the for the teammate next to you and you don't really go in and regulate and really implement that culture across the board and make sure everybody's either on the bus or gets the hell off the bus, then you're not going to be effective.

One person can't be the culture. They have to be the champion that causes the entire culture to grow across the board top to bottom, left or right. Yeah. And Brandon, again, kind of thrown up some good comments, should companies allow employees to put up something that essentially looks like a vote of no confidence if their leadership sucks. Like shouldn't, shouldn't companies have more mechanisms to throw red flags about their leadership performance and then power ground level employees and power ground level employees to be part of that conversation. That's hard to grow a, or to scale an organization, have a place where you can say things and not necessarily feel like you're singled out and reprimanded.

I don't know. I feel like more organizations need this. Brian, do you have any solutions at all? Yeah, I mean, like, so I got two, right? So one of the more, you know, six Sigma super Jack Donigee corporate ways of doing it, is the 360 degree reviews, right? And those are really valuable. Okay, so 360 degree review is where a person that they're placing the org chart. They're reviewed by their superiors, right? Their bosses, right? They're reviewed by their colleagues. So like if I was a VP in the organization, my previous organization, right? I'd be reviewed by the CIO, right? Who is my boss? I'd be reviewed by the VP of data analytics and the VP of IT operations, right?

So my colleagues and then reviewed by many of of the folks that are beneath you in the org chart, that roll up to you. So I'd be also re-ed by a junior developer, my architect, my product manager. And so like by doing that, you go and get feedback from across the board, right? And it can be anonymized or not, right? So that's one way of doing it, right? And that's a more formal way. Good leaders, you do it in their one-on-ones, right? I mean, every one of my one-on-ones, I end with, you know, what can I do to make your life better and what can I do to be better?

Right? So good leaders should be soliciting that feedback, right? Now the problem is generally the ones that are soliciting the most are the ones that need it the least. So that's where it's a challenge. But again, that comes back to more of what's your organizational culture, right? like, you know, one of the great things about my former boss, he had an open door policy with everybody in the IT department and he meant it, right? Like, if you have any questions or concerns about your manager, you could walk in and talk to him and say, this is, look, he wasn't going to go and ratchet out until the manager of the details, right?

But like, he would take that and see if there's any way he could provide constructive feedback during the one-on-ones with the managers, right? So, seeing those kinds of things, seeing those servant leaders like top to bottom, seeing those open door policies and they actually mean it and then actually taking advantage of the open door. You know, there's ways to do it in the right cultures. But again, it comes down to the culture from top to bottom. Yeah, absolutely. So fourth and one. Let's talk about it again. Like I said, fourth and one look over where's your head at when you sent that to me? Yeah.

So my college football coach, Andy Fry, great guy. I'm not Amy Fry if you're watching. Yeah, exactly. If you just happen to watch Taylor stream here. But one of those go-to sayings, I've heard it 400 times in the last 20 years, is when it's fourth and one and the games on the line, you don't look over to the coach and point at him and say, hey, coach, this one's for you. You look at the guys next to you. I think that's so important when you're building an engineering team that really wants to accomplish something because there are times in engineering where it's fourth in one right where you're tired you've been putting out a production fire you've got some major deliverable and you've been going through crunch time and you know you got to find that you know pull up that last bit of strength concentration you know you just want to go to bed and it's it's how do you look over to the people next to you that you've been sweating with you know you know mentally right you've been working so hard together as a group to get some deliverable over the finish line and say, you know what, I'm not really doing this for the coach.

I'm not really doing this for the company. You know what I mean? Like I'm doing it for my team here. My team's relying on me. I'm relying on them. You know, let's look at each other and use that as motivation to find the way to get this done, right? And if you're doing strong teams that really like appreciate each other and respect each other and, you know, expect each other's abilities. When it comes to that crunch time, you do that and you look over and that's what you want, right? Those are the teams that come to play that fourth in one situation and make the stop, right?

Or pound the ball in, right? So that's what that would mean. I love that. I love that. Let's see here. I'm gonna go to another one here. Let's see here. First, I'll see here. Lane exhausted in the field of battle. That sounds super epic. What were your thoughts on that? Yeah. So I mean, that's a that's a Lombardi quote, which I'm going to go into butcher. And it basically is, there's no better feeling than, at the end of the game, lie exhausted on the field of battle victorious. And this is what you want to really shoot for. In your career, in whatever you're pursuing with passion, you want to know that when the whistle blows, when the deliverables deliver, that you did everything you can, that you did everything that was in your power to make your team, your company, your product successful.

Obviously within reason, we want to sacrifice your work-life balance or your family, all that. But you are laying there at the end saying, I did everything I could and you know what, we ended up pulling it off. And there's no greater feeling in the world than knowing you gave it at at all when you're beat up, you're tired, you're bloody, you're exhausted and you know, that's the best feeling there is, right? Is knowing you left it all in the field, you did everything you could to get something done and you succeeded, right? That's what I... Yeah, I love that. Next thing, aim small, miss small.

Curious on that one. Aim small, yes small. Yeah, so this was something that was originally a football thing and then like, I think Mel Gibson co-opted it in like the movie The Patriot back in the day, right? But it's this concept that, yeah. We're all over the place today. We're talking about football, Mel Gibson, The Patriot. We're just a band marching band. Yeah, everything, it's perfect, right? Everything goes. Be a little variety. So it's this concept of when you're setting out to do something, right? Accomplish the task, right? And football, it's, you know, I play defensive end and so much comes down to what the first movement of the player is in front of me, right?

So, rather than focusing on the entire player, take a very small part of the player, maybe it's just a little hole in their jersey, right, and focus on where that hole goes. Okay. Now, if you're focusing on the whole player, right, and they move one way, you might completely miss them. But if you're focusing on something very specific, that by a little bit, and you're still going to hit the player, right? So, going to do something, don't just look at the whole project and say, all right, we're going to go knock out this whole thing, right? It's all right, break it down in small pieces and really focus on how are you going to hit those, right?

How are you going to knock those at? You know, when you're when you're doing product and figuring out what a feature should be, right? Don't just be like, okay, cool, they're going to interact with the system. Get down to the granularity you need to where even if you don't 100% nail what the customer is giving you, you're still going to be close enough to be effective, right? So that's a small miss ball and obviously in the Patriot that was a shooting thing to wear like you know aim at a button not at the not at the person but sure sure and and what and talk to me too because I feel like that's so I feel like this this is systematically in tech in general right like basically when it comes to you know I could talk about during the interview process and people can't explain things they have done in detail right I you know a lot of times within delivery I think there's a lot of times where there's more of just a general way of thinking or a general oversight and people aren't being attention to detail.

How can, I guess, an individual help improve that mindset or how can someone work on aiming small? Yeah, so I think it's first figure out what matters. Right? I mean, it comes back to the why you're actually doing what you're trying to do. Like I don't want a person to move in front of me. The why I'm doing this is because if they move this way, it's probably going to be one of these plays. If they move at me, it's going to be one of these plays. Like sure, I understand the why I need to know which direction they're going, right? And so then I know how to really look at them and detect that as quickly as possible, right?

When you're explaining something to an interviewer, it's kind of the same thing. It's like, all right, why are they asking me this question? Right? do they really want to understand my level of technical expertise in this area? Do they want to understand, have I faced adversity in a situation? I need to give that example. Do they want to understand, have I completed something before? Are they trying to understand if I have a creative aspect of this? So it's a little bit on the fly, at least in the interview setting, saying, all right, what are they trying to get at? Then that can hone you into that small area.

It's like, okay, they really want to make sure I understand what a three-tier architecture is. It's like, okay, cool. Now I've got three places to aim, right? Like, I can talk about the front end, I can talk about the middle tier, right? And just narrow it down that way. And then it's really easy to say, cool, what are the high points around this, right? So does that help? That's kind of good. It does. Yeah. And I think that's my advice to all people watching this now in the future. I think it really good at getting really granular. Yeah. And I think, I think one of the way, I mean, I, I talk about this all time.

I'm gonna be honest with you, tweeting has helped me a ton. Like learning how to write, learning how to communicate in small like micro pieces, micro like, you know, thoughts, Twitter's really helped with that. So, you know, if you're wanting to try to get better communication and people are talking about how to get better communication, honestly, journaling, writing, like all that stuff helps a ton. Another thing I want to ask too, as we wrap up here in the last five minutes, because I'm curious where your head was at when you sent this to me. Cause I'll give my thoughts as well. Play any position. Yeah.

I have some thoughts on this, but I definitely interview you. So I want to hear your thoughts first. Sure. I mean, this is like, this is really important when you're starting out, but it's also equally important when you've been doing it for years. Right. Like, so when you're starting out playing the game, you know, especially like you're in high school, right? You're not going to be as developed physically, right? You're pretty much just fodder for the seniors and juniors and first team, right? So there's going to be lots of opportunities to jump in and play different positions on the field. And football is one of those unique sports where like, every position is very different, right?

Like the quarterback is playing a different game than the defensive tackle who's playing a different game than the wide receiver who's playing a different game than the linebacker is completely different, right? So taking that opportunity when the coach says, is hey, I need a player for a ball to hop in and get exposure, right? Like, yeah, you're not going to know what you're doing, but you can go out there and try. You can learn more about how the position works. And that makes you a better player later, even if you don't want to play in that position, because you know what that position does. You've got at least some context and awareness of it, right?

That goes over completely the same way to when you're starting out your career, right? If you're a junior developer somewhere, and you look, well, I really like front end, whatever, right? If they need somebody to help on the back end, hop over, throw your hand up. gladly do this and learn how to write some store procedures or write some sequel periods, right? Yeah. Yeah. You know, we need help in the middle. You're great. I will totally take and start writing some API hooks, right? Like whatever, like be willing to just do good outside of your position and get exposure to all this. One, you might find out you like another position better.

And two, it's going to be more effective your position because you know how the other positions play. When you get the, when you get to be a manager, right, and higher up, it's also important. Take that time to go and shadow other people in the organization, especially outside your department, right? Go watch the users, go watch other leadership and see how they manage their teams. Go understand how ops work, how the finance team work, how things work through the business processes, right? It's so important because getting that context, it doesn't take much time and it makes you so much more effective and valuable to the organization to do that.

So throw your hand up and say, yeah, put me out, I'm gonna try that position for a little bit, right? Yeah, yeah, I love that. And I think that's something that I like to do on my team. So, you know, not that Will Muschamp did a great job at South Carolina. But one thing that he was known for is cross-training his defensive backs and, you know, safety's corners, basically cross-training them to where that they can fill in if somebody's hurt, needs a break or something. And I've kind of taken that mentality with my team is that for me, I like to cross-train my people on both sales and recruiting.

Because what I have seen is that our best sales people have come from a recruiting background and understand the technical aspect of it and who can also sell. And then, you know, and so for me, I'm always trying to cross-train my people and play different positions because I think that also invokes a level of buy-in. Right. Now everyone's on the same team. And appreciation, right? Yeah, definitely appreciation. So all right, Brian, as we wrap up here, so I started asking this question to people since you've come on the show, because it's Guidance Councilor 2.0 and basically wanna give specific feedback. what would you tell your younger self, like what is a career tip or something you would encourage your younger self to do before you started on your professional journey?

Yeah, I think it's validation's got to come from within. Right? Like, you know, it's, you always want to be hungry. You always want to be driving, you know, success of your team, of your org, you know, and it's great to get the headpats and everything, but if you can't be like, what's the word, satisfied by like you knowing when you're doing your best and you knowing when you're adding value, then there's no amount of work, achievement, recognition, hours put in the job that's gonna convince you of that. So really making sure you're working on your own mental health and looking for that as you go, right?

Cause it's easier to start that earlier than try to figure it out later, right? Especially for some damages that have been done. Absolutely. Absolutely. Awesome. Awesome. All right, y'all. Well, thank you, Brian. Thank you, man. I appreciate it. That was fun. Yeah, I really like that. I really like that. Anytime I can talk sports with tech is a blast. I'm y'all go connect with Brian. He's a great resource. And and y'all have a wonderful weekend. And I will see y'all next week for another great week of guest and yeah. Talk to you soon. Thanks y'all. I'm just feeling peace. Hey, you did it. You listened to an entire episode and I am very grateful, because you know why?

There's a lot of podcasts out there. There's a lot of episodes, and I myself rarely finished an entire episode, so I appreciate you so, so much for listening. Quick reminder, please rate and review this podcast in the App Store. I want this to be discoverable to others, and the only way that happens is if you take the time right now and rate and review it. Please, like, right now. unless you're driving, then don't do it. So thank you again. If you need to reach out to me, Taylor at Vaco.com or at T-dastin on all social media handles. And I hope you have a fantastic day.

liked this one? get the next in your inbox

850+ readers get the takeaways, the prompts and a straight read on the market. no spam, leave whenever.

or subscribe at taylordesseyn.beehiiv.com · no spam, unsubscribe anytime.