Leading by Letting Go: The Power of Hands-Off Engineering Management | The Pair Program Ep26

Tim Winkler: 00:00:05

Welcome to the PAIR program from hatchpad, the podcast that gives you a front row seat to candid conversations with tech leaders from the startup world. I'm your host, Tim Winkler, the creator of Hatchpad,

Alan Deitch: 00:00:15

and I'm your other host, Mike Gruin. Join

undefined: 00:00:17

us

Tim Winkler: 00:00:17

each episode as we bring together. Two guests to dissect topics at the intersection of technology, startups, and career growth. What's up everyone? We are back for another episode of the Pair program. I'm your host, Tim Winkler, accompanied by my co-host Mike Gruin. What's going on?

Alan Deitch: 00:00:41

How are you? I'm doing

Mike Gruen: 00:00:42

great. Uh, in the middle of, uh, remodeling, well, redecorating, I should say, redecorating my office. So, uh, we just got some fresh paint on there. And then, uh, have furniture being delivered today. Uh, and then maybe I'll even hang some pictures. So we'll break some. I was gonna say, yeah, looks pretty barren right now. Right? Don't even have the bottle of whiskey back there right now. So, uh,

Tim Winkler: 00:01:02

let me know when the whiskey comes in. um, I was gonna, I was gonna throw you a line about, uh, chat G p T right now. So like, uh, how many hours a day do you think you're spending just experimenting in

Mike Gruen: 00:01:14

chat G p T? Oh, I mean, that was a, that was like two months ago or month ago. Uh, I've moved on to crayon and just having it generate pictures for me. So, uh, that's been

Alan Deitch: 00:01:23

a lot of fun.

Tim Winkler: 00:01:26

So you're not still, you know, using it for all your one-on-one? No, no. I, I

Mike Gruen: 00:01:30

mean, I do plan to use it come mid-year reviews. That'll be, it'll be helpful then. But I mean, you're blowing up my pairing come June, right?

John Barrile: 00:01:41

Yeah. Did you have me cracking up with that?

Tim Winkler: 00:01:43

That was funny. Um, um, cool. Let's jump. Let's give our listeners a quick heads up on today's episode. So today's episode is all about letting go, um, specifically for tech leaders and startups. You know, knowing when to let go of certain task, uh, and duties. Um, you know, so like over the course of, of helping, you know, a number of startups and early stages scale up. You know, a common trend that we see with, with founders or executive leaders is that it can be quite difficult to. A pass off processes and responsibilities that maybe you've owned since inception or like those early on stages. Um, you know, you may feel like nobody. Can do what you do quite like you do it, um, which is oftentimes true. How, however, it's, it's, you know, very difficult to get to that next level of growth if you're not willing to let go of those tasks and trust, which would probably be a big key word that we use a lot here. Um, trust that your team can handle it. Um, and so we have a couple of guests with us here to provide their insights on this topic. Uh, we have Alan Diet, um, a senior Director of engineering, a Spot Hero, um, a popular digital parking app. And then John Bur, uh, Barilla, uh, sorry, Burrell. It's okay. It's Barilla, uh, the Chief Technology Officer of Heartbeat Health, uh, a health tech startup based in New York. Uh, I am excited to get their perspectives on this topic today. So Alan and John, thank you both for spending time with us on the Para Program.

Alan Deitch: 00:03:12

Thank you for the invitation.

Tim Winkler: 00:03:13

Yeah, of course. Um, alright, so before we dive into the discussion, we do like to kick things off with a fun segment that we call Pair me Up. Pair pair me up. That's where we're gonna go around the room. We'll shout out a couple of complimentary pairings. And Mike, you, uh, always lead us off. So what do you got for us today? All right. I

Mike Gruen: 00:03:29

am, uh, dipping back into my childhood. Uh, I do not recommend this, but pledge and wood floor. Uh, we had a lot of fun growing up, uh, putting place down on the wood floor and then sliding around with socks. Uh, nearly killed my dad. I feel bad about this, uh, but he like slipped and fell on the stairs. Um, but yeah, uh, it was a lot of fun. Um, step, you know, get into like a pillowcase and somebody would put pillows down the hall and you try and jump over it and then like when you land, you play those

Alan Deitch: 00:03:56

just loads of fun.

Mike Gruen: 00:03:57

Uh,

John Barrile: 00:03:58

so pledge and wood floor. So

Tim Winkler: 00:04:01

nearly pledged floors and broken wrists. Exactly.

Alan Deitch: 00:04:07

Nice.

Tim Winkler: 00:04:08

Nice. I'm not gonna lie, I had an immediate flashback too. Yes. As a kid, like once, you know, mom would, you know, those floors would just be freshly touched up, just flying through with some socks on. Like you're right, you can get

undefined: 00:04:19

some

Mike Gruen: 00:04:19

good distance. Yeah. But we do it with like the furniture, like we would go with the heavy spray, like it. It wasn't like what you were supposed to be using to clean the floors. It was nice. Like bowling alley, like

John Barrile: 00:04:31

That's good.

Tim Winkler: 00:04:32

Alright. Yeah. We'll, we'll accept that. That's nice. I'm, I'm glad

John Barrile: 00:04:36

it was acceptable.

Tim Winkler: 00:04:41

Um, alright, I'm, I'm gonna jump in. So my pairing today is, uh, uh, new parents and espresso machines. Um, and. You know, for, for some of those listeners, you know, this, this is, uh, the third episode now since I've had my, my first child. So we're going into month two now of being parents to our, our, uh, new daughter Alice. And, you know, one of the things that, you know, everybody always preaches is like the lack of sleep and kids are expensive, right? Like, uh, kind of knew that going into it, but we weren't really sure how to, how to tackle some of these problems. And, um, we would. You know, for the most part, I, you know, I go to coffee shops quite a bit. For me, it was a good way of just getting outta the house during the pandemic, um, or, or post pandemic just to, you know, working from home. Uh, I spent a lot of money on, on, uh, on coffee, my wife drinking a latte. Um, and so we invested in a, in an espresso, espresso machine. Uh, and it's been a game changer for us. So um, Saw how fast, like you, you know, the, you, you save money, uh, you know, not, not not going and getting those lattes from, from the coffee shop. Um, you know, getting, getting pretty creative with how we, we, you know, make our own like different syrups and whatnot. Um, and then obviously, you know, the, the lack of sleep is catching up on us. So the, uh, can report that ca the caffeine level in the Winkler household's been flow. Um, so, uh, that's my, my pairing for today is, uh, new, new parents and, uh, expresso machines. Very nice. Um, cool. Let's pass it over to the guest. Um, Alan, why don't you give us a quick intro and then, and tell us, uh, your

Alan Deitch: 00:06:22

pairing. Sure, thanks. Uh, and, and again, thanks for. Inviting me to the podcast. My name is Alan Diet. I am one of the senior directors of engineering at Spot Hero. I oversee our, uh, all of the software that drivers will interface with. So whether that be our mobile apps or our website or emails or anything at all, that has to do with the driver's experience, one of my teams or building that and, um, continuing to. My pairing. So we're almost in March, which means spring out here in Chicago. And for me that means racing season is starting. Uh, I'm an amateur triathlete, so for me, my pairing is actually three elements. It's swimming, biking, and running and getting, um, getting really into the flow of, of training. And all three would be my. My current pairings. Wow. Hey,

Mike Gruen: 00:07:11

Tim, are we gonna accept that? Is that, is that acceptable

Tim Winkler: 00:07:16

I was kinda leaning into like cleaning products would be more acceptable, but, um, what, what are those, would you say is your, your biggest strength and which one's your, your biggest weakness of those three?

Alan Deitch: 00:07:27

I think my strengths are swimming and biking. They're pretty close. Um, and running is my weakest of the three discipl.

Tim Winkler: 00:07:34

Interesting. Yeah. Yeah. I've, I've know a few folks that have done tries and, uh, swimming's always the weakest for them. They just, either they never had access to a pool to, to train or, or to, to practice. And, um, I, you know, I've been going to a, a rec center over the last year that has a pool, and it's, it's crazy. You know, how, you know, you, I don't know. I, I don't go swimming that often, uh, since I was a kid. Right. So then getting back into that, You know, it's a lot of mental, uh, of, you know, making sh telling yourself you're not, you're not, you know, you're, you're, you're losing that breath, but you're gonna be able to take that next breath. And once you lose that, you know, you start to panic a little bit. Breath gets shorter and shorter. And so, um, a lot of swimming is, is kind of just like, yeah, a lot of mental training, uh, is what, what I've kind of. Um, but I'm sure the same applies to, you know, something that's wild enough to do a triathlon. I mean, it takes a pretty, pretty large amount of mental strength.

Alan Deitch: 00:08:31

The open water swim is where it gets real interesting swimming in a pool and swimming in, in a lake or an ocean. Oh yeah. It's, there's a difference there. And so, um, but I think it's my, one of the reasons why it is one of my strengths is cause I have been swimming my whole life and so I, I understand the water well, but then it puts me ahead in the first, you know, in the first element of the race. And then by the time I get to the run, I'm zo and that's when everyone catches up. So it's like, it's an interesting equilibrium. Um, but yeah, for sure. Just keep moving forward, you know? That's cool. Keep

Tim Winkler: 00:09:02

moving forward. John, have you ever done a try? Anything like that? I have never

John Barrile: 00:09:06

done a try. Nope. Wow. I've run, that's about it. I'll run, I'll swim, I'll bike, but yeah. Not together. Yeah. Cool.

Alan Deitch: 00:09:15

All right.

Tim Winkler: 00:09:15

Good pairing. Good Try pairing Um, let's, uh, let's pass it over to, to John about a quick intro in your pairing. Yeah.

John Barrile: 00:09:23

Um, thanks for having me. Um, it, um, I'm John, I'm the, the CTO at Heartbeat Health. Uh, it's, uh, virtual first cardiology startup. Um, and, um, you know, I, I've been there for about a year. I think we're, uh, we're actually starting to get some traction here. So I think, uh, we're, we're grown. Grown pretty good right now. Um, I've got the engineering team, um, and, uh, as far as my pairing goes, I was gonna say product and engineering, but I figured y'all think that was incredibly lame. So um, good call. I was gonna go

Mike Gruen: 00:09:53

with, uh, good call

Alan Deitch: 00:09:55

I was gonna go with, um,

John Barrile: 00:09:58

bourbon and college football.

Tim Winkler: 00:10:00

Yes. Bourbon made the cut

Mike Gruen: 00:10:01

again. Yeah, there we go. I thought we were gonna make an entire, entire episode without saying whiskey

John Barrile: 00:10:09

Oh man. We're

Tim Winkler: 00:10:10

brewing football, man. Who's, who's your squad? Who's your team? Alabama. Oh Ben, roll

John Barrile: 00:10:16

tide. Yeah, roll tide. Alright. There's a lot of bourbon this season though. Yeah, so I'm

Tim Winkler: 00:10:23

actually a Tennessee fan, so we were quite, quite thrilled for oh, for one, one time, uh, you know, in years that there was a victory. That was probably a tough one for you to watch, huh? Oh yeah. What kind of burger were you drinking at that on that night?

John Barrile: 00:10:38

It was, it was Woodford Reserve, but uh, you know, our COO is. As a big Tennessee fan,

Tim Winkler: 00:10:43

so, oh, so you guys have some, some words, uh, every so often. Uh, once my phone was

John Barrile: 00:10:48

just blowing up with

Alan Deitch: 00:10:50

memes,

Tim Winkler: 00:10:52

Good stuff. Yeah, I mean, that's a great pairing. Uh, my business partner Will, will love that. Uh, big college football guy. Big bourbon guy. So, we'll that'll, that'll kind of wrap up the pairing. Let's, uh, let's jump into, um, the actual episode here. So, as I mentioned, you know, we're gonna be talking about letting go. Um, and, and you know, breaking that down a little bit so, you know, when is the right time to let go of certain tasks, you know, what are these different tasks or responsibilities that you may want to consider handing off, uh, as a tech leader and how, how do you go about it? What I love about, you know, both of our guests who are, who are with us, is that, um, you know, we're able to come at this topic from a couple of different perspectives. Alan, you know, you've been in a role where, you know, you're at the top of your engineering org. Uh, just a heartbeat away from the Ct o uh, John, you know, you've had a similar situation in previous companies like Rally. Now you're, you sit as the CTO of Heartbeat Health and, uh, you've likely had to hand off some of those, you know, your tasks to a senior person on the team. Um, and so I think we're gonna be able to tackle this from a few different angles. Um, why don't we start with you, Alan, uh, maybe give the listeners just a little bit of context on some of the types of roles and, and the companies that you've been a part of and, and how in those positions, That you've had to maybe take over certain responsibilities from leadership, you know, like kind of what goes into that transition and what stands out for you for that to happen successfully? Yeah,

Alan Deitch: 00:12:25

so, um, when I was at Groupon before Spot Hero, I was, I was at a. Uh, and the founding stages of Groupon, like in the first two to 400 people, full company. And this was a time when it was just, um, innovation all over the place. Very unorganized in terms of teams, but we had a mission and, and everyone just went to build, just go build, build, build. And we'll all figure out what happens next, right? This is super early days, and after a while you get to. organically form these groups. And so now you have these groups of people working on certain areas. And now we would call them teams, right? Um, and so as with teams, sometimes you look around and you go, well, I'm looking for leadership. Um, should I do A, should I do B? Should I prioritize this or that? And it just felt natural to me to start stepping up in that regard. And this is a little bit of just. over the top with making sure to review every poll request, uh, making sure that everyone felt comfortable, uh, and then understanding where people's challenges were. And so not with a title, but more of a responsibility, like I formed into a tech leader within our little group. And then we as a company at the same time, more coincidentally, we're just growing, growing, and maturing. And so a bunch of leaders above me said, Hey, we see you. We see you stepping up. We see you taking. Uh, a bunch of these engineers and moving them into a specific direction. Would you like to be a manager, And like, that's just, just a weird thing to think about. You're so good at this one thing. We're gonna ask you not to do that anymore, but to do this other thing, uh, and manage a bunch of people. And, and as as my story goes, I told them, sure, but only for like three months. And if I hate it or if it's a disaster, I wanna go back to building. Um, and they're like, yeah, sure we can, you know, we can do that. And within the first couple of weeks, I really found love and. Managing people and helping them. But to the point of this topic, letting go of all those building and engineering responsibilities was so difficult. Y it took years, years, and years to be like, okay, I'm not responsible for building this feature, this task, this piece of software. I'm responsible for solving problems without code building teams and bringing humans together to solve. um, in their way, but ultimately get us to the next, next evolutionary step. And um, yeah, it was just really difficult for a while personally, and I'm sure later we'll talk about how we get through some of those personal challenges. But that's basically how I got into engineering management. Uh, coming up through like an individual contributor role, did you,

Mike Gruen: 00:15:06

um, were you asked to manage people that had previously been your peers or were you asked to manage

Alan Deitch: 00:15:12

like, oh, yeah, yeah, yeah.

Mike Gruen: 00:15:13

Cause I, when I got into management, like I had some conversation, boss came to me, what do you think about being a manager? I was like, sure. Uh, someday, like, I didn't think it was gonna happen next week. Um, and then the next week I was basically managing, but I got lucky in that as a Java developer, I ended up managing a bunch of mainframe engineers, couldn't do what they were doing, forced me to learn, like to not do any of that So, uh, so yeah, I think that's also, yeah, a good thing that's can be a challenge for a lot of people being asked to manage people that you previously worked with and letting go of the things that used to build and now managing the people that are building the things you built. I could see that being a big.

Alan Deitch: 00:15:51

Yeah, absolutely. Uh, the team was my peers and now I was their boss. We were still building the same thing, using the same technologies. Uh, I remember, I don't have 'em with me, but I remember I bought three books and it was like managing 1 0 1 and all of these things, and I was looking for chapters specifically around, so now you're the boss of your friends. I couldn't find any resources and so. uh, we could talk about that later if you'd like, but yeah, that was, that was a very interesting challenge of like shifting that dynamic. Mm-hmm.

Tim Winkler: 00:16:21

Yes. What's so interesting is that, you know, something that you've been doing, you know, and, and really crafting, you know, rounding out your, your skillset around for years, you're asked to do something else and to start to build back, build that muscle. Um, and so, but that, that muscle is so important that you focus on. Right? That, that, that, that building of other people around you, solving problems, making decisions, um, those are all traits that y you know, it's tough to focus on that if you're still trying to get in the weeds of, of, of the building. Um, and so it's just interesting to think through of, you know, what do you mean? You know, I, I can't get my hands dirty over there anymore. Like, you really do have to kind of like completely pull, pull yourself into that. Direction. Uh, John, how about yourself? Like, um, you know, talk, talk to me a little bit about, uh, you know, that transition for you as well, and then we can obviously talk about, um, you know, what goes into, you know, delegating that stuff off.

John Barrile: 00:17:17

Yeah, yeah. Um, so great question. Um, so I guess my, my first management role, it's been, what, 14 years now? Uh, something like that. It's been a while. Um, it was, uh, similar. I, I, I sort of. Pushed into the role, I just got told that I was going to be managing this team. Um, and the team had really struggled in a lot of ways. It was sort of, um, it was a large corporation and, um, you know, struggling to deliver, you know, production down twice a day. Um, all kinds of fun. And, um, you know, so, so really what happened, um, you know, to your point about being a peer and then suddenly managing this group, Um, I was very, very hands-on. Uh, way too hands-on, I think. Um, and, I would even go as far as say that I sort of micromanage the team a good bit. Mm-hmm. Um, there came a point when, um, there was a, a, a college hire that actually was the, um, one of the best hires I've ever made. This, this guy. Um, he actually pulled me, settle day. He called me a tyrant. Uh, um, yeah.

Tim Winkler: 00:18:27

Um,

John Barrile: 00:18:29

and you know, I just kind of brush it off. Anyways, after that role, I, I stepped back into like an IC role, uh, in my next job. And, um, what's interesting is that I worked for somebody who was exactly like the way that I was. Um, and I realized, oh man, I would've hated to work for me. This would've been miserable. I ran into, I ran into that guy who called me a two years ago. Um, uh, you know, we, we, we caught up and had a beverage and, uh, I was like, you remember when you called me a, I was like, no, I said that So, um, Yeah. I was like, oh, you completely changed the way that I manage people now. But hey, thanks So, um, yeah, I think, I think it's, it's always a struggle and I, I think, I think about it even, even for like, um, you know, even with engineers on a team, you sometimes you get, um, you know, so you know, somebody putting together a proof of concept as a principal engineer, senior engineer, somebody like cranking something out, and then it's time to hand it off. A lot of times people don't wanna let go of it. Um, it's a skill for sure. It's, it's, I think it's one of the hardest things to learn. Mm-hmm.

Tim Winkler: 00:19:29

What, what was the, um, so, uh, Alan, you kind of alluded to, you know, you were with Groupon in those early stages. Um, you know, was the, was there like a hierarchy of a cto, a VP of engineering? Um, you know, when did those start to, uh, evolve or when did those start to take place? Because, you know, what we've seen is like, it's harder the, the earlier the company, right? Uh, you're a 10 person company. It's gonna be that much harder for a C T O to have faith that this VP or principal engineer is gonna be able to. You know, help build this visionary product that they're, that they're, that they're, you know, they've had their hands in for years. Um, you know, to pass that off. I feel like as the company evolves in size, like the, those, those next layers might become a little bit easier. But what was your experience with, with Groupon and, and then maybe, um, you know, what is it that you're seeing currently at Spot?

Alan Deitch: 00:20:26

Yeah. Um, so at that time when I first joined, there was a bit of structure. There was definitely layers of the, uh, management chain. Um, but then once you got to a certain layer, let's call it, you know, engineering, right? And then you might have had like three or four big buckets, right? Mobile. Web or, or even like application, right? Like huge buckets. And there wasn't really division in their customer service sales, right? Something of these massive like suitcase terms. And then you had engineers and then they were on a hiring spree, right? They were just hiring everyone. Everyone who could do a, do a job or knew the tech. Here in Chicago at the time it was Rubion Rails. There was a big boom in Rubion Rails engineers. And so if you knew. And you were a relatively straightforward human. You could get, like, you know, you knew the craft, you could get into the company, right? And then later, within the first six or 12 months, like, okay, hey, you know what? You have interest over here. We're gonna slide these pieces over here. But in terms of like direct line managers and a one to eight ratio or anything like that, it was way too early for any of that. Um, at, at, at Groupon. Now at Spot Hero, we have a very, We're only a 250 ish person, company all in. But we have a much more thought around the organizational design. We have an engineering department. We've broken it up into five different leagues. Each league has a very specific focus. There's a director on top of the league that is, you know, again focused on a specific area and often we cross collaborate, which is great. Each league now has multiple squad. Or small teams, autonomous teams that can mostly, for the most part, do what they need to do to, you know, meet their goals and their, their OKRs. Um, and we try to keep them about eight to 10 total people. That's all in product engineering, qa, uh, different disciplines to to, to meet those challenges because we know. That engineering managers, when they get to a certain threshold of seven or eight or more, it's really hard to have those authentic relationships where you can really drive career development and get something done. And so we kind of have this mental model. Are there some exceptions? Of course. Um, but that's kind of our, our way of thinking about it. Mm-hmm.

Tim Winkler: 00:22:47

Mike, you don't know anything about that? Not at all capacity of people that you manage

Alan Deitch: 00:22:53

Not at all. We generally don't talk about

Mike Gruen: 00:22:56

what I do.

Tim Winkler: 00:23:01

Um, John, you're, you're in a smaller company. Uh, what, what, what is the size of, of heartbeat? Yeah,

John Barrile: 00:23:09

so engineering wise, we're at, uh, we're at 12 right now. Uh, you know, we're, we're trying to be conservative with how we grow the team. Um, so right now we're actually really flat. It's basically. Me managing. Um, and, uh, we haven't really built that hierarchy yet. And I think part of it is really a, a testament to the engineers we've got as far as, you know, um, being very self motivated, very, very talented, and just being able to kinda crank things out and, and, um, we, we've we're split up into a, a couple of teams, um, likely gonna split out a third here in the near future. But, um, you know, trying to keep the teams fairly small. But, um, yeah, I I was thinking about like how many people. Can you directly manage? I was just laughing with Mike's comment there cause I think we're, we're probably getting close to that point. Um, I think we had a 13 probably gonna end up, um, with some leads. I think, you know, rally actually did a really good job. Um, as far as our, our, our org structure there, um, in my opinion it was. It was really flat as far as like, it was sort of based on like the Amazon model where you sort of have like a lead over, you know, a, a team and then you might have a manager with one to three teams that's senior, your manager with, you know, five or six teams and, and, and so on. Um, and that, I think that worked, that worked pretty well. Um, and so, you know, I think that's, that's sort of the model that, that, that we're going.

Mike Gruen: 00:24:36

It's more similar to the model on that. I have five

Alan Deitch: 00:24:38

teams,

Tim Winkler: 00:24:42

So John, everybody reports to you. Do you, do you have, like, who would you say is your right hand person?

John Barrile: 00:24:48

Um, I mean, right now, so it's interesting. Oh, a lot of the, um, I've actually got, uh, Right now I've got two, two or three engineers, uh, that, that have served as a manager in the past. And, you know, when we were interviewing, said, Hey, you know, I really wanna go back to being in icu. I really wanna go back to engineering. Mm-hmm. Um, and so, you know, we, we haven't really had an issue with that yet, but yeah, right now it's sort of, it's sort of, you know, very distributed model. Mm-hmm. It depends on what it is. Yeah.

Tim Winkler: 00:25:19

So I, I guess I'm trying to break this down a bit more specifically here. Um, we talk about like, specific task and, you know, we don't, we don't have a product person per se, um, uh, on the, on this, uh, episode, Mike, you've, you've, you've served in, in product roles before, but, um, what, what, what are some of these like specific tasks? You know, I guess coding, you know, we, we can, we can break that down a little bit more too, but, you know, what is it? That's so difficult to hand this off or to pass something off. Uh, as you're transitioning into, into more of a people manager, um, Alan, like if, if you could dissect your, you know, your experience a little bit more on that because, um, you know, a product person might have something different, um, and, and, and maybe there is like certain tasks that, that, you know, off the top of your head, if you have product folks that you've, you've led as well. But what are some of those specific items? You know, tech folks are, are struggling or would, could potentially struggle to pass off?

Alan Deitch: 00:26:16

I th I think when it comes to the, the struggles of, of a person recently moved into management, it would be to actually execute on the work being asked. And so instead of, instead of time hands on keyboard, it's more. understanding from the product side the why and the when is something due, and then working with those engineers to understand that they know. What I have to do and how am I gonna go do it? One of the biggest struggles I had early on was I disagreed with so much of their how? right? But if we align to the other three, if we had a solid, like where I got to was, if we have a solid understanding of why this thing needs to be built or why it's important, when does it, it need to go out the door? And what fundamentally, what high level are we. I had to get better at going. Okay. I can't zoom in on the how, they're definitely gonna do it differently than I am. And of course my way is the right way, but they're definitely gonna do it a different way. But let, let's just try this out. And this is what actually say engineers, I don't know how you're planning on doing it, but I'm not gonna tell you how I'm gonna do it. And we're gonna meet at the finish line, right? We're gonna meet at the end. And, and, and I'm hoping you're gonna surprise me. Along the way. If you have questions, of course I'm here. I'm here to support you. I'm not, we're not doing it together to see who's better. But I know that you're gonna do it differently cuz you just think differently. And that's part of why we have a diverse team and you know, and it adds on into, um, you know, d and i there. But let's see what you can, do You understand the other three? I'm gonna step back on the how and I'm gonna trust that we. I'm gonna check in because that's what I do. I don't know if I would call it micromanagement. You might have to ask the team but, uh, we're gonna check in somewhat often to say like, okay, how's it going? Um, are you gonna hit that deadline? Are you still understanding the why and the what? Um, but it's that how piece that I had to remind myself often early days not to get involved in the how, on the, how it turned out to be successful that way. Yeah.

Mike Gruen: 00:28:21

On the, how, like one of the areas that, um, I think. Is some can be a struggle is on technology choice. So a lot of engineers mm-hmm. they want to go off and pick like whatever cargo cult thing is out there, um,

John Barrile: 00:28:37

oh let's do this all on microservices. Like

Mike Gruen: 00:28:40

whatever. Um, or like a specific technology or whatever. Like I think that's one area where it can be a little bit of a challenge. Cause if you just leave it up to the engineers, of course they wanna do the new, some not. Wanting to do the new

Alan Deitch: 00:28:52

cool tech, um, as an engineering

Mike Gruen: 00:28:55

leader, as an experienced person, like I'm a big fan of just boring tech. Like let's use something that's done this before. So I'm curious how you, where on that, how, where do you draw that line? How do you know what to let go and when to trust the team to make those decisions? And this is, I I'm sorry. It's, it is a

Alan Deitch: 00:29:11

question for both of you. Um, but yeah, just, yeah. Jump in. I'll take the first stab of it for sure. So, um, I've always leveraged our community of engineers in the, in the company to say we have standards in terms of big guardrails, right? For example, at Groupon we were Ruby on rail shop at at Spot Hero, we're a Python, Django for the most part. Chop. If you come into that and you go, Hey, I know what I, I know the why. I know the, when I know the what, and I'm gonna go build it in Scala, brand new to Spot. I'm gonna leverage the things I've learned in a book called Nudge to say, okay, if you wanna introduce a new tech stack here, here's the small mountain of work that you're gonna need to do to prove that a Scala is the right tech for this, that it can scale to what we need it to, that it can still meet the deadline of when, and that when you're done with. The engineers around you are going to be so familiar with how to evolve it, fix bugs, uh, iterate on it, that it makes sense. But if you can't prove that to me early, then we're gonna have to default back to the technologies that we already have in place. And so Nudge is a great book where basically says you. Can give a limited amount of choice and opportunity to people for them to make. But on the side, if you really want to, you can nudge them in the right direction by putting small roadblocks in their way. Now, I'll say this, to their credit, some of these engineers are like, cool, challenge, accepted. And they've brought really interesting new cha, uh, new solves into the environment. And, and now we have incorporated them. Um, but if, but if they're that hungry for it, they're gonna do it and still meet the deadline. And so, um, that's how I would handle, you know, those tech choices. Those big tech choices. Um, yeah. I'll let, I'll let, I'll let John kinda wrap on that. Yeah. Yeah, I think

John Barrile: 00:31:05

I think of it similarly. Um, I, I look at it as like, you know, um, you know, I, I, I encourage the engineers to experiment on different things and, you know, uh, small proof of concepts and, um, you know, and learn from it. So it's like, if you know, uh, I like, I'm actually living this right now. I've got an engineer who loves Rust and has been, he has been begging me to use Rust. Um, I, I worked with him before, so he's been begging me to use Rust for four years now. Um, and a lot of our backend right now is, uh, is Kotlin. So, um, you know, we came to a point, where're doing some refactoring and. you know, he said like, let's do this proof of concept with Russ. So he did some performance benchmarks and, you know, some poking around on it. And, um, so far it's, it's been great. I think the engineers are, he even organized sort of like a, a book club and, and sort of has, you know, getting all the engineers into rust. Um, so that's, uh, that's been exciting to see. I think, you know, if, if, if it fails, I've also been on the other side where we, and it fail. You know, at least we learned not to do that again, um,

Alan Deitch: 00:32:08

Mm-hmm. So, um,

John Barrile: 00:32:10

but yeah, I think, uh, you know, I, I think it's important, uh, to, to have some, some risk tolerance for failure in those types of things. Um, but, but also within some, some parameters, uh, whether that's time or, or, um, or, or whatnot. Yeah. For sure.

Tim Winkler: 00:32:28

Yeah. Good luck finding more rust engineers as well. I I mean, and that's,

Mike Gruen: 00:32:32

that's one of the, right, that's one of those things that I like, like that's one of those obstacles that I say is like, Hey man, like I'm gonna need to hire people. Like, think about like you, you're not the only person who's gonna have to work on this,

Alan Deitch: 00:32:42

but Okay.

John Barrile: 00:32:43

Yeah. Yeah. Well, the last company was scholar. We had the same firm. We would actually hire good engineers and then have to teach them scholar, so, yeah. Yeah.

Tim Winkler: 00:32:52

Yep. Um, you know, it's also, I think, should, you know, thinking about a lot of this comes to management style, right? Mm-hmm. uh, a lot of folks are just like micromanagers and, and micromanagers can oftentimes be synonymous with like, I'm not letting it go. I'm not gonna let go because I need to make sure like I'm involved in every single decision. And so when I think about this, this topic, sometimes it leads me to down this path of like, what's the company culture like too? There's, there's a culture of, um, you know, next person up, you know, like, Hey, look like you've earned the, you know, you've earned the, the, the right here to, uh, to, to, you've got my trust now, right? Like you've been a part of the company for X amount of. You know, that you should have be, you should be spending this amount of time with somebody, um, to where you feel comfortable that they could step in. If you were, you know, God, who knows what happens that day. And like, you can't, you can't sit in your seat. Um, there, there has to be, in my opinion, the good leaders are always kind of like building somebody to kind of mirror what they do in the event that they can't be there for something. Um, and at the end of the day, like, you know, you do. Uh, you, you, you want to feel good about passing some of that stuff on so that you can build your own skillset in other areas that will help grow the business at large. So I think there's a lot of this that, when I think about it, if like, you know, when, when we're helping a company that's hiring, it's like, okay, so, you know, this person comes in, you know, we always ask like, what's the upward mobility? What, you know, what is it that they can expect from their own growth? And if there's, you know, always a lot of kickback of like, well, you know, it's gonna do, it's gonna be a long time for anything for, for them, you know, this is it. This is their role. Which maybe it's just that type of position. But, um, you know, I'd just bring it back to my point is, you know, there, there's a lot of selling points here for those companies that are willing to embrace that culture of like, yeah, we're open to, you know, letting go a little bit and take, let somebody else kind of take on the reins, uh, as needed.

John Barrile: 00:34:47

Yeah.

Tim Winkler: 00:34:49

Um, cool. Well, Mike, what, you know, what have you say? I mean, I know you're, you're, you've got a number of, you know, large, large distributed teams as well, and, um, you know, anything that's specific that comes to mind on, on your end or, yeah,

Mike Gruen: 00:35:02

I mean, going back to the, the, one of the first earlier questions you asked, which is like, where are the different places where you're letting go? Right. There's the. We touched on it a little bit. There's the hands-on coding aspects, the like, how are we gonna do this? There's the technology stuff. Um, career development is an interesting one. Um, that's

Alan Deitch: 00:35:18

where like I think, you know, there's

Mike Gruen: 00:35:20

team leads and you know, there's, there's different ways you can sort of carve up like what an engineering manager does. So I'm just curious what you guys think, like just off the top of your head, like what are those different, what would you say are some of the different areas where you might be able to carve out and give opportunity to, to folks on your team to. Um, and we

Alan Deitch: 00:35:39

can start with you, John.

John Barrile: 00:35:41

Yeah. Yeah. So I think, um, I, I, I'm, I'm a little bit fuzzy on the

Alan Deitch: 00:35:46

question, to be honest. sorry. Yeah, no, it's fine. Like, so like when you think about, like, as you're, as, as you're moving up and, and you're, um, yeah.

Mike Gruen: 00:35:53

How do you, what are some of the things that you can let go of? What are those areas? Um, we talked about hands-on

Alan Deitch: 00:35:59

coding. We talked about Yeah.

John Barrile: 00:36:02

Yeah, yeah. Yeah. So I think, I think, you know, um, I, I look at it as sort of, uh, it's really about unblocking the team and the people that, that are, you know, working for you. So, um, you know, I think when you've got like a lead or a manager that's leading a team, um, they might be spending some amount of time coding. Um, Definitely not all of it, but I do think that, um, you know, as you move up and, and, and sort of, um, you know, I, I look at it as, as, you know, kind of handing things off that maybe aren't the best. It's really a prioritization exercise, right? It's sort of like, what, what is the best use of my time right now? And, um, So a as those things, you know, as schedules get busy, I think it's, you know, you have to look for, look for ways you can hand things off and, you know, I think in a lot of cases get to ease folks into, to different things. For example, um, you know, with, with tech leads or managers, uh, I, I love that Alan mentioned that, um, you know, in, in your first management role you had, you had a. You had the support to be able to go back to an IC role if you didn't like it. I think that's important. Um, you know, you wanna make sure that people are supported in what they're doing and, um, yeah, I, I look at it as, as really, you know, when you hand those things off, making sure that folks have what they need to, to do the job. Yeah.

Alan Deitch: 00:37:20

Yeah. I'd say like, um, on my list of things, I would not let go of very similar to what John is saying. I, I would not let go of career development pieces. and I maybe, maybe I'm one step a little bit higher as a director now. I've been there for a while thinking about that, but I would not let go development pieces down to individual contributors. I feel like that is definitely core to what engineer manager to icontinue safety net, right. In the companies and the startups I've worked. Failure is a learning, not a dismissal. Right. And so what I have to continue to remain a safety net so that people can take those big bets and those risks and we'll see if they cash in. I also then feel like I can't let go of the protection I do, so that other distractions don't come into that team so that they can focus on the, the mission at hand. The areas where I feel like they, I can let go are of course at the day-to-day coding decisions. Maybe not technology decisions, but like. do we write in, do we write these three lines this way or this way? Mm-hmm. I'm not gonna weigh in on PRS anymore. I'm gonna, I'm gonna assign an a strong up and coming motivated individual to be the project leader, the tech lead. And with that, the responsibilities are of course, building, architecting, but also presenting, defining, and, and I'm gonna, Give that person all of the energy I can to make them successful, but I'm letting that part go. I don't need to claim ownership or credit, um, but I will accept blame, right? And so there's a very, you know, there's a very thin line there. If something goes south, I'm gonna be the first one to explain why and what we're gonna do to fix it. If it's a massive success, I'm gonna let that individual shine and let them present. as high as as they need to, right? Uh, internally, externally. So that's kind of where I would draw the line between what I'm ready to let go of. and things that I just wouldn't let go of, um, in the engineering manager capacity. Yeah, I, I

Mike Gruen: 00:39:16

couldn't agree more than like, on the career path and the career development and like, while it's nice to have some senior engineers who can do some mentoring and some other things, I think that that's sort of on the side. Um, and I agree that like engineering manager, like your role is to develop people and help them and guide them in their

Alan Deitch: 00:39:32

career. Um, One of the areas that like, you know, the day-to-day tasking, like,

Mike Gruen: 00:39:37

what are you, what are you guys gonna be working on? And all of that, that's up to the team and, and stuff like that.

Alan Deitch: 00:39:42

Um, so I, I tend to agree with

Mike Gruen: 00:39:44

what you were saying and, um, trying to think if there's any other sort of areas where I, I definitely feel strongly that I don't let go, but my, my job is to block and tackle my job is to, to, I, I like to say I, I meet so that my team doesn't have. Um,

Alan Deitch: 00:39:57

like I

Mike Gruen: 00:39:59

like, right? Like my job is to try and protect their time as much as possible, um, and, you know, create the time and space for them to, to collaborate and, and, and do what they do best. Um, and try and protect them from the, from the.

John Barrile: 00:40:12

Distractions. Yeah. Um,

Tim Winkler: 00:40:14

ha. Have you all, uh, found yourself in a situation where, let's talk the, the opposite of the spectrum here, where somebody's trying to maybe take on some of the decisions that you tend to make or, uh, you know, maybe overextend, like, you know, their. Authority into an area where it's like, you know, some, sometimes you gotta put 'em back into their lane. Um, has that happened or, and how do you, yeah. I guess how do you approach that? How do you communicate that? Hmm. Hmm. Stay in your lane, bro. Is that

Alan Deitch: 00:40:45

what you

John Barrile: 00:40:46

stay exactly what I say.

Alan Deitch: 00:40:49

get out. Um, I, I'm curious cuz I haven't had too many, like engineers really step up and want.

John Barrile: 00:40:59

Oh man. I, I can think, I can think of, um, a couple folks that, you know, uh, maybe a little bit, um, Yeah, a little bit eager to, you know, for promotions and, and that kinda thing that, um, sort of wanted to, uh, I, I, I had somebody actually email you one time about sort of campaigning for why they needed like a double promotion or something over where they were at. But I think, you know, it, it's really that that was, we had to have a talk about, you know, Skills needed for different levels and like, you know, let's do this. Let's bring it back to skills and like, here's where ICU having the skills and here's where I think you need to work on things. And the proof

Mike Gruen: 00:41:40

and the proof that you're not, you need to ask. Yeah.

Tim Winkler: 00:41:46

Well, I could say in like early stages, maybe there's battles over like feature, uh, like feature prioritization of like, you know, someone really wanting to work on something that isn't really core to, you know, pushing the product, uh, at that time or something. Yeah.

Alan Deitch: 00:42:01

Yeah. So I would tell you that like, Wherever I've been and, and most specifically at, you know, at SPOT here, we really enforce, like leading with curiosity. So if that person comes and they're like, I have these lofty things, like I just meet it with a bunch of curious questions and going back to the nudging, I might be nudging them in a direction to not necessarily stay in their lane. I, I don't know if I subscribe to that, but more. Just like, do you understand the chess move you're about to make? And can you think two and three steps ahead? And let's like, let's put it on a whiteboard and let's talk about it, because by the time you do X, someone else is gonna come in and are you ready to handle that stakeholder? Oh, and then when you, if that's successful, are you ready to handle the next stakeholder? And now all of a sudden, this becomes overwhelming. We lead with curiosity. We like to say that there's a second API and it's assumed positive intent. And so like, I'm not thinking about it as someone trying to like land grab or, or, or, or boast or whatever. It's let's, let's figure out like what you're trying to solve and are we solving the right problems? And if usually we get back to those core basic questions of the why and are we solving the right thing? We usually find like, okay, let's take a step. Let's execute well on that, and then we can have the conversation about what's next. Um, but yeah, a couple of times people have stepped in it and we just gracefully apologize and, and, and then move forward. Like, another piece is that we fail forward, right? We don't always revert everything. Like in software, we don't always revert our last change. Sometimes we fail forward and we just make another hot fix on top of it. And, and we think about that in a very similar way, or at least I do when, when thinking about, you know, these people. You know, might be trying to take on a lot in, in a very short period of time with, with maybe not understanding what, what's behind door number two, you know? Mm-hmm. Mm-hmm. It's a good way, good way to thinking about

undefined: 00:43:50

it

Tim Winkler: 00:43:50

like that. That's, uh, that, that second API isn't a part of this really neat, cool microservices architecture, uh, like start trying to build I like that. Assume positive intent. That's good. All right, cool. Um, well, I think we can, uh, yeah, we can kind of put a bell on it at this point. I, I, I am curious though, um, do you all have product folks that report in to. Or, or team kind of on a separate product, A little bit of separate side. Yep.

John Barrile: 00:44:20

We've got a parallel, parallel structure for that. I'd love to,

Tim Winkler: 00:44:22

I'd love to get a product perspective on some of this stuff too, and just see, um, see what kind of things pop up on their, oh man. On their, uh, thoughts on, on the topic as well. Um. But yeah, we, we've got, uh, a little bit of time left. So let's, let's go ahead and transition ourselves to, um, to our final segment here. Uh, so this is called the Five Second Scramble. So, uh, this is a, a fun little rapid q and a. Um, I, I'm gonna fire off some questions to both of You'all. On a one-on-one. Uh, you'll gimme your response, you know, ideally within five seconds, um, some will be business, some will be personal. Um, I'm gonna go ahead and start, uh, with. Um, Alan, what problems are you solving at Spot

Alan Deitch: 00:45:06

Hero? Well, at Spot Hero, we are building a two-sided marketplace to solve parking challenges. So we're solving, making parking reservations easier for everyone. Who are your users? Our drivers are anyone who has a car trying to park their car, or someone who has a garage or a lot who wants someone to park in their space.

Tim Winkler: 00:45:30

what type of engineers thrive at Spot Hero?

Alan Deitch: 00:45:34

Curious ones.

Tim Winkler: 00:45:37

Do you tend to hire for a specific skillset or for a specific position? Both. What's your favorite aspect of working at Spot Hero?

Alan Deitch: 00:45:50

The people and culture.

Tim Winkler: 00:45:53

What's your favorite programming language?

Alan Deitch: 00:45:59

Um, Ruby,

Tim Winkler: 00:46:04

if you could only eat one food for the rest of your life, what would it be?

Alan Deitch: 00:46:12

Portillo's chocolate cake.

Tim Winkler: 00:46:15

Not gonna be a long Shout out Portillos. Damn. What is there no sponsorship there? Um, that was specific.

Alan Deitch: 00:46:23

Um, it's good. It's real good. I dunno if you've ever had it. It's

John Barrile: 00:46:27

real good.

Tim Winkler: 00:46:27

I'm about to. I'm about get it tonight. Um, if you could switch lives with any person for a day, who would it be and why?

Alan Deitch: 00:46:42

A captain in the army, um, army reserve or army Seals, and I think the level of intensity that they go through every day would teach me a whole hell of a lot on how, um, how, how that side of our, of our country operates. Yeah.

Tim Winkler: 00:46:56

Good answer. Do you believe there's life on other planets? Yes. Favorite Disney character?

Alan Deitch: 00:47:08

In the spirit of today. It's gotta be, um, Elsa, let it go.

Tim Winkler: 00:47:18

Oh man. With the mic drop on the last question. Solid. All right, John, you got, you got some tough, uh, you got some tough competition here. This isn't a competition. Um, um, let it go. Oh my goodness. All right. We'll, we'll, we'll start with some similar questions. So John, what problems are you solving at Heartbeat Health?

John Barrile: 00:47:40

Yeah, we're, uh, we're trying to, to change the way that the cardiovascular disease is treated and, um, and diagnosed.

Alan Deitch: 00:47:48

Who are your users?

John Barrile: 00:47:51

Um, really anybody out there? Uh, you know, you look at the, the numbers out there, cardiovascular disease is one of the most un, un uh, most common undiagnosed, uh, issues out there.

Tim Winkler: 00:48:02

Hmm. What type of engineers thrive at Heartbeat

Alan Deitch: 00:48:06

Health? You know, I think is

John Barrile: 00:48:08

two things, I think is one self-motivation and the other one is ability to deal with

Alan Deitch: 00:48:12

ambiguity.

Tim Winkler: 00:48:15

What is your favorite aspect of working at Heartbeat?

John Barrile: 00:48:18

The, the team. The team, yeah. I think, uh, we've got a great group of folks.

Tim Winkler: 00:48:25

What would you say is your favorite stage of a startup? C a B, or C? Ooh.

John Barrile: 00:48:32

You know, I'm really enjoying things right now. Um, like I said, we, we've, we've gotten, you know, a lot of really good traction, a lot of positive momentum right now, so it's just kind of exciting right now. It's, it's really weird, like, think about, but. A lot of times on Friday, I'm kind of disappointed that it's the weekend

Tim Winkler: 00:48:49

That's, that's a great thing. Yeah. What, uh, uh, favorite country that you've ever traveled to?

John Barrile: 00:48:56

Ooh, um, Cambodia.

Tim Winkler: 00:49:02

Oh. If you had one day left to live, would you rather spend it with Morgan Freeman or Denzel Washington? Oh man.

John Barrile: 00:49:13

Uh, I'm gonna go with, uh, Morgan Freeman. I think

Alan Deitch: 00:49:19

she Shank,

Tim Winkler: 00:49:20

right? Yeah. It, it says a lot about you. Like, you know, some folks will say like, they're going out, you know, guns blazing, like Denzel style party. Morgan Freeman is a little bit more of like, you know, read me a story, you know, the last few hours. Um, do you have a celebrity Doppel gang?

John Barrile: 00:49:38

I don't know. I know I've got plenty of Dopel Gangers out there. I've seen pic Actually one time I saw a picture of someone that I thought was a picture of me.

Tim Winkler: 00:49:49

Uh, do you have any phobias?

John Barrile: 00:49:52

Mice. Interesting rodents. Ugh.

Tim Winkler: 00:49:56

Would you rather have a pet dragon or pet unicorn

John Barrile: 00:50:02

dragon? I think, yeah. Favorite superhero. Oh, favorite. Super, super. You know, I was always big fan of Spider-Man when I was a kid.

Tim Winkler: 00:50:12

Oh. Good stuff. Not, not, uh, Elsa from Frozen No, no.

Alan Deitch: 00:50:20

This the first time we haven't had Batman is the answer.

Tim Winkler: 00:50:23

Yeah, that's true. Batman's always the go-to.

Mike Gruen: 00:50:25

Batman's a pretty good answer.

Tim Winkler: 00:50:27

Yeah. Uh, cool. All right. That is, uh, that's a wrap. You guys both passed the five second scramble. That was, that was good. There were some good answers in there. Um, Thanks again for, for spending time with us. Um, you know, if there's anywhere specific, you know, that you, you want, uh, our audience to find you, feel free to shout it out. I dunno if there's areas on Twitter, uh, you know, LinkedIn, um, but uh, feel free to do so now. Uh, if you'd like to.

Alan Deitch: 00:50:56

I'm good. Yeah. I'm not really on social media. I'm good. Good.

Tim Winkler: 00:51:03

Uh, John. Same

Alan Deitch: 00:51:04

Nah, yeah. I'll pass

Tim Winkler: 00:51:07

Good stuff. Alright. I keep, keep it a discreet. Well, again, appreciate your, your time and, and, and sharing, uh, your, your insights with, uh, with our audience and, uh, yeah, looking forward to push this one live. Yeah. All

Alan Deitch: 00:51:20

right. Cool. Thanks again for having me. Yeah, thank you.