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

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,

and I'm your other host, Mike Gruin.

Join

us

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?

How are you?

I'm doing

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: let me know

, 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

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

a lot of fun.

So you're not still, you know, using it for all your one-on-one?

No, no.

I, I

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?

Yeah.

Did you have me cracking up with that?

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.

Thank you for the invitation.

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

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

just loads of fun.

Uh,

so pledge and wood floor.

So

nearly pledged floors and broken wrists.

Exactly.

Nice.

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

some

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: That's good.

Alright.

Yeah.

We'll, we'll accept that.

That's nice.

I'm, I'm glad

it was acceptable.

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

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,

Tim, are we gonna accept that?

Is that, is that acceptable

? Tim Winkler: I was kinda leaning into

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?

I think my strengths are swimming and biking.

They're pretty close.

Um, and running is my weakest of the three discipl.

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.

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

moving forward.

John, have you ever done a try?

Anything like that?

I have never

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: All right.

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.

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

with, uh, good call

. Alan Deitch: I was gonna go with, um,

bourbon and college football.

Yes.

Bourbon made the cut

again.

Yeah, there we go.

I thought we were gonna make an entire, entire episode without saying whiskey

Oh man.

We're

brewing football, man.

Who's, who's your squad?

Who's your team?

Alabama.

Oh Ben, roll

tide.

Yeah, roll tide.

Alright.

There's a lot of bourbon this season though.

. Yeah, so I'm

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?

It was, it was Woodford Reserve, but uh, you know, our COO is.

As a big Tennessee fan,

so, oh, so you guys have some, some words, uh, every so often.

Uh, once my phone was

just blowing up with

memes,

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,

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,

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

your peers or were you asked to manage

like, oh, yeah, yeah, yeah.

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.

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.

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.

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.

Um,

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: What, what was the,

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?

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: Mike, you don't

? Not at all capacity of people that you manage

? Alan Deitch: Not at all.

. We generally don't talk about

what I do.

Um, John, you're, you're in a smaller company.

Uh, what, what, what is the size of, of heartbeat?

Yeah,

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.

It's more similar to the model on that.

I have five

teams,

So John, everybody reports to you.

Do you, do you have, like, who would you say is your right hand person?

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.

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?

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.

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,

oh let's do this all on microservices.

Like

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

cool tech, um, as an engineering

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

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

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: Mm-hmm.

. So, um,

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.

Yeah.

Good luck finding more rust engineers as well.

I . I mean, and that's,

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,

but Okay.

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: 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.

Yeah.

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,

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

where like I think, you know, there's

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

can start with you, John.

Yeah.

Yeah.

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

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.

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

coding.

We talked about Yeah.

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.

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

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

career.

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

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.

Um, so I, I tend to agree with

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,

like I

, Mike Gruen: 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.

Distractions.

Yeah.

Um,

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

what you

stay exactly what I say.

, Alan Deitch: get out.

Um, I, I'm curious cuz I haven't had too many, like engineers

really step up and want.

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

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

Yeah.

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.

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

it

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.

We've got a parallel, parallel structure for that.

I'd love to,

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

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.

what type of engineers thrive at Spot Hero?

Curious ones.

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?

The people and culture.

What's your favorite programming language?

Um, Ruby,

if you could only eat one food for the rest of

your life, what would it be?

Portillo's chocolate cake.

Not gonna be a long . Shout out Portillos.

Damn.

What is there no sponsorship there?

Um, that was specific.

Um, it's good.

It's real good.

I dunno if you've ever had it.

It's

real good.

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?

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.

Good answer.

Do you believe there's life on other planets?

Yes.

Favorite Disney character?

In the spirit of today.

It's gotta be, um, Elsa, let it go.

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?

Yeah, we're, uh, we're trying to, to change the way

that the cardiovascular disease is treated and, um, and diagnosed.

Who are your users?

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.

Hmm.

What type of engineers thrive at Heartbeat

Health?

You know, I think is

two things, I think is one self-motivation and the

other one is ability to deal with

ambiguity.

What is your favorite aspect of working at Heartbeat?

The, the team.

The team, yeah.

I think, uh, we've got a great group of folks.

What would you say is your favorite stage of a startup?

C a B, or C?

Ooh.

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

That's, that's a great thing.

Yeah.

What, uh, uh, favorite country that you've ever traveled to?

Ooh, um, Cambodia.

Oh.

If you had one day left to live, would you rather spend it with

Morgan Freeman or Denzel Washington?

Oh man.

Uh,

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

I think

she Shank,

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?

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.

Uh, do you have any phobias?

Mice.

Interesting rodents.

Ugh.

Would you rather have a pet dragon or pet unicorn

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.

Oh.

Good stuff.

Not, not, uh, Elsa from Frozen . No, no.

. Alan Deitch: This the first time we

Yeah, that's true.

Batman's always the go-to.

Batman's a pretty good answer.

. Tim Winkler: 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.

I'm good.

Yeah.

I'm not really on social media.

I'm good.

Good.

Uh, John.

Same

. Alan Deitch: Nah, yeah.

I'll pass

. Tim Winkler: 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

right.

Cool.

Thanks again for having me.