Hello everybody. I'm Jonathan Kirschner and this
is a podcast about leadership. And on this podcast we talk
about the skills and mindsets required to become not just a
regular old leader, but an excellent leader.
And today we are talking, we're taking on a a very important
topic, the climb from start up to scale up and ultimately the
leap to the public markets, the IPO.
We always typically hear about the financial side of an IPO,
the bell ringing, the stock price, the capital raise, the
big party, the confetti. What we rarely talk about is the
human toll and the leadership culture required to start a
company is often very different from the culture required to
lead a public organization. And so to help us navigate this,
we have two incredible heavy hitters with us today.
First, I'm going to go with got to get, we got to get a drum
roll. I'm doing drum roll Gary
service. So Gary is an operating partner
at Insight Partners, which is one of the world's largest
venture capital and private equity firms.
So Gary, Gary does not watch from the sidelines.
Gary's deep in the trenches with his portfolio companies, and
he's helping them navigate the messy, complex journey of what
we'll call scaling up. And he's bringing the unique
perspective of seeing this play out across not just like one or
two, but hundreds of organizations knowing exactly
where the plot twists are. And so it's incredible to have
you on the show today, Gary. Thank you so much for joining
From what looks like New York City in the background.
Indeed it is. Thank you Jonathan.
Super excited to talk about one of my favorite topics.
Awesome. OK, and then joining Gary as as
though it was wouldn't be enough.
We have Katherine Williamson. It's weird saying Katherine
cause Kat, I know you for for years.
And Kat is currently the VP of talent development at Gong.
Kat's previously held roles at Hashicorp, Pinterest, and other
high growth tech firms. She's an expert practitioner who
has lived through the IPO transition from the inside and
recently actually collaborated with us.
Thank you so much, Kat, for the collaboration and partnership on
the white paper that we wrote titled The IPO Evolution, which
looks specifically at how talent and culture needs to mature in
order to survive public scrutiny.
Kat knows exactly what it takes to get a leadership bench ready
for the big leagues. So Gary Cat, welcome to the
show. This is I'm pumped.
I'm going to I'm going to field the first question to to Gary.
So Gary, you work with so many companies at that critical scale
up phase. Is there a specific like
inflection point or moment, a specific kind of failure where a
founder realizes like, Oh no, like all that's fun dopaminergic
scrappy chaos that got me here is now actually like, hurting
us. It's getting in our way.
Yeah. I, I think that's such a great
question because as as Cat well knows, there is points at which
we have discussions just about talent in general at these
businesses that say this person in this role probably is not the
person that's going to get you to the next level.
They may be great at this range, not so much to this next leg of
the journey. And that goes throughout all the
growth, not just IPO. And I think, you know, as
companies are working through their scale of journey and
they're trying to figure out what they need to continue to
scale, what happens typically, I mean, unfortunately is the the
KPI start to be telling a different story.
And that doesn't mean the company has lost product market
fit. It doesn't mean that the
business is not a good business, but we start to see some
degradation in the core KPIs. Those KPIs can be the rate at
which ARR is changing. So we were growing at, you know,
a doubling every year, and now that's kind of coming down as
the rate of change is going. And that may be a lot of
numbers, by the way. It's not just simply that we
might see it in little bits of retention issues, which tells
you that maybe your onboarding isn't great.
Maybe you have telemetry data that tells you your engineering
team is working super hard, but people aren't using all the new
features that are being introduced into your.
And so these are just examples across any of the functional
areas which give you leading indicators that something within
the organization has changed. And the solution is not always
simple. It's not necessarily I need a
new person or may not mean that you need to change how you've
done things and you need someone in a senior role who is not just
managing for today, but managing for what's next.
That's, that's really interesting.
So I can actually, you know, being, being a founder and, and
CEO of two organizations, air analytics and air consulting,
Air analytics being 3 year old, three years old.
So it's really still kind of a, a, a baby Air consulting being
much more mature. But like I, I, I know how
amazing it feels to move fast to like out innovate.
It's, it's just, it's a, it's pleasure full.
It's, it's actually like incredibly gratifying to lead
through innovation and to always being like always doing new
things. And I remember the first time
somebody was trying to explain to me, I didn't get my MBA.
So no, no MBA here, no formal training psychologist tried to
start a company and, and, and barely made it.
And, and now here I am right when somebody was trying to
explain to me what a KPI it was, I was like that.
That is like the most like de energizing, like concept means
you're going to just sit and like measure the same thing, you
know, like every month and then like we're going to look at a
report or a dashboard on a quarterly basis.
And that's what success or failure is.
It's not like what we innovative or did we have fun or did we
move fast and break things. So it's like you're so de
energizing. I'm curious, you know, from from
both of you, you know, like, like cat you, you being sort of
operating internally in an organization and helping like
leaders at scale develop with, with some major implications to
culture and, and Gary, you, you know, looking at investment
choices and and helping founder CE OS like let's unpack that
concept a little bit like how the the the founders, let's
start with this. The founders become sort of
obsessed with just like the, the, the, the, the allure of
chasing the shiny object, moving fast and breaking things and
sort of resist this like slowing down and attending to the boring
stuff like KPIs and OK Rs. I can start, but I, but I'm sure
Gary's got got tons to contribute as well.
I think so. And I, I think at least sort of
in some of my experiences, I think it's less about like the
excitement, but more about the perception of slowing down to do
these things. And I think sort of sometimes
it's been my job to say we might need to slow down initially, but
in in order to scale and in order to, you know, ramp fast or
like get after some of the things that you want to do,
which might be more exciting for you in terms of innovation and
and growth. We need to set these foundations
so that we don't have to keep like reiterating things or
duplicating work across the system because this person built
something, we haven't shared it centrally.
We don't have a central ownership.
Maybe they leave the company or they get bored of it and it goes
away and somebody else has built the same thing over here,
someone else has built the same. So there's like a place here
which is like sometimes you need to kind of slow down and get
your foundations in order to get back to doing some of the stuff
that you love doing. Like once this stuff runs well,
then you know, go for it. Go innovate.
Be excited about those things. It makes a ton of sense, but
like, do you ever, do you ever like meet up with resistance
when you're saying to a founder or to a leadership team, like,
Hey, we need to slow down and get our processes right.
Or, you know, we need to, you know, do some interviews and
scope out the right, you know, solution here.
Like, does that feel like bureaucracy or like we're we're
we're not what we're like slowing ourselves down?
Yeah, Yeah, absolutely. Yeah.
I think that's, that's partly our job is to, is to kind of
paint the picture of the future and really, really get to why
this is important, particularly if it's a topic that the CEO
found. I've worked in tech a lot.
So a lot of tech CEOs might not have had been able to see or had
experiences where HR ran this way, operations ran this way.
They've seen Rev OPS working at scale.
Like I think sometimes it's our job to, you know, to educate in
that if you, you know, if you slow down and create this stuff,
it doesn't have to seriously impact your culture.
Your culture can still be exciting and innovative and
trying new things. And there is some benefit to
getting some of these pieces in place.
I think it's a mistake to paint the entrepreneur with a single
brush stroke. And I think that you're going to
get I, I, I, I talk about four archetypes of the entrepreneur.
And because they are so different that they will respond
to these things quite differently.
So archetype #1 especially in, in my business is the technical
founder. And so the technical founder may
come from an engineering background, may come from just
much more of, of the the the product focus.
The second one is going to be the go to market founder.
And this is a founder that may have come up more through sales
and found a technical Co partner, but you know, they're
leading and they're like their focus is go to market and
selling. The third is the finance someone
who is may have been ACFO or may just know the the finances of
growing businesses and how to do acquisitions and figure out how
to integrate them and how to manage all of the numbers.
And then the the last one is sort of in in by the way, this
may not be all MISI. You may see overlaps of Navs is
what I'll just simply call the visionary.
And the visionary is, is that person that is thinking out to
the solutions and is really just incredible at creatively solving
for problems. And you may have a single one of
these or some melange of them, and they're going to respond to
the scaling challenge differently.
They're going to look for different things and they're
going to bring different skills to it as well.
I I love that. So I imagine there's not one,
you know, silver bullet, like there's not one archetype that's
better than the others. Like each one, you know, has its
own, you know, pluses and trade-offs.
And I really do appreciate that. It's not, it's not like every,
you know, founder, CEO or entrepreneur is, is, is just
chasing squirrels, right? You, you know, that that product
person may actually need to chase more squirrels, right?
They might be like 2 heads down, focused on their product and not
looking out enough and exercising like creativity or
visionary thinking. But so, so you know, there's,
there's like these, you know, like strengths and, and, and
trade-offs probably to each archetype.
So, you know, independent of the archetype or the melange of, of,
of, of, of the mix. Gary, I'm just curious, like
you, you've probably had a conversation or two with the
founder, you know, that goes along the lines of like, you
know, what got you here is not going to get you there.
Can you help us understand? Like, what does that look like?
And maybe if you had a conversation, you don't have to
say the name or company or anything like that, but you
know, what does that conversation look like?
And, and, and how, and have you seen founders take that feedback
and, and run with it? And you know, or, or conversely,
like they just can't do it. They can't.
They can't make it happen. So when you get to the point of
having a conversation with the founder about their role or what
their team looks like or how their scaling is going, you
know, typically they're in pain and and you know, they're in
pain, they are expressing their pain.
It could be that they're working crazy hours.
It could be that they're having a hard time delivering on key
initiatives like they're in pain.
And so the, the the discussion with ACEO that in some cases
it's them, they are not the right person to take it to the
next level. In other cases it could be their
Co founder who was incredible in product.
But now you need a different kind of product organization or
any of these combinations. And so you need to be in a place
of first and foremost getting to the joint recognition that
indeed there is an issue. Indeed we've isolated where the
issue is and we have several options of how we could address
this. You want to empower the CEO and
in most cases, even if the CE OS the issue, they know they're the
issue. They've they're they're very few
who are not self aware to know where their challenges are.
And so I think that you know, you you can make it into this
beautiful drama, but it doesn't really have to be a drama.
And it doesn't mean that the the the things that got you here
won't get you here in the future.
Needs to that discussion doesn't mean need to be a game ender.
It can be the beginning of that next level of collaboration with
that founder, which can be equally as beneficial.
And I'll say one last thing, which is, you know, a long time
ago, and I'm sure you know, Jonathan, you, you say this with
some frequency. You know, I worked with a coach
and, and you know, the, the, the key focus of that coach was
getting me to identify my highest and best use.
And if you can, if you can focus on highest and best use of an
individual, then it's a very different discussion.
Because now you're saying, look at all the amazing things you
bring. Remember I told you the four
archetypes? Maybe they've been forced to be
all four of them and they really should just be one of them.
And that may be just a load taken off their shoulders.
So in many ways, these aren't just, you know, these aren't
just difficult conversations, these are coaching
conversations, Gary, that you're having with the founder.
The board should be a coach. If you're going to use a board
in the best possible way, the best possible way is not to like
use your decks to March them through all the slides and show
them the performance that you could have emailed them and it.
And if they're doing their job, they're reading what you want to
use the board is as a coach, as an advisor, as having more data
points than you do to be able to, to give you recommendations.
I love it. I love, I love orienting to the
I mean, a board is scary. You know, I've been just again,
talking from, you know, the, the, the shoes of, of, of a
founder. It's it's like an intimidating
thing to have a board and to be coming in and reporting to the
board, but that that shift in mindset and orienting to the
board as as sort of a a. You got to move beyond it being
a report card and and move it to being everyone is on the has the
same goal to make this business successful.
Let's all get together and have that discussion and I'm going to
be super transparent about where things are going well and where
they're not. That's where many founders go
awry is they try to couch what they're saying and put it in a
in a language there versus taking ownership, saying I tried
this thing, it didn't work. Here's where I think the next
direction is. So that that transparency, that
candor and us all, we're all on the same team here.
This isn't just like a, a quarterly report card in front
of a bunch of people where I need to, you know, put spin on
every message and slide. This is for us to come together
to move the needle forward together.
That's that's actually really valuable for the founders
listening to this podcast, but also I think for board members
as well, because I think board members sometimes do come to
these meetings approaching it like a, like a, a scorecard
report card activity. So I really appreciate that cat.
I you know. Of course, I read the white
paper that that you contributed so heavily to before this
podcast to freshen up. I was shocked by this statistic
that basically 60% of founders are no longer CEO by the time of
IPOII mean, I guess I'm just curious, you know, for, for all
the founders listening and, and, and those who are fascinated
with, you know, scale up ecosystems, like what's the
shift in mindset that you've seen that is needed by the
founder in order to be part of like that 40% that that are, you
know, surviving? Yeah, I, you know, I think, you
know, and I think we were talking about this before.
It's, it's really quite a different job.
I think it is that shift from, I think we say it in the white
paper, you know, from sort of chaos to organization and maybe
from sort of short term mindset to more of a sort of structured
longer term focus. I think that's that's really the
big shift, which can feel honestly like a completely new
job sometimes. And I think that that is sort of
the risk and there's lots of different pieces to it.
But to Gary's point, like if there was things that you loved
doing, you loved being, you know, if you're maybe the
engineering archetype, like you love being in there solving the
problem, you know, sitting with teams, actually doing the work.
And now suddenly your role is much more numbers and reporting
out and being, you know, questions and possibly judged in
a way on on your success in a way that you haven't
experienced, you know, in, in the times that you're really
enjoying work. It can, you know, it can be sort
of a lonely job and suddenly you're not doing any of the cool
stuff you wanted to do. And so sort of I think that's
that's one of the biggest challenges I think.
Yeah. I mean, when I, I, I, I work
with a, a, a founder CEO that IPO and like one of the biggest
like disenchanting surprises was, you know, all of a sudden
you've got to now like report on a quarterly basis to the public
and 1 penny off. Or even now, you know, with the
pressure that in the markets, like if you just meet
expectations or, or maybe you're like exceeding expectations, but
not exceeding enough for your forward guidance wasn't strong
enough that it could just like send you back 20% like like
that. And then all of a sudden
everybody's like all of a sudden short term focused and and then
it you know, you get to the next quarter, maybe you, you, you,
you, you crushed it. You tell a better narrative.
The stock goes up, but then the next quarter down it it the the
the cycle and the the volatility of this can create this like
very like short term thinking. And now all of a sudden like
this expansive, especially for the visionary archetype.
I imagine this would be like particularly hard for a lot of
that spark gets diminished. And I'm just curious from both
of you like, how do we mitigate, you know, that risk, that risk
of becoming as maybe like Jeff Bezos and the Amazonians might
say becoming like a day 2 company, right?
How do we mitigate the risk of becoming a Day 2 company where
that initial vibe and and that energy is is diminished?
Well, so I, I'm not sure the goal is to preserve the vibe
and, and, and, and what I mean by that is the, the concept of,
of a company pre IPO and a company post IPO cannot by his
very nature be the same thing. Now you and I can talk about
culture and preserving core tenants of our culture, but you
literally if you're a strong leader of a IPOA company that
IPOs, you need to be the kind of leader that says we were an
amazing startup, we had a journey, we grew, we created and
our job isn't over. We are ready to move to our next
level of growth, our next arc. And it won't be the same as our
previous arc, but it can't, it can be just as rewarding, but in
different ways. And that message to your
employee base, because one of the the things that's really
hard for companies is actually retaining those employees post
IPO. Cat knows this more so than I
do. And that, you know, you need to
it. And it's not simply money now,
because some of them may have done incredibly well in AIPO and
now you need to reinvigorate the organization with new incentives
and new excitement. That was not what people were
there originally. And there's nothing wrong with
that. And that's sort of my message
that there's nothing wrong with that.
Yeah, and and spot on. And, and what I'd add is like, I
think sometimes where things lag or sometimes where you can get
this kind of disrupted vibe or, you know, maybe even culture is
when you have a set of leaders or a CEO, founder or somebody
who like won't make that shift says, no, we have to keep
everything exactly as it was when we're a private company.
But also, you know, that's not the reality everybody's living
in. And so employees get this weird
mix of, no, we're still the same.
We're still, you know, cool and innovative, but what they're
seeing in reality is something that that looks and feels
different. So you have this kind of push
and pull moment. And I think that's one of them.
The mistakes as a, you know, at least you sort of see out there
around, you know, the 60% is maybe the not recognizing and
making that shift when they need to.
And then like Gary just said, reinvigorating towards it.
Success is is, you know, a huge motivator.
Sometimes the success looks different in startup than it
might do in a scaling public company.
But success is success. And so how do you start talking
about, you know, the public company's success in a way
that's just as invigorating as maybe it was in the past?
And I and I would say like it's really interesting people talk
about IP OS being milestones. Now a milestone just to keep
everyone on using our words correctly is not an end point.
It's a point on the journey. And so when you think about the
milestone of IPO hell, we're just getting started.
And so I think it's really important for folks to think
about this in the, in the, the journey that this organization
is on. And while this is an important
milestone, it is certainly not the end point.
That's really important. I'm wondering going back to a
point you may go, which I I found to be like, you know,
personally resonant like we're not solving for vibe.
So many founders can can get sort of caught in the trap where
they're solving for vibe and they're sort of like clinging to
that that, you know, kind of like founder energy.
And I'm just curious, like, can that be a derailleur, you know,
is in, in some ways, have you seen this like where, where
founders are doing that in some way to resist the natural
maturation to the next level? You know, could it be some kind
of like unconscious change resistance, you know, and from,
from, from actually growing up, right?
Like, I don't want to grow up. It's scary.
It's scary to be an adult. It's scary to be, you know, with
the big boys. Like, I want to go back to the
to the playground. I'm just curious, you know, I'm,
I'm playing with this idea. Yeah, no, no, no.
There are plenty of founders who find themselves in the
predicament that they solved a really important problem at one
point and the world is changing super quickly.
And the solution to that problem is not what they came up with or
the market their product is targeted to is no longer the
right market. And in and in so doing this,
there's this massive amount of like I, I was giving a talk last
week and I was talking about AI transformation.
And I, I said transformation used to be a project, like it
had a beginning and end. We're going to do project Opus
and project Opus is going to come from here to here.
And when all of a sudden magically we'll be in the cloud
or magically, you know, we'll be doing this with, with AI and the
world we're in, we're in constant transformation.
And so those founders who find it hard to create the culture of
reinvention and constantly pushing the boundaries for
themselves personally as well As for their teams are going to
struggle. And this has nothing to do with
IPO. This is just leadership in
general and what it's going to take to be successful in a world
where the idea that we're transforming our business is
never done. Right.
It's not, it's, it's, it's not a, you know, transformation
where we start here and and here and then we're done and, and now
we're, we're there and maybe there's another transformation a
few years later. We're we're in constant and
continuous change. So what I'm hearing from you is
that right again, put, put IPO, scale up, start up.
All that aside, like table stakes, to be a leader today is
like you said, Gary, to be in like creating a cultural
constant reinvention, which is that's hard.
If you're not disrupting yourself, if you're not
disrupting yourself, there are many little AI native companies
and competitors and the folks that used to not be competitors
say, what the hell? This looks like a juicy market.
I'm going to go into this market like we're in a hyper
competitive world. And so if you are not like
thinking of it in this world and I'm not picking on Gong in any
way. I'm just saying Gong did this
one great little thing. It recorded calls.
Wasn't that amazing? Well, if that's the only thing
it continued to do today, no one would care.
And so as you sort of think about like just what is going on
in a regular cadence of Business Today, the the great leader is,
is the leader that is paranoid. Paranoia is actually a powerful
tool for a leader. Like you need to see all this
risk and you need to see all this change and you need to
understand like the world is changing and I'm not sure where
it's going. And I'm OK with that.
And I know how to lead through that.
And so I think that you know what, what you're left with
today is a very different kind of operating world that every
leader of every business is going to need to, you know, up
their skills to be successful. Even if they've had successful
exits before, whatever they did there probably not going to work
now. And so you got to get to that
level. That actually that makes me
think about like, you know, Kat, you've been doing this for a
long time. I mean, you, you've led the
leadership development and talent development functions in,
in numerous start up to scale up organizations.
And you know, in that capacity, like you've got to like decide
like at this level, we're going to focus on these attributes and
competencies and then this level we're going to focus on these
leadership skills. And at this level of our
emerging leader, we're going to work on these skills.
It's like a, it's, it's like a jigsaw puzzle specific to the
context of, of being, you know, in this in motion from start of
the scale up. And then of course, specific to
the organization, whether it's Hashic or Pinterest gone,
whatever it is, right? I, I'm just curious from, well,
I got 2 questions. Like one help me understand how
this like how do you get this accepted into the system, into a
system that's always like working harder than like their
actual capacity that's always under tons of pressure?
How do you get people to like slow down to basically learn
leadership skills? Like I'm wondering, you probably
get a lot of resistance. Like no, like we don't have time
for that. We don't have budget for that.
We're we're putting that into, you know, our marketing budget,
like the people figured out given this book, you know, like,
so I'm just curious like how you, you know, get buy in at the
broadest level of of a start up to scale up.
And then my second question really to to to both of you,
just like thinking about the skills we need right now in this
point in time. So if we had a magic wand and
can create like the the ultimate leadership development
experience for a, a pre IPO or or just recently post IPO
organization in the year 2026, like what would that look like?
So, so, but let's go to the first question for yeah, just
like table sticks. How do you get adoption of
leadership development and that investment of time and budget in
in an organization that's moving at like 120 miles an hour?
Yeah, yeah. I think, you know, I think as
the world's changing, you know, our development models need to
change as well. You know, I think in the past it
was OK to grab a bunch of leaders and take them out of the
business for a week and, you know, take them on a track and
learn team development skills and, and things like this.
And, you know, very common set of skills that we're going to
lead to success as a leader. I think that is all kind of out
the window now. I think really, really good
leadership development is when you can sit alongside a leader
for a period of time and really understand what are they doing
in their business, what are their business challenges, How
is their team around them operating?
How you know, what are some of the struggles that they have
with their particular business and then being able to sort of
OfferUp those little bits of, I call it in the flow of work kind
of moments or practice or support that helps them get
their job done. And that's, that's really where
I think leadership development is going is around getting much
closer to the business and to the leaders that we're there to
help develop, understand where the business is going.
Like really put a business lens on and then create just little
moments of support, almost like sort of sitting with, with your
courage to help them get the job done that they've got in front
of them. But at the same time, keeping an
eye on the future, which is, OK, you've got a problem today,
Let's practice a new skill. How does that feel?
What does that look like? What's some feedback?
And then when that challenge comes up again, let's practice
that skill again, building over time rather than thinking
there's sort of a silver bullet. It's just it's not that way.
So it's not about, you know, carving out the three days and
going off site to the mountains or something like that, that
that's, I mean, does that work? I think it depends on the
challenge that the, that the leader or the leadership team is
facing. I am and I don't, you know, I'm
not saying that sometimes it's, it's necessary to take a group
of leaders, maybe a leadership team out of the business for a
second so they can all figure out how do I work together?
Maybe they have instead of conflict that is starting to get
in the way of their decision making.
OK, so it's OK to say, yo, time out.
Let's step away here for a second.
Let's figure out why we keep running into conflict here as an
executive team, how that's slowing down our decision making
and what impact is that having on the business and how do we
start to get past this so that this conflict isn't slowing us
down anymore? And so if that's the problem, I
might say, yeah, those in the moments like little hints and
tips might not get them over this hurdle.
You might need to pull them out and say, hey, we need to really
fix this and then get them back in.
But that's you being very close to the business and starting to
understand the root cause of how some of this is happening.
So in the in that instance, you might come in for an hour, see a
meeting, understand decision making is the problem, and then
create an operating process for them to start decision making.
But if the conflict is actually the problem there no operating
model in the world is going to help because there's, you know,
contrarians and things like this in the group that are that are
disrupting decision making. But that's about getting close
and then finding the solution that meets the need.
And I and I would, I would add Kat on that piece there.
I think you make some really important points here. the IT
really depends on the problem and what is the best tactic to
have progress. So I'm, I guess because I'm so
over rotated to AI today that I believe very strongly that we
need to work harder to have the human to human pieces, which I
think actually can be more impactful.
And so as you like, look at your like tool belt of ways that you
can drive change and impact on management teams, on leaders.
Some of it can be done async and could be training that you do
online, but that has limits it I think if you do it on Prem,
awesome, maybe that you take some time on Prem and do it.
But when you're on Prem, you sort of have all the business
pressure in the meetings and people knocking on the door and
all those pieces. And so you may need to get to
the mountains just because the problem demands dedicated time.
It can't be just your sort of side hustle, so to speak.
It needs to really have a dedicated way.
To solve for that leadership issue.
So again, you know, I'm, I'm not trying to overcomplicate it, but
I also don't want us to take, you know, a single point of view
because the problems are just so different as Kat was indicating,
you know, it really depends. That's I love that.
I love the concept of tool belt and having like multiple, you
know, sort of options and tools depending on the problem we're
trying to solve for. And, and, and one of those being
the mountains, but others being, you know, bite sized learning in
the flow of work. Fantastic.
I mean, maybe we could just come back to this topic of leadership
in, in our current times. You know, we're, we're getting
towards the end of the year, about to start a new year 2026.
We're all experiencing the like incredible disruptive power,
which presents both an opportunity and, and, and
perhaps challenges at the same time concurrently with regard to
AI and then and the, the, the massive force of innovation that
brings. What Yeah, like are the
leadership skills that leaders need to be developing and
learning the same as they were 10 years ago?
Or like, do we need to be focused on, you know, some
distinctive skills or attributes right now to be successful?
You know, Gary, I, you mentioned, you know, we got to
be a little more paranoid. Like should we be taking like a
paranoia one O 1 class? And I'm just being cheeky with
you, but curious. Like, I don't know, like what
what, what does a leader need to do right now to be successful
to, to, to lead effectively? I don't think it's ever been
harder to be a leader of a business than it is today.
You know, I, I mentioned about the transformation, the constant
transformation, managing that is incredibly challenging.
And I think, you know, when you look at the skill sets that we
have always valued, whether it be communication skills or maybe
it's the the capacity to know how to navigate an organization,
or maybe it's the skill of truly creating leadership and goals
and, and endpoint, like none of those have changed.
I think what you know, people misunderstand about AI today is
they think that it's a technology challenge when in
reality it's a change management challenge.
So all the things that you've leveraged in the past to manage
change need to be in the leaders tool belt again, like this needs
to you need to be able to have the right kind of training and
you need to create the right kinds of incentives.
And you need to understand that, you know, the organization is
probably going to lose some people because there's not the
right fit. And, you know, these are not
I'm, I'm not minimizing these in any way to say that these are
easy choices or that these are are are decisions that leaders
take lightly. But the in the in a world that
is accelerating in the pace of change, this is not the time to
just put yourself on the side and say, you know, I'm going to
wait and I'm going to figure it out.
I'm going to see how things work.
Because you may wake up and your market's gone.
Your customers are gone. Like because someone moved
quicker, more decisively, created the right kind of goals.
And I, and you know, you've heard the, you know, move quick
and break things thing that reality has never been more
important because your customers are under a different set of
pressure. They're getting the, have you
adopted AI yet? Or where's my ROI from my AI
initiatives and investment and all this?
And are you someone that can help them with that?
Are you someone that could be net plus as long as you're
transparent? You know, I'm never one to
advocate for like vaporware products.
I'm here to advocate for clear direction and road map, like a
very clear direction that you know, I'm going to stick with
you because you have a place and you may not have all my
functionality I need today, but you're going to bring that in.
All good. Yeah, I think, I think that's
always been there and I think more so than ever, right.
If you're sitting in an environment where not not only
are your customers changing and moving and getting new things,
but you and in your flow of work, like in your work, you're
getting asked to, you know, AI tools, things like this, get
your work more efficient, move faster.
Having a leader that creates this, this calmness in a world
that is chaotic and, and, and you know, fast-paced.
I think that is just such a skill that that if leaders have
it and can kind of harness that without slowing anything down,
but just this calm voice that says things are moving.
The way we approach it might look different next week, but we
are focused, we are clear, we are confident and we are moving
forward in this direction. I I just think there's there's
such a skill and when you see it done well, it just settles
everybody down and they can move through change.
Knowing that like somebody's somebody's at the helm and
they're confident we're in the right direction.
It's really paradoxical. Yeah.
It is. It is.
Because on the one hand, I'm hearing like.
You know, it's, it's, it's really the leader's job to, to
not just navigate change. I mean navigate change.
That's so like, you know, 2020, you know, it's the leader's job
to keep the ball in motion during constant transformation.
So the leader is actively changing and moving the
organization towards something. And at the same time, what I'm
hearing is like the leader needs to be a, a, a, a stabilizer to
the people in the organization, right?
So how does the leader move and propel the organization through
this context of constant change while also grounding people?
That's like a real Jedi skill. I want to add one other word
here. Cat use the word, but I, I, I
would almost juxtapose the, the calmness for the word I'm
thinking of, which is clarity. I think clarity makes everyone
more comfortable. I think we're we're
organizations struggle is when they're like, you know,
squirrels chasing, you know, a different nut every day that
feels super uncomfortable and and and not calming.
But I think clarity drives calmness.
And I think that those leaders that commit are also comfortable
in recognizing if they commit and they need to pivot there,
there is less shame in that than ever.
Like you should be rigorous at solving the problem, not about.
Rigorous on staying on the path, Rigorous about solving the
problem, not just. Staying on the path, I love that
because the path is like, you know, that's.
That's really that's. Really profound.
OK, this is this is fantastic. So I, I want us to just as we
get towards the end of the of, of the hour here to, to channel
your experiences working with a start up to scale up that is,
you know, about to go IPO or really just any kind of
inflection point. It could be a private equity
investment, it could be a fundraising event, but something
that is going to create this discontinuous moment and propel
the organization into sort of a new level of growth.
What advice? So I'll start with you, Gary.
What advice would you give to a founder CEO who is about to
embark on that process and is saying, Gary, I got this, we're
good, we're solid. What advice would you give that
founder CEOII think the. Most dangerous thing for most CE
OS is to stop questioning their assumptions.
And so they need to be constantly challenging their
assumptions. And again, this gets back to all
the things we were talking about, the assumptions about
what got us here that may not get us there, the assumptions
about who on our team are the right people versus not.
It's also about our business model and our markets and our
solutions. Like you, you know, I always
tell this story about bias and how dangerous it is it is to
organizations. And let's say you had an
employee and they're always late to every meeting and that really
bothers you and you finally are fed up.
I'm firing that employee and now you're going to hire a new
employee. And guess what?
That employee is, God damn it, going to be on time every time.
And you hire them and guess what?
They're on time every time and they can't spell.
And So what you've done is traded 1 issue for a different
issue and you haven't really, you know, thought about like
really without all the bias, without all the things that you
think made you successful, How do I now navigate this next
journey if I don't feel comfortable, empowered and part
of my daily existence to challenge what I believe are my
truths so constantly? Scrutinizing and challenging
one's assumptions. I I think that's incredible.
Sage advice, Gary, thank you. Thank you.
OK, Cat, you could go with the founder, CEO or or CHRO or chief
talent officer of an organization about the IPO.
They say like we got this, we're fine, it's all good.
We're we're ordering the confetti now.
It's going to be amazing. You know, all I need advice on
is like, you know, what are we going to have for our appetizers
at the, at the the post IPO party?
What advice would you give to that person?
First, I'd say you need to delegate, maybe a.
Little bit more effectively. That doesn't seem like the
decision making. You should be focused one of
that moment. That might be a separation
conversation. I, you know, I think if, if
you're leading a people team that's, you know, scaling
rapidly, it, it might be a little bit boring, but I think
it's like, go and check out your foundations.
Do you know what great looks like in leadership?
Do you have a clear, solid, you know, very wide, very deep bench
of leaders who are either building to be ready for that
sort of executive level job or are ready now when you're sort
of like keeping them warm? I think we talked about it a
little bit, but attrition is a really big, you know, really big
risk when you go through all these changes and all the
changes we sort of talked about. And so managing your risk around
attrition, particularly at that executive level.
I that would be my like #1 to get after and just really being
clear on sort of who, who is your succession slate?
Don't do 1 to 1 replacements, but really think about that next
leadership bench. I think sort of there's twofold.
1 is you may lose an executive. You don't really know how any
one person is feeling and things are changing.
And so I'm being prepared to have somebody to step into that
role. So that business continuity is
there as much as possible, I think is important.
And then I also think these executives are about to move
into maybe the biggest role of their lives, maybe adding much
more complexity to their role in the day-to-day.
The CEO, you know, we talked about is sort of going to go
have this different, different job, if you will.
And so if you've got a super strong set of leaders that are
there supporting and lifting up that executive group as they
step into this new moment, I think, you know, that's that's
huge as well. So yeah, focus on your bench,
get you ready now leaders set up and, and, and good to go.
And then sort of following from there.
Excellent advice SO. Have a like sort of a deep
talent pipeline. Like don't just assume that like
this All Star team that that sits at the C-Suite that they're
going to be there forever. Like we need to have good talent
at multiple levels and to be thoughtful about, you know,
readiness and and succession is what I'm hearing like that, that
that, you know, like who wants to think about that when we're
about to like all become, you know, gazillionaires?
But like, that's actually what we need to be thinking about
creating a really healthy, robust talent pipeline.
Exactly. And I feel like in these.
Moments because they are so exciting and everybody's like
ready for the next thing that sometimes that can slip away
like, Oh no, our executives are super excited to be here.
They've worked so hard to get to this moment.
They're going to carry on doing this, you know, be here forever.
And, and actually, what we see in the data is sort of the
opposite of that. And so that can be yeah, that's,
that's sort of the recommendation.
Really, really good advice. Any parting thoughts?
Any, you know, we, we covered a lot of ground here.
Gary and Kat, any, any parting thoughts or, or other advice
that you would give to our listeners who are keen to
understand leadership in general, 'cause this is a
podcast about leadership, but also specifically in this
context of, of start up the scale up and how do we mature
effectively, right? How do we mature effectively and
intentionally? Cat Sart.
Oh God. Well.
You know, one thing that we haven't really, I don't think
we've touched on necessarily. So I'll throw it out there as,
as something to think about and, and not necessarily, you know,
final words of wisdom or anything like that.
But I I've been thinking a lot about lately how we help
founders and executive teams that have been going through a
shift from the start up to more scale is how do we help them
really trust the experts that they have brought in and put in
place around them with the intention that these are experts
in this particular thing. And you know, maybe it's what,
yeah, it could be anything marketing, you know, accounting,
treasury, whatever, legal, but like hiring an expert at senior
levels and then how do you trust them and take their advice and
stay curious and know your own limitation in that space?
I think it's something that that at least instead of in my
experience is sometimes it's so hard for the CEO to say
actually, I don't have an expertise in this area.
Maybe I don't know the rights of decision here.
I've hired all these really expensive talent.
Let me get them in a room and they can tell us how we move
forward. And so I, you know, there's
something here around. Stay curious, stay humble and
trust your experts. You've paid a lot of money for
them. You should be listening to them.
Yeah, I, I, I have a a similar idea, but a bit of A twist,
which is to say you should really try to match your exit to
your leadership capability. And the, the, the fact that an
IPO seems bright and shiny and amazing and you have this image
of yourself ringing the damn bell like that's amazing.
But you may not be that kind of leader.
And there is no shame in you saying that.
My monetization of my business may come through other means
which are just as fulfilling, but not maybe the IPO.
It's not like the IPO is the only exit.
It's not like the IPO is the best exit.
Like you need to really match a little bit and and to using
Cat's word, being humble enough to recognize where your skill
set is and what is the exit that's going to match on what
you can actually deliver you. You need to really be honest in
the end about that. Wow, the great.
The great irony, you know, we're talking about IPO, which is this
like ecstatic moment. You know, you see, you know,
usually, I mean, not always, usually you need to see this
like big pop in the stock price and overnight, you know, people
become, you know, millionaires or, or, you know, that that
there's, there's this opportunity to get liquidity and
something they worked so hard for.
And wow, I imagine that could be something that could, could go
to, you know, one's head quickly.
But yet we're talking about, we're ending this podcast about
leadership on the topic of humility being, you know,
really, really significant, really important self-awareness,
humility, trust. And so I, I this is, this is
fantastic. I think it's the perfect place
to, to stop. And I just want to thank you,
Gary and Kat, for taking the time to share your experiential
wisdom. So everybody knows you guys are
wicked smart and wise, but there's experience in the
trenches with these organizations, with these
founders and CE OS that you bring to bear.
And it's just so valuable for us.
So, so thank you so much and thank you to all of our
listeners. This is a podcast about
leadership and looking forward to our next episode.
Bye for now. Thank you.