Video summary
The video explores the fundamental shift required for effective leadership, moving away from the traditional mental model of a leader as an authoritarian captain steering a machine-like organization toward viewing them more like a gardener cultivating a living ecosystem. Many leaders initially operate under the illusion that they can control every variable through strict instructions and measurable outcomes, but eventually reach a turning point where they realize this approach fails because organizations are complex systems rather than simple machines. To survive entropy and adapt to change, these leaders must let go of the reins and understand that their role is not to command from above but to create an environment where people can connect, find meaning, and exercise agency within clear boundaries. This transition involves recognizing that while certain functions may seem mechanical, the core of any successful organization is a living entity driven by relationships and shared purpose rather than rigid control.
A crucial distinction made in the discussion is between complicated systems, which follow predictable instructions like building a watch or assembling Legos, and complex systems, such as raising a teenager or leading an innovative company, where outcomes emerge from interactions that cannot be fully predicted beforehand. In complex environments, relying solely on information gathering is insufficient; instead, leaders must learn through experience by probing the system to identify emerging patterns known as attractors. The transcript illustrates this with historical examples like Emperor Hadrian's attempt to groom a successor versus Marcus Aurelius and Antoninus Pius developing an affinity through long-term apprenticeship without prior instructions. These stories highlight that complex systems require humility, experimentation, and the willingness to navigate uncertainty rather than seeking straight-line solutions or trying to control every outcome from the start.
To foster this kind of complexity-driven growth, leaders must actively cultivate moments where individuals feel they matter and belong to an enchanted circle of shared value, which often sparks transformative energy in history and personal lives. This is achieved not by leaving a door open as a mere gesture but by intentionally designing spaces that invite feedback and support people who might otherwise remain silent due to fear or hierarchy. The video cites the example of Navy SEAL commander Dave Cooper, who would admit his own mistakes on purpose to create psychological safety where team members felt empowered to correct him without retribution. Conversely, leaders like Elon Musk are criticized for punishing dissenters publicly, which destroys trust and prevents future communication of critical issues, demonstrating that true leadership involves constantly humbling oneself and inviting the least powerful voices into the conversation rather than asserting dominance or vindictiveness.
Ultimately, effective leadership requires mastering the art of surrendering control to engage our relational attention system instead of being trapped in a narrow task-focused mindset driven by an evolutionary urge to win immediate interactions. Leaders must learn to flip between short-term desires for correctness and long-term goals like maintaining relationships or organizational health, recognizing that winning every argument often leads nowhere significant while losing the bigger picture matters immensely. By embracing Stoic practices such as admitting fault, asking questions of subordinates, and viewing leadership as a journey of experimentation rather than a static position of power, leaders can unlock their potential to guide living systems toward flourishing outcomes without relying on ego or false certainty about controlling every aspect of reality.
Read the full video transcript
What do you think goes into the
cultivation
of becoming a leader? When
we talk about leader, there's a mental
model that comes in all of our minds
that we're kind of been trained on,
which is like captain of the ship,
right? I'm steering, I'm controlling,
I'm
I'm in charge of things. And I think a
lot of us start out with that model, and
a lot of our systems are built with that
model. And what happens, at least as
I've experienced it in the three books
that I've written that connect with
this, is that most leaders go through
this process where they do that for a
while,
and it then they then they reach kind of
a turning point, and all of a sudden
that they realize they have some
insight, some
road to Damascus? Is that Is that the
correct road? Some road to Damascus
moment where it's like, "I This is not
working. I'm running it like it's a
machine. I'm trying to put levers and
get instructions and have measurable
outcomes and absolutely push push push."
And what they do is they let go of the
reins a little bit. And that's the time
when they start cluing into how
I would argue the world actually works,
which is that it's not a machine. It's
more like a garden that you can grow and
cultivate and have move in a certain
way. And all the good organizations An
organization is not a machine. An
organization is ultimately it it has
machine-like functions, but ultimately
like down super deep it's a living
thing, right? And if you're going to
beat entropy, if you're going to like
keep surviving and adapting in this
changing world, if you operate like it's
a machine, you can steer, you'll reach
the end. Like it will stop working. So,
what these leaders do is they realize a
couple things.
The first is that they need to create a
sense of meaning and mattering. They
need to to really have people connect
and build relationships. That ends up
being area number one. Area number two
is they need to design space for agency.
They need to create spaces.
Organizations aren't machines, they're
they function more like rivers. Like you
need to have clear boundaries, what
we're not going to do.
River banks going to just stand strong,
it's not going to What we're not going
to do. We need to have a gradient, like
a horizon we're going toward, right?
We're We're going that direction. And
anything you do in that space,
go do it. Have some agency. And the good
organizations, when you look at the
Seals, when you look at Pixar, when you
look at top-performing organizations,
what their leaders do inevitably, I
think, is they create that sense of
mattering and meaning, which you can
think of as almost like
that's the connective energy. Like
that's the the cells that are alive,
that are connected. And now, we're going
to channel that energy into this
direction, not here, not here, in this
space, and now it's up to you guys, go
do it. One of the things I learned for
me with this with looking at this stuff
has been the difference between
complicated and complex. Hm. We use that
as like synonyms, right? It ain't. This
This was like my little I still walk
around thinking about this all the time.
Complicated things come together the
same way every time.
A set of Legos. Instructions to build a
Ferrari.
>> A watch.
>> A watch. Same every single time, right?
You put it together, you'll get a watch.
Complex things change as you interact
with them. Hm. So, the question asked is
it more like building a watch? Is it
more like raising a teenager?
Because everything there's no set of
instructions, there's no 1 2 3 4 5. So,
yet we walk through life, because of the
way our brains are built, always sort of
seeing machines. And the way we're also
kind of trained, I think, we're always
looking for machines, always assuming
things are machines, we're always
looking for that straight-line solution
that will fix it, like that will allow
us that sense of control that we want.
And I think leaders especially who
realize
there's it's not complicated, it's
actually complex. We're on this journey
of experimenting that's going to take us
left and right and around, and there'll
be new stuff, and when that new stuff
appears, I need to be ready for it. If
it's complex, you want as much
information
as you could possibly have. And you want
to learn by experience. The best what a
mathematician would say is in complex
systems dynamic theory would say is the
best way to learn when it's complicated
is find the expert. Mhm. Like find the
expert who's a watchmaker. When it's
complex, you actually have to learn
through experience. Probe is the word.
So, do an experiment. Do an experiment,
see what happens. And then you'll get
what they would call attractors, like
patterns will come up that you notice,
and you're like, "Oh, that's cool." or
"Oh, that sucks." And then you kind of
follow where that takes you. And that's
kind of how we live [clears throat] our
lives, actually, when you zoom way out.
What's funny maybe where some of this
stuff intersects with what I write
about, I'm fascinated by this sort of
brief period of Roman history where
Hadrian's the emperor,
and he is having to choose a successor.
There's a a handful of Roman emperors
who don't have sons, and they have to
choose their successor. So, he's having
to choose, you know, somebody for a job
that only like 15 other people have ever
had.
And so, you know, who does he pick? And
for some reason, he picks this kid who
would become Marcus Aurelius, you know,
a privileged but otherwise, you know,
unremarkable person. And he decides to
to groom him for power, but he
understands he doesn't have enough time
left. So, he adopts this older Roman
senator named Antoninus, on the
condition that Antoninus in turn adopt
Marcus Aurelius. He's not just choosing
his successor, he's choosing his
successor's successor. And he probably
thinks that Antoninus is going to live
for, I don't know, 5 years or something.
Or maybe he even thinks like at some
point Marcus will kill him, and then
he'll take over. Like just the brutality
of the ancient world is going to handle
this problem. Yeah. But instead,
Antoninus lives for two decades. And
these two men, Marcus Aurelius and
Antoninus, who have no affiliation other
than they were just thrown together by
this
guy who they're also not related to,
they develop an incredible affinity for
each other. So, so Antoninus rules, he
takes seriously that he's going to tutor
this kid, and at some point Marcus
becomes co-emperor.
Again, like this has never happened
before in human history. So, so
Antoninus ruling and teaching, then then
they're co-ruling together, but it's
basically this this two-decade
apprenticeship. And then eventually
Marcus Aurelius becomes emperor. And
then, this is where the story gets
interesting, he has a son. His son is
Commodus. So, one version is Commodus
gets a 15-year head start of on-the-job
training. But instead, it actually goes
horrendous, like it's it's as bad as
Joaquin Phoenix's character portrays it
in in Gladiator. And so, you know, what
goes wrong? History is not a science
experiment.
You don't get to control for your
variables.
>> Yes. But here, you have like this sort
of compare and contrast. It works in one
case, and then it doesn't work in this
other case. I'm just endlessly
fascinated with,
you know, first off the idea of like
actually
saying like, "Hey, I want to learn
everything I can about this job I'm
about to take." And then, you know, how
somebody else who decides not to do it
goes so terribly. Springsteen's been in
the news lately, and it's like he talks
about the moment he saw Elvis on the
television. Yeah. Like the moment,
right? These moments of ignition, and
they're not about information. They're
not about like learning some fact or
seeing some person. It is about this
energized relationship where you are you
find yourself mattering. You find this
sense you're you're you're seeing some
immense value, some enchanted circle.
And those moments, I think, they happen
all the time,
and they end up driving these big things
that happen both in history and in our
lives individually. And cluing into
them, as as a parent, I think about that
a lot. As a as a community member, I
think about that a lot. As somebody
who's in in a high-performing
organization, it's like, how do we
cultivate those? Like where did that
happen I don't I can't help but wonder
like where did that happen for you? Cuz
you got lit up at a pretty young age.
>> I did. I mean, someone handed me the
ideas from the Stoics, and I was like,
"Oh, where's this been?"
>> I'm in. And And so, I think
>> What Go back an inch, but like what led
you to be in? What led me to see it, or
what led me to be excited Why were you
craving? Or why why did it What itch did
it scratch for you? Or where did it
Where did it resonate? Why one thing
lights us up and another doesn't, I
think there is I I do think there's
something
sort of otherworldly about I I don't
know how much choice we have over that.
Like
>> Elvis through the TV. That's the
feeling. Yeah, there's this sometimes it
lines up. Like why this person loves
physics and this person loves, you know,
physical education, you know, who knows?
But like the decision to me that's
interesting is what do you do next? Like
cuz how many people go, "Oh, well,
that's impossible." or "Oh, well, that
seems like a lot of work." or "Oh,
that's not for people like me." or you
know, it's What do you
What do you do with it? That's what
ultimately matters. Right. I talked to a
guy named Dave Cooper one time who
headed up the people who got Bin Laden,
Navy SEAL Team 6 commander, and he said
the most foremost important words that a
leader can say are, "I screwed that up."
And they go It goes two directions.
You are you are fallible, you have wrong
instincts, you screw things up, but to
everybody around you, it creates that
space
where they can step in and say, And next
time I can help you,
they can help you before you screw it
up, because they know you're okay with
being wrong. You got to talk to me. He
would stand next to a window and kind of
do it on purpose, and then there'd be
someone new in the room, he would say,
"Hey, you got to tell me to move away
from the window. I didn't realize I was
standing by the window, that's a
dangerous place for me to stand. Grab
me. If you have to grab me, grab me."
Creating that space where you're saying,
you know, "Hey, you have a voice. I
don't need [clears throat] to
This is not just safe for you to speak
up, but it's you have a role here. It's
really important that you speak up."
Yeah, there's a story about Hadrian, who
was actually not that great of a leader.
He was problematic. Not ironically not
the model that Marcus Aurelius wants to
model himself after. It's It's
ultimately Antoninus, but there's a
story about Hadrian arguing with one of
his advisors over some philosophical
question or mathematical question, some
something that they're arguing over. And
they go back and forth, and eventually
the advisor says, you know, "Actually,
you know what? You're right. I'm wrong,
you're right." And uh a friend comes and
he says, "Why did you Why did you do
that? You You're like objectively right
here. There's no Yeah.
Let me show you you know why you're
actually correct." And and the advisor
goes, "I think you're mistaken." He
says, "The man who commands 40 legions
is always correct." And that is the
problem with being the the leader or the
the person in charge, especially if you
are intimidating or vindictive or you
know, withholding or any of those things
that can serve as a sort of not just a
deterrent, but then also a punishment to
people who correct you or you you end up
not getting the thing you desperately
want. And so to do that that jujitsu
that is required of do that of
constantly humbling yourself, of
constantly asking the least powerful
person what they think, of constantly
invoking stories where you screwed up
>> Yes. is like ends up being like the
stoic practice maybe of like this sucks,
but God it creates conditions for this
for this group brain to light up a
little bit and and knocks us out of our
reflexive hierarchical kind of wince
that we all do around power. And so
these the leaders that I've been around
have got those jujitsu moves down. They
always are saying, "I'm probably off on
this. I don't know what do you what do
you think, Bob?" And they're constantly
deflecting. They're constantly walking
around and saying, "Hey, if you could
change one thing about what we do here,
what would it be?" Yeah.
>> One thing. Change one thing. Like little
They're they're like a little firehose
of little signals that are like, "I'm
I'm an idiot." It's kind of what all of
them say, you know, "Help me out." What
they're what they're not doing is what
leaders think works. They go like, "My
door is always open." Nope. And and then
they think that's what's going to create
a culture of feedback and criticism and
you know, sharing. No. Right. Exactly.
It doesn't come close. You have to
actually build spaces, platforms,
support people to get in that room and
say those things cuz we don't typically
want to.
>> Yeah. There's a story I think I told in
Wisdom Takes Work about Elon Musk or
someone. He just shared something
horrendously offensive and stupid on on
Twitter and one of his employees is
like, "Hey, I got
I'm genuinely worried that you shared
this, you know, like 1% of the
population would fall for this thing and
you fell for you know, he's like sort of
laying into him. And and Elon Musk like,
"You're [ __ ] fired." You know, he
fires him, kicks him out of the room.
And then later in that same meeting he
he says like, "Why isn't anyone else
talking?" You know, it's like because
you just executed someone in front of
them. Like they're not only not going to
share in this meeting, they're not going
to share some safety concern or some
legal concern 9 months from now or 9
years from now that could prove
catastrophic because you just gave them
a very powerful demonstration of what
you do when people criticize you to your
face. Unbelievable
the lack of awareness of some of that
stuff is almost hard to believe. Our
capacity for self-deception is And the
timelessness of it, right? This is This
is what
>> kings were doing uh
10,000 years ago and you know, it's also
what you know, parents do. We go like,
"I want you to come to me with
anything." And then and then the last
time they came to you, you grounded them
and then you wondered why they're not
opening up to you. And underneath it all
like I'm I'm I'm so fascinated by that
moment those moments because
one [sighs and gasps]
another sort of big unlock for me
besides is is like this idea that our
that we've got two attention systems.
Like we have kind of a task attention
system that likes to do that kind of
stuff. That likes control that is built
to get who will know and rid me of this
priest, you know, that says bold things
and that sees the world through a very
very narrow tube.
>> Yeah. And that is built The evolutionary
part is fascinating me. That is built to
grab food. Is built to
spot something valuable, control it. Win
the win the interaction you're currently
in. Task attention. Win it, right? And
then there's this other form of
attention, you know, relational
attention where it's like, "Oh,
evolutionarily I need to pay attention
to the sky, to the social fabric. I need
to be nuanced. I need to really connect
to what's going on." Right. And the the
unlock was that they compete. You can't
have both on at the same time.
And in all these moments, they're all
like examples of people who are feeling
super strong.
Cuz that's how you feel when you're
controlling. It feels great to say that.
Musk felt awesome when he said that.
>> Cuz he was he was reveling in his power.
So much control. And the move over and
over again is to like
surrender that and and and say, "Well,
wait a minute. Wait a minute. I really
can't control it. I'm I'm really not the
center of everything. I can't control
everything. I'm I'm I'm just a person in
this space. What's going What's What is
this? What's actually going on here?"
And the leaders who have the ability to
make that move Yeah. where they Every
they they got to be a leader something
because they like control a lot of
times, but to have that move where they
can actually sort of let go or parents
who can have that move and actually sort
of let go. It's like the short-term the
the flipping between short-term
long-term. Do I want to Do I want to be
right about the couch or do I want to
stay married, you know? Do I want to
decide my kids' major or do I want them
to bring their grandkids around
>> [laughter]
>> 20 years from you know, like like are
you in the trap of the present moment or
can It's funny cuz we think philos like
we go, "They're philosophical." It's not
like they know Aristotle. It's like the
lower case philosophical I think to me
it's like, "Can you see the big picture?
Can you go to what really matters?" And
so often you're in these exchanges where
the thing you're trying to win doesn't
[ __ ] matter at all. Right. And our
society is sort of increasingly built
around those types of exchanges.