Startups don’t get easier with age—they just get more complex. Much like teenagers, scale-ups are constantly outgrowing their structures, still figuring out their identity, and not always great at setting realistic goals. But this awkward “in-between” stage isn’t a failure—it’s a rite of passage on the path to becoming a mature company.
In this episode, Hannah sits down with Matt Wensing, Head of Product and Design at Customer.io, who has seen scaling from nearly every angle: founder, product leader, and now executive. Matt shares how to bridge the gap between lofty strategy and day-to-day execution, why your org’s real capacity is often higher than you think, and how to turn constant experimentation from chaos into sustainable growth.
Resources from this episode:
- Subscribe to The Product Manager newsletter
- Connect with Matthew on LinkedIn
- Check out Customer.io and Matthew’s website
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Hannah Clark (00:01):
Ah, growing pains.
I'm sure we've all heardone parent say to another,
"if you think it's hard whenthey're little, just wait
until they're teenagers." Andfrankly, that's as true of
startups as it is of children.
The challenges don't get easier,they just get more complex.
In fact, scale-ups tend to havea lot in common with teenagers.
They're constantly outgrowingthings, they're still
figuring out who they are,and they're not quite mature
(00:22):
enough to have a firm graspon things like realistic
goals and how to reach them.
And don't get me wrong, I'mnot knocking them because
ultimately, this stage isn't afailure, it's a rite of passage.
Reaching that teen stageof maturity is a signal
that things are movingforward as they should.
But being responsible forthat growing org is not
for the faint of heart.
My guest today is MattWensing, Head of Product
and Design at Customer.io.
(00:44):
Before joining Customer.io, Matthas worn just about every hat
in the product leader closet.
He's founded two startups andheld leadership roles at several
others, so he's had plenty oftime to observe and deconstruct
the ways that scaling orgsnavigate the long and awkward
transition period from earlystage to mature enterprise.
You'll hear what experience hastaught Matt about the connection
(01:04):
between high level strategyand frontline leadership, why
your org's actual capacity isprobably much higher than you
realize, and how to turn a cycleof endless failed experiments
into an engine that actuallypowers sustainable growth.
Let's jump in.
Oh, by the way, we holdconversations like this
every week, so if thissounds interesting to
(01:24):
you, why not subscribe?
Okay, now let's jump in.
Welcome back to TheProduct Manager podcast.
Matt, thank you for making timeon your Friday to talk to me.
Matthew Wensing (01:35):
Thanks so much for having me.
Hannah Clark (01:37):
So can you tell us a little bit about
your background and howyou got to where you are
today at Customer.io?
Matthew Wensing (01:41):
Sure.
I joined Customer.ioeight months ago now.
And when I initially joined, Iwas technical director, was the
title on the engineering team.
Really part of a small teamwith the CTO and another
technical director looking athow AI could be used throughout
the product and platform.
So really AI innovation.
(02:02):
Before that, I hadstarted a startup.
Ran that for five years,had raised some funding.
It was a low-code, no-codestartup, so a lot to do with
marketing automations as well.
And then prior to that, theprevious 15 years, I started a
startup out of kinda my firstor second job outta college.
I decided I wanted to do oneof these web 2.0 things and
started a startup that was thefirst interactive maps on the
(02:23):
internet that had weather onthem or the first interactive
weather maps on the internet.
And that was a reallyinteresting ride.
We ended up going out marketand selling of all things B2B
SaaS for supply chain, anddid that for quite a while
and really have done, hadto do as a founder and have
done pretty much every rolefrom engineering to sales.
Hannah Clark (02:42):
I remember when that came out.
That was crazy.
Wow.
Okay.
Well, what an honor.
I'm learning things and I'mbecoming more starstruck as
we get talking anyway we won'tbe talking about weathers and
maps and that kind of thing.
We're gonna be focusing todayon what it's like to lead
and manage products in this.
Very tricky stage.
I feel like we've all had thisexperience of being in this
(03:03):
between stage of startup andscale up when things are really
starting to ramp up and thingsstart to go off the rails.
So in the past, we chattedbefore and you talked about
Customer.io as being sort ofthis frontier town where it's
past the wild west kind ofstartup days, but not quite
into fully established city.
So, in your experience, whatare some of those key leadership
(03:23):
challenges that really emerge inthis specific stage of maturity?
Matthew Wensing (03:27):
I think it depends a little bit
on how you got here.
There's a certain amountof culture that you bring
into that situation.
Where is everybody on thesame page or is everybody
understanding that?
We are in this phase.
We're not a city yet, and bycity, to extend the metaphor,
those are the places where yougo and everyone has their box.
(03:49):
You know where to get your mail.
Everything's delivereda certain way.
And the thing I say internallyto the folks that I work
with directly is in thisphase and this in-between
phase, you have two jobs.
One of them is your core job,the function that you perform
that creates value for thecompany and the business.
But the other part of yourjob is figuring out the
best way to do your job.
(04:09):
And you might even say to figureout what your job is because
you have a title, and thattitle is probably the umbrella
over the core of your focus.
This transition phase.
If you come from the earliestdays that this, figuring
out what I should do todayis the most of the job.
I mean, I would say that's 95%plus of your job most days.
(04:29):
You're really justmaking it up as you go.
This is a bit in between andyou can end up hiring people
who are used to the WildWest, where they're figuring
it out every single day.
And then you can hirepeople who are really, you
could say, leaning intothe future and saying, I'm
even more comfortable themore established it gets.
And I think it's just importantto recognize and for each
(04:50):
person to know that, hey, thatfeeling you're feeling of not
knowing for sure if the thingyou're doing is the right thing.
That's actually part ofthe job and that's normal.
We want your help in figuringout the full definition of your
roles and responsibilities,and that's how you
participate in building thecompany you wanna work at.
Hannah Clark (05:08):
Oh, that's an interesting take.
I feel like it's a questionthat tends to linger, that
doesn't communicate it oftenbetween leadership and ics.
So, that's interestingthat you point that out.
I wanna dig a little bit furtherinto that, if that's okay.
So when you're working with,say, a new hire, for example,
that's come onto the team duringthat stage and like maybe you're
(05:29):
building their job descriptionout or getting a sense of what
their main contribution tothe company needs to be, how
does that ideally need to go?
Like where do you see the, theboundary between how much the
IC should be participating intheir, just kinda dictating
what their role shouldbe versus what leadership
should be dictating to them.
Matthew Wensing (05:48):
If you can tolerate more metaphors.
Hannah Clark (05:51):
Oh, I love them.
I love them.
Matthew Wensing (05:51):
Yeah.
The way I think about theseearly hires, and by early I
mean less than 500 people,which means each department,
if you break it down, youcould all fit into a pretty big
room or an auditorium togetherand you know everyone's name.
You're under that Dunbarnumber where you know every
single engineer by name and youknow a little bit about them.
So it's still small comparedto a large company scaled.
(06:12):
And in those situations, if Iam leading a group like that, I
try not to make many assumptionsabout how the future's gonna
unfold, what their full scope ofresponsibilities are gonna be.
We're trying to ultimatelyget as much contribution
out of each individual.
We're trying to give as muchindividual as much opportunity.
(06:33):
As we can.
And in that case, there isa job description as you
put out in order for them torespond to and join the team.
But what I will often do isinitially you're trying to
learn how this person works andwhat they're comfortable with.
And I like to startwith, and this can happen
in a period of days.
This doesn't haveto take months.
In fact, when you're atthis stage, you can't take.
(06:55):
But you really try to figureout what is the most ambiguous
direction that this personcan comfortably work under.
Hannah Clark (07:04):
Oh, interesting.
Matthew Wensing (07:05):
Not because you're trying
to be ambiguous, right?
You actually, if you'reinterfacing, say if you're
reporting to a VP or a CPOor maybe the CEO, depending
on where you are, thedirection you're getting is
often extremely high level.
And it's because thosepeople have such a wide
purview that they have tobe extremely parsimonious
(07:25):
in how they share direction.
So we need to do something aboutX. What I try to do initially
is say, okay, I'm not gonnaput this person into a box
or create a ceiling on them.
I'm gonna take what I justgot given, and I'm not gonna
just pass it along as is.
I'm going to bring it downone level into make it a
little bit more concrete,put some boundaries on it,
but not much more becauseideally they can run with it.
(07:50):
And I like to see how peoplerun with or don't run with
that kind of direction.
And it's very interesting tosee what the follow through
or responses are to that.
I think you can learn a lotin, like I said, days, not
weeks, in terms of how peoplehandle that kind of direction.
And again, you're not abdicatingyour responsibility, but
what you're looking for isthis a person who can thrive
(08:13):
with a lot of autonomy?
Or is this a personthat actually needs more
supervision, more management,more clear direction and
boundaries in order to thrive.
And you need both kinds withan organization, but you can
either frustrate or you canreally dishearten a person
that needs one or the otherif you don't test for that.
Hannah Clark (08:31):
That makes sense to me.
I think that's, I actually feelthat's a really good indicator
for a strong leader to have thatkind of emotional intelligence
to get a sense of, like how.
Be able to read someone'sability and comfort level
with a level of ambiguityand kind of see and be
perceptive to how theykinda rise to that occasion.
I kind of wanna take a littlestep back here and I apologize.
(08:53):
I'm throwing you a curveball because what this
is making me think of is.
The role of strategy andhow it evolves from that
really early stage startupas you start to get more
mature as an organization.
And I think this is an arealike where we're talking about
deployment of personnel andthat kind of thing and how that
kind of can be so individual.
But I, I see kinda a patternof strategy being a little
(09:15):
bit more, it gets morecomplex, as when you're a
small team, a strategy can bereally just an action plan.
And then as you get bigger.
The components of a strategybecome more diffuse across
different organizations and itbecomes more challenging for
someone kind of in senior, butnot, executive leadership or
a director level to interpretthat strategy and kind of be
(09:36):
able to fulfill their end ofit, especially in a remote
organization where people justaren't quite communicating as
fluidly as they would be inmaybe in an office situation.
So what have you seen in thefield as far as managing the
role of strategy in terms ofdeploying and translating a
vision into actual outcomes.
Matthew Wensing (09:55):
What I've learned is you cannot
afford to play the game oftelephone with strategy.
And what I mean is you reallyneed to have that the spine of
the organization, meaning thereneeds to be continuity and to
end in terms of, maybe there'sa few gaps or levels between.
This manager and the CEO orthis VP and this director,
(10:18):
but you can't afford tohave that understanding.
Shared or communicatedin a low fidelity way
between those participants.
So what I mean is you should beable to draw a line from sort
of the lowest level managerall the way to the CEO of
conversations that have happenedwhere that understanding
really got cemented byin between those people.
(10:39):
Let me tell you what'sthe opposite of this is.
So the anti-pattern wouldbe, here's this vision,
here's this understanding.
This is our strategyat a very high level.
So maybe it's thecompany strategy.
We want to be the greatestX. Insert your company here.
That's often the kindof thing that comes
from board to the CEO.
And then maybe the C-levelsocializes it a bit.
And then one failure modewould be you then convene
(11:03):
your S team, 'cause we want toimitate Amazon in this case.
And we say, okay,here's our strategy.
And you just hand it out to eachperson and you say, go implement
this, or go run with this,make this real in your world.
And you will essentially createa gap in understanding where
the way it gets carried out.
Then on the ground, itdoesn't end up looking and
(11:23):
feeling the way that it wasintended to, because people
will interpret things.
Change is hard, right?
And if that strategy involvestrade-offs or hard decisions,
or we're gonna focus on thiscustomer instead of this
customer, if you really haven'tcemented that knowledge between
each level of the chain.
You will end up withreinterpretations that
happen along the way.
(11:44):
That end up accommodatingcertain realities on
the ground, such as.
Well, Bill's not gonna be reallyexcited about this because
this essentially puts aside theproject he's been working really
hard on for the last year.
So I'm sure I can figure outa way to work this in here
and have these be compatible.
And what you end up doing isyou can end up creating what
(12:04):
I think of as think of it as.
If anyone's a Star Trek fan,the Borg, it assimilates, right?
Yeah.
It synthesizes things.
It absorbs things, and whatyou end up doing is you
have a strategy at the topthat is extremely, maybe
it's more disciplined orit's part of what makes, I
almost said strategic, right?
What makes a strategy strategicis that it forces trade-offs.
It makes hard decisions.
It says, we're not gonna dothis, we're not gonna do that.
(12:26):
The sign that you haven'tdone the cementing as
I call it, is that.
Somewhere in the chain, someonegoes, it must not mean that we
can't do this, or we must beable to also accommodate that,
and they will glom on, or itbecomes the sticky ball, right?
Where there's really nothingthat isn't in play anymore.
It's, of coursewe wanna do this.
And that's how you knowyou haven't done this part.
(12:48):
This part is the people reallycoming to grips with what
this says we're not doing.
Maybe anymore, or we're notgonna do instead of this.
If that person understandsthat, then there's an
accountability chain as well.
It's very hard if you don't havethat come to grips with moment.
I think especially for remoteteams, this is easy to skip, is
(13:08):
did that person really go away?
Understanding the trade-offsand what we're gonna have to
give up in order to do this.
And I think that'show you prevent that.
But we can also dothis of course, right?
Or this doesn't say thatwe can't keep doing this.
And then you have aleader that goes, how
come we have the strategy?
That we're only gonna do thisand we're gonna focus on this.
There's the word, right?
Everyone wants focus.
We're gonna focus on this.
(13:29):
But then when I'm lookingat how we're spending our
time, I don't see that focus.
And it's because somewherealong the way that chain got
broken and someone assumed thatit didn't mean that we can't
also do these other things.
Right?
Hannah Clark (13:40):
Yeah.
Okay.
This makes sense to me.
And I think part of why Iasked this and why that kind
of came to me as we're talkingabout folks sort of choosing
their own adventure, so tospeak, about how they can
contribute best to the company.
I think that when we misfirein that area, that tends to
be where work gets duplicatedor people who are well-meaning
tend to spend time serving thestrategy to their understanding.
And then we get some breakdownin terms of, again, what's
(14:02):
the right process and howdo we really show value or
present value if we don'thave a very clear picture
about the scope of our.
Influence withinthat bigger picture.
And that kinda leads me intowhen should we introduce
process versus maintaining thiskinda like startup agility.
Like I feel like this isjust a constant struggle.
Like how do you make ajudgment call about avoiding
(14:23):
this chaos versus death bycommittee kind of battle?
Matthew Wensing (14:26):
I like to introduce process on
the heels of success.
So something worked, Ithink of process and I
was explaining this tosomebody earlier this week.
This gives a helpful way tointroduce process without even
using the process word, is Ilike to think of process as
it is writing down a storyof what success looks like.
That we want to repeat.
So you say, wow, thatcall between product and
(14:49):
sales went really well.
That call where we got broughton to have that conversation,
that customer went really well.
It wasn't written down.
There was no process.
Thank goodness we have somepeople on the team who can
just leap headfirst into thosesituations without a playbook.
And have it go well.
And maybe we've tried it threeother times that it didn't
go well and this time it did.
Writing down the processis simply then saying to
(15:10):
the company, Hey, here'swhat just happened.
This was awesome.
So let me tell you whythis went so well or why
I think this went so well.
It went so well because first,Glenn and I got together and
we did this, or the next thingwe did is, Sam and I did this.
You just tell a story ofthe success that you had.
And naturally, peoplewant to imitate.
(15:31):
Success process is really justa way for people to imitate a
successful story, and thereforeeveryone wants that, right?
Yeah.
And it's what salespeople,when people are on their,
educational products orinfo products, right?
What are they sellingyou recipe for success.
And a lot of those obviouslyare not real, a great manager.
Calls a timeout ornotices success and says,
(15:52):
how did you do that?
Please write it down andteach it to the team.
And then I like to separate.
So that's the process isjust repeating the story.
I like think of ops.
Ops is also extremely helpful.
Ops is a way of saying thatis the story we wanna have at.
We want these three peopleto get into a room together
and reconcile why thisthing wasn't done on time.
Not in a bad way,but in a good way.
(16:14):
That's a healthy conversation.
We need to have that.
How often should we have that?
Yeah, I think we shouldhave that at least
every couple weeks.
Great Ops, can you help?
Yes.
Ops comes in and says, I'mgoing to essentially create
the structure, the contextthat allows us to repeat this.
And it seems really simple,but this is the part
about saying out loud whatotherwise is just assume.
(16:35):
It's very easy for a lessexperienced manager to assume
that, hey, they had success.
They're gonna do that again.
They want that to happen again.
I think this phase is about.
Saying, Hey, write thatdown, share that story.
And then, Hey, ops, how do wetry to recreate that success?
Let's get them in a room.
How long should theconversation be?
What's the agenda?
(16:56):
And before you know it,you have this process, but
everyone sees the valuebecause it was organic.
You've productized essentiallya human interaction by
just starting with a story.
Hannah Clark (17:06):
Kind of the takeaway that I'm hearing here
is that as opposed to thinkingabout processes strictly a
checklist or just an objective,you're thinking about.
Ops is developing that sortof process guide, but what
we really need to be thinkingabout process as sort of
like the beats of the story.
Okay, what beats did we have tohit for this to have happened?
Yes, for it to be replicated.
And then fromthere, that's your.
(17:27):
Outline, and then from thereto create like a repeatable
process when ops comes in,that's more the checklist, izing
of things like the actual, thethings that can help you scale,
the things that kind of helpyou to standardize something.
As invariably your teamgrows or people turnover.
Matthew Wensing (17:41):
Ops makes it manageable, right?
Without ops, you're not trackingit you're not measuring it.
Ops is what lets you go.
Oh, so that means we couldhave up to this many beats
per whatever with this group.
This, and I loveyour beats analogy.
I just have to say that tome is the story is the movie.
The beats are the scenesthat you need to create.
And if we don't have this scene,if the scene doesn't happen, the
(18:02):
story falls apart and everyonewants to be a part of that.
Hannah Clark (18:06):
Yeah.
Well, everyone wantsto be in a good mood.
Matthew Wen (18:08):
Yeah, that's right.
Hannah Clark (18:09):
Okay.
Let's talk a little bit aboutbecause you'd mentioned,
creating process outof success, but success
also creates problems.
And so if we think about theways that companies tend to
attribute sometimes their winsto the processes, but maybe it
was more due to, the timing thattheir product came out or the
market fit, then they happenedupon how do you separate,
(18:31):
what is actually working?
How do we verify that thisprocess is functional rather
than it just happened towork at the right time.
Matthew Wens (18:39):
That's a good one.
I think you're getting, I mean,this is a fundamental fallacy
or one of the fundamentalfallacies of people is you're
misattributing results to acertain way of doing things.
And I think to some extent,congratulations, you're
succeeding, which most peopledon't get to that place.
And I think Customer.iofor sure where I work is
at the place where it'sworking and that's awesome.
What you have to be open to.
(19:01):
I mean, unless you have agroup of people who just
love attending meetings andprocess, and most people don't.
You are going to end upwith feedback on is this
working for us or not?
I do think that there's atime for kind of molting, if
you will, in shedding thoseprocesses that got us to
now, but won't get us there.
And I think you can.
(19:23):
These are even the good ones.
So that story worked when weonly had one product manager
and three salespeople.
It doesn't work anymore.
I think if you don't havethat operational mindset.
You will just coast intothose and before you know it,
people will start to say, Idon't really see the success.
The success is not coming out.
We're still doing thebehavior, but I don't
(19:44):
see the success there.
I think what you're talkingabout is almost the world where
we continue to have the samelevel of success and we're
going through these motions.
There's worse problemsto have in the world.
What I think people arereally worried about is we're
starting to see the top ofthat S-curve in terms of.
Things just don't feelas quick as they used to.
Or decisions are takinglonger than they used
to, or frustrationswill start to come out.
(20:08):
And I think that these are thegear shifts or the metamorphosis
or these moments in time whereit takes a deliberate action on
behalf of the leadership teamto say, it's time to reorganize.
It's time to reboot or refactorthe way this is working,
it's not working anymore.
And there's a certain foundermentality or there's a certain.
Pioneer that you needmentality in those cases to
(20:30):
say, Hey, the well that wehave, it's not gonna work.
That's not gonna get thepopulation has, we've, it's
outlived its purpose andthere is a moment there where
you have to be willing toremove the well and replace
it with something else.
And that's risk.
There has to be a certainamount of appetite for risk
that says we don't wanna lockin our gains at this point.
(20:52):
And I would say a techniquethat I've used in terms of.
Having this conversation withpeople where it's already
working is you say, okay,put aside what's working.
What are our aspirations?
How big do you want this to get?
And most of the time peoplewill not say, oh yeah, I
just want it to be like 5% or10% more than we have today.
Most people, if you askthem, where do you want this
(21:14):
to really go, they'll sharesomething very grand with you,
and then you have that new.
Vision or that new version ofthe story where you go, okay,
so you can see how a well isn'tgoing to, like, how is that
gonna work when we have 20,000people living on this street?
Well, clearly it's not right.
And so if you want toget to that, if those
(21:34):
are your aspirations, wehave to take more risk.
And how much risk a company'swilling to take internally is
unfortunately not something thatany one individual can decide.
That's where the seniorleadership has to
come in and really.
Have that groundingconversation again and say,
if our aspirations are tobe a public company, or our
aspirations are to be this,we've got to take more risk.
(21:54):
And then letting yourself wipethe slate clean in some cases,
or reboot what you've beendoing that got you here and
say, this isn't going to getus where we need to go next.
But I think just being sensitiveto those frustrations and
intellectually honest withthe results you're getting.
And then thirdly.
Can we actually get towhere we're trying to go?
(22:14):
Using what we're using now?
And this all comes downto the right people.
And answering those questionshonestly is itself a challenge.
But that's the job.
Hannah Clark (22:24):
Yeah.
Well, okay, so this is makingme think of this let's say.
Thing that happens sometimeswhere when we decide to
change course, the companyis scaling, we decided
that whatever processes orsomething needs to be replaced.
We tend to look at biggercompanies, larger companies,
more successful companies assort of like our North star.
How can we copy and pastesome of their playbook and
(22:46):
replicate those resultsin our own organizations.
But of course, like thosecan also be subject to the
same kind of stipulationsof maybe they, yeah, right.
Time, market fit, et cetera.
How do we evaluate or how maybe,how specifically, how have you
evaluated what practices thatwe borrow from big company
playbooks are worth adopting?
Matthew Wensing (23:04):
I think in those cases, the best scenario
is you bring in a leaderthat has lived and done that
before, elsewhere, and youdramatically reduce the risk
that they copy the form butnot the substance of that.
Because they know.
They know that if you wereon the outside and you had
your understanding of Apple,you thought that it was just
Steve Jobs walking around andtelling everybody what to do.
(23:27):
What you don't know iswe actually had these
conversations like this, andthese used to take hours and
we would do this and that.
And what you find out isthat the fictionalized
or the depiction of that.
It's so superficial becauseeverybody wants to believe
that if you just imitate, youcan have, and we just talked
about how that mimetic natureinternally can be used for
(23:49):
good to replicate success.
It can be used very dangerouslyto try to imitate success as
external to you because theamount of information that you
lose by observing across andeven reading business books, or
a really inspiring blog post.
There's some weird thingshere too to consider that's
maybe the company's doingthat because they have to,
because it's compensating fora weakness that we don't have.
(24:11):
There's all kinds ofreasons why people do
certain things, and if you.
Assume the reasons you can endup in a dangerous situation.
I think OKRs is one of thosethat is, this is a great
example of there are so manyimplementations of OKRs and
we all know them, but findingsomebody who's done it before
and then can build a departmentand do it the same way they've
done it and hire peoplewho have done it that way.
(24:32):
That's one thing.
An excited CEO or CPO readinga book by John Doer and saying,
we need to do OKRs too, andthen trying to implement
them for the first time.
It can work, butjust consider that.
What you're doing isyou are experimenting.
You are trying to figureout if this imitation is the
solution for your problem.
Do you even have the samesets of problems that they
(24:54):
had when they started toadopt those tools and those
rituals and you don't know yet.
So it's okay, try that.
But somehow you need to tryit with a very light hand or
grip on it and say, if thisdoesn't work this quarter, if
this doesn't work, this sprint.
We are not going to stickto it because it's not about
our ego, it's not aboutour pride, like we're gonna
try it and see if it helps.
(25:15):
So I would recommend thosethings in very small doses
with a light grip, unless youhave someone that's lived it
and can really tell you theinside story of, we tried those
and this is what didn't work.
I'm gonna do it the way thatI've known has worked before.
And also, I'm gonnahire the people that
work this way because.
If you could hire someonefrom Google that's familiar
with OKRs and if this personuses them at a completely
(25:36):
different company, even thatmight not be compatible.
So I think there's alot of danger there.
We know that.
I also think thatit's worth trying.
We don't need to learneverything over again ourselves.
There are certain risks thatwe figured out how to avoid.
Just be careful.
Hannah Clark (25:51):
Yeah.
Matthew Wensi (25:51):
In terms of that.
Hannah Clark (25:52):
I'm gonna press you a little bit more on
kind of a related angle here.
I like the way that youmentioned using a light
hand when piloting tacticsor strategies that.
You're not a hundredpercent sure gonna be
compatible with the mission.
I have seen the oppositeextreme of that, of what I
would refer to as too muchtoo fast and not enough time.
(26:15):
So how do we avoid the issueof perpetually being in an
experimentation phase, but.
Managing our timeline so that wecan really evaluate the outcome.
I've seen this happen acrossmany organizations and with
people that I've spokento as well, where it's
we tried this experiment.
(26:36):
It's almost like we havea 10 step experiment.
We get to step three.
Leadership gets concerned thatit's not giving us the results
yet that we're aiming for, andthen we decide, you know what?
Nevermind, we're gonnago back to step one on
a different experiment.
And it's like we don'tever get that real
learning from the payoff.
Matthew Wensing (26:54):
Yeah.
And this is true.
Even if it's this is a patternof how do we learn and test.
That's true.
All the way down to thefeature level, right?
And all the way up to thecompany As product and
product, product as product.
I have adopted a technique.
The technique isn't new to me,so I'm a big fan of the observe,
orient, decide, act framework.
(27:15):
Food loop, which is reallyjust a way of, and I use
this all the time in life.
This helps me in my personallife, even of saying we've
got to split the observationsfrom the orientation around
those observations fromthe decision about those,
and then from the actions.
And I'll also say thereare failure modes, and
you just described one,which is if you take a
single letter out of that.
Equation.
(27:36):
There are the companiesthat just observe, and
they never decide anything.
And what you just describedis a company that maybe
observes, does some reasoningaround those observations
and then makes a decision tojust go a different direction
and kind of starts over.
You want to make sure you gothrough all of those, and we
can certainly talk about whatall those are, but it's tough.
Organizations are only asstrong as the leaders that.
(27:59):
Get to run them.
And so I don't know necessarilywhat to do if leadership doesn't
do these sorts of things, butwhat should be happening is
someone needs to say, I'm goingto lay this out and if everyone
else is too busy, this could bea special assignment of someone
where as the company, I like tosay the Jane Goodall approach
of, I'm going to go observe.
(28:20):
I'm the ethnographerof the company.
I'm gonna go talk to everyone.
I'm gonna observe, I'mgonna study, I'm gonna
write everything down.
I'm gonna be a scientist.
Right.
Capture that and thenlay that all out.
And if you lay it out in acertain way, if you can really
split out the observationsfrom the judgements, and I see
this fail a lot in terms ofpeople who are frustrated and
say, we shouldn't move on tothe next thing next, right?
(28:41):
They'll lead with that.
They'll say, here's 13 reasonswhy we shouldn't do this next,
and people immediately put uptheir guard in defenses to that
because you've, you're treatingit like a court case, and as
soon as it's a court case.
Where I'm going to show thatmy client is innocent or
why that person's guilty,people put up their defenses.
I would highly recommenda more scientific approach
(29:02):
where you say, I observethis, I observe that, and
you can catch yourself.
If you get good at writing thisway, you will catch yourself
halfway through a sentenceabout observations going,
that's not an observation,I'm making a judgment.
Or that's actually like I'mthinking about the observation.
If you can come and leadwith observations, people's
minds will open up.
(29:23):
A lot more because now they'realmost eager to know, I'm
seeing the same things you are.
Right.
Because you'veleft that part out.
Take me now.
Okay.
Why are thoseobservations there?
Oh yeah.
I believe that too.
Yeah.
That's this way because we didthis and that's this way because
he did this and then you finishwith your, and so we should
recommendation or decisions.
Very helpful techniquein terms of writing more
(29:45):
persuasively internally, andsometimes all it takes is
this kind of, Hey, the pen ismier than the sword, right?
All it takes sometimes forthose of you who are in
those situations, maybearen't the senior leader.
If you can lay that out in thatway, you might be surprised
at the kind of impact that canhave where the right people
reading it in the right ways,and there's a lot of management
there of making sure that it'sreceived in the right way.
(30:07):
But those are very,those are powerful.
Companies can sometimes.
These are groupsof people, right.
Group dynamics are real,but leading everyone through
that thought process takesa very disciplined approach
to laying the informationout, and I don't think it's
practiced often enough.
Hannah Clark (30:23):
Yeah.
Okay.
Again I wanna reiteratewhat I'm hearing here.
Like the takeaway that'semerging from this for me is,
it's silly to, to reframe itlike this because what you're
saying is you should treatexperiments as experiments.
Yes.
Which sounds obvious, butI think it's not obvious
because oftentimes experimentsare treated like coaching
conversations or vague guidance.
(30:45):
It's kinda like weshould try this.
And someone takes thatas a marching order.
And I think that's, it's reallythe communication breakdown and
kind of the failure to treatit like an experiment in which,
if you say we're gonna run anexperiment between a group of
leaders versus we're gonna runan experiment around a group
of researchers, they're gonnathink very different things with
regards to what you just said.
And I think what you'resaying is you gotta think
(31:08):
about it like a researcherwould say, we're gonna
communicate about what exactlywe are setting out to do.
We're gonna set benchmarksand timelines according
to what we're going totry, when we're going to
reevaluate, and we're goingto be researching throughout
the whole thing, right?
We're going to bemaking observations and
communicating about whatthose observations are.
What I'm hearing isprobably where a lot of
(31:28):
this breakdown is happeningis that there is no real
management of the experiment.
And so it makes sense why therewould be frustration between
the leader saying this isn'tworking, and then you know,
the managers or ics, et cetera,who are trying to, work on
that experiment going, well,hold on, we're not finished.
And so who would've thoughtexperiments should be
treated like experiments?
Matthew Wensing (31:49):
Yeah.
I will say I have astrong belief that we
adopted as product people.
We adopted the wholelean startup methodology.
So I know Eric wrotethat book in 2007.
It was amazing.
It was amazing.
At the time, I think it wasso amazing that a lot of us
adopted scientific language.
We learned to, once again,imitate the craft of being
(32:12):
scientific when it comes tobusiness and validation and
feature building and productdevelopment without the
discipline of, okay, I cansay we're gonna test this.
If I say, Hey, we have thisidea for a feature and there's
three ways we could do it, Ireally believe that we have to
have include this deep researchfunction, which is gonna be a
(32:33):
lot more expensive to build.
And so we're gonna testthat theory by first
releasing a version.
That's where wedo that manually.
And see if peoplelike it or not.
There should be red flags oralarm bells or whatever it is.
Butterflies going off inyour stomach right now if you
think about it, because whatI just did, I'm not testing
the right thing at all.
What I should be testing is.
(32:54):
This is really expensive.
What we should be testing is canour customers live without it?
But I use language ofexperimentation and fooled
you into thinking thatI was being scientific.
Now obviously, maybe Ididn't actually, but like
this happens all the timein product management where
someone will say somethinglike that and be like, yeah,
we should do it manually.
'cause then we're not reallyproductizing it, which avoids
that research and like wedon't have to build it yet.
(33:16):
That's lightweight.
Yeah, that's smart.
That's a good experiment.
That's a terrible experiment.
All you're gonna get is theperson going this is awesome.
You're like, yeah, we thoughtyou would think it was awesome.
Oh shoot.
What were we testing again?
You weren't actuallytesting the thing.
You should be testing.
You just tested.
Do people like the thingthat I think they're gonna
yeah, don't do that test.
Can they live without thething that's really expensive
(33:37):
that we hope we don't have tobuild because we're not here
to build really cool stuff.
We're here to build a businessand if that business is more
profitable and can executefaster, because we don't
have to build certain things.
Let's not.
And so I think thatintellectual honesty or that,
are we really experimenting?
It is a pervasive thing in ourzeitgeist as product people
(33:58):
to be using words like this.
But we didn't reallystudy the book.
We highlighted the book andstarted using the language and.
We weren't mentored about how toactually apply those principles.
So if that's you,we've all done it.
But see if you can catchthe next person that you're
working with saying words likeexperiment and test and theory
and hypothesis, and see ifthey're really testing a thing
(34:19):
that, wow, if this ends upbeing false, I'm uncomfortable
because I thought it was gonnabe true, but I'm willing to test
if it's false because that wouldbe better for the business.
What we like to do is we liketo put our opinions out there
and test and see, can I findvalidation for my opinion?
That's my test.
Hannah Clark (34:37):
Yeah.
It's like how can we put AIinto this product instead of
how do we solve this problem?
Matthew Wensing (34:42):
That's right.
I have a strong opinion thatwe need to do X, therefore
we're gonna do some cheapversion of X. And when people
like it, I'm gonna get to showall of you that I was right.
Hannah Clark (34:51):
Yeah.
Matthew Wensing (34:51):
That's the actual thing going
on behind in our minds.
And science and ego don'thave a lot in common.
Hannah Clark (34:57):
Oh, that, that's a quote.
I think that this wholeconversation, a lot of it
hinges to decision making.
So you've seen the evolutionfrom founder-driven
decisions to moredistributed decision making.
Organization grows, decisionmaking power changes.
What's your approach tofinding decision rights and
ensuring that everyone's gotthe right context to make good
(35:17):
decisions within their capacity?
Matthew Wensing (35:19):
I think it goes back to what I started with is
you were sending out feelersall the time as a leader,
as a manager to understand.
How much context can this personhandle and what do they do with
the autonomy they're given?
I used to manage developersand I had a scale for how
autonomous is this developer,and you could work your way
off that ladder starting with,do I know what code to write?
(35:41):
If they need help withthat, then they're
junior by definition.
That's okay.
But they're anassociate in that sense.
Up to the level of I know whywe did this work, and I know
how it fits our strategy.
That person is theperson who you're hoping
you hired or found.
Maybe you know that youhired The other one.
Where I'm going with thisis, remember I said at the
beginning, you're testingto see what level of
ambiguity it can handle.
(36:02):
I also like to test how muchcontext can they absorb?
Are they taking full advantageof all the information that's
being said on all the meetings,all the calls, and all the
notion docs and all the strategydocs that are being written
by the CEO in our mandate?
Are they starting to finddiscrepancies between
things where they're going,I was reading this and
I was reading that, andthese kind of don't agree.
These are good signs.
If you find someone thatnotices the wrinkles or the
(36:25):
air bubbles in your strategyor in your thinking, they're
paying attention, right?
They can reconcile things,and that means they're ready
to work at a higher level.
The other tests I like torun is when you give them
something, Hey, we needto make it over that lake.
Do they disappear from view run?
And suddenly you hear asplashing sound and they get,
there's a bunch of screamingand stuff, and then maybe
they come back half torn upand they bring you the thing
(36:46):
that was on the other sideof the lake, and it's okay.
You did it.
Thank you for doing it.
Or do they disappear for halfa day and then come back and
say, so I took a survey of thelake and I wanted to understand,
when you say we need to getacross it, are you intent on
crossing it at the widest part?
Is there a reason thatwe need to do that?
Or can we cross it over here?
'cause we cancross it over here.
Now you found someone whoknows how to take that autonomy
(37:08):
where you gave them the roomto go do all of that, right?
You weren't checking in onthem six hours later saying,
Hey how are you doing?
But did they know enoughto run a survey first?
Did they know enough tosay he can't really meet?
I see alligators in there.
They can't really mean thatI should just swim across.
I should probably grabhim on Slack and say,
Hey, I took a look.
Quick look, and thisis what I found.
(37:30):
As a senior leader, you arenot necessarily looking for
someone who throws himselfinto the water kind of thing.
Hannah Clark (37:36):
The Labrador Fever approach.
Matthew Wensing (37:38):
Yes.
Super heroic, super friendly,your best friend in that
sense, but painful from a coststandpoint, and that could
lead to some bad outcomes.
And I think the thing is this,if this is you, if you're
the, if you're that personwho's reporting to someone
knowing this, there's a, Ithink, and I know 'cause I've
been there, my first jobs.
They're in your gut.
You're like, I don'twanna bother them.
Like I don't wanna seem likeI don't know what to do.
(37:59):
Don't worry about that.
If you come back with smartquestions, having done your
research, having taken itdown the field, if you will,
and saying, Hey, I wannaunderstand a little bit better
why you think we should dothis, what, et cetera, et.
What you're doing is you'regiving them the opportunity
to give you a little bitmore clarity, give you some
boundaries, explain whythey were asking for that.
All these things whichyou should not be making
(38:20):
assumptions about, don'tmake assumptions about.
Just 'cause they didn'tsay it yet doesn't mean
they don't have opinions.
And I've seen a lot offailures in that case.
So back to your question,if you do this right and you
find someone who uses theirautonomy wisely and can work
their way up that ladder, itcan absorb a lot of context.
Now you know who you can trustwith localized decisions.
(38:40):
Because you can truly delegateand say, in this case, I don't
have to be in all those details.
But if you don't do thiswork as a leader, if you
don't test, if you don'tgive them the opportunity
to fail, you won't discover.
And then as a leader, you'renot gonna know how much capacity
do we really have because.
I'm holding back on delegatingbecause I haven't really
(39:01):
tested the resources thatI have, but if you test
them, you'll find out, andif you don't have enough of
one kind, you can augment.
If you don't have enoughof kind of another,
you can fix that too.
But I think distributed decisionmaking is the dream, but if you
haven't done the research onwho can handle it and who can
make a better decision than Iwould have had I done it myself,
then you're just flying blind.
(39:21):
Then you're just hoping thatthey make great choices and
that's where you get the chaos.
Hannah Clark (39:26):
What I'm hearing here is and I also tend to
think that sort of compatiblewith this theory is that most
people have a lot more capacitywithin their existing headcount
than they think because...
Matthew Wensing (39:36):
Absolutely.
Hannah Clark (39:37):
...you're not doing that investigative
work or that collaboration toreally discern what someone's
true capacity is and whattheir capabilities are to
operate within that scope.
It sounds really likeyou have someone in mind
when you're saying this.
I do wanna say, before I ask youfurther, this actually reminds
me a lot about an episodeon systems thinking that we
recently did with Sheryl Cababa,because what you're describing
(39:58):
to me sounds very much like thesystems thinking mindset, which
I think is, I'm sure that itcan be trained, but I think a
lot of people tend to be veryjust adept at that kind of
ability to hold a lot of contextat once and be able to work
with it sort of simultaneouslyto find win-win situations.
So for anyone listening whowants to dive further into
that, we did that a few weeksago, it was a great episode.
(40:19):
It puts it all into perspective.
But I do wanna ask, doyou have an anecdote or
an example of somebody whoreally embodied that trait
that kind of stands out toyou when you tell us this?
Matthew Wensing (40:28):
I'll use a friend of mine.
When I started my firstcompany, at some point I needed
a director of marketing andhe joined me, having been a
consultant at Deloitte andwas really good at that job.
And crushed it and itdid all the things that
consultant needs to do.
One of the job interviewquestions was like,
Hey, develop it.
And I didn't know much better.
So I didn't ask thebest questions when
I was interviewingfolks at that point.
So I said, yeah, developa go to market plan or
(40:50):
a marketing plan for us.
And back came like this 15 pageGoogle doc of here's the go
to market plan, and I think Istill have a copy of it because
we ended up working togetherfor 12 years after that.
I still have a copy ofit somewhere, which is
like the classic case of.
He got a direction.
Now, it wasn't an interviewquestionnaire, so he
couldn't really do a backand forth, and he just
(41:10):
blew it out of the water.
Right.
The reality is we didn'tend up using almost any of
that because two things.
One, it was a startup, andtwo, we didn't have that
collaborative conversation.
Later on, he becameextremely good.
He's now making a career outof working for C-level execs
or next to executive vicepresidents, et cetera, high
level senior level execs andsaying, I heard you say this.
(41:32):
And what he was doing bythe time I worked on him
through two startups.
By the second one, I wouldsay something on a 30
minute call on a Friday.
He wouldn't even ask me aboutit then, and he wouldn't do
anything else with it otherthan he'd write it down
and on our Monday morningcall he'd say, I heard you
mention this on Friday.
What made you think about that?
Like, why did you do that?
And so when I share theselessons with you, I'm
(41:53):
actually, I'm sharing thelessons that he learned by
working together with me.
We learned by working togetheron two startups that he
got better at not runningwith those things, and I
got better at appreciating.
I'm glad he didn't justrun with it because that,
I didn't even know enoughto tell him at first, so.
Those are the anecdotes.
I like the funny one.
By the end of it, we had sucha great working rhythm in
(42:16):
that sense where I could trusthim with extremely high level
direction and then I wouldknow he was gonna, we were
gonna work it through togetherand then he would run and
perform at a very high level.
But one last tip, if you dothis, I think a lot of managers.
Come from the wrong direction.
What I mean is you start atthe low level and you say,
ah, I have this employee.
I hired them to be an ic.
They're a product manager oran entry-level product manager.
(42:38):
I'm gonna give them this andI'm gonna see how they do, and
then I'm gonna give 'em a littlebit more and see how they do.
You're building up what youthink is their capability level.
That is a very slowpath to discovering
their ceiling, right?
Much faster is to challengethem with something where if
they succeed, they have shownyou that they are six levels
bigger than you thought.
And now you can meet themthere, you have now leapt there.
(43:00):
The only risk is that theyscrew up that one task
that you ask them to do.
And again, you might discoverthis in a week, but how much
better to discover in a weekthat they're capable of knocking
something outta the park thatyou think they can't handle
than to spend six months onthis thing level and then
six months on this level, andthen six months level that's
the slow path to discoveringwho your top performers are.
If you as a leader can findthings that are challenging
(43:22):
but low risk if they fail.
Because what happensotherwise is they leave.
You're like, oh, okay.
They left.
I didn't really think of themmaybe as a top performer.
Then they go join some companyand they're like leading some
huge initiative and completelycrushing you go, what happened?
It's like they were alwaysthat person, you just didn't
discover their ceilingand you can discover this.
There's a lot of differentways to do that aren't
(43:42):
necessarily live fire exercises.
They're gonna costyour company a bunch of
production costs, dollars,karma credit, et cetera.
But I think it's theopposite direction that
most people start becausethey think about the ladder.
I wanna make themclimb the ladder.
I would say I'd rather givethem the chance to grab the top
one of the higher rungs and ifthey can reach it, fantastic.
You're looking forthose kinds of people?
Hannah Clark (44:01):
Yeah, absolutely.
Well, at the very least,you've stretched that
person and help them developand create a trajectory
for their development.
Another one of those thingsthat's it sounds like it should
be so obvious, but we don'tsee that happen in practice.
Oh, Matt, this has been aphenomenal conversation.
I've learned a lot.
I appreciate yourwisdom so much.
Where can folks who are alsoappreciating your wisdom
(44:22):
right now find you online?
Matthew Wensing (44:23):
If I'm online at mattwensing.com is where
I have a bunch of essays thatI've written over the years.
You can also find me onLinkedIn, @wensing is my handle.
But you can just look forMatt Wensing there and I'd
love for you to connect.
Hannah Clark (44:35):
Awesome.
Well, thank you so much formaking the time and yeah,
hope to talk to you soon.
Matthew W (44:38):
Thanks for having me.
Hannah Clark (44:41):
Thanks for listening in.
For more great insights,how-to guides and tool reviews,
subscribe to our newsletter attheproductmanager.com/subscribe.
You can hear more conversationslike this by subscribing to
The Product Manager whereveryou get your podcasts.
Ah, growing pains.
I'm sure we've all heardone parent say to another,
"if you think it's hard whenthey're little, just wait
until they're teenagers." Andfrankly, that's as true of
startups as it is of children.
The challenges don't get easier,they just get more complex.
In fact, scale-ups tend to havea lot in common with teenagers.
They're constantly outgrowingthings, they're still
figuring out who they are,and they're not quite mature
(00:22):
enough to have a firm graspon things like realistic
goals and how to reach them.
And don't get me wrong, I'mnot knocking them because
ultimately, this stage isn't afailure, it's a rite of passage.
Reaching that teen stageof maturity is a signal
that things are movingforward as they should.
But being responsible forthat growing org is not
for the faint of heart.
My guest today is MattWensing, Head of Product
and Design at Customer.io.
(00:44):
Before joining Customer.io, Matthas worn just about every hat
in the product leader closet.
He's founded two startups andheld leadership roles at several
others, so he's had plenty oftime to observe and deconstruct
the ways that scaling orgsnavigate the long and awkward
transition period from earlystage to mature enterprise.
You'll hear what experience hastaught Matt about the connection
(01:04):
between high level strategyand frontline leadership, why
your org's actual capacity isprobably much higher than you
realize, and how to turn a cycleof endless failed experiments
into an engine that actuallypowers sustainable growth.
Let's jump in.
Oh, by the way, we holdconversations like this
every week, so if thissounds interesting to
(01:24):
you, why not subscribe?
Okay, now let's jump in.
Welcome back to TheProduct Manager podcast.
Matt, thank you for making timeon your Friday to talk to me.
Matthew Wensing (01:35):
Thanks so much for having me.
Hannah Clark (01:37):
So can you tell us a little bit about
your background and howyou got to where you are
today at Customer.io?
Matthew Wensing (01:41):
Sure.
I joined Customer.ioeight months ago now.
And when I initially joined, Iwas technical director, was the
title on the engineering team.
Really part of a small teamwith the CTO and another
technical director looking athow AI could be used throughout
the product and platform.
So really AI innovation.
(02:02):
Before that, I hadstarted a startup.
Ran that for five years,had raised some funding.
It was a low-code, no-codestartup, so a lot to do with
marketing automations as well.
And then prior to that, theprevious 15 years, I started a
startup out of kinda my firstor second job outta college.
I decided I wanted to do oneof these web 2.0 things and
started a startup that was thefirst interactive maps on the
(02:23):
internet that had weather onthem or the first interactive
weather maps on the internet.
And that was a reallyinteresting ride.
We ended up going out marketand selling of all things B2B
SaaS for supply chain, anddid that for quite a while
and really have done, hadto do as a founder and have
done pretty much every rolefrom engineering to sales.
Hannah Clark (02:42):
I remember when that came out.
That was crazy.
Wow.
Okay.
Well, what an honor.
I'm learning things and I'mbecoming more starstruck as
we get talking anyway we won'tbe talking about weathers and
maps and that kind of thing.
We're gonna be focusing todayon what it's like to lead
and manage products in this.
Very tricky stage.
I feel like we've all had thisexperience of being in this
(03:03):
between stage of startup andscale up when things are really
starting to ramp up and thingsstart to go off the rails.
So in the past, we chattedbefore and you talked about
Customer.io as being sort ofthis frontier town where it's
past the wild west kind ofstartup days, but not quite
into fully established city.
So, in your experience, whatare some of those key leadership
(03:23):
challenges that really emerge inthis specific stage of maturity?
Matthew Wensing (03:27):
I think it depends a little bit
on how you got here.
There's a certain amountof culture that you bring
into that situation.
Where is everybody on thesame page or is everybody
understanding that?
We are in this phase.
We're not a city yet, and bycity, to extend the metaphor,
those are the places where yougo and everyone has their box.
(03:49):
You know where to get your mail.
Everything's delivereda certain way.
And the thing I say internallyto the folks that I work
with directly is in thisphase and this in-between
phase, you have two jobs.
One of them is your core job,the function that you perform
that creates value for thecompany and the business.
But the other part of yourjob is figuring out the
best way to do your job.
(04:09):
And you might even say to figureout what your job is because
you have a title, and thattitle is probably the umbrella
over the core of your focus.
This transition phase.
If you come from the earliestdays that this, figuring
out what I should do todayis the most of the job.
I mean, I would say that's 95%plus of your job most days.
(04:29):
You're really justmaking it up as you go.
This is a bit in between andyou can end up hiring people
who are used to the WildWest, where they're figuring
it out every single day.
And then you can hirepeople who are really, you
could say, leaning intothe future and saying, I'm
even more comfortable themore established it gets.
And I think it's just importantto recognize and for each
(04:50):
person to know that, hey, thatfeeling you're feeling of not
knowing for sure if the thingyou're doing is the right thing.
That's actually part ofthe job and that's normal.
We want your help in figuringout the full definition of your
roles and responsibilities,and that's how you
participate in building thecompany you wanna work at.
Hannah Clark (05:08):
Oh, that's an interesting take.
I feel like it's a questionthat tends to linger, that
doesn't communicate it oftenbetween leadership and ics.
So, that's interestingthat you point that out.
I wanna dig a little bit furtherinto that, if that's okay.
So when you're working with,say, a new hire, for example,
that's come onto the team duringthat stage and like maybe you're
(05:29):
building their job descriptionout or getting a sense of what
their main contribution tothe company needs to be, how
does that ideally need to go?
Like where do you see the, theboundary between how much the
IC should be participating intheir, just kinda dictating
what their role shouldbe versus what leadership
should be dictating to them.
Matthew Wensing (05:48):
If you can tolerate more metaphors.
Hannah Clark (05:51):
Oh, I love them.
I love them.
Matthew Wensing (05:51):
Yeah.
The way I think about theseearly hires, and by early I
mean less than 500 people,which means each department,
if you break it down, youcould all fit into a pretty big
room or an auditorium togetherand you know everyone's name.
You're under that Dunbarnumber where you know every
single engineer by name and youknow a little bit about them.
So it's still small comparedto a large company scaled.
(06:12):
And in those situations, if Iam leading a group like that, I
try not to make many assumptionsabout how the future's gonna
unfold, what their full scope ofresponsibilities are gonna be.
We're trying to ultimatelyget as much contribution
out of each individual.
We're trying to give as muchindividual as much opportunity.
(06:33):
As we can.
And in that case, there isa job description as you
put out in order for them torespond to and join the team.
But what I will often do isinitially you're trying to
learn how this person works andwhat they're comfortable with.
And I like to startwith, and this can happen
in a period of days.
This doesn't haveto take months.
In fact, when you're atthis stage, you can't take.
(06:55):
But you really try to figureout what is the most ambiguous
direction that this personcan comfortably work under.
Hannah Clark (07:04):
Oh, interesting.
Matthew Wensing (07:05):
Not because you're trying
to be ambiguous, right?
You actually, if you'reinterfacing, say if you're
reporting to a VP or a CPOor maybe the CEO, depending
on where you are, thedirection you're getting is
often extremely high level.
And it's because thosepeople have such a wide
purview that they have tobe extremely parsimonious
(07:25):
in how they share direction.
So we need to do something aboutX. What I try to do initially
is say, okay, I'm not gonnaput this person into a box
or create a ceiling on them.
I'm gonna take what I justgot given, and I'm not gonna
just pass it along as is.
I'm going to bring it downone level into make it a
little bit more concrete,put some boundaries on it,
but not much more becauseideally they can run with it.
(07:50):
And I like to see how peoplerun with or don't run with
that kind of direction.
And it's very interesting tosee what the follow through
or responses are to that.
I think you can learn a lotin, like I said, days, not
weeks, in terms of how peoplehandle that kind of direction.
And again, you're not abdicatingyour responsibility, but
what you're looking for isthis a person who can thrive
(08:13):
with a lot of autonomy?
Or is this a personthat actually needs more
supervision, more management,more clear direction and
boundaries in order to thrive.
And you need both kinds withan organization, but you can
either frustrate or you canreally dishearten a person
that needs one or the otherif you don't test for that.
Hannah Clark (08:31):
That makes sense to me.
I think that's, I actually feelthat's a really good indicator
for a strong leader to have thatkind of emotional intelligence
to get a sense of, like how.
Be able to read someone'sability and comfort level
with a level of ambiguityand kind of see and be
perceptive to how theykinda rise to that occasion.
I kind of wanna take a littlestep back here and I apologize.
(08:53):
I'm throwing you a curveball because what this
is making me think of is.
The role of strategy andhow it evolves from that
really early stage startupas you start to get more
mature as an organization.
And I think this is an arealike where we're talking about
deployment of personnel andthat kind of thing and how that
kind of can be so individual.
But I, I see kinda a patternof strategy being a little
(09:15):
bit more, it gets morecomplex, as when you're a
small team, a strategy can bereally just an action plan.
And then as you get bigger.
The components of a strategybecome more diffuse across
different organizations and itbecomes more challenging for
someone kind of in senior, butnot, executive leadership or
a director level to interpretthat strategy and kind of be
(09:36):
able to fulfill their end ofit, especially in a remote
organization where people justaren't quite communicating as
fluidly as they would be inmaybe in an office situation.
So what have you seen in thefield as far as managing the
role of strategy in terms ofdeploying and translating a
vision into actual outcomes.
Matthew Wensing (09:55):
What I've learned is you cannot
afford to play the game oftelephone with strategy.
And what I mean is you reallyneed to have that the spine of
the organization, meaning thereneeds to be continuity and to
end in terms of, maybe there'sa few gaps or levels between.
This manager and the CEO orthis VP and this director,
(10:18):
but you can't afford tohave that understanding.
Shared or communicatedin a low fidelity way
between those participants.
So what I mean is you should beable to draw a line from sort
of the lowest level managerall the way to the CEO of
conversations that have happenedwhere that understanding
really got cemented byin between those people.
(10:39):
Let me tell you what'sthe opposite of this is.
So the anti-pattern wouldbe, here's this vision,
here's this understanding.
This is our strategyat a very high level.
So maybe it's thecompany strategy.
We want to be the greatestX. Insert your company here.
That's often the kindof thing that comes
from board to the CEO.
And then maybe the C-levelsocializes it a bit.
And then one failure modewould be you then convene
(11:03):
your S team, 'cause we want toimitate Amazon in this case.
And we say, okay,here's our strategy.
And you just hand it out to eachperson and you say, go implement
this, or go run with this,make this real in your world.
And you will essentially createa gap in understanding where
the way it gets carried out.
Then on the ground, itdoesn't end up looking and
(11:23):
feeling the way that it wasintended to, because people
will interpret things.
Change is hard, right?
And if that strategy involvestrade-offs or hard decisions,
or we're gonna focus on thiscustomer instead of this
customer, if you really haven'tcemented that knowledge between
each level of the chain.
You will end up withreinterpretations that
happen along the way.
(11:44):
That end up accommodatingcertain realities on
the ground, such as.
Well, Bill's not gonna be reallyexcited about this because
this essentially puts aside theproject he's been working really
hard on for the last year.
So I'm sure I can figure outa way to work this in here
and have these be compatible.
And what you end up doing isyou can end up creating what
(12:04):
I think of as think of it as.
If anyone's a Star Trek fan,the Borg, it assimilates, right?
Yeah.
It synthesizes things.
It absorbs things, and whatyou end up doing is you
have a strategy at the topthat is extremely, maybe
it's more disciplined orit's part of what makes, I
almost said strategic, right?
What makes a strategy strategicis that it forces trade-offs.
It makes hard decisions.
It says, we're not gonna dothis, we're not gonna do that.
(12:26):
The sign that you haven'tdone the cementing as
I call it, is that.
Somewhere in the chain, someonegoes, it must not mean that we
can't do this, or we must beable to also accommodate that,
and they will glom on, or itbecomes the sticky ball, right?
Where there's really nothingthat isn't in play anymore.
It's, of coursewe wanna do this.
And that's how you knowyou haven't done this part.
(12:48):
This part is the people reallycoming to grips with what
this says we're not doing.
Maybe anymore, or we're notgonna do instead of this.
If that person understandsthat, then there's an
accountability chain as well.
It's very hard if you don't havethat come to grips with moment.
I think especially for remoteteams, this is easy to skip, is
(13:08):
did that person really go away?
Understanding the trade-offsand what we're gonna have to
give up in order to do this.
And I think that'show you prevent that.
But we can also dothis of course, right?
Or this doesn't say thatwe can't keep doing this.
And then you have aleader that goes, how
come we have the strategy?
That we're only gonna do thisand we're gonna focus on this.
There's the word, right?
Everyone wants focus.
We're gonna focus on this.
(13:29):
But then when I'm lookingat how we're spending our
time, I don't see that focus.
And it's because somewherealong the way that chain got
broken and someone assumed thatit didn't mean that we can't
also do these other things.
Right?
Hannah Clark (13:40):
Yeah.
Okay.
This makes sense to me.
And I think part of why Iasked this and why that kind
of came to me as we're talkingabout folks sort of choosing
their own adventure, so tospeak, about how they can
contribute best to the company.
I think that when we misfirein that area, that tends to
be where work gets duplicatedor people who are well-meaning
tend to spend time serving thestrategy to their understanding.
And then we get some breakdownin terms of, again, what's
(14:02):
the right process and howdo we really show value or
present value if we don'thave a very clear picture
about the scope of our.
Influence withinthat bigger picture.
And that kinda leads me intowhen should we introduce
process versus maintaining thiskinda like startup agility.
Like I feel like this isjust a constant struggle.
Like how do you make ajudgment call about avoiding
(14:23):
this chaos versus death bycommittee kind of battle?
Matthew Wensing (14:26):
I like to introduce process on
the heels of success.
So something worked, Ithink of process and I
was explaining this tosomebody earlier this week.
This gives a helpful way tointroduce process without even
using the process word, is Ilike to think of process as
it is writing down a storyof what success looks like.
That we want to repeat.
So you say, wow, thatcall between product and
(14:49):
sales went really well.
That call where we got broughton to have that conversation,
that customer went really well.
It wasn't written down.
There was no process.
Thank goodness we have somepeople on the team who can
just leap headfirst into thosesituations without a playbook.
And have it go well.
And maybe we've tried it threeother times that it didn't
go well and this time it did.
Writing down the processis simply then saying to
(15:10):
the company, Hey, here'swhat just happened.
This was awesome.
So let me tell you whythis went so well or why
I think this went so well.
It went so well because first,Glenn and I got together and
we did this, or the next thingwe did is, Sam and I did this.
You just tell a story ofthe success that you had.
And naturally, peoplewant to imitate.
(15:31):
Success process is really justa way for people to imitate a
successful story, and thereforeeveryone wants that, right?
Yeah.
And it's what salespeople,when people are on their,
educational products orinfo products, right?
What are they sellingyou recipe for success.
And a lot of those obviouslyare not real, a great manager.
Calls a timeout ornotices success and says,
(15:52):
how did you do that?
Please write it down andteach it to the team.
And then I like to separate.
So that's the process isjust repeating the story.
I like think of ops.
Ops is also extremely helpful.
Ops is a way of saying thatis the story we wanna have at.
We want these three peopleto get into a room together
and reconcile why thisthing wasn't done on time.
Not in a bad way,but in a good way.
(16:14):
That's a healthy conversation.
We need to have that.
How often should we have that?
Yeah, I think we shouldhave that at least
every couple weeks.
Great Ops, can you help?
Yes.
Ops comes in and says, I'mgoing to essentially create
the structure, the contextthat allows us to repeat this.
And it seems really simple,but this is the part
about saying out loud whatotherwise is just assume.
(16:35):
It's very easy for a lessexperienced manager to assume
that, hey, they had success.
They're gonna do that again.
They want that to happen again.
I think this phase is about.
Saying, Hey, write thatdown, share that story.
And then, Hey, ops, how do wetry to recreate that success?
Let's get them in a room.
How long should theconversation be?
What's the agenda?
(16:56):
And before you know it,you have this process, but
everyone sees the valuebecause it was organic.
You've productized essentiallya human interaction by
just starting with a story.
Hannah Clark (17:06):
Kind of the takeaway that I'm hearing here
is that as opposed to thinkingabout processes strictly a
checklist or just an objective,you're thinking about.
Ops is developing that sortof process guide, but what
we really need to be thinkingabout process as sort of
like the beats of the story.
Okay, what beats did we have tohit for this to have happened?
Yes, for it to be replicated.
And then fromthere, that's your.
(17:27):
Outline, and then from thereto create like a repeatable
process when ops comes in,that's more the checklist, izing
of things like the actual, thethings that can help you scale,
the things that kind of helpyou to standardize something.
As invariably your teamgrows or people turnover.
Matthew Wensing (17:41):
Ops makes it manageable, right?
Without ops, you're not trackingit you're not measuring it.
Ops is what lets you go.
Oh, so that means we couldhave up to this many beats
per whatever with this group.
This, and I loveyour beats analogy.
I just have to say that tome is the story is the movie.
The beats are the scenesthat you need to create.
And if we don't have this scene,if the scene doesn't happen, the
(18:02):
story falls apart and everyonewants to be a part of that.
Hannah Clark (18:06):
Yeah.
Well, everyone wantsto be in a good mood.
Matthew Wen (18:08):
Yeah, that's right.
Hannah Clark (18:09):
Okay.
Let's talk a little bit aboutbecause you'd mentioned,
creating process outof success, but success
also creates problems.
And so if we think about theways that companies tend to
attribute sometimes their winsto the processes, but maybe it
was more due to, the timing thattheir product came out or the
market fit, then they happenedupon how do you separate,
(18:31):
what is actually working?
How do we verify that thisprocess is functional rather
than it just happened towork at the right time.
Matthew Wens (18:39):
That's a good one.
I think you're getting, I mean,this is a fundamental fallacy
or one of the fundamentalfallacies of people is you're
misattributing results to acertain way of doing things.
And I think to some extent,congratulations, you're
succeeding, which most peopledon't get to that place.
And I think Customer.iofor sure where I work is
at the place where it'sworking and that's awesome.
What you have to be open to.
(19:01):
I mean, unless you have agroup of people who just
love attending meetings andprocess, and most people don't.
You are going to end upwith feedback on is this
working for us or not?
I do think that there's atime for kind of molting, if
you will, in shedding thoseprocesses that got us to
now, but won't get us there.
And I think you can.
(19:23):
These are even the good ones.
So that story worked when weonly had one product manager
and three salespeople.
It doesn't work anymore.
I think if you don't havethat operational mindset.
You will just coast intothose and before you know it,
people will start to say, Idon't really see the success.
The success is not coming out.
We're still doing thebehavior, but I don't
(19:44):
see the success there.
I think what you're talkingabout is almost the world where
we continue to have the samelevel of success and we're
going through these motions.
There's worse problemsto have in the world.
What I think people arereally worried about is we're
starting to see the top ofthat S-curve in terms of.
Things just don't feelas quick as they used to.
Or decisions are takinglonger than they used
to, or frustrationswill start to come out.
(20:08):
And I think that these are thegear shifts or the metamorphosis
or these moments in time whereit takes a deliberate action on
behalf of the leadership teamto say, it's time to reorganize.
It's time to reboot or refactorthe way this is working,
it's not working anymore.
And there's a certain foundermentality or there's a certain.
Pioneer that you needmentality in those cases to
(20:30):
say, Hey, the well that wehave, it's not gonna work.
That's not gonna get thepopulation has, we've, it's
outlived its purpose andthere is a moment there where
you have to be willing toremove the well and replace
it with something else.
And that's risk.
There has to be a certainamount of appetite for risk
that says we don't wanna lockin our gains at this point.
(20:52):
And I would say a techniquethat I've used in terms of.
Having this conversation withpeople where it's already
working is you say, okay,put aside what's working.
What are our aspirations?
How big do you want this to get?
And most of the time peoplewill not say, oh yeah, I
just want it to be like 5% or10% more than we have today.
Most people, if you askthem, where do you want this
(21:14):
to really go, they'll sharesomething very grand with you,
and then you have that new.
Vision or that new version ofthe story where you go, okay,
so you can see how a well isn'tgoing to, like, how is that
gonna work when we have 20,000people living on this street?
Well, clearly it's not right.
And so if you want toget to that, if those
(21:34):
are your aspirations, wehave to take more risk.
And how much risk a company'swilling to take internally is
unfortunately not something thatany one individual can decide.
That's where the seniorleadership has to
come in and really.
Have that groundingconversation again and say,
if our aspirations are tobe a public company, or our
aspirations are to be this,we've got to take more risk.
(21:54):
And then letting yourself wipethe slate clean in some cases,
or reboot what you've beendoing that got you here and
say, this isn't going to getus where we need to go next.
But I think just being sensitiveto those frustrations and
intellectually honest withthe results you're getting.
And then thirdly.
Can we actually get towhere we're trying to go?
(22:14):
Using what we're using now?
And this all comes downto the right people.
And answering those questionshonestly is itself a challenge.
But that's the job.
Hannah Clark (22:24):
Yeah.
Well, okay, so this is makingme think of this let's say.
Thing that happens sometimeswhere when we decide to
change course, the companyis scaling, we decided
that whatever processes orsomething needs to be replaced.
We tend to look at biggercompanies, larger companies,
more successful companies assort of like our North star.
How can we copy and pastesome of their playbook and
(22:46):
replicate those resultsin our own organizations.
But of course, like thosecan also be subject to the
same kind of stipulationsof maybe they, yeah, right.
Time, market fit, et cetera.
How do we evaluate or how maybe,how specifically, how have you
evaluated what practices thatwe borrow from big company
playbooks are worth adopting?
Matthew Wensing (23:04):
I think in those cases, the best scenario
is you bring in a leaderthat has lived and done that
before, elsewhere, and youdramatically reduce the risk
that they copy the form butnot the substance of that.
Because they know.
They know that if you wereon the outside and you had
your understanding of Apple,you thought that it was just
Steve Jobs walking around andtelling everybody what to do.
(23:27):
What you don't know iswe actually had these
conversations like this, andthese used to take hours and
we would do this and that.
And what you find out isthat the fictionalized
or the depiction of that.
It's so superficial becauseeverybody wants to believe
that if you just imitate, youcan have, and we just talked
about how that mimetic natureinternally can be used for
(23:49):
good to replicate success.
It can be used very dangerouslyto try to imitate success as
external to you because theamount of information that you
lose by observing across andeven reading business books, or
a really inspiring blog post.
There's some weird thingshere too to consider that's
maybe the company's doingthat because they have to,
because it's compensating fora weakness that we don't have.
(24:11):
There's all kinds ofreasons why people do
certain things, and if you.
Assume the reasons you can endup in a dangerous situation.
I think OKRs is one of thosethat is, this is a great
example of there are so manyimplementations of OKRs and
we all know them, but findingsomebody who's done it before
and then can build a departmentand do it the same way they've
done it and hire peoplewho have done it that way.
(24:32):
That's one thing.
An excited CEO or CPO readinga book by John Doer and saying,
we need to do OKRs too, andthen trying to implement
them for the first time.
It can work, butjust consider that.
What you're doing isyou are experimenting.
You are trying to figureout if this imitation is the
solution for your problem.
Do you even have the samesets of problems that they
(24:54):
had when they started toadopt those tools and those
rituals and you don't know yet.
So it's okay, try that.
But somehow you need to tryit with a very light hand or
grip on it and say, if thisdoesn't work this quarter, if
this doesn't work, this sprint.
We are not going to stickto it because it's not about
our ego, it's not aboutour pride, like we're gonna
try it and see if it helps.
(25:15):
So I would recommend thosethings in very small doses
with a light grip, unless youhave someone that's lived it
and can really tell you theinside story of, we tried those
and this is what didn't work.
I'm gonna do it the way thatI've known has worked before.
And also, I'm gonnahire the people that
work this way because.
If you could hire someonefrom Google that's familiar
with OKRs and if this personuses them at a completely
(25:36):
different company, even thatmight not be compatible.
So I think there's alot of danger there.
We know that.
I also think thatit's worth trying.
We don't need to learneverything over again ourselves.
There are certain risks thatwe figured out how to avoid.
Just be careful.
Hannah Clark (25:51):
Yeah.
Matthew Wensi (25:51):
In terms of that.
Hannah Clark (25:52):
I'm gonna press you a little bit more on
kind of a related angle here.
I like the way that youmentioned using a light
hand when piloting tacticsor strategies that.
You're not a hundredpercent sure gonna be
compatible with the mission.
I have seen the oppositeextreme of that, of what I
would refer to as too muchtoo fast and not enough time.
(26:15):
So how do we avoid the issueof perpetually being in an
experimentation phase, but.
Managing our timeline so that wecan really evaluate the outcome.
I've seen this happen acrossmany organizations and with
people that I've spokento as well, where it's
we tried this experiment.
(26:36):
It's almost like we havea 10 step experiment.
We get to step three.
Leadership gets concerned thatit's not giving us the results
yet that we're aiming for, andthen we decide, you know what?
Nevermind, we're gonnago back to step one on
a different experiment.
And it's like we don'tever get that real
learning from the payoff.
Matthew Wensing (26:54):
Yeah.
And this is true.
Even if it's this is a patternof how do we learn and test.
That's true.
All the way down to thefeature level, right?
And all the way up to thecompany As product and
product, product as product.
I have adopted a technique.
The technique isn't new to me,so I'm a big fan of the observe,
orient, decide, act framework.
(27:15):
Food loop, which is reallyjust a way of, and I use
this all the time in life.
This helps me in my personallife, even of saying we've
got to split the observationsfrom the orientation around
those observations fromthe decision about those,
and then from the actions.
And I'll also say thereare failure modes, and
you just described one,which is if you take a
single letter out of that.
Equation.
(27:36):
There are the companiesthat just observe, and
they never decide anything.
And what you just describedis a company that maybe
observes, does some reasoningaround those observations
and then makes a decision tojust go a different direction
and kind of starts over.
You want to make sure you gothrough all of those, and we
can certainly talk about whatall those are, but it's tough.
Organizations are only asstrong as the leaders that.
(27:59):
Get to run them.
And so I don't know necessarilywhat to do if leadership doesn't
do these sorts of things, butwhat should be happening is
someone needs to say, I'm goingto lay this out and if everyone
else is too busy, this could bea special assignment of someone
where as the company, I like tosay the Jane Goodall approach
of, I'm going to go observe.
(28:20):
I'm the ethnographerof the company.
I'm gonna go talk to everyone.
I'm gonna observe, I'mgonna study, I'm gonna
write everything down.
I'm gonna be a scientist.
Right.
Capture that and thenlay that all out.
And if you lay it out in acertain way, if you can really
split out the observationsfrom the judgements, and I see
this fail a lot in terms ofpeople who are frustrated and
say, we shouldn't move on tothe next thing next, right?
(28:41):
They'll lead with that.
They'll say, here's 13 reasonswhy we shouldn't do this next,
and people immediately put uptheir guard in defenses to that
because you've, you're treatingit like a court case, and as
soon as it's a court case.
Where I'm going to show thatmy client is innocent or
why that person's guilty,people put up their defenses.
I would highly recommenda more scientific approach
(29:02):
where you say, I observethis, I observe that, and
you can catch yourself.
If you get good at writing thisway, you will catch yourself
halfway through a sentenceabout observations going,
that's not an observation,I'm making a judgment.
Or that's actually like I'mthinking about the observation.
If you can come and leadwith observations, people's
minds will open up.
(29:23):
A lot more because now they'realmost eager to know, I'm
seeing the same things you are.
Right.
Because you'veleft that part out.
Take me now.
Okay.
Why are thoseobservations there?
Oh yeah.
I believe that too.
Yeah.
That's this way because we didthis and that's this way because
he did this and then you finishwith your, and so we should
recommendation or decisions.
Very helpful techniquein terms of writing more
(29:45):
persuasively internally, andsometimes all it takes is
this kind of, Hey, the pen ismier than the sword, right?
All it takes sometimes forthose of you who are in
those situations, maybearen't the senior leader.
If you can lay that out in thatway, you might be surprised
at the kind of impact that canhave where the right people
reading it in the right ways,and there's a lot of management
there of making sure that it'sreceived in the right way.
(30:07):
But those are very,those are powerful.
Companies can sometimes.
These are groupsof people, right.
Group dynamics are real,but leading everyone through
that thought process takesa very disciplined approach
to laying the informationout, and I don't think it's
practiced often enough.
Hannah Clark (30:23):
Yeah.
Okay.
Again I wanna reiteratewhat I'm hearing here.
Like the takeaway that'semerging from this for me is,
it's silly to, to reframe itlike this because what you're
saying is you should treatexperiments as experiments.
Yes.
Which sounds obvious, butI think it's not obvious
because oftentimes experimentsare treated like coaching
conversations or vague guidance.
(30:45):
It's kinda like weshould try this.
And someone takes thatas a marching order.
And I think that's, it's reallythe communication breakdown and
kind of the failure to treatit like an experiment in which,
if you say we're gonna run anexperiment between a group of
leaders versus we're gonna runan experiment around a group
of researchers, they're gonnathink very different things with
regards to what you just said.
And I think what you'resaying is you gotta think
(31:08):
about it like a researcherwould say, we're gonna
communicate about what exactlywe are setting out to do.
We're gonna set benchmarksand timelines according
to what we're going totry, when we're going to
reevaluate, and we're goingto be researching throughout
the whole thing, right?
We're going to bemaking observations and
communicating about whatthose observations are.
What I'm hearing isprobably where a lot of
(31:28):
this breakdown is happeningis that there is no real
management of the experiment.
And so it makes sense why therewould be frustration between
the leader saying this isn'tworking, and then you know,
the managers or ics, et cetera,who are trying to, work on
that experiment going, well,hold on, we're not finished.
And so who would've thoughtexperiments should be
treated like experiments?
Matthew Wensing (31:49):
Yeah.
I will say I have astrong belief that we
adopted as product people.
We adopted the wholelean startup methodology.
So I know Eric wrotethat book in 2007.
It was amazing.
It was amazing.
At the time, I think it wasso amazing that a lot of us
adopted scientific language.
We learned to, once again,imitate the craft of being
(32:12):
scientific when it comes tobusiness and validation and
feature building and productdevelopment without the
discipline of, okay, I cansay we're gonna test this.
If I say, Hey, we have thisidea for a feature and there's
three ways we could do it, Ireally believe that we have to
have include this deep researchfunction, which is gonna be a
(32:33):
lot more expensive to build.
And so we're gonna testthat theory by first
releasing a version.
That's where wedo that manually.
And see if peoplelike it or not.
There should be red flags oralarm bells or whatever it is.
Butterflies going off inyour stomach right now if you
think about it, because whatI just did, I'm not testing
the right thing at all.
What I should be testing is.
(32:54):
This is really expensive.
What we should be testing is canour customers live without it?
But I use language ofexperimentation and fooled
you into thinking thatI was being scientific.
Now obviously, maybe Ididn't actually, but like
this happens all the timein product management where
someone will say somethinglike that and be like, yeah,
we should do it manually.
'cause then we're not reallyproductizing it, which avoids
that research and like wedon't have to build it yet.
(33:16):
That's lightweight.
Yeah, that's smart.
That's a good experiment.
That's a terrible experiment.
All you're gonna get is theperson going this is awesome.
You're like, yeah, we thoughtyou would think it was awesome.
Oh shoot.
What were we testing again?
You weren't actuallytesting the thing.
You should be testing.
You just tested.
Do people like the thingthat I think they're gonna
yeah, don't do that test.
Can they live without thething that's really expensive
(33:37):
that we hope we don't have tobuild because we're not here
to build really cool stuff.
We're here to build a businessand if that business is more
profitable and can executefaster, because we don't
have to build certain things.
Let's not.
And so I think thatintellectual honesty or that,
are we really experimenting?
It is a pervasive thing in ourzeitgeist as product people
(33:58):
to be using words like this.
But we didn't reallystudy the book.
We highlighted the book andstarted using the language and.
We weren't mentored about how toactually apply those principles.
So if that's you,we've all done it.
But see if you can catchthe next person that you're
working with saying words likeexperiment and test and theory
and hypothesis, and see ifthey're really testing a thing
(34:19):
that, wow, if this ends upbeing false, I'm uncomfortable
because I thought it was gonnabe true, but I'm willing to test
if it's false because that wouldbe better for the business.
What we like to do is we liketo put our opinions out there
and test and see, can I findvalidation for my opinion?
That's my test.
Hannah Clark (34:37):
Yeah.
It's like how can we put AIinto this product instead of
how do we solve this problem?
Matthew Wensing (34:42):
That's right.
I have a strong opinion thatwe need to do X, therefore
we're gonna do some cheapversion of X. And when people
like it, I'm gonna get to showall of you that I was right.
Hannah Clark (34:51):
Yeah.
Matthew Wensing (34:51):
That's the actual thing going
on behind in our minds.
And science and ego don'thave a lot in common.
Hannah Clark (34:57):
Oh, that, that's a quote.
I think that this wholeconversation, a lot of it
hinges to decision making.
So you've seen the evolutionfrom founder-driven
decisions to moredistributed decision making.
Organization grows, decisionmaking power changes.
What's your approach tofinding decision rights and
ensuring that everyone's gotthe right context to make good
(35:17):
decisions within their capacity?
Matthew Wensing (35:19):
I think it goes back to what I started with is
you were sending out feelersall the time as a leader,
as a manager to understand.
How much context can this personhandle and what do they do with
the autonomy they're given?
I used to manage developersand I had a scale for how
autonomous is this developer,and you could work your way
off that ladder starting with,do I know what code to write?
(35:41):
If they need help withthat, then they're
junior by definition.
That's okay.
But they're anassociate in that sense.
Up to the level of I know whywe did this work, and I know
how it fits our strategy.
That person is theperson who you're hoping
you hired or found.
Maybe you know that youhired The other one.
Where I'm going with thisis, remember I said at the
beginning, you're testingto see what level of
ambiguity it can handle.
(36:02):
I also like to test how muchcontext can they absorb?
Are they taking full advantageof all the information that's
being said on all the meetings,all the calls, and all the
notion docs and all the strategydocs that are being written
by the CEO in our mandate?
Are they starting to finddiscrepancies between
things where they're going,I was reading this and
I was reading that, andthese kind of don't agree.
These are good signs.
If you find someone thatnotices the wrinkles or the
(36:25):
air bubbles in your strategyor in your thinking, they're
paying attention, right?
They can reconcile things,and that means they're ready
to work at a higher level.
The other tests I like torun is when you give them
something, Hey, we needto make it over that lake.
Do they disappear from view run?
And suddenly you hear asplashing sound and they get,
there's a bunch of screamingand stuff, and then maybe
they come back half torn upand they bring you the thing
(36:46):
that was on the other sideof the lake, and it's okay.
You did it.
Thank you for doing it.
Or do they disappear for halfa day and then come back and
say, so I took a survey of thelake and I wanted to understand,
when you say we need to getacross it, are you intent on
crossing it at the widest part?
Is there a reason thatwe need to do that?
Or can we cross it over here?
'cause we cancross it over here.
Now you found someone whoknows how to take that autonomy
(37:08):
where you gave them the roomto go do all of that, right?
You weren't checking in onthem six hours later saying,
Hey how are you doing?
But did they know enoughto run a survey first?
Did they know enough tosay he can't really meet?
I see alligators in there.
They can't really mean thatI should just swim across.
I should probably grabhim on Slack and say,
Hey, I took a look.
Quick look, and thisis what I found.
(37:30):
As a senior leader, you arenot necessarily looking for
someone who throws himselfinto the water kind of thing.
Hannah Clark (37:36):
The Labrador Fever approach.
Matthew Wensing (37:38):
Yes.
Super heroic, super friendly,your best friend in that
sense, but painful from a coststandpoint, and that could
lead to some bad outcomes.
And I think the thing is this,if this is you, if you're
the, if you're that personwho's reporting to someone
knowing this, there's a, Ithink, and I know 'cause I've
been there, my first jobs.
They're in your gut.
You're like, I don'twanna bother them.
Like I don't wanna seem likeI don't know what to do.
(37:59):
Don't worry about that.
If you come back with smartquestions, having done your
research, having taken itdown the field, if you will,
and saying, Hey, I wannaunderstand a little bit better
why you think we should dothis, what, et cetera, et.
What you're doing is you'regiving them the opportunity
to give you a little bitmore clarity, give you some
boundaries, explain whythey were asking for that.
All these things whichyou should not be making
(38:20):
assumptions about, don'tmake assumptions about.
Just 'cause they didn'tsay it yet doesn't mean
they don't have opinions.
And I've seen a lot offailures in that case.
So back to your question,if you do this right and you
find someone who uses theirautonomy wisely and can work
their way up that ladder, itcan absorb a lot of context.
Now you know who you can trustwith localized decisions.
(38:40):
Because you can truly delegateand say, in this case, I don't
have to be in all those details.
But if you don't do thiswork as a leader, if you
don't test, if you don'tgive them the opportunity
to fail, you won't discover.
And then as a leader, you'renot gonna know how much capacity
do we really have because.
I'm holding back on delegatingbecause I haven't really
(39:01):
tested the resources thatI have, but if you test
them, you'll find out, andif you don't have enough of
one kind, you can augment.
If you don't have enoughof kind of another,
you can fix that too.
But I think distributed decisionmaking is the dream, but if you
haven't done the research onwho can handle it and who can
make a better decision than Iwould have had I done it myself,
then you're just flying blind.
(39:21):
Then you're just hoping thatthey make great choices and
that's where you get the chaos.
Hannah Clark (39:26):
What I'm hearing here is and I also tend to
think that sort of compatiblewith this theory is that most
people have a lot more capacitywithin their existing headcount
than they think because...
Matthew Wensing (39:36):
Absolutely.
Hannah Clark (39:37):
...you're not doing that investigative
work or that collaboration toreally discern what someone's
true capacity is and whattheir capabilities are to
operate within that scope.
It sounds really likeyou have someone in mind
when you're saying this.
I do wanna say, before I ask youfurther, this actually reminds
me a lot about an episodeon systems thinking that we
recently did with Sheryl Cababa,because what you're describing
(39:58):
to me sounds very much like thesystems thinking mindset, which
I think is, I'm sure that itcan be trained, but I think a
lot of people tend to be veryjust adept at that kind of
ability to hold a lot of contextat once and be able to work
with it sort of simultaneouslyto find win-win situations.
So for anyone listening whowants to dive further into
that, we did that a few weeksago, it was a great episode.
(40:19):
It puts it all into perspective.
But I do wanna ask, doyou have an anecdote or
an example of somebody whoreally embodied that trait
that kind of stands out toyou when you tell us this?
Matthew Wensing (40:28):
I'll use a friend of mine.
When I started my firstcompany, at some point I needed
a director of marketing andhe joined me, having been a
consultant at Deloitte andwas really good at that job.
And crushed it and itdid all the things that
consultant needs to do.
One of the job interviewquestions was like,
Hey, develop it.
And I didn't know much better.
So I didn't ask thebest questions when
I was interviewingfolks at that point.
So I said, yeah, developa go to market plan or
(40:50):
a marketing plan for us.
And back came like this 15 pageGoogle doc of here's the go
to market plan, and I think Istill have a copy of it because
we ended up working togetherfor 12 years after that.
I still have a copy ofit somewhere, which is
like the classic case of.
He got a direction.
Now, it wasn't an interviewquestionnaire, so he
couldn't really do a backand forth, and he just
(41:10):
blew it out of the water.
Right.
The reality is we didn'tend up using almost any of
that because two things.
One, it was a startup, andtwo, we didn't have that
collaborative conversation.
Later on, he becameextremely good.
He's now making a career outof working for C-level execs
or next to executive vicepresidents, et cetera, high
level senior level execs andsaying, I heard you say this.
(41:32):
And what he was doing bythe time I worked on him
through two startups.
By the second one, I wouldsay something on a 30
minute call on a Friday.
He wouldn't even ask me aboutit then, and he wouldn't do
anything else with it otherthan he'd write it down
and on our Monday morningcall he'd say, I heard you
mention this on Friday.
What made you think about that?
Like, why did you do that?
And so when I share theselessons with you, I'm
(41:53):
actually, I'm sharing thelessons that he learned by
working together with me.
We learned by working togetheron two startups that he
got better at not runningwith those things, and I
got better at appreciating.
I'm glad he didn't justrun with it because that,
I didn't even know enoughto tell him at first, so.
Those are the anecdotes.
I like the funny one.
By the end of it, we had sucha great working rhythm in
(42:16):
that sense where I could trusthim with extremely high level
direction and then I wouldknow he was gonna, we were
gonna work it through togetherand then he would run and
perform at a very high level.
But one last tip, if you dothis, I think a lot of managers.
Come from the wrong direction.
What I mean is you start atthe low level and you say,
ah, I have this employee.
I hired them to be an ic.
They're a product manager oran entry-level product manager.
(42:38):
I'm gonna give them this andI'm gonna see how they do, and
then I'm gonna give 'em a littlebit more and see how they do.
You're building up what youthink is their capability level.
That is a very slowpath to discovering
their ceiling, right?
Much faster is to challengethem with something where if
they succeed, they have shownyou that they are six levels
bigger than you thought.
And now you can meet themthere, you have now leapt there.
(43:00):
The only risk is that theyscrew up that one task
that you ask them to do.
And again, you might discoverthis in a week, but how much
better to discover in a weekthat they're capable of knocking
something outta the park thatyou think they can't handle
than to spend six months onthis thing level and then
six months on this level, andthen six months level that's
the slow path to discoveringwho your top performers are.
If you as a leader can findthings that are challenging
(43:22):
but low risk if they fail.
Because what happensotherwise is they leave.
You're like, oh, okay.
They left.
I didn't really think of themmaybe as a top performer.
Then they go join some companyand they're like leading some
huge initiative and completelycrushing you go, what happened?
It's like they were alwaysthat person, you just didn't
discover their ceilingand you can discover this.
There's a lot of differentways to do that aren't
(43:42):
necessarily live fire exercises.
They're gonna costyour company a bunch of
production costs, dollars,karma credit, et cetera.
But I think it's theopposite direction that
most people start becausethey think about the ladder.
I wanna make themclimb the ladder.
I would say I'd rather givethem the chance to grab the top
one of the higher rungs and ifthey can reach it, fantastic.
You're looking forthose kinds of people?
Hannah Clark (44:01):
Yeah, absolutely.
Well, at the very least,you've stretched that
person and help them developand create a trajectory
for their development.
Another one of those thingsthat's it sounds like it should
be so obvious, but we don'tsee that happen in practice.
Oh, Matt, this has been aphenomenal conversation.
I've learned a lot.
I appreciate yourwisdom so much.
Where can folks who are alsoappreciating your wisdom
(44:22):
right now find you online?
Matthew Wensing (44:23):
If I'm online at mattwensing.com is where
I have a bunch of essays thatI've written over the years.
You can also find me onLinkedIn, @wensing is my handle.
But you can just look forMatt Wensing there and I'd
love for you to connect.
Hannah Clark (44:35):
Awesome.
Well, thank you so much formaking the time and yeah,
hope to talk to you soon.
Matthew W (44:38):
Thanks for having me.
Hannah Clark (44:41):
Thanks for listening in.
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