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March 19, 2024 35 mins

On this week’s episode, host Conor Bronsdon sits down with Emily Nakashima, VP of Engineering at, to discuss how you can prepare to be a VP of Engineering, and how the role differs among companies. Being a VPE varies based on company size, culture, and the existing team's makeup, and Emily provides valuable advice for engineers aspiring to leadership positions.

Emily also discusses using personality tests for better team dynamics and the need for regular self-evaluation as an integral part of career advancement. The conversation closes by talking about the impact of AI on the workforce, the importance of aligning engineering and business goals, and the potential of AI to enhance rather than replace human skills.

Episode Highlights:

01:27 Why does Emily think there isn't a standard VP of Engineering role?
06:29 The archetypes of the VPE role
10:15 How does the VPE role change as an organization grows?
14:46 Preparing to become a VP of Engineering before you get the role
20:11 How you can use personality tests in organizational design
26:00 How is the VP of Engineering role changing in 2024?
30:53 Teams are having to accept realities about production software with regards to AI

Show Notes:

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Emily Nakashima (00:00):
I think that this was actually a mistake I

made when I first took on anexecutive role where I really
expected to show up,representing my function, and
fairly quickly I went, oh, thisis the wrong way to think about
Once I sort of switched andsaid, Hey, this is a team that's
trying to solve a problemtogether, and most of the time
we actually can kind of like setaside the hat that we wear when
we're out in the rest of thecompany and just sort of work
together, as you know, fivepeople who have different

expertise but are trying tosolve the same problem, that
ended up being a much healthierapproach.
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Conor Bronsdon (01:06):
Hey everyone, welcome back to Dev Interrupted,
live from Leading Eng Sf.
I'm your co host Conor Bronsdon,and I'm joined today by Emily
Emily is the VP of Engineeringat Honeycomb.
io, also known as Honeycomb.
Emily, thanks for coming on theshow.
Really happy to be here.
It's my pleasure.
Because you have a background inproduct engineering, performance

optimization, client sidemonitoring design, and I love
that you kind of describeyourself as this dev tools nerd.
Uh, because frankly, so are wehere.
We, we love talking to folkslike yourself, and I understand
that you have identified amisconception that you're
seeing, in how we all apply notjust dev tools, but dev

Because we talk a lot about howCTO roles can vary company to
Some CTOs sit over multiple VPsof engineering and they're
running the whole engineeringorg.
Others have a special ops group,or maybe some other roles here
where they're focused onsecurity.
There's a variety of ways youcan look about it, depending on
the size of the company, thetype of company.

Yet we like to think about VPsof engineering as kind of
standard like, okay, you're VPof engineering.
Your size of the company may bedifferent.
You don't think that's the case?
You think there's a a differencebetween VP of engineering across
the board?

Emily Nakashima (02:20):
I do think that, and I don't think it's
just developer tools, companies,I really think, especially
startups, but really, any kindof like scaling company.
I think so often the roles arereally defined by who's there
and what the organization doeswell.
You know, there's this realunderstanding'cause we've sort
of, I think, idolized foundersand CTOs that we have sort of
become more aware of all thedifferent shapes.
Um, but you know, the reality isthat the VP of engineering can

take on almost as many shapes asthe CTO.
And I don't want people to missthat.
'cause I think like people caneither be drawn to the
opportunity for the wrongreasons or they can sort of
think it's not for them becausethey have the wrong picture of
in their head of what it

Conor Bronsdon (02:54):
could be.
Well, let me just say to VPs ofengineering who are watching and
We think about you too.
we we're big fans, uh, andthat's why Emily, I'm, I'm
really glad you're here to kindof talk, uh, to us about some of
this almost antiquated views ofthe role that we have.
How do you think about the VP ofengineering role?
How does it break down for you?

Emily Nakashima (03:12):
I do think that, you know, some of the kind
of, sort of maybe stereotypethat people have in their head,
there is some truth in that.
Like, I think in general, thisidea that.
the VP of Engineering is thelead manager for either
engineering as a whole in asmaller company or, you know, a
portion of the technical teamsin a larger company.
It rounds to true in mostplaces, I think.

I think the thing that peoplemiss is how much the actual role
is shaped by other people on theleadership team.
And sometimes other people whoaren't on the leadership team,
Probably if you think about theVP and CTO relationship.
That kind of like makes moresense naturally to people.
Like I work with charity majorswho's Honeycomb CTO, um, Charity

is very well known to come from,uh, a really strong operational
She was A DBA at one point, youknow, she was like a sys admin
back in the day.
She understands backendengineering very well.
And so when I tell people, Hey,because Charity has that
background, I can kind of comefrom more of a front end
background, be more of aspecialist in like engineering
and product collaboration.
That makes a lot of sense.

But a thing that people missthat I think is really important
is that I can also have my rolebecause we had some early
employees at the company whowere relatively senior, who also
had really strong operationalchops, who, made sure that the
platform was like runningreliably, who made sure that we
didn't have major architecturalchallenges.
And because those weren't thetop concerns when they went to

go pick a VP of engineering, Ihad a profile that made sense.
So I think it's really, youknow, it's both.
It's up, down and sideways thatall kind of like shape the role.
It's not just who's the CTO,which I think people focus on.

Conor Bronsdon (04:44):
That's a really great point that there are all
these different dimensions wedon't necessarily think about.
And you also mentioned theinteractions with other
organizations, other businessunits and how that impacts how
the role of VP of engineeringfunctions.
Can you talk a bit about that?

Emily Nakashima (05:00):
I think that, um, people really,like I said, focus on that
V-P-N-C-T-O relationship.
I see that same sort ofreciprocal shaping happening
with the VP of product as well.
Sometimes you have a reallystrong VP of product and then
there's sort of a healthytension between the two roles,
and they're sort of shaped inopposition to each other.

Conor Bronsdon (05:17):
Usually healthy

Emily Nakashima (05:18):
or, you know, tension of some sort one, one
flavor or another.
Um, and then sometimes, youknow, you have a, a product
function that, you know, maybeengineering has been at the
company for longer.
The product function is a littleless mature.
And then the VP of engineeringis almost senior to the VP of
And there's a little bit more ofa, you know, you're sort of
under my umbrella kind ofrelationship.
But it can be really different,and no matter what the shape of

the VP of product is, it alwaysshapes that VP of engineering
role in turn.
And to a lesser extent it's truefor other roles on the senior
leadership team as well.

Conor Bronsdon (05:49):
Yeah, I mean, I'm not an executive, but I
imagine that when you're in thatexecutive leadership meeting,
The, the strengths and weaknessof that team has been my
You know, the one time I didfound a company and that didn't

go well, let's just saylisteners, Um, I, I wonder how
you've seen that impact youpersonally in your role.

Emily Nakashima (06:15):
Yeah, you know, I think that this was actually a
mistake I made when I first tookon an executive role where I
really expected to show up,representing my function, you
know, and fairly quickly I went,oh, this is, this is the wrong
way to think about this.
Um, once I sort of switched andsaid, Hey, this is a team that's
trying to solve a problemtogether.
And most of the time we actuallycan kind of like set aside the
hat that we wear when we're outin the rest of the company and

just sort of work together, asyou know, five people who have
different expertise but aretrying to solve the same
That ended up being a muchhealthier approach.
And then it's not about like, Irepresent engineering, you
represent marketing.
It's like.
you're the funny one, who'sgonna add levity when we're all
like arguing with each other, orI'm the person who's gonna
remember to like retrospect andlook back.
Like that kind of stuff oftencomes more, much more to the

And having that sort of balanceand sort of like skillset and
perspective, I think is, asimportant as the kind of
functional balance.

Conor Bronsdon (07:04):
I just wanna say it's very kind of you to, to
picture me as the funny one.
So, so thank you for that.
Um, I don't know if it'sdeserved, but, it sounds like
you have a few differentarchetypes in mind as far as how
VPs of venturing function,depending on company size,
makeup, et cetera.
What are those differentarchetypes?

Emily Nakashima (07:23):
I feel like the more I dig, the more I find more
ones then okay.
I'll say I'm, I'm coming from,I'm more of a startup person.
And there, there really is a bigdifference between being, um,
the VP of engineering at asmaller company versus being a
VP of engineering at a biggercompany.
Um, I, you know, I know a littlebit about that divide, but I
haven't been that VP ofengineering at a bigger company

and, um, I think that, you know,it can really change Often at a
larger company you have a muchbigger scope, you know, you have
more people under you and youare managing a lot more
Cross functional relationshipsare often more complex, but in
some ways you also have lessautonomy.
You know, you can't just gorewrite the travel policy on a
whim on a Friday afternoon, youknow?

So that really can shape therole.
I think you get a wider array ofarchetypes sometimes at smaller

Conor Bronsdon (08:10):

Emily Nakashima (08:10):
And then you get more, there's such a range
of, from internal facing toexternal facing.
Oh, trailblaze versus steward isa dynamic I really like.
My COO, Jeff Gray uses thatdescription of the two different
possible flavors where thetrailblazer is the person who is
like out, you know, innovatingnew technology, like coming up
with new product lines.
And then someone needs to be inthat steward position where

they're like, this is theproduct that makes us money
I'm, I'm gonna make sure itkeeps doing that.
You know,

Conor Bronsdon (08:37):
And I imagine there's this, I mean, use this
phrase healthy tension, uh, withthe role when there's technical
co-founders too.
So, I mean, like, I'll say likelinear B, we have a, a VP of
We also have a CEO as a formerVP of engineering.
We have A-A-C-P-O as a former ofVP of engineering.
So this creates differentdynamics than I'm sure other

companies where maybe.
It's a, a more business-mindedco-founder.
And not to say that our, ourco-founders are business-minded,
but maybe they came from salesand have hired a VP of
engineering to build out theproduct.
That that absolutely will createa different dynamic in product
and engineering organizations.

Emily Nakashima (09:13):
Yeah, absolutely.
A lot of times, like where thevision comes from can be the
biggest thing that kind ofshifts around.
And I think often if you havefounders in those roles, they
can often like, look into thefar future forever and tell you
like what the product should beand then, you know, if you get
to a certain point where all ofa sudden that's a hat that needs
to be assigned to a specificexecutive and that wasn't what
you were hiring for.
When you like hired that personinto the role.

That can be an interesting thingthat really kind of forces
people to grow or sometimesforces a, a change.

Conor Bronsdon (09:39):
So how do you identify the archetype that your
company needs when you come onboard or when you're hiring?
I suppose.

Emily Nakashima (09:47):
It's a good question.
I'll, I'll say when I was sortof a, manager, Director, Senior
IC, I was not tuned in to the,you know, even to the idea that
I could ask my VP of Engineeringto be different, or that I could
evaluate whether theorganization had picked the
right shape, and only now I lookback and I see, you know,
moments where we really had theright shape of person for the
job, and moments when we didn't,and it made a big difference to

the health of the company.
It's hard to do when people havesuch a narrow understanding of
the job.
The big thing I would look forif I were trying to understand
that, is really those crossfunctional relationships and how
they're working, and especiallywhich ones seem to be strong and
which ones seem to be, likethere's not connective tissue
there, or they're fraying alittle bit.
You know, that's often thebiggest clue that something

needs to change, where like,maybe you see an organization
where you really think productand engineering need to be
tight, or engineering reallyneeds to be, you know, very
closely aligned with the revenuegoals and shipping certain
things that, you know, you knowthere's revenue behind, and you
don't see that happening.
Those kinds of things are oftenthe sort of The really concrete
warning signs that maybe there'sbeen a misalignment in the


Conor Bronsdon (10:50):
And I imagine the needs, I mean, we know the
needs evolve over time, uh, forroles.
So I can see how this wouldreally shift as organizations
grow in scale.

Emily Nakashima (11:01):
One of the interesting things about being a
startup VP versus potentiallybeing in a bigger company is
like, the pace at which you needto kind of become an entirely
different shape or archetype canbe a lot faster.
You know, I do think the role isalways evolving no matter what
company you're at, just becausebusinesses, business conditions
are changing.
But I think at a startup you cankind of have a completely

different, most importantproblem every maybe six months.
Sometimes it's just, I need tothink about X and, and now I
need to think about Y.
But sometimes it's, I need to besomeone who's like the planner,
who's so organized, who'sputting the right systems into
place and all of a sudden youneed to become like the
visionary leader.
Who's like inspiring people.
It can really kind of push youto grow maybe faster than, than

Everyone's comfortable with thepace.

Conor Bronsdon (11:44):
I mean, for folks who are at startups or
have been at startups for awhile, and the audience, you're
probably gonna resonate withthis.
So often people join a seedcompany or a Series A or Series
B and they find around later thecompany looks very different.
Some people want to grow withthat company and some people
want to have all this change andreally keep growing with it.
But some folks are really like,Hey, I love a Series B startup.

You know, I want a little bit ofscale.
Uh, or maybe I love that SeriesA seeder.
I want, I want to build.
And once we get to Series B,Series C, I'm like, ah, there's
too much red tape.
It's not what I want anymore.
And we see that happen at IClevels, but we also see it
happen at management levelswhere some folks will scale with
the company and others will moveforward on different areas.

Emily Nakashima (12:25):
Yeah, I really, honestly, I wish we were better
at celebrating when peoplenotice that dynamic and make the
call for themselves.
That the company's no longer theright fit.
Uh, at Honeycomb, we, we try tobe really positive when people
choose to leave.
We always frame it as like agraduation and not like, this
person quit or like thisperson's leaving.
We always say like, theygraduated from the team because

we always want to, we want themto feel positively about that
We want them to sort of likeclose the book at a moment that
like feels good and feels likethey can celebrate it.
And we want to make it clearthat we don't expect anyone to
stay forever.
You know, I think sometimespeople always feel like there's
that one more important thingthat they can't leave behind.
And, you know, when you stay toolong, I think it's, it's not
good for you, but a lot of timesit also holds back growth at the

Um, so yeah, it can, it can besometimes hard when you, when
you, you've really grownattached.
When you've grown with thecompany, a lot of times you get
really attached to the team.
You get attached to the product.
And you can stay in thatsituation where kind of the
day-to-Day isn't working for youfor a long time.
And I, you know, I think we tryto put as much positive framing
around that as possible toremind people that it is a

choice, right?

Conor Bronsdon (13:27):
Are there particular signs that you've
seen of when someone maybe doesneed to move on?

Emily Nakashima (13:33):
You know, it's hard to say.
I think it manifests differentlyfor each person.
I got some advice from a coachat one point, which was.
You feel this way now, maybe youfeel really strongly that
something isn't working, and itcan be hard to tell if that's
just a momentary thing that'sreally bothering you, or if
something has really changedabout the company.
And she said, go to yourcalendar right now, put a
calendar reminder 30 and 90 daysout, write down how you feel,

and then when that calendarreminder pops back up, ask
yourself, am I still in theexact same place, or did I have
a moment where I was frustratedwith this one problem, and it's
actually pointed in the rightdirection?

Conor Bronsdon (14:06):
That's a great perspective to kind of gather
that qualitative data fromyourself and say, you know,
where am I here?
Because it is easy to getfrustrated in a moment.
And, you know, sometimes otherthings in life are happening
that are affecting how you'reviewing your work.
It's very common.
How does that continue?
Because if it becomes sustained,that's where you know there's an

Emily Nakashima (14:26):
Yeah, exactly.
When I've seen people realizethat it's time, they realize
that they have been upset aboutthe same problems over and over
and they kind of can't put themaside, they can't bring them to
a resolution, and they lookaround and feel like their
coworkers, they feel alone,right?
They feel like their coworkersdon't see this big problem I
see, but the reality is everyoneelse has a different perspective
on it.
And so I do think checking backin with yourself to make sure

that that perspective issustained and that sort of delta
from maybe the people around youis sustained is the thing that
kind of helps you go, okay, wehave grown in different

Conor Bronsdon (14:57):
Yeah, and I think that alignment is
something that is usually feltby others on the team, right?
Like, your manager probably seesthat if you're feeling that way.
And it is better to find theright spot for you instead of
struggling to make it fit ifthis is a sustained issue.
That said, there are ways thatyou can, you know, grow and

prepare yourself for roles thatscale like this.
And, you know, Startup VP ofEngineering is absolutely a role
that will often scale from, youknow.
Maybe you're hired at the SeriesA and you scale the series B and
you keep growing the team.
It's an exciting time.
How should people prepare tobecome a VP of Engineering
whether at a startup or anenterprise?

Emily Nakashima (15:36):
You know, it's a great question, and I think a
lot of people don't realize thatthey actually can start
preparing before they, they getthe role, you know?

Conor Bronsdon (15:43):

Emily Nakashima (15:43):
They sort of put the title up on a pedestal
and then don't sort of breakapart the skills that are, that
are involved.
And I actually think even as asenior IC or engineering
manager, or certainly as anengineering director, you can
take on a lot of efforts thatwill help you be ready.
The biggest one is generallyjust sort of identifying across
organization management problem,and then you know, going to your

VP or going to your director andsaying, Hey, can I work on this?
I didn't realize I could do thatfor so long.
I always felt like I would bestepping on someone's toes.
And now, you know, now that I'mon the other side, I'm like,
yes, please.
Like, please, like you want tosolve a big, important problem
and you just want some authorityand support in doing it great,
I'm here for you.
Um, and for me, you know, sooften my job is a little kind of
So when someone wants to kind ofpartner and solve a big problem

for the organization, it can bea lot of fun.
You get to work together andthen hopefully they get a little
taste of what it's like to be inthat role too.

Conor Bronsdon (16:31):
Yeah, I think there are a couple ways to think
about this.
Like one, like, solve yourboss's problems.
Don't, don't be one.
Like that's an, that's anobvious one, right?
Like, let's try to help solvetheir problems and usually.
I mean, people differ.
Some, some people are veryauthoritarian or hierarchical
and don't want you to take onproblems yourself.
And also to differs culture toculture, whether that's, you

know, internationally where,where you're working or company
to company.
But in startups, people want youto solve problems.
That's what they hired you for,They're really excited for you
to start solving.
It's like you identified thisproblem.
You saw a problem that maybe Isaw too, maybe I didn't, and
you're going to go solve it.
Now maybe I'll give you somefeedback and I'll solve it a
different way slightly because Ithink there's this thing you're
missing, this piece of context.

but usually I'm just stokedyou're you're doing it.

Emily Nakashima (17:15):
And you touched on somethingreally important, which is, you
know, sometimes it has solveyour boss's problems, but even
more exciting than that is like,Hey, I see this big problem that
maybe you don't see from yourvantage point.

Conor Bronsdon (17:25):
Oh, I love that.

Emily Nakashima (17:25):
Um, you know, I'm so used to it since I sort
of grew with the company and somany of the folks on the team
are people that like I hired orI worked with directly as a
manager back in the day.
Like, I can have that sort offalse sense that I still know
how everything works in theorganization.
And it's actually changed a lotsince I was up close with it.
And when someone comes to me andthey surprise me with a problem,
like that's my favorite moment.

Conor Bronsdon (17:43):
That is an awesome call out.
And I think it's something weunderrate because we think, oh,
we have so much context we'reexposed to leadership, we also
have been here for a while, andthings are changing on the
And ICs have not just differentframes, but also depth in
certain areas that maybe youdon't have, and so do managers

in different areas.
However, I also think there areskills that are really crucial
to develop that are not justthis problem solving piece.
start to develop those managerof manager skills, uh, as you
work towards that next stage ofyour career, if that's what you


Emily Nakashima (18:26):
You know, for me, one of the hardest things
was figuring out how to buildthe same degree of visibility of
the organization as a manager ofmanagers.

Conor Bronsdon (18:35):

Emily Nakashima (18:36):
Like, you know, you're used tobeing able to kind of go verify
directly, you know, you can lookat pull requests, you can go
talk to the engineer the moreyou move up the ladder, the more
it becomes really disruptive todo those things.
Or the more you create chaos bylike, Hey, I saw this on this pr
what does it mean?
You know, like, you don't,

Conor Bronsdon (18:51):
Someone's gonna be worried about that.

Emily Nakashima (18:52):
You don't wanna be the problem.
Um, but it, it is a totallydifferent skill to build that
picture of what's actuallyhappening in the organization
and where things are workingand, and not, from secondary
sources versus from going andtalking to people directly.
So sometimes it means, you know,it's a lot of reading status
updates, it's trying to makesense of them.
It's trying to verify that basedon what you hear from other

managers, but it can be a reallydifferent way of collecting
And I do see some managers andmanagers who have never figured
out how to make that leap.
And I always feel like the, theend result is paying for their
So I think you can practice it,you can try to make sense of
what's going on in like anadjacent part of the
organization and sort of seewhat you come away with and try
to develop that picture.
So I think that like, that, thatpiece is one you could try

I also think just sort ofbuilding your, your context
about the business, even thoughit may not be directly related
to the specifics of managingpeople who are managing people,
it is one of those skills you'regonna be trying to build at the
same time.
And it's nice to get the jump onthat when it's not you know,
when you're not already in thehot seat.

Conor Bronsdon (19:52):
Yeah, and I know a lot of folks who listen to
We, I mean, we have plenty offounders and CTOs, VPs of
We also have a lot of folks whoare maybe engineering managers
and looking to kind of scalethat senior engineering manager,
director level and say, yeah, Ido want be the manager of
You gave some great insightsabout how to approach building
that skillset.
If you were to give like acouple of actionable tips of
like, okay, try this, try that.

What would you say to thosefolks listening who are, are
trying to build that skillset?

Emily Nakashima (20:16):
Number one is definitely just like literally
pick a project or pick a part ofthe company.
And say, I'm gonna develop areally nuanced picture of what's
working and not working overthere.
And then, you know, I'm gonnatry to like read the status
I'm gonna go try and look at theship work, look at the change
I'm gonna, you know, look at themetrics I can see in, in, you
know, linear B or whateverengineering metrics tool is, and

then go talk to the manager ofthat team and go, Hey, I'm just
trying to understand thisbetter.
And see how much like what youhave come away with matches
their perception.

Conor Bronsdon (20:44):
You know, I hear you talk about archetypes.
I've also heard that you likeusing personality tests in how
you think about yourorganizational design and, and
helping prepare people.
How are you leveraging those?

Emily Nakashima (20:55):
So there, there's a backstory for, for our
executive team by how we gotinto these, um, you know, there
was a period where we had sortof hired, our exec team has a
nice balance of sort of folkswho grew into the role
internally, and then we've hireda number of seasoned folks from
outside of the company who havebeen VPs or c-levels before.
Um, and that's really nice, but,you know, it takes a while to
get the group to gel.

So, you know, we had gonethrough a period where we had
brought on a couple of new, um,executives who were new to the
company but not new to theirjobs.
And we were sort of trying tofigure out how to gel as a team.
And I think it was our, our CEOChristine Yen who decided, you
know, we were, we started to doquarterly offsites as an exec
And she was like, great, we'regonna do a personality test and

we're gonna all talk about theresults and that's how we're
gonna get to know each other.
I can't even remember which oneit was at this point.
It might've been Myers-Briggs.
But somehow that started tobecome a recurring thing that we
did almost every offsite.
So there was like, maybe a yearand a half where every quarter
when we got together, the thingwe would do before we saw each
other in person was take apersonality test and then
discuss theirselves.
A new one.
Different time.

Love It was a different one eachtime.

Conor Bronsdon (21:58):
I love that.
That's kind of fun.

Emily Nakashima (21:59):
So we did, uh, Myers-Briggs, wedid Insights Discovery.
We did the Working GeniusFramework.
At one point, I, um, you know,just to be cheeky, I got
everyone to do their astrologychart.
Oh yeah.
And I talked people through whatthat meant.
And the funny thing is you getabout as much value out of that
as you do the other ones.
At first I was a littleskeptical, but I really see

judiciously deployed thatthere's real power for certain
teams, especially for managementteams in those tools.
And so I have come around to, Ithink there maybe not every
quarter, but there's really goodmoments to play.

Conor Bronsdon (22:30):
It's a great conversation starter.
If nothing else.
Like yes, it's not always gonnabe a hundred percent accurate,
but it can help you frame.
And I think I've found also whenI, when I've done it, and I'm
not advocating you spendingspend much time on this, I
agree, but it is kind of fun.
Um, you can say, okay, like.
I got, for example, I got EN tj,um, or I got IN tj and I've,
I've gotten both on thatMyers-Briggs test.

Like, do I agree with that rightnow or is this a reflection of
how I'm feeling in the moment?
And interrogating that result isreally interesting, I find.

Emily Nakashima (22:58):
And another reason that I reallylike them, there's two
situations that I'll deploy themin that, uh, I think not every,
everyone thinks of when theythink about these as tools.
Number one is if you have a teamthat you think is really
talented, but there may belacking a little bit of
Like sometimes, you know, thosetests are really good at just
sort of holding up a mirror.
And this is gonna sound silly,but like they just remind you

that you are good at somethings.
Or potentially, you know, wehave a number of very senior
engineers and sometimes peoplecould come into the company and
feel this sense of, oh gosh,everyone here knows so much.
Like, what can I contribute?
And just reminding people, Hey,you're a different shape.
You know, no matter how, howmuch you respect your teammates,
there's something you bring thatthey don't have, can be really
powerful and can really remindpeople that, like as a team you

are, you know, bigger than thesum of the parts of the people
on the team.

Conor Bronsdon (23:45):
You're stronger together.

Emily Nakashima (23:46):
Yeah, exactly.
So that's one case.
The other case I think they canbe really powerful for, um,
underrepresented employees, whomay be, you know, because of
biases in the workplace, peopledon't always recognize the sort
of leadership skills they mightbring.
'cause they're sort of expectingthem to come in a different
StrengthsFinder is actually myfavorite framework for this.
You know, I think certainpeople, people just, you know,

jump to the conclusion that ifyou're strategic or you're
ambitious or you know, you're,achiever, like you might look
like something different.
And you know, because thesetests are just, you know, you
fill in the bubbles, you get thescore.
They can identify anyone asthose things.
You know, there's always likecultural biases and that kind of
thing to worry about, but Istill think that like they can
be a really good tool forhelping people see themselves in

a way that maybe they haven'tbeen stereotyped in the past.
I feel like sometimes they cankind of help level the playing
field and help people seethemselves in a way that they

Conor Bronsdon (24:35):
I also like your point about the mix of
personalities and skill sets youneed on a team.
Because, um, if everyone on ateam is, you know, one Myers
Briggs category, that teamprobably has some issues.
Like, it's true it's got somestrengths, but it's gonna have
some weaknesses, too.

Emily Nakashima (24:48):
Yeah, and especially, like, it can be so
easy to miss this until you seeit, like, on the chart of your
exec team.
Uh, our CEO Christine Yen andthe COO Jeff Gray, when we do
the Insights discovery profile,we're all blue, which means
you're very analytical.
You love to work with data, youknow, you love to like solve
problems and like makedecisions.

And when we're all like jamming,the three of us are like jamming
on something together.
It feels so good'cause we thinkthe same way.
But it's so easy for us to miss,uh, you know, to sort of have
blind spots and like miss thatperspective that a coworker who
thinks different way is gonnaadd.

Conor Bronsdon (25:22):
Well, I have to ask, since she's been a guest in
the show before, uh, what'sCharity Majors?

Emily Nakashima (25:28):
that's a good question.
Charity and I are generallyopposites, which is kind of
'cause it means we, we, we worktogether well.
Chair, there's a, there's a redone, which is sort of like, you
just wanna like go, go, go andget it done.
You're fiery.
I think like the tagline forthat one.
Be brief, be bright, be gone, orsomething like that.
like they wanna get it done.
They, you know, they're like,they'll be in awe of your
They'll encourage you.

But they also are just likealready moving on to the next
thing with their minds Um,totally different than the
analytical blue where you justwanna like stew in the data.

Conor Bronsdon (25:58):
This is great.
I, I'm gonna have to go, listen,we've actually done two episodes
with Charity on previousseasons.
I'm gonna have to go back andlisten to them in this context
and be like, okay.
You're red, I think.
All right.
How's, how do you work withEmily here?
How does this work?
So this is, this is wonderful.
I really appreciate theperspectives you brought to this
conversation about the changingrole of VPs of engineering and,
you know, how that impacts therest of the executive team.

And something else we shouldalso mention is that, uh, there
is a lot of change happeninggenerally in the world right
The role of a VP of engineeringis changing.
We're being asked more to bebusiness leaders, not just
bringing engineering efficiency,at least in many companies, of
course, it may vary as we'vebrought up.
What are you thinking aboutgoing into 2024, Emily, that you
see changing either the VP ofEngineering role or the

technology space in general?

Emily Nakashima (26:44):
Yeah, I, I think as you said, it certainly
is a very interesting time andit can be really hard to kind
of, even like at this point putyour finger in the air and kind
of know where things are going.
And I'll say an interestingconversation that keeps popping
I did a meetup a few months backthat was with other engineering
leaders and people who were justsort of, you know, making
It was one of the firstin-person meetups a lot of
people had been to in a numberof years.

And, um, the question came out,uh, is your board pressuring
To lay off 30% of yourengineers, ah, or more and
replace them with AI Yeah.
I have a lot of respect for ourboard and I think they bring a
good sort of measuredperspective to things and we are
not getting that exact flavor ofpressure.
But a number of people just puttheir hands up and some people
said, I'm being asked to lay off50% of my team and replace'em

with ai.
Um, so that's definitely.
Whether you're excited about itor not, and I'm, I'm a little
It's something that people haveto have an answer to.

Conor Bronsdon (27:36):
I, I think that's a really great point.
I, I talked to a CEO, uh, justin the last couple days, who
told me that he had laid off 80%of his team.
And yes, new innovation is down.
He's like, Hey, we're keepingthe lights on.
You know, I'm still retainingthe value.
And I mean, that's a, you know,three, three rounds, brutally
deep cuts.
But there's a financialincentive for, for some of this

behavior and, because of howmost organizations are
constructed, that will oftenhappen.
So it's important that we thinkabout how we're allocating
resources, both, you know,financial and, and human
Um, I, I know it's a littledemeaning to say it that way,
but it's that conversation isn'tgoing away.

Emily Nakashima (28:17):
I, I think this is unfortunatelylike the painful fallback to
reality and a lot of teams aremoving.
They're moving back to operatingin the mode that they kind of
maybe should have been allalong, like.
We should understand the impactof investments that we've made.
We should make sure that we arespending our time and energy on
the things that have the mostbusiness impact.

We should make sure that we canlook at our data and observe
that that's really true.
Those things sound so obviouswhen I say them out loud, but I
think a lot of engineeringteams, there was a real moment
of pressure to just grow, grow,grow, and people really stopped
focusing on those fundamentals.

Conor Bronsdon (28:51):
I mean, ZURP, Zero Interest Rate phenomenon,
The big dogs, the Microsofts,the Googles, the Apples, the
Facebooks of the world do then.
And we were just going, ohshoot, we gotta, we gotta get
our engineers in here.

Emily Nakashima (29:07):
I'm certainly not someone asking, you know,
can we lay off the engineers andreplace them with ai?
I think that's, in general, Ifeel like that's quite a
horrible approach.

Conor Bronsdon (29:14):

Emily Nakashima (29:14):
But I do think that honestly, engineering is a
craft, much more fun and muchmore engaging when you are
trying to respond to businessconstraints.
So, um, there that part.
I welcome.

Conor Bronsdon (29:23):
Yeah, it's really interesting.
We partnered with Google ontheir Dora research this year.
Uh, that reports recently out.
Highly recommend, But one of theinteresting things that I heard
Nathan Harvey, who's the headof, uh, Dora's team over at
Google talk about when he and Ibroke down the report is, okay,
like, we're seeing AI beleveraged in about 50 percent of
the companies in our 33, 000person survey.

However, we don't have a clearcorrelation to efficiency gains
at this point.
Now, what they did find is acorrelation to increased dev
is being leveraged to helpdevelopers get rid of annoying
I think there's a ton ofopportunities for that.
And maybe help devs feel moreefficient or feel like they're

not having to spend as much timeon things that aren't equate to
value in their mind.
So as someone who's a DevToolsnerd myself, that gets me kind
of excited.
But there is so much pressurethat you mentioned from
shareholders, from the board,from CEOs and CFOs sometimes,
quite often.
To say, okay, well we can bemore efficient, we think the

data's not quite there, thatit's for sure bringing
efficiency gains, though.

Emily Nakashima (30:35):
Yeah, that's a good call out.
There are fundamentally somedifferent philosophies and I do
totally, I think people willhave to kind of pick which one
they align with.
Like, for us specifically atHoneycomb, Christine, our CEO,
um, says we wanna build likemeta suits and not like.
Autonomous robots.
You know, we wanna build toolsthat make people feel more
awesome at their job and, youknow, make the things that they

have to do easier, but they'resort of still in control.
'cause we think that like thereare so many things about human
judgment that just, uh, can't,there's just not a good
replacement for it.
Especially, you know, so much ofwhat we do is engineers is
about, making challengingtrade-offs and you have so much
context that I think is justvery hard to translate at this
point to a machine.
I'm much more optimistic aboutthose use cases that are about

empowering humans and makingtheir job better and easier than
the ones that are like, how canyou replace the people with
'cause I think it's, it's, theoutcomes are quite

Conor Bronsdon (31:25):
I think you can replaceprocesses with code sometimes.
Like, that's where I'm excited.
Policy as code is an idea is, isa huge opportunity to cut down
some of these process pieces.
In the end.
I, I agree with you.
I think, you know, humandecision making, human context
is important, and we willperform better if everyone gets
a copilot like thing for theirjob.

Whether that's an engineer,whether that's a marketer like.
Whether that's someone workingin an entirely different role,
let, let's give everyone a toolthat's tuned to how they need to
approach the world to help them.
Because yeah, that's gonna see alot of efficiency gains that's
gonna make people happier.
It's going to, you know, seethese improvements.
But there is this conversationhappen thing where it's like,

oh, well why can't we justcompletely replace the humans?
'cause humans are expensive fora corporation because we have to
spend the money.
Um, but, but I agree with you.
I think it's a littleshortsighted at, at least for
now, the tech, tech doesn't seemto be there yet in my mind.

Emily Nakashima (32:20):
I agree with that.
There is one aspect of this thatI'm, I'm welcome and I'm really
excited about, and this issomething that, that our CTO
Charity Majors sort of clued meinto, where she pointed out that
all of these software teamsbuilding with ai, building with
They are starting to have toaccept the certain realities
about production software thatactually I think, have been true
for a long time.

Um, you know, there's sort ofmyths that we tell ourselves
about our software that haven'tbeen true for a while.
You know, the idea that, youknow, our software is perfectly
deterministic that if the testpass it works, that, you know,
once you ship it to production,what the software does doesn't
change until you ship again.
All of those things have becomesort of like less and less true
over time in the cloud era.

And, you know, LLMs really sortof put those issues in the
And so I, you know, she's kindof excited and I, and I agree
that I think we're gonna havemore of a conversation where we,
we sort of evolve how we thinkabout supporting software and
production and how we ship.
And I think that's gonna bereally cool and interesting part
of this.

Conor Bronsdon (33:20):
Emily, I've, I've really enjoyedthis conversation.
I appreciate the thoughtfulnesswith which you've approached,
this topic, and I hope everyonewho's interested in being a VP
of engineering in the audiencehas listened to this and has
found some value, and maybe VPsof engineering in the audience.

Emily Nakashima (33:39):
I think, you know, one of the things I'm
really excited about as I lookout is just I do think that
there's a return to reallywanting to make sense of, of the
data that you're seeing.
Like it is a moment that reallycalls for that.
And so I think that like, um,all of a sudden.
You know, our tools become somuch more important.
They become so much moreprecious to us.
And I always wanna encouragepeople to sort of dream big for

their tools.
I think it's so, so easy to sortof, um, get used to dealing with
your tools in a certain way.
And I think like the nice thingabout AI is it's, it's forced us
to sort of re-envision whatthose experiences can be like.
I think you can do that witheverything you use.
You don't necessarily have tolimit it to, you know, the, the
AI that's coming to, you know,replace typing in your text
So I think it's a good time tokind of look around and go, what

else can we upgrade in our livesto, to make our jobs a little

Conor Bronsdon (34:24):
Well it sounds like you thinkupgrading to linear B is a good
call, so I'll, I'll take that,the implied guess on that one.
So thank you.
Emily, where can our guestsfollow your work?

Emily Nakashima (34:33):
Oh, that's a good question.
The social media landscape isvery weird at the moment.

Conor Bronsdon (34:37):
I believe we had David Yee we talked to earlier
and he called it the socialmedia hellscape.

Emily Nakashima (34:42):
That feels very accurate.
I think a good place to find meif you are on Blue Sky, I'm
there at EA Nakashima.
I think, you know, I'm also justall over the place at Honeycomb
So come find me in a boothsomewhere and I'd be very happy
to talk to you about data and AIand anything else.

Conor Bronsdon (34:58):
That sounds great, Emily.
Thanks for coming on the showand spending the time with us.
I've really enjoyed Emily.

Emily Nakashima (35:04):
Thanks for having me.
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