April 1, 2024 • 42 mins
Part of a founder's job is to care more about the business than anybody else. That alone can bring a lot of intensity to work. But when you're an ex-banker to boot, things can get into overdrive. How do you make sure you don't burn out your employees that way, especially if they're not used to the pace? How do you trust your team to regulate their own work while maintaining a rapid pace? And how can a leader harness the power of "why" to resolve all this?
These are the questions we get into in this coaching session with Olga Chin, founder and CEO of Interprice Technologies. Enjoy!
Watch this entire session on YouTube.
Enjoyed this episode? Ready to take your leadership and personal growth to the next level? Please visit my website to learn more about coaching with me.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Founders are obsessed with their companies by default
, and that obsession can be anincredible source of energy and
motivation just through itssheer intensity.
But when it comes time for afounder to build a team around
them, how important is it forthe others to match that
intensity?
Can one go too far?
How does one build a culture ofintensity without burning out?
Those are the questions that weexplore in today's coaching
session with Olga Chin, thefounder and CEO of Enterprise
(00:22):
Technologies.
If this is your first time here, I'm Brian Wang, the host of
this show, and I'm also anexecutive coach who helps
founders grow by working throughtheir biggest challenges.
On this show, we have one-timecoaching sessions where you will
hear things that my clientsnever say elsewhere, because
they're working throughreal-life current issues.
I ask everyone who comes onthis show to dig deep and trust
that by the end, they will learnsomething new about themselves
(00:45):
and gain new insight on how tomove their business forward.
Okay, let's dive in.
Hey, olga, it's great to seeyou today.
Speaker 2 (00:51):
Good to see you too.
Thanks, Brian, for having me.
Speaker 1 (00:54):
Yeah, absolutely so.
Just to speak a little bit tothe audience, olga Chin, you're
the founder CEO of a companycalled Enterprise and you and I
we've known each other for gosh,I want to say, a couple years
now.
I'm really excited to get onthis session with you.
I just want to hand it to youand just ask, based off of our
previous conversation, what youwanted to bring in and what you
(01:15):
really wanted to take a look attoday.
Speaker 2 (01:17):
I'm excited as well, brian, one of the things that
you and I have spoken in thepast about is when you are a
founder, especially when you'rea solo founder, the company is
your baby.
You are obsessed.
I use this word obsession quitea bit.
You think about it all the time, but yet you're building the
team around you that's maybe notas obsessed with the company as
(01:40):
you are, which is completelyhealthy, and we can talk about
how that equates to sports lateron.
But I want to talk about acouple of different aspects.
So, first of all, how do youbuild a healthy team, knowing
that you are the person who isthinking about the company all
the time, 24-7?
But also, how are you thenmanaging this obsession, because
the buck ultimately stops withyou in almost every situation,
(02:04):
and I think it's relevant topretty much every founder I know
.
Speaker 1 (02:07):
Yeah, I would agree with that.
Pretty much every founder Iknow has that certain level of
obsession with the business, forbetter or for worse, and so I
hear you talking a little bitabout how that obsession shows
up and you notice that it'sdifferent than how others treat
the business and the attitudesthat they bring.
There's two things that youspoke to.
(02:27):
One is like how do you manage ateam like a healthy team, given
the obsession, and how do youmanage the obsession itself?
I'm wondering it sounds likethere might be a couple of
different threads there whichthread is feeling more salient
for you right now?
Speaker 2 (02:46):
Maybe let's start with the latter one.
So let's unpack the founderjourney right.
Because you're the founder, youhave this obsession with your
company.
Some of the best founders Iknow tell me that the best ideas
come to them in the shower,which means that you're thinking
about it when you're in theshower, which is entirely true.
There are several instancesthat I can recite to you when I
(03:10):
woke up at night thinking aboutthe company and I dream about it
.
So there's obsession.
As long as it doesn't becomeaddiction, it's actually healthy
because you are this invested.
So it's similar to almost likea child in a way, because you're
just constantly thinking aboutit.
But you're pretty much the onlyone Most of the time.
(03:31):
Yes, you have employees and theteam and I have partners in the
company, but there's a lot ofpressure and it can feel quite
lonely.
Speaker 1 (03:40):
I want to say yeah, and so that loneliness that
you're describing, is that partof what makes the obsession
challenging, or is it somethingelse?
Speaker 2 (03:51):
I think it's a little bit more of the fact that
ultimately, the buck stops withyou.
So I always you know it's funnybecause when I started the
company I never used to watchsports or be into sports, but
somebody gave me this analogy inthe past and I think about this
a lot, and so I've actuallystarted reading up on this.
But it's like leading a sportsteam.
(04:11):
So think about you know afootball team.
You are the quarterback.
The problem is that you're alsoa little bit of a coach too,
and so when you watch a game andthe team wins, most of the time
they talk about the quarterback, and if the team loses, most of
the time they talk about thequarterback's mistakes.
It's the same kind of pressurefor the founder.
Speaker 1 (04:35):
So we started this conversation talking about the
obsession and now we're talkingabout pressure.
In listening to you, I'mcurious about what are you
trying to figure out at themoment.
I hear a lot of these thingsthat are very familiar to me,
(04:56):
that are pretty present in a lotof founder experiences, but I'm
curious for you specifically,Olga what are you trying to
figure out at the moment?
Speaker 2 (05:05):
How do you take all of this, the pressure and the
obsession and how do you createa healthy work environment for
the rest of your team?
Right?
So how do you create thisfootball team where you are the
quarterback, you are partially acoach and you lead a team and a
(05:27):
lot of times you have to havethe mental strength to deal with
it, but you also want to makesure that the team is
functioning?
And when they look at you andthey see that you're spending
24-7 on your company, how do youensure that their minds are
healthy and they see you as ahealthy leader versus somebody
(05:50):
who's maybe just a little crazy?
Speaker 1 (05:52):
What is it about them seeing you be obsessive?
That would lead them to be anunhealthy team.
Speaker 2 (06:00):
I think there's good obsession, there's bad obsession
, right Obsession with thecompany is good as long as it
does not become addiction.
And good obsession means, youknow, look, taking even a step
back right, when a person joinsa startup to work with a startup
, most of the time they'rebetting on the founder, they're
(06:23):
betting on the company and thereis a very certain persona that
joins it.
But they want to see yourenergy as the founder.
They want to see that you'reinvested.
That's partially why peoplejoin startups.
That's partially why investorsinvest in startups.
They want to see this energy.
This energy can be verycontagious, but if you take it
(06:43):
past a certain point so, forexample, if you expect everybody
else to be thinking about this24 seven then it becomes.
Then it's just not a healthyenvironment, right.
So there's a, there's a veryfine line there.
Speaker 1 (06:57):
Yeah, yeah, and I, and I get all of that
conceptually.
So I want to locate where youare, olga, when you think about
the spectrum of healthy versusunhealthy obsession.
Where would you place yourselfrelative to that line?
Speaker 2 (07:16):
I think it can swing both ways.
I've spent a lot of time tryingto figure out what can I do
outside of work to get my mindoff of this, how not to have a
knee-jerk reaction whensomething either good or bad
happens and maintain kind of avery steady pace, thinking that
(07:36):
it's a marathon and not a sprint, that nothing is an overnight
success.
So you definitely, you know youcan obsess all you want, but
ultimately it's a long game thatyou're playing.
I had to learn a couple ofdifferent things for myself.
So, yeah, I guess that's kindof where I'm at.
So I'm not sure if I think it'sfairly healthy from that
(07:58):
perspective.
Like I have tons of energy whenit comes to that, I want to
succeed, but you know, I wouldsay and I hope many people
relate to this it is quitelonely.
Speaker 1 (08:11):
I'm hearing you and you're saying all the ways in
which you want to create somedistance, not be too taken in by
the journey or the experiencewhich I think a lot of founders
ultimately find themselves inthat place, and yet I'm also
noticing that you're going backto the loneliness piece right,
(08:34):
Just being in that sort of soleposition of the one who cares
the most.
Can you just speak a little bitmore about what that's like for
you personally?
Speaker 2 (08:44):
Ooh, that's a really good question.
So I do have a couple ofpartners, uh, that have started
the company with me, so Iwouldn't say that I'm entirely
lonely.
Um, I do have a lot of support.
Um, I also am very lucky to bemarried to somebody who can
actually listen about this,although it's interesting, there
(09:05):
are days when I want to talkabout it and there are days when
I just want to just be bymyself.
You know if that makes sense.
So, but in terms of loneliness,I think it comes down to that.
Every decision, even if we voteby and do things by consensus,
ultimately the decision restswith me.
(09:27):
So if we decide to do something, if we decide to launch a new
product, if we have a toughnegotiation with a customer and
we figure out price one way oranother, ultimately, at the end
of the day, I have the fullresponsibility and if things go
right, try to give credit to theteam.
(09:49):
But I have this big belief thatif things go wrong and I talk
about this actually a lot whenwe hire people if things go
wrong, it is on me, andeverybody knows that, that it's
100% on me and that's theresponsibility that you take on
when you're a founder, itdoesn't mean that it's easy day
to day.
What's?
Speaker 1 (10:09):
it like for you just to reflect on that right here,
just like the sense that it allkind of is at your feet.
Speaker 2 (10:14):
You know what?
It's interesting, because whenI talk about it it's not
actually as hard as it seems.
Maybe you just get so used toit.
I think at the end of the day,it maybe you just get so used to
it.
Speaker 1 (10:25):
I think at the end of the day it's funny.
It's like the water that youswim in.
It doesn't seem like that bigof a deal when that's your
day-to-day reality.
Speaker 2 (10:36):
That's true, and there's also one of the things
that I learned is that there areonly so many decisions that you
make and so many choices thatyou make as a founder during the
course of the company's lifethat are just incredibly
important.
Everything else is kind of likeit affects the course
trajectory a little bit, butit's not a make it or break it
(10:57):
and, funny enough, one of thethings that I keep thinking
about, especially this year, isthat when I first started the
company and Dylan joined, mychief product officer joined we
made one product decisionwithout going into specifics
that we literally I'll neverforget, we were just literally
sitting on the phone one day andbe like, hey, why don't we try
(11:17):
this, brian?
That is what made enterpriseinto what it is right now, and
if you had asked me that day, Iwould have thought there was
such minutiae details.
Speaker 1 (11:29):
Yeah, it's often the case that we can't predict what
certain decisions will lead todown the line.
Yeah, it's, it's.
It's wonderful to reflect onthat and and at the same time,
I'm wondering right now, Olga,as we're as we've been kind of
talking about all of this, wheredo you want to go next?
Like we've touched on a fewdifferent things and I sense
that we're sort of in this stillkind of like reflective thing,
(11:52):
but reflective mode, but wheredo you want to go now?
What?
Speaker 2 (11:55):
about the people, though, because that's the most
important piece, right?
So my team sees me making thesedecisions.
They're very supportive.
Some decisions are easy, somedecisions are tough.
We have good days, we have baddays, just like any company.
But how do you create thisreally, really healthy
environment where you well,first of all, the team has to
(12:18):
trust you, and you're the oneperson who is obsessed that
you're making these decisionsand you care about the company
so much.
You're thinking about this 24-7.
But you do not require yourteam to do that, and yet you
have to give them enough of yourenergy every single day to keep
(12:39):
going.
Speaker 1 (12:40):
You've mentioned this a few times now how do you
create a healthy team?
So you've mentioned this a fewtimes now, like how do you
create a healthy team?
And I want to ask you what isit in your experience right now
that's making you ask thequestion, meaning like I hear
you ask it as if you don'talready know.
Speaker 2 (12:57):
I guess some of it is .
Let's pretend that I'm hiringsomebody, right, and they say
well, what kind of culture doyou have?
It's like, well, we're astartup, we work a lot, yeah,
but you don't have tonecessarily, we only care about
the output.
But we don't want them to getscared, right, because we want
(13:17):
to have this culture where, um,people are not afraid to
experiment, people are notafraid to have lives outside of
work, but at the same time, weare also incredibly driven.
We are all ex-bankers.
So if you ever watch any ofthese TV shows bankers, lawyers
they work a lot of hours andyour stamina becomes incredibly
(13:38):
high to working a lot.
And fortunately, orunfortunately, my core group of
business and product folks areex-bankers.
Okay, and so we tend to work alot.
It's very demanding and we alsohave a lot of high stamina.
So, going back to the sportsanalogy, I often think about
(14:02):
when a team is training right.
I often think about you know,when a team is training right
and you recruit team players.
(14:23):
Well, folks, for various otherroles, you're not necessarily
going to get people like that,and that's totally okay, but how
do you work together?
Speaker 1 (14:31):
So that feels like we're going into a little bit of
a different question, but itsounds like you're saying, given
that much of the core team isthat sort of Ironman athlete, is
that sort of Ironman athleteand as we hire for various roles
that might not require thatsort of level of stamina and
(14:51):
grit drive, how do you bring inpeople that work a little bit
differently, in a way that where, like, they work well together?
Is that a fair up at, I think,four o'clock in the?
Speaker 2 (15:07):
morning every day he checks all his email for, I
think, a good hour.
So I can expect four o'clockemails from him or Slack
messages.
Then he goes to do his CrossFitexercise and then he comes back
(15:31):
and he's online at six and hepretty much works through the
evening.
Now imagine another team playerjoining and seeing this pattern
and unfortunately, Dylan and Ihave had several conversations
at four o'clock in the morning.
It's not unusual for us toactually do that, but as much as
(15:51):
it's really good in terms ofproductivity and because we're
so driven and everybody cares somuch, it's not necessarily what
everybody else wants to do.
Speaker 1 (16:00):
Okay.
So going back to that originalquestion of like, how do you
create a healthy team given thatyou and other people on your
team operate with this level ofobsession and intensity?
If I were to interpret, itsounds like you don't want to
send the message that that iswhat is required.
4 am emails.
(16:21):
6 am uh work.
Uh, working throughout thenight.
Like it sounds like that's notthe message that you want to
send to people.
Speaker 2 (16:32):
Yeah, not at all, and in fact, if somebody's up at
four o'clock in the morning aswell, we would think it's very
weird.
So we don't.
It's not.
Not only is it not expected,it's, we don't anticipate that.
Speaker 1 (16:45):
So what is the message that you want to send to
the people that you're hiringat the company?
Speaker 2 (16:51):
That it's an inclusive environment.
We care a lot aboutintellectual stimulation and the
output, but it's notnecessarily.
Our culture is very muchex-banker culture.
Very, very driven, Very drivenyeah.
Speaker 1 (17:10):
So it sounds like two things at once.
We have a lot of bankers here.
The culture is informed by that.
We're driven and we'reinclusive.
We're open to different ways ofworking is what I heard you say
yes and what makes thatstatement not enough for the
question of how do you build ahealthy team?
Speaker 2 (17:30):
um, because the team is still going to see us on
slack with a green button atfour o'clock in the morning and
so.
So the question is do you hidethat or not?
Really, and so we do.
We have done a lot of teambuilding events, so people know
us very well.
(17:50):
I know everything about thepersonal stuff from most
employees, right, so we try.
Speaker 1 (17:57):
Well, let me.
Sorry to jump in here, but solet, okay.
So I hear you.
You, you make that statement.
Like you, you want to beinclusive.
You're also like acknowledgingthat there's a certain working
style that a lot of people heretake.
So let's just say I'm justgoing to be very on the nose
(18:19):
about it.
So let's say, you say all thatand then you're telling
teammates hey, you will see usprobably up at 4 am or 5 am or
whatever, working, and I don'twant you to take that to mean
that you need to be workingright now.
I'm not saying that's what youneed to say, but let's just
pretend that that's whathappened.
(18:40):
Why would that not besufficient in communicating what
you're trying to communicate orsetting the culture that you're
trying to set here?
Speaker 2 (18:49):
Because it's do as I say, not do as I do, kind of
principle, right, because you'resaying one thing and you're
sort of doing another, but theflip side of that, brian.
So let's talk about the otherpiece of it.
What I mentioned is that whensomebody joins a startup,
usually they join because of thefounder and the vision and the
(19:10):
market and they see this thingsucceeding.
I don't think anybody reallyjoins just because you know you
get a paycheck and that's aboutit.
Startups tend to attract acertain breed of people and
that's a well-known fact.
What if they see the oppositesituation?
What if the founder is notobsessed and kind of like,
checked out, right?
Speaker 1 (19:31):
Generally not a good sign.
Speaker 2 (19:33):
It's not a good sign, right?
And so, as much as I think alot about kind of how do I not
overwhelm people with all thisenergy, and constantly like I
have all these ideas, like if Ithink of something at 11 o'clock
at night, you know, I mightactually post it on Slack saying
, hey, what do you guys thinkabout it?
And that's the energy that Iwant to give to my people, that
(19:53):
I'm fully invested in.
And does it mean that they haveto respond to me at 11 o'clock
at night?
No, absolutely not.
So you're balancing out thesetwo things and that's very
difficult.
Speaker 1 (20:06):
So here's what I'm curious about what do you think
would happen on your team if youwere to say look, I'm going to
work really hard.
Some people on this team aregoing to work really, really
hard.
That's going to be representedby working at lots of hours,
just like we talked about.
Also, I want you to find yourown pace.
(20:27):
You simply allowed them tofigure that out by themselves.
I get the part about do as Isay, not as I do, component.
Let's say you just experimentedwith that.
You made that statement andthen you kind of went about the
next few weeks working the wayyou normally do, and then you
(20:48):
allow others to work the waythey want to do.
What do you think would happenon the team?
Speaker 2 (20:53):
I don't think it would change anything right now.
I think it only matters reallyfor new hires or some of the
newer folks.
I believe that most of theexisting people already know
kind of where the working styleis.
In fact, there was a funnystory.
One of my partners, ann.
She mentioned to me somethingrecently.
She said you know, I wake up at7 o'clock and I check Slack to
(21:16):
see what Olga posted at 5.
And it comes out funny, butit's actually true, yeah they
can laugh about it, they knowyou.
Oh yeah, no, they know exactlywhat's going on, but I think it
scares some of the newer hires.
So when we try to build theteam initially, that's the tough
piece.
So it might be something thatjust needs to be communicated
(21:37):
individually until people trustme.
So the longer they're in thecompany they trust what I
actually say.
Speaker 1 (21:44):
It sounds like.
Correct me if I'm wrong, butpart of the fear is that you'll
say, hey, you don't need to workthese hours, that I work, but
people will still see thatyou're working all these hours
and that they're going to bescared because you use that word
like it sounds like you'reconcerned that they're going to
(22:05):
be scared and they will feellike pressured that they have to
work that many hours yeah andthen that's what you don't want
is that accurate.
Speaker 2 (22:13):
That's right, but I still want the productivity yeah
.
Speaker 1 (22:16):
So that's interesting because because part of what I
hear is that there's a part ofyou that that does want them to
be working really hard and apart of you that doesn't want
them to, like, get burned out orto overdo it.
Is that accurate?
Speaker 2 (22:29):
yeah, that is very accurate yeah, so what like what
?
Speaker 1 (22:33):
what comes up for you ?
As I just point out the factthat there's like there's a
little bit of an internalconflict on your end about this.
Speaker 2 (22:40):
My first gut reaction is that maybe that barometer is
a very personal thing for eachindividual where they want to be
on that scale Like how much canthey put in versus the?
Speaker 1 (22:59):
productivity, and how much can they?
Speaker 2 (22:59):
get back Right, and that's going to depend on so
many different factors for eachindividual person, and so maybe
there is no consistent messagethat everybody kind of has to
figure it out for themselves.
Is that fair that?
Was my reaction when you saidthat.
Speaker 1 (23:17):
It doesn't matter if I think it's fair.
What do you think, as you'resaying that?
Speaker 2 (23:22):
I think that's probably true, because
everybody's motivated bydifferent things and everybody
has a very different situationpersonally, and there are some
times when somebody can put inmore, somebody can put in less.
There are some days whensomebody is more focused versus
(23:42):
another days, and that's a veryindividual, specific thing.
Speaker 1 (23:47):
What I hear is that you're acknowledging that people
will vary a lot in terms ofwhat they need, what they want,
how hard they want to work and,um some sense that you can trust
that they'll figure it out ontheir own.
Speaker 2 (24:02):
Maybe just yeah, I think so.
I think maybe it's anindividual thing and it's not a
one day type item too, becausewhen I focus on new hires, the
reason I'm doing this is becausewhen somebody first comes in,
yes, they probably will buy intothe vision and mission
Otherwise they wouldn't haveaccepted the offer.
But for them to trust me, totrust the rest of the team,
(24:25):
that'll take a little bit oftime and that's a very mutual
thing, by the way, it's verynormal.
So, as they build this trust,perhaps they have to figure out
where, on the scale, how muchthey can handle of this team
right, or this marathon, howfast can they push themselves.
(24:45):
So, as you think about, againgoing back to sports, if
somebody is running a marathon,it's their choice and their
ability in terms of how fast andhow much you push yourself, how
much you train for that andwhat you want as an outcome.
Speaker 1 (25:02):
Although I want to challenge that for a moment,
though.
Right, because marathons areindividual.
It's an individual race.
Each individual is kind oftrying to beat their own time,
right, but you're working on ateam, and so the work that one
person does is going to impactthe rest of the team as well.
So what happens when you havesome people who are, you know,
working double duty and reallypushing the envelope, and others
(25:23):
who are sort of hanging backbecause they've decided that
they're just going to work at adifferent pace?
What does that end up lookinglike for the team and for you?
Speaker 2 (25:31):
I think that the people who decide to work double
time get more responsibility,more rewards, I guess, better
positions, and the interestingpart is that in a company you
need to have a balance right,and if we had everybody who was
(25:52):
working 24-7, I think that wouldbe an insane asylum here at
Enterprise, just because it'sjust not healthy in every kind
of way asylum here at enterprise, just because it's just not
healthy in every kind of way.
Speaker 1 (26:02):
And so this balance, this diversity of working styles
and preferences, I think isactually really, really helpful
but I also hear, though, thatthat you value the whole working
double duty, pushing theenvelope side of things.
Um, you talked about rewardingpeople, getting more opportunity
, getting more promotions.
Speaker 2 (26:23):
Brian, I would be careful, though, because it's
not just the hours right, soit's about productivity.
Speaker 1 (26:28):
Say more about that.
What does that mean to you?
Speaker 2 (26:31):
We care about the output.
We actually have it in ourcompany.
We call it company ethos as wepublish this, and so it's about
productivity.
So everybody's responsible fora particular project.
We're a pretty small team still, so it's about 30, 40 of us and
everybody's responsible fortheir own piece, and we talk
(26:54):
about that.
A lot like accountability.
It doesn't matter how long ittakes a person to get things
done.
A lot like accountability.
It doesn't matter how long ittakes a person to get things
done.
But if somebody wants to moveup and advance and we've had
situations where that actuallyhappened very, very quickly if
they finish their project withina shorter amount of time, they
can take on more, they can helpthe team, and that's actually
(27:15):
happened quite a bit.
Speaker 1 (27:17):
Yeah, yeah.
So it sounds like one aspect isyou really value output If we
use a crude measure of outputover time as productivity?
Speaker 2 (27:28):
That's right.
The problem in a startup isthat there's always more that we
can do.
Always, the work doesn't end.
Speaker 1 (27:37):
So far, you've talked a little bit about how there's
always more to do and you valuepeople who will be very
productive, create a lot ofoutput, and that, on some level,
having folks who are working alittle bit less intensely is a
good thing, as it creates somebalance on the team, creates a
(28:01):
healthier environment andsomewhere there's kind of like a
gray it's not black or white,right.
It's like you don't want allcrazy intensity across the team.
You don't want everyone to bevery laid back.
You want to be somewhere in themiddle.
So I guess, if we tie it backto that question of how do you
(28:21):
create a healthy team whenobsession and hyperactivity are
things that are really importantaspects, where are you now on
that question?
Speaker 2 (28:33):
So we actually have a fairly good balance.
To be honest, in terms of thecore group of folks, I would say
some of it has to do withmutual respect, some of it
probably has to do with theopenness.
So I'm really reallytransparent, besides salaries
and things like that open book,completely open book with a team
(28:56):
, that open book, completelyopen book with a team and I
think that's helpful, becausethen if I am pinging, you know
at 11 o'clock at night, allthese ideas, then the team knows
where it's coming from, so it'snot just some random thought
that I have, and so they alwaysknow like this is what led to
all the saying all this.
Um, so yeah, I think it's aboutmutual respect and that's not
(29:20):
something that you get overnight, I think.
And so for some of the coreveterans because if you think
about how, like, for example,somebody like dylan joined
enterprise before I even wentfull-time a couple of weeks
before, but still it's poor theamount of respect and trust
there is pretty huge.
Speaker 1 (29:40):
Because he took that risk.
Speaker 2 (29:42):
Yes, yeah, a hundred percent.
And when somebody new joins,that I didn't know before, it
takes a while to build thattrust, build that level of
respect.
Once you do, I thinkeverybody's kind of on the same
page and at the same time theyprove that like I see where they
are in terms of the output ofwhat they want to do.
So it's really helpful.
(30:03):
But being patient during thatfirst onboarding, that's hard
too.
As you're exploring differentways of working together.
Speaker 1 (30:14):
What I'm hearing from you is that transparency and
respect are pretty criticalingredients for creating a
healthy environment for yourteam.
And that doesn't come for free,doesn't come from the beginning
.
It requires time, investment,it requires a process where
(30:37):
people spend this time togetherto feel each other out,
calibrate, and so on and soforth.
Speaker 2 (30:44):
I think so, and I think that me translating that
into the company culture as wellis important, because, now that
we're talking about it, one ofthe things that I mentioned is I
have this group of originalgangsters, as I call them.
So these guys have been withEnterprise since day one.
They know everything that'sgoing on without their roles
being super defined just becausethey were the original folks.
(31:06):
And what sometimes happens isthat when new folks join, we can
kind of fix everything prettyquickly within this original
group right, without letting theperson figure it out, and so
it's not just about me, it'skind of translating that
throughout the company that wehave this culture.
That's incredibly driven, butit's all about the output and
(31:30):
you have to be respectful anddevelop this mutual trust,
because mutual trust developmentis maybe the primary goal here
and maybe that is not even theoutput.
Speaker 1 (31:40):
A little lost.
Can you just repeat what yousaid?
Speaker 2 (31:44):
So I guess teaching the folks and coaching them that
when we're building out theteam and as we even work on
being a team, this respect andtrust building amongst everybody
in the company and not just meit's not just me to to a person
I think that's really importantand vocalizing that Okay, that
(32:07):
it's like a goal.
Speaker 1 (32:09):
Trust and respect yeah, okay, oh and respect are
really critical for team health.
And with yourself what?
And with yourself, what'scoming up for you?
Where are you in this question?
What feels like it's notresolved right now?
Speaker 2 (32:28):
I think what's coming up for me is that I think
transparency has actually helpedme quite a bit with that.
So I literally run it in themost transparent way.
We have company meetings everyThursday and I lay it out in
terms of our developers know,like, where we're in terms of
customer contracts, like it's avery open book, and I thought
(32:51):
sometimes that maybe I don'tever need to do that right,
because I've never worked inorganizations that did that.
So why would I have to do that?
But when, a couple of monthsago, we had a situation where
something in the product had abug and I had to call one of the
main developers on it and gethim to stay, you know pretty
(33:13):
late to work on it and fix it,but he understood, my team
understood right away like what?
Why I'm asking that?
Because they, because I'vetalked about what this means,
and I think that that's actuallywhat created the trust.
Is this transparency that maybethey didn't necessarily need,
(33:35):
but because they did need it itsounds like.
Speaker 1 (33:37):
It sounds like that transparency provides the
context and the understanding ofwhy they need to work late in
the first place.
Speaker 2 (33:46):
Yeah, I think so.
I think that's there are noquestions and they all
understood, and I think that abig part of it, too, is creating
this empathy that why do I care?
I want them to understand why Icare, because I have customers
that I love and I care about thecustomer.
(34:08):
So it's all, at the end of theday, it's all about our clients,
and I want to make sure that ittranslates throughout the
organization, and so it's notjust me being obsessed for the
sake of being obsessed.
There's this mission.
Speaker 1 (34:18):
So let's say that you were to indicate that to your
team over and over and overagain.
Transparency here's why we careabout this.
Here's why it matters.
Here's why we're doing whatwe're doing.
How would that impact thiswhole thing that you're talking
about around?
People are going to work toohard or not hard enough, or it's
(34:41):
going to be unclear, like ifyou simply just were as
transparent as you could beabout why you're doing what
you're doing all day long.
How would that impact things?
Speaker 2 (34:53):
Well, you make it sound really simple.
I didn't say it was simple well,you make it sound really simple
.
I didn't say it was simple, butthe reality um is, I think it
would have two different effects, right?
So if, if people on my team whodon't actually talk to
customers all the time hear thisfeeling that that's what I'm
experiencing, that's why I'mdoing this, then they're free to
(35:14):
make their own decisions, howobsessed they want to be Right,
and I'm empowering them to makethat decision to based on where
they are in their life and, atthe same time, by talking to
them why I'm doing this and whythis matters, then they can
(35:37):
calibrate where they are in thatproductivity scale and where
they need to be, because it'snot just about hey, I want to
just check the box.
Speaker 1 (35:45):
Mm-hmm.
Speaker 2 (35:46):
And I'm essentially putting that responsibility on
them, and they're free to maketheir decision.
Speaker 1 (35:55):
Well, I like what you said around empowerment because
, just to reflect for a second,it sounds like a couple of
things I'm picking up.
One is when you provide thiscontext around the customers,
especially for people who don'thave a lot of contact with them,
when you explain the context,what matters or why it matters,
(36:17):
or even when you are transparentabout what gets rewarded to
enterprise, what doesn't getrewarded, you're essentially
giving your team and new hiresthe relevant information that
they need in order to make fullyinformed decisions.
Speaker 2 (36:33):
So another way of describing that is empowerment.
Yes, and I think that I'm alsotaking that pressure off of
myself.
Speaker 1 (36:39):
How do you mean?
Speaker 2 (36:39):
Because, instead of me deciding what to tell this
person in terms of the workhours or not, what I'm doing is
I'm telling them why thismatters to me and how much this
matters and what the mission is.
And here are our clients andwhy they care clients and why
(37:00):
they care, and it's up to theperson to decide where they want
to be in this company, assumingthat they get their job done,
of course, right.
So there's minimal requirementsthere that they have to meet,
but it's their decision and notmine, and all I can do is tell
them that I'm okay, regardlessof their work structure, style,
you know.
However they want to do it, butthen I'm taking that load off
of my shoulders.
Speaker 1 (37:20):
Yeah, so I want to just invite you to take a moment
right here, present moment, tosee what that feels like to take
that load off, because you'velaid it all out.
Speaker 2 (37:30):
Yeah, no, it's interesting because then I'm no
longer thinking about dictatinghow somebody works and what they
do.
How does?
Speaker 1 (37:39):
that feel for you right now.
Speaker 2 (37:42):
It's a little easier.
Speaker 1 (37:44):
Yeah, just a little bit.
Speaker 2 (37:45):
There's also a level of human empathy, I think, there
in terms of this empowermentand me, I like being transparent
with the team because I wantthem to fully understand where
it comes from, like where deepdown inside my heart it comes
(38:05):
from, and I think that I've donethat.
But you, what you're showing me, is that there's another layer
where I'm giving them all thisinformation, not just so that
they have empathy and understandclients, but so that they can
see where they are on the in inon this map, like where they are
on the team.
Speaker 1 (38:25):
And so when they have all that information, then they
can decide for themselves.
Speaker 2 (38:31):
Yes, knowing that I have their back, no matter what.
Speaker 1 (38:34):
So go back to this original question of how do I
make sure my team is healthywhen there's all this obsession
on it?
How does that question sit withyou right now?
Speaker 2 (38:45):
I think that as long as I tell them why, how, then
I'm harnessing the positiveeffects versus dictating what
everybody does, in which case itbecomes negative.
Right, but I like the obsessionconcept, I like the energy of
it.
I think it's really important.
Speaker 1 (39:05):
Your job isn't to tell people how obsessed they
ought to be.
Your job is to simply share howcommitted, how obsessed you are
currently and what will berewarded here, and allow them to
make a choice.
And so long as that decision isin their hands, not in yours,
(39:25):
then that weight that youmentioned, that's on your
shoulders, can be just a littlebit lighter, because you're not
carrying that decision for them.
Speaker 2 (39:33):
Yes, and then the flip side is that we started out
this conversation talking abouthow it's lonely being a solo
founder and how every decisionis yours, but maybe this one
doesn't have to be mine.
Speaker 1 (39:53):
Very nice, just going to let that one hang out for a
second.
Very nice, just gonna let thatone hang out for a second.
Yeah, so just we're gonna startto wrap here.
So take a moment to take inwhat we just explored and I want
to ask you what's the maintakeaway for you, olga?
Speaker 2 (40:13):
I think the main takeaway is that the
transparency that you'reallowing your team to have
probably has more benefits thanI realized.
When we started thisconversation, I knew, going into
it, that, talking about thefounder obsession, I wasn't
going to say that it's a badthing, because I truly believe
that it's not, that that's whystartups exist.
(40:36):
But at the same time, I think Iwould imagine that most people
realize why founders do this andif you're just giving people
benefit of doubt and creatingthis transparency and talking
about why and how, I imaginethat it probably empowers people
more than I originally thought.
Speaker 1 (40:57):
Yeah, I'm excited to see how that unfolds for you, as
you really practice that.
Speaker 2 (41:03):
Appreciate it.
Speaker 1 (41:03):
All right, olga, it was a pleasure to be with you.
Speaker 2 (41:06):
Thank you so much, brad, you got it.
Speaker 1 (41:08):
One of the things that really struck me in the
session was that sense ofloneliness that comes with being
a founder.
It's this feeling like you'reresponsible for every single
thing that happens in thebusiness, and as a former
founder myself, I totally getthat.
I think part of what made thisexperience harder than it needed
to be for Olga was the tensionof embracing intensity and not
(41:28):
wanting to scare off employeeswho don't necessarily want to
make work their everything.
Olga internalized that tensionby taking responsibility for how
her employees worked, even ifjust implicitly.
But when she leans ontransparency to create trust and
help her team understand thewhy behind her own actions, she
ultimately empowers her team tofind their own balance.
Now Olga doesn't need to beresponsible for all their
(41:49):
choices.
She can leave it up to them andwith that, find some relief.
Thank you for listening to SlowDown to Speed Up.
If you enjoyed this episode,please rate it in your favorite
podcasting app or give it a likeand subscribe on YouTube.
And if you're a founder lookingto reach the next level through
coaching or you'd like to comeonto the show, please reach out
to me at dashingleadershipcom.
Founders are obsessed with their companies by default
, and that obsession can be anincredible source of energy and
motivation just through itssheer intensity.
But when it comes time for afounder to build a team around
them, how important is it forthe others to match that
intensity?
Can one go too far?
How does one build a culture ofintensity without burning out?
Those are the questions that weexplore in today's coaching
session with Olga Chin, thefounder and CEO of Enterprise
(00:22):
Technologies.
If this is your first time here, I'm Brian Wang, the host of
this show, and I'm also anexecutive coach who helps
founders grow by working throughtheir biggest challenges.
On this show, we have one-timecoaching sessions where you will
hear things that my clientsnever say elsewhere, because
they're working throughreal-life current issues.
I ask everyone who comes onthis show to dig deep and trust
that by the end, they will learnsomething new about themselves
(00:45):
and gain new insight on how tomove their business forward.
Okay, let's dive in.
Hey, olga, it's great to seeyou today.
Speaker 2 (00:51):
Good to see you too.
Thanks, Brian, for having me.
Speaker 1 (00:54):
Yeah, absolutely so.
Just to speak a little bit tothe audience, olga Chin, you're
the founder CEO of a companycalled Enterprise and you and I
we've known each other for gosh,I want to say, a couple years
now.
I'm really excited to get onthis session with you.
I just want to hand it to youand just ask, based off of our
previous conversation, what youwanted to bring in and what you
(01:15):
really wanted to take a look attoday.
Speaker 2 (01:17):
I'm excited as well, brian, one of the things that
you and I have spoken in thepast about is when you are a
founder, especially when you'rea solo founder, the company is
your baby.
You are obsessed.
I use this word obsession quitea bit.
You think about it all the time, but yet you're building the
team around you that's maybe notas obsessed with the company as
(01:40):
you are, which is completelyhealthy, and we can talk about
how that equates to sports lateron.
But I want to talk about acouple of different aspects.
So, first of all, how do youbuild a healthy team, knowing
that you are the person who isthinking about the company all
the time, 24-7?
But also, how are you thenmanaging this obsession, because
the buck ultimately stops withyou in almost every situation,
(02:04):
and I think it's relevant topretty much every founder I know
.
Speaker 1 (02:07):
Yeah, I would agree with that.
Pretty much every founder Iknow has that certain level of
obsession with the business, forbetter or for worse, and so I
hear you talking a little bitabout how that obsession shows
up and you notice that it'sdifferent than how others treat
the business and the attitudesthat they bring.
There's two things that youspoke to.
(02:27):
One is like how do you manage ateam like a healthy team, given
the obsession, and how do youmanage the obsession itself?
I'm wondering it sounds likethere might be a couple of
different threads there whichthread is feeling more salient
for you right now?
Speaker 2 (02:46):
Maybe let's start with the latter one.
So let's unpack the founderjourney right.
Because you're the founder, youhave this obsession with your
company.
Some of the best founders Iknow tell me that the best ideas
come to them in the shower,which means that you're thinking
about it when you're in theshower, which is entirely true.
There are several instancesthat I can recite to you when I
(03:10):
woke up at night thinking aboutthe company and I dream about it
.
So there's obsession.
As long as it doesn't becomeaddiction, it's actually healthy
because you are this invested.
So it's similar to almost likea child in a way, because you're
just constantly thinking aboutit.
But you're pretty much the onlyone Most of the time.
(03:31):
Yes, you have employees and theteam and I have partners in the
company, but there's a lot ofpressure and it can feel quite
lonely.
Speaker 1 (03:40):
I want to say yeah, and so that loneliness that
you're describing, is that partof what makes the obsession
challenging, or is it somethingelse?
Speaker 2 (03:51):
I think it's a little bit more of the fact that
ultimately, the buck stops withyou.
So I always you know it's funnybecause when I started the
company I never used to watchsports or be into sports, but
somebody gave me this analogy inthe past and I think about this
a lot, and so I've actuallystarted reading up on this.
But it's like leading a sportsteam.
(04:11):
So think about you know afootball team.
You are the quarterback.
The problem is that you're alsoa little bit of a coach too,
and so when you watch a game andthe team wins, most of the time
they talk about the quarterback, and if the team loses, most of
the time they talk about thequarterback's mistakes.
It's the same kind of pressurefor the founder.
Speaker 1 (04:35):
So we started this conversation talking about the
obsession and now we're talkingabout pressure.
In listening to you, I'mcurious about what are you
trying to figure out at themoment.
I hear a lot of these thingsthat are very familiar to me,
(04:56):
that are pretty present in a lotof founder experiences, but I'm
curious for you specifically,Olga what are you trying to
figure out at the moment?
Speaker 2 (05:05):
How do you take all of this, the pressure and the
obsession and how do you createa healthy work environment for
the rest of your team?
Right?
So how do you create thisfootball team where you are the
quarterback, you are partially acoach and you lead a team and a
(05:27):
lot of times you have to havethe mental strength to deal with
it, but you also want to makesure that the team is
functioning?
And when they look at you andthey see that you're spending
24-7 on your company, how do youensure that their minds are
healthy and they see you as ahealthy leader versus somebody
(05:50):
who's maybe just a little crazy?
Speaker 1 (05:52):
What is it about them seeing you be obsessive?
That would lead them to be anunhealthy team.
Speaker 2 (06:00):
I think there's good obsession, there's bad obsession
, right Obsession with thecompany is good as long as it
does not become addiction.
And good obsession means, youknow, look, taking even a step
back right, when a person joinsa startup to work with a startup
, most of the time they'rebetting on the founder, they're
(06:23):
betting on the company and thereis a very certain persona that
joins it.
But they want to see yourenergy as the founder.
They want to see that you'reinvested.
That's partially why peoplejoin startups.
That's partially why investorsinvest in startups.
They want to see this energy.
This energy can be verycontagious, but if you take it
(06:43):
past a certain point so, forexample, if you expect everybody
else to be thinking about this24 seven then it becomes.
Then it's just not a healthyenvironment, right.
So there's a, there's a veryfine line there.
Speaker 1 (06:57):
Yeah, yeah, and I, and I get all of that
conceptually.
So I want to locate where youare, olga, when you think about
the spectrum of healthy versusunhealthy obsession.
Where would you place yourselfrelative to that line?
Speaker 2 (07:16):
I think it can swing both ways.
I've spent a lot of time tryingto figure out what can I do
outside of work to get my mindoff of this, how not to have a
knee-jerk reaction whensomething either good or bad
happens and maintain kind of avery steady pace, thinking that
(07:36):
it's a marathon and not a sprint, that nothing is an overnight
success.
So you definitely, you know youcan obsess all you want, but
ultimately it's a long game thatyou're playing.
I had to learn a couple ofdifferent things for myself.
So, yeah, I guess that's kindof where I'm at.
So I'm not sure if I think it'sfairly healthy from that
(07:58):
perspective.
Like I have tons of energy whenit comes to that, I want to
succeed, but you know, I wouldsay and I hope many people
relate to this it is quitelonely.
Speaker 1 (08:11):
I'm hearing you and you're saying all the ways in
which you want to create somedistance, not be too taken in by
the journey or the experiencewhich I think a lot of founders
ultimately find themselves inthat place, and yet I'm also
noticing that you're going backto the loneliness piece right,
(08:34):
Just being in that sort of soleposition of the one who cares
the most.
Can you just speak a little bitmore about what that's like for
you personally?
Speaker 2 (08:44):
Ooh, that's a really good question.
So I do have a couple ofpartners, uh, that have started
the company with me, so Iwouldn't say that I'm entirely
lonely.
Um, I do have a lot of support.
Um, I also am very lucky to bemarried to somebody who can
actually listen about this,although it's interesting, there
(09:05):
are days when I want to talkabout it and there are days when
I just want to just be bymyself.
You know if that makes sense.
So, but in terms of loneliness,I think it comes down to that.
Every decision, even if we voteby and do things by consensus,
ultimately the decision restswith me.
(09:27):
So if we decide to do something, if we decide to launch a new
product, if we have a toughnegotiation with a customer and
we figure out price one way oranother, ultimately, at the end
of the day, I have the fullresponsibility and if things go
right, try to give credit to theteam.
(09:49):
But I have this big belief thatif things go wrong and I talk
about this actually a lot whenwe hire people if things go
wrong, it is on me, andeverybody knows that, that it's
100% on me and that's theresponsibility that you take on
when you're a founder, itdoesn't mean that it's easy day
to day.
What's?
Speaker 1 (10:09):
it like for you just to reflect on that right here,
just like the sense that it allkind of is at your feet.
Speaker 2 (10:14):
You know what?
It's interesting, because whenI talk about it it's not
actually as hard as it seems.
Maybe you just get so used toit.
I think at the end of the day,it maybe you just get so used to
it.
Speaker 1 (10:25):
I think at the end of the day it's funny.
It's like the water that youswim in.
It doesn't seem like that bigof a deal when that's your
day-to-day reality.
Speaker 2 (10:36):
That's true, and there's also one of the things
that I learned is that there areonly so many decisions that you
make and so many choices thatyou make as a founder during the
course of the company's lifethat are just incredibly
important.
Everything else is kind of likeit affects the course
trajectory a little bit, butit's not a make it or break it
(10:57):
and, funny enough, one of thethings that I keep thinking
about, especially this year, isthat when I first started the
company and Dylan joined, mychief product officer joined we
made one product decisionwithout going into specifics
that we literally I'll neverforget, we were just literally
sitting on the phone one day andbe like, hey, why don't we try
(11:17):
this, brian?
That is what made enterpriseinto what it is right now, and
if you had asked me that day, Iwould have thought there was
such minutiae details.
Speaker 1 (11:29):
Yeah, it's often the case that we can't predict what
certain decisions will lead todown the line.
Yeah, it's, it's.
It's wonderful to reflect onthat and and at the same time,
I'm wondering right now, Olga,as we're as we've been kind of
talking about all of this, wheredo you want to go next?
Like we've touched on a fewdifferent things and I sense
that we're sort of in this stillkind of like reflective thing,
(11:52):
but reflective mode, but wheredo you want to go now?
What?
Speaker 2 (11:55):
about the people, though, because that's the most
important piece, right?
So my team sees me making thesedecisions.
They're very supportive.
Some decisions are easy, somedecisions are tough.
We have good days, we have baddays, just like any company.
But how do you create thisreally, really healthy
environment where you well,first of all, the team has to
(12:18):
trust you, and you're the oneperson who is obsessed that
you're making these decisionsand you care about the company
so much.
You're thinking about this 24-7.
But you do not require yourteam to do that, and yet you
have to give them enough of yourenergy every single day to keep
(12:39):
going.
Speaker 1 (12:40):
You've mentioned this a few times now how do you
create a healthy team?
So you've mentioned this a fewtimes now, like how do you
create a healthy team?
And I want to ask you what isit in your experience right now
that's making you ask thequestion, meaning like I hear
you ask it as if you don'talready know.
Speaker 2 (12:57):
I guess some of it is .
Let's pretend that I'm hiringsomebody, right, and they say
well, what kind of culture doyou have?
It's like, well, we're astartup, we work a lot, yeah,
but you don't have tonecessarily, we only care about
the output.
But we don't want them to getscared, right, because we want
(13:17):
to have this culture where, um,people are not afraid to
experiment, people are notafraid to have lives outside of
work, but at the same time, weare also incredibly driven.
We are all ex-bankers.
So if you ever watch any ofthese TV shows bankers, lawyers
they work a lot of hours andyour stamina becomes incredibly
(13:38):
high to working a lot.
And fortunately, orunfortunately, my core group of
business and product folks areex-bankers.
Okay, and so we tend to work alot.
It's very demanding and we alsohave a lot of high stamina.
So, going back to the sportsanalogy, I often think about
(14:02):
when a team is training right.
I often think about you know,when a team is training right
and you recruit team players.
(14:23):
Well, folks, for various otherroles, you're not necessarily
going to get people like that,and that's totally okay, but how
do you work together?
Speaker 1 (14:31):
So that feels like we're going into a little bit of
a different question, but itsounds like you're saying, given
that much of the core team isthat sort of Ironman athlete, is
that sort of Ironman athleteand as we hire for various roles
that might not require thatsort of level of stamina and
(14:51):
grit drive, how do you bring inpeople that work a little bit
differently, in a way that where, like, they work well together?
Is that a fair up at, I think,four o'clock in the?
Speaker 2 (15:07):
morning every day he checks all his email for, I
think, a good hour.
So I can expect four o'clockemails from him or Slack
messages.
Then he goes to do his CrossFitexercise and then he comes back
(15:31):
and he's online at six and hepretty much works through the
evening.
Now imagine another team playerjoining and seeing this pattern
and unfortunately, Dylan and Ihave had several conversations
at four o'clock in the morning.
It's not unusual for us toactually do that, but as much as
(15:51):
it's really good in terms ofproductivity and because we're
so driven and everybody cares somuch, it's not necessarily what
everybody else wants to do.
Speaker 1 (16:00):
Okay.
So going back to that originalquestion of like, how do you
create a healthy team given thatyou and other people on your
team operate with this level ofobsession and intensity?
If I were to interpret, itsounds like you don't want to
send the message that that iswhat is required.
4 am emails.
(16:21):
6 am uh work.
Uh, working throughout thenight.
Like it sounds like that's notthe message that you want to
send to people.
Speaker 2 (16:32):
Yeah, not at all, and in fact, if somebody's up at
four o'clock in the morning aswell, we would think it's very
weird.
So we don't.
It's not.
Not only is it not expected,it's, we don't anticipate that.
Speaker 1 (16:45):
So what is the message that you want to send to
the people that you're hiringat the company?
Speaker 2 (16:51):
That it's an inclusive environment.
We care a lot aboutintellectual stimulation and the
output, but it's notnecessarily.
Our culture is very muchex-banker culture.
Very, very driven, Very drivenyeah.
Speaker 1 (17:10):
So it sounds like two things at once.
We have a lot of bankers here.
The culture is informed by that.
We're driven and we'reinclusive.
We're open to different ways ofworking is what I heard you say
yes and what makes thatstatement not enough for the
question of how do you build ahealthy team?
Speaker 2 (17:30):
um, because the team is still going to see us on
slack with a green button atfour o'clock in the morning and
so.
So the question is do you hidethat or not?
Really, and so we do.
We have done a lot of teambuilding events, so people know
us very well.
(17:50):
I know everything about thepersonal stuff from most
employees, right, so we try.
Speaker 1 (17:57):
Well, let me.
Sorry to jump in here, but solet, okay.
So I hear you.
You, you make that statement.
Like you, you want to beinclusive.
You're also like acknowledgingthat there's a certain working
style that a lot of people heretake.
So let's just say I'm justgoing to be very on the nose
(18:19):
about it.
So let's say, you say all thatand then you're telling
teammates hey, you will see usprobably up at 4 am or 5 am or
whatever, working, and I don'twant you to take that to mean
that you need to be workingright now.
I'm not saying that's what youneed to say, but let's just
pretend that that's whathappened.
(18:40):
Why would that not besufficient in communicating what
you're trying to communicate orsetting the culture that you're
trying to set here?
Speaker 2 (18:49):
Because it's do as I say, not do as I do, kind of
principle, right, because you'resaying one thing and you're
sort of doing another, but theflip side of that, brian.
So let's talk about the otherpiece of it.
What I mentioned is that whensomebody joins a startup,
usually they join because of thefounder and the vision and the
(19:10):
market and they see this thingsucceeding.
I don't think anybody reallyjoins just because you know you
get a paycheck and that's aboutit.
Startups tend to attract acertain breed of people and
that's a well-known fact.
What if they see the oppositesituation?
What if the founder is notobsessed and kind of like,
checked out, right?
Speaker 1 (19:31):
Generally not a good sign.
Speaker 2 (19:33):
It's not a good sign, right?
And so, as much as I think alot about kind of how do I not
overwhelm people with all thisenergy, and constantly like I
have all these ideas, like if Ithink of something at 11 o'clock
at night, you know, I mightactually post it on Slack saying
, hey, what do you guys thinkabout it?
And that's the energy that Iwant to give to my people, that
(19:53):
I'm fully invested in.
And does it mean that they haveto respond to me at 11 o'clock
at night?
No, absolutely not.
So you're balancing out thesetwo things and that's very
difficult.
Speaker 1 (20:06):
So here's what I'm curious about what do you think
would happen on your team if youwere to say look, I'm going to
work really hard.
Some people on this team aregoing to work really, really
hard.
That's going to be representedby working at lots of hours,
just like we talked about.
Also, I want you to find yourown pace.
(20:27):
You simply allowed them tofigure that out by themselves.
I get the part about do as Isay, not as I do, component.
Let's say you just experimentedwith that.
You made that statement andthen you kind of went about the
next few weeks working the wayyou normally do, and then you
(20:48):
allow others to work the waythey want to do.
What do you think would happenon the team?
Speaker 2 (20:53):
I don't think it would change anything right now.
I think it only matters reallyfor new hires or some of the
newer folks.
I believe that most of theexisting people already know
kind of where the working styleis.
In fact, there was a funnystory.
One of my partners, ann.
She mentioned to me somethingrecently.
She said you know, I wake up at7 o'clock and I check Slack to
(21:16):
see what Olga posted at 5.
And it comes out funny, butit's actually true, yeah they
can laugh about it, they knowyou.
Oh yeah, no, they know exactlywhat's going on, but I think it
scares some of the newer hires.
So when we try to build theteam initially, that's the tough
piece.
So it might be something thatjust needs to be communicated
(21:37):
individually until people trustme.
So the longer they're in thecompany they trust what I
actually say.
Speaker 1 (21:44):
It sounds like.
Correct me if I'm wrong, butpart of the fear is that you'll
say, hey, you don't need to workthese hours, that I work, but
people will still see thatyou're working all these hours
and that they're going to bescared because you use that word
like it sounds like you'reconcerned that they're going to
(22:05):
be scared and they will feellike pressured that they have to
work that many hours yeah andthen that's what you don't want
is that accurate.
Speaker 2 (22:13):
That's right, but I still want the productivity yeah
.
Speaker 1 (22:16):
So that's interesting because because part of what I
hear is that there's a part ofyou that that does want them to
be working really hard and apart of you that doesn't want
them to, like, get burned out orto overdo it.
Is that accurate?
Speaker 2 (22:29):
yeah, that is very accurate yeah, so what like what
?
Speaker 1 (22:33):
what comes up for you ?
As I just point out the factthat there's like there's a
little bit of an internalconflict on your end about this.
Speaker 2 (22:40):
My first gut reaction is that maybe that barometer is
a very personal thing for eachindividual where they want to be
on that scale Like how much canthey put in versus the?
Speaker 1 (22:59):
productivity, and how much can they?
Speaker 2 (22:59):
get back Right, and that's going to depend on so
many different factors for eachindividual person, and so maybe
there is no consistent messagethat everybody kind of has to
figure it out for themselves.
Is that fair that?
Was my reaction when you saidthat.
Speaker 1 (23:17):
It doesn't matter if I think it's fair.
What do you think, as you'resaying that?
Speaker 2 (23:22):
I think that's probably true, because
everybody's motivated bydifferent things and everybody
has a very different situationpersonally, and there are some
times when somebody can put inmore, somebody can put in less.
There are some days whensomebody is more focused versus
(23:42):
another days, and that's a veryindividual, specific thing.
Speaker 1 (23:47):
What I hear is that you're acknowledging that people
will vary a lot in terms ofwhat they need, what they want,
how hard they want to work and,um some sense that you can trust
that they'll figure it out ontheir own.
Speaker 2 (24:02):
Maybe just yeah, I think so.
I think maybe it's anindividual thing and it's not a
one day type item too, becausewhen I focus on new hires, the
reason I'm doing this is becausewhen somebody first comes in,
yes, they probably will buy intothe vision and mission
Otherwise they wouldn't haveaccepted the offer.
But for them to trust me, totrust the rest of the team,
(24:25):
that'll take a little bit oftime and that's a very mutual
thing, by the way, it's verynormal.
So, as they build this trust,perhaps they have to figure out
where, on the scale, how muchthey can handle of this team
right, or this marathon, howfast can they push themselves.
(24:45):
So, as you think about, againgoing back to sports, if
somebody is running a marathon,it's their choice and their
ability in terms of how fast andhow much you push yourself, how
much you train for that andwhat you want as an outcome.
Speaker 1 (25:02):
Although I want to challenge that for a moment,
though.
Right, because marathons areindividual.
It's an individual race.
Each individual is kind oftrying to beat their own time,
right, but you're working on ateam, and so the work that one
person does is going to impactthe rest of the team as well.
So what happens when you havesome people who are, you know,
working double duty and reallypushing the envelope, and others
(25:23):
who are sort of hanging backbecause they've decided that
they're just going to work at adifferent pace?
What does that end up lookinglike for the team and for you?
Speaker 2 (25:31):
I think that the people who decide to work double
time get more responsibility,more rewards, I guess, better
positions, and the interestingpart is that in a company you
need to have a balance right,and if we had everybody who was
(25:52):
working 24-7, I think that wouldbe an insane asylum here at
Enterprise, just because it'sjust not healthy in every kind
of way asylum here at enterprise, just because it's just not
healthy in every kind of way.
Speaker 1 (26:02):
And so this balance, this diversity of working styles
and preferences, I think isactually really, really helpful
but I also hear, though, thatthat you value the whole working
double duty, pushing theenvelope side of things.
Um, you talked about rewardingpeople, getting more opportunity
, getting more promotions.
Speaker 2 (26:23):
Brian, I would be careful, though, because it's
not just the hours right, soit's about productivity.
Speaker 1 (26:28):
Say more about that.
What does that mean to you?
Speaker 2 (26:31):
We care about the output.
We actually have it in ourcompany.
We call it company ethos as wepublish this, and so it's about
productivity.
So everybody's responsible fora particular project.
We're a pretty small team still, so it's about 30, 40 of us and
everybody's responsible fortheir own piece, and we talk
(26:54):
about that.
A lot like accountability.
It doesn't matter how long ittakes a person to get things
done.
A lot like accountability.
It doesn't matter how long ittakes a person to get things
done.
But if somebody wants to moveup and advance and we've had
situations where that actuallyhappened very, very quickly if
they finish their project withina shorter amount of time, they
can take on more, they can helpthe team, and that's actually
(27:15):
happened quite a bit.
Speaker 1 (27:17):
Yeah, yeah.
So it sounds like one aspect isyou really value output If we
use a crude measure of outputover time as productivity?
Speaker 2 (27:28):
That's right.
The problem in a startup isthat there's always more that we
can do.
Always, the work doesn't end.
Speaker 1 (27:37):
So far, you've talked a little bit about how there's
always more to do and you valuepeople who will be very
productive, create a lot ofoutput, and that, on some level,
having folks who are working alittle bit less intensely is a
good thing, as it creates somebalance on the team, creates a
(28:01):
healthier environment andsomewhere there's kind of like a
gray it's not black or white,right.
It's like you don't want allcrazy intensity across the team.
You don't want everyone to bevery laid back.
You want to be somewhere in themiddle.
So I guess, if we tie it backto that question of how do you
(28:21):
create a healthy team whenobsession and hyperactivity are
things that are really importantaspects, where are you now on
that question?
Speaker 2 (28:33):
So we actually have a fairly good balance.
To be honest, in terms of thecore group of folks, I would say
some of it has to do withmutual respect, some of it
probably has to do with theopenness.
So I'm really reallytransparent, besides salaries
and things like that open book,completely open book with a team
(28:56):
, that open book, completelyopen book with a team and I
think that's helpful, becausethen if I am pinging, you know
at 11 o'clock at night, allthese ideas, then the team knows
where it's coming from, so it'snot just some random thought
that I have, and so they alwaysknow like this is what led to
all the saying all this.
Um, so yeah, I think it's aboutmutual respect and that's not
(29:20):
something that you get overnight, I think.
And so for some of the coreveterans because if you think
about how, like, for example,somebody like dylan joined
enterprise before I even wentfull-time a couple of weeks
before, but still it's poor theamount of respect and trust
there is pretty huge.
Speaker 1 (29:40):
Because he took that risk.
Speaker 2 (29:42):
Yes, yeah, a hundred percent.
And when somebody new joins,that I didn't know before, it
takes a while to build thattrust, build that level of
respect.
Once you do, I thinkeverybody's kind of on the same
page and at the same time theyprove that like I see where they
are in terms of the output ofwhat they want to do.
So it's really helpful.
(30:03):
But being patient during thatfirst onboarding, that's hard
too.
As you're exploring differentways of working together.
Speaker 1 (30:14):
What I'm hearing from you is that transparency and
respect are pretty criticalingredients for creating a
healthy environment for yourteam.
And that doesn't come for free,doesn't come from the beginning
.
It requires time, investment,it requires a process where
(30:37):
people spend this time togetherto feel each other out,
calibrate, and so on and soforth.
Speaker 2 (30:44):
I think so, and I think that me translating that
into the company culture as wellis important, because, now that
we're talking about it, one ofthe things that I mentioned is I
have this group of originalgangsters, as I call them.
So these guys have been withEnterprise since day one.
They know everything that'sgoing on without their roles
being super defined just becausethey were the original folks.
(31:06):
And what sometimes happens isthat when new folks join, we can
kind of fix everything prettyquickly within this original
group right, without letting theperson figure it out, and so
it's not just about me, it'skind of translating that
throughout the company that wehave this culture.
That's incredibly driven, butit's all about the output and
(31:30):
you have to be respectful anddevelop this mutual trust,
because mutual trust developmentis maybe the primary goal here
and maybe that is not even theoutput.
Speaker 1 (31:40):
A little lost.
Can you just repeat what yousaid?
Speaker 2 (31:44):
So I guess teaching the folks and coaching them that
when we're building out theteam and as we even work on
being a team, this respect andtrust building amongst everybody
in the company and not just meit's not just me to to a person
I think that's really importantand vocalizing that Okay, that
(32:07):
it's like a goal.
Speaker 1 (32:09):
Trust and respect yeah, okay, oh and respect are
really critical for team health.
And with yourself what?
And with yourself, what'scoming up for you?
Where are you in this question?
What feels like it's notresolved right now?
Speaker 2 (32:28):
I think what's coming up for me is that I think
transparency has actually helpedme quite a bit with that.
So I literally run it in themost transparent way.
We have company meetings everyThursday and I lay it out in
terms of our developers know,like, where we're in terms of
customer contracts, like it's avery open book, and I thought
(32:51):
sometimes that maybe I don'tever need to do that right,
because I've never worked inorganizations that did that.
So why would I have to do that?
But when, a couple of monthsago, we had a situation where
something in the product had abug and I had to call one of the
main developers on it and gethim to stay, you know pretty
(33:13):
late to work on it and fix it,but he understood, my team
understood right away like what?
Why I'm asking that?
Because they, because I'vetalked about what this means,
and I think that that's actuallywhat created the trust.
Is this transparency that maybethey didn't necessarily need,
(33:35):
but because they did need it itsounds like.
Speaker 1 (33:37):
It sounds like that transparency provides the
context and the understanding ofwhy they need to work late in
the first place.
Speaker 2 (33:46):
Yeah, I think so.
I think that's there are noquestions and they all
understood, and I think that abig part of it, too, is creating
this empathy that why do I care?
I want them to understand why Icare, because I have customers
that I love and I care about thecustomer.
(34:08):
So it's all, at the end of theday, it's all about our clients,
and I want to make sure that ittranslates throughout the
organization, and so it's notjust me being obsessed for the
sake of being obsessed.
There's this mission.
Speaker 1 (34:18):
So let's say that you were to indicate that to your
team over and over and overagain.
Transparency here's why we careabout this.
Here's why it matters.
Here's why we're doing whatwe're doing.
How would that impact thiswhole thing that you're talking
about around?
People are going to work toohard or not hard enough, or it's
(34:41):
going to be unclear, like ifyou simply just were as
transparent as you could beabout why you're doing what
you're doing all day long.
How would that impact things?
Speaker 2 (34:53):
Well, you make it sound really simple.
I didn't say it was simple well,you make it sound really simple
.
I didn't say it was simple, butthe reality um is, I think it
would have two different effects, right?
So if, if people on my team whodon't actually talk to
customers all the time hear thisfeeling that that's what I'm
experiencing, that's why I'mdoing this, then they're free to
(35:14):
make their own decisions, howobsessed they want to be Right,
and I'm empowering them to makethat decision to based on where
they are in their life and, atthe same time, by talking to
them why I'm doing this and whythis matters, then they can
(35:37):
calibrate where they are in thatproductivity scale and where
they need to be, because it'snot just about hey, I want to
just check the box.
Speaker 1 (35:45):
Mm-hmm.
Speaker 2 (35:46):
And I'm essentially putting that responsibility on
them, and they're free to maketheir decision.
Speaker 1 (35:55):
Well, I like what you said around empowerment because
, just to reflect for a second,it sounds like a couple of
things I'm picking up.
One is when you provide thiscontext around the customers,
especially for people who don'thave a lot of contact with them,
when you explain the context,what matters or why it matters,
(36:17):
or even when you are transparentabout what gets rewarded to
enterprise, what doesn't getrewarded, you're essentially
giving your team and new hiresthe relevant information that
they need in order to make fullyinformed decisions.
Speaker 2 (36:33):
So another way of describing that is empowerment.
Yes, and I think that I'm alsotaking that pressure off of
myself.
Speaker 1 (36:39):
How do you mean?
Speaker 2 (36:39):
Because, instead of me deciding what to tell this
person in terms of the workhours or not, what I'm doing is
I'm telling them why thismatters to me and how much this
matters and what the mission is.
And here are our clients andwhy they care clients and why
(37:00):
they care, and it's up to theperson to decide where they want
to be in this company, assumingthat they get their job done,
of course, right.
So there's minimal requirementsthere that they have to meet,
but it's their decision and notmine, and all I can do is tell
them that I'm okay, regardlessof their work structure, style,
you know.
However they want to do it, butthen I'm taking that load off
of my shoulders.
Speaker 1 (37:20):
Yeah, so I want to just invite you to take a moment
right here, present moment, tosee what that feels like to take
that load off, because you'velaid it all out.
Speaker 2 (37:30):
Yeah, no, it's interesting because then I'm no
longer thinking about dictatinghow somebody works and what they
do.
How does?
Speaker 1 (37:39):
that feel for you right now.
Speaker 2 (37:42):
It's a little easier.
Speaker 1 (37:44):
Yeah, just a little bit.
Speaker 2 (37:45):
There's also a level of human empathy, I think, there
in terms of this empowermentand me, I like being transparent
with the team because I wantthem to fully understand where
it comes from, like where deepdown inside my heart it comes
(38:05):
from, and I think that I've donethat.
But you, what you're showing me, is that there's another layer
where I'm giving them all thisinformation, not just so that
they have empathy and understandclients, but so that they can
see where they are on the in inon this map, like where they are
on the team.
Speaker 1 (38:25):
And so when they have all that information, then they
can decide for themselves.
Speaker 2 (38:31):
Yes, knowing that I have their back, no matter what.
Speaker 1 (38:34):
So go back to this original question of how do I
make sure my team is healthywhen there's all this obsession
on it?
How does that question sit withyou right now?
Speaker 2 (38:45):
I think that as long as I tell them why, how, then
I'm harnessing the positiveeffects versus dictating what
everybody does, in which case itbecomes negative.
Right, but I like the obsessionconcept, I like the energy of
it.
I think it's really important.
Speaker 1 (39:05):
Your job isn't to tell people how obsessed they
ought to be.
Your job is to simply share howcommitted, how obsessed you are
currently and what will berewarded here, and allow them to
make a choice.
And so long as that decision isin their hands, not in yours,
(39:25):
then that weight that youmentioned, that's on your
shoulders, can be just a littlebit lighter, because you're not
carrying that decision for them.
Speaker 2 (39:33):
Yes, and then the flip side is that we started out
this conversation talking abouthow it's lonely being a solo
founder and how every decisionis yours, but maybe this one
doesn't have to be mine.
Speaker 1 (39:53):
Very nice, just going to let that one hang out for a
second.
Very nice, just gonna let thatone hang out for a second.
Yeah, so just we're gonna startto wrap here.
So take a moment to take inwhat we just explored and I want
to ask you what's the maintakeaway for you, olga?
Speaker 2 (40:13):
I think the main takeaway is that the
transparency that you'reallowing your team to have
probably has more benefits thanI realized.
When we started thisconversation, I knew, going into
it, that, talking about thefounder obsession, I wasn't
going to say that it's a badthing, because I truly believe
that it's not, that that's whystartups exist.
(40:36):
But at the same time, I think Iwould imagine that most people
realize why founders do this andif you're just giving people
benefit of doubt and creatingthis transparency and talking
about why and how, I imaginethat it probably empowers people
more than I originally thought.
Speaker 1 (40:57):
Yeah, I'm excited to see how that unfolds for you, as
you really practice that.
Speaker 2 (41:03):
Appreciate it.
Speaker 1 (41:03):
All right, olga, it was a pleasure to be with you.
Speaker 2 (41:06):
Thank you so much, brad, you got it.
Speaker 1 (41:08):
One of the things that really struck me in the
session was that sense ofloneliness that comes with being
a founder.
It's this feeling like you'reresponsible for every single
thing that happens in thebusiness, and as a former
founder myself, I totally getthat.
I think part of what made thisexperience harder than it needed
to be for Olga was the tensionof embracing intensity and not
(41:28):
wanting to scare off employeeswho don't necessarily want to
make work their everything.
Olga internalized that tensionby taking responsibility for how
her employees worked, even ifjust implicitly.
But when she leans ontransparency to create trust and
help her team understand thewhy behind her own actions, she
ultimately empowers her team tofind their own balance.
Now Olga doesn't need to beresponsible for all their
(41:49):
choices.
She can leave it up to them andwith that, find some relief.
Thank you for listening to SlowDown to Speed Up.
If you enjoyed this episode,please rate it in your favorite
podcasting app or give it a likeand subscribe on YouTube.
And if you're a founder lookingto reach the next level through
coaching or you'd like to comeonto the show, please reach out
to me at dashingleadershipcom.
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