THE LEADER AND THE PARADOX - The Art of Leading Between Contradictory Styles
- Dec 16, 2025
- 7 min read
I’ve been working for many years with founders, teams, and investors.
And even though the industries differ, the numbers change,
and the level of enthusiasm varies depending on how close payday is,
there’s one thing I keep seeing, over and over again:
paradoxes.
In entrepreneurship, there is no perfect calm.
There is movement.
There is tension.
There are contradictions that sometimes show up before you even manage to put them into words.
As a company grows, they grow too.
And from what I see in the projects I work on,
leadership starts to mature exactly at the moment when you stop trying to choose between them and begin learning how to use all of them.
Not in a static, artificial balance,
but in a living integration.
One day you need… people.
Another day… results.
Sometimes… innovation.
Other times… order.
A good leader is, at the same time,
a mentor and a visionary,
a competitor and a builder of processes.
Not one after the other.
Not according to a manual.
But depending on the moment.
Because leadership isn’t a single skill.
It’s a repertoire of complementary styles,
… and sometimes deeply contradictory ones.
Styles you practice until you can use them without fear.
PEOPLE
When the team needs to be seen before it can be guided
There are periods when the real center of the business is people and how they feel.
And you start hearing comments, often said with a mix of honesty and self-irony:
“For me, success is simple:
if I didn’t upset anyone today, it was a good day.”
Or:
“I feel like I’m doing my job well when colleagues come to me not just with problems,
but because they actually enjoy working together.”
In moments like these,
leadership needs more
warmth, patience, and presence.
People need to feel they’re moving toward you, not away from you.
And this does wonders for morale and collaboration.
But this is where the paradox shows up.
If you stay here for too long, you start to:
delay decisions,
over-protect,
avoid necessary truths,…
and carry too much emotional weight.
So the need for clarity appears.
Not instead of empathy, but alongside it.
And this is where good leaders start asking themselves:
“Where do we need ‘let’s talk’… and where do we need ‘let’s decide’?”
“When am I helping people… and when am I protecting them too much?”
“Which conversation needs patience… and which one needs a bit of courage?”
“Where am I keeping the peace… but losing progress?”
Leadership here becomes a living balance between closeness and orientation toward meaning.
DIRECTION
When the future brings more possibilities than the present can carry
There are periods when ideas come faster than you can put post-its on the wall.
A good idea appears, then another one, then two more,
and you barely have time to ask whether anyone can actually carry them.
Someone once told me, smiling:
“If one more new idea shows up this week,
I’ll open a separate folder: ‘Ideas 2028+.Not for now.’”
Another one, more pragmatic:
“We’re not against change.
We’re against Wednesday changes that get changed again on Friday.”
Here’s the paradox:
without new ideas, you don’t innovate;
with too many ideas at the same time, you don’t move forward.
The problem isn’t the team’s pace.
It’s unpredictability.
From what I’ve seen, mature leaders don’t suppress their ideas.
They discipline them.
They test them step by step.
They anchor them in reality instead of throwing them into chaos.
And they start asking questions like:
“How do I keep space for new ideas… without losing the finish line for the old ones?”
“What’s truly urgent… and what’s just today’s enthusiasm?”
“When do I bring the visionary forward… and when do I let them step back so I don’t confuse people?”
“How much freedom can I offer without losing direction… and how much direction without suffocating freedom?”
Direction doesn’t have to be rigid.
But it does need to be clear enough for people to understand what matters today,
not just what you dream about for tomorrow.
RESULTS
When reality demands speed… but people need to stay whole
There are moments when the business asks for a sprint, not a walk.
Clients are pushing.
Competitors are breathing down your neck.
The goals are very concrete.
This is where performance-oriented leadership comes into play:
clarity, focus, rhythm, execution.
But people feel immediately when we cross an invisible line.
And comments start to surface, like:
“The problem isn’t that there’s a lot of work.
The problem is that we don’t really know what done means.”
Or, with disarming honesty:
“At this speed… I’m no longer looking for solutions.
I’m just trying not to make mistakes.”
There’s a thin line between
productive pressure
and pressure that quietly demobilizes.
Good leaders sense the moment when they need to slow the pace without losing direction.
They feel it in the team’s energy.
In the silences between meetings.
They know when to push — and when to leave a bit of space.
And they start asking themselves:
“Where am I asking for speed… but haven’t ensured clarity?”
“How much of this is real urgency… and how much is just my own pressure to close things fast?”
“Who am I pushing too hard simply because they can handle it — and for how long?”
“Where do I really need to increase the pace… and where do I just need to clear the noise?”
“Which result is truly urgent… and which one is just my anxiety to finish quickly?”
Leadership here is about holding the rhythm,
not imposing it at any cost.
ORDER
When you need structure… so you can be flexible again
There are moments when you realize that “we’ll figure it out” no longer works.
You need structure.
You need clarity.
You need processes
that protect people’s time
and reduce dependence on improvisation.
People often ask for this in a very natural way:
“I’d really like to know what comes next,
instead of finding out on the way to the client.”
“Sometimes it feels like procedures live in everyone’s head,
not in a place where we can all find them.”
They’re not asking for bureaucracy.
They’re asking for predictability.
This is where the paradox appears:
Without order, chaos shows up.
Without flexibility, rigidity takes over.
Good leadership needs to hold both.
And leaders start asking:
“Where does a process genuinely help…
and where does it become just one extra step invented on someone’s bad day?”
“What needs to be standardized so we stop firefighting…
and what should stay flexible so we don’t put out good ideas as well?”
“What’s worth putting on paper…
and what’s better left in people’s hands so we don’t kill initiative?”
“Where do we actually need rules…
and where do we just need common sense and communication?”
“Which process clarifies things…
and which one only complicates them to give the impression of order?”
Order doesn’t mean slowing down.
It means removing friction so you can move faster.
DIAGNOSIS
How to know what kind of leadership makes sense today,
without swinging between extremes
To simplify things,
I often use two simple questions:
“Is the pressure coming from the inside or from the outside?”
“And does this situation require a big change, or just a small adjustment?”
From the combination of these two, direction starts to emerge.
If the pressure comes from inside and the change is big,
you need people and collaboration.
When morale is low.
When tensions show up or the team starts working in silos.
Neither procedures nor vision really help here.
This is where you rebuild trust.
Real conversations.
Listening.
Space for people.
If the pressure comes from outside and the change is big,
you need vision and innovation.
When the market is shifting.
When the product can no longer keep up.
When a new competitor enters the scene.
This is where you rethink the game.
You test.You reposition.
You take courage.
If the pressure comes from inside and the change is small,
you need order and processes.
When errors repeat.
When information gets lost.
When everyone is working hard, but nothing feels clear.
This is where you bring structure.
Roles. Simple steps. Clarity.
If the pressure comes from outside and the change is small,
you need speed and results.
When there’s an opportunity.
When you need to respond quickly.
When the goals are short-term, monthly or quarterly.
Here, what matters is focus.
Decision. Execution.
None of this is a universal recipe.
It’s just a way to make the context clearer.
Because the answers to these two questions can point you toward the leadership style that makes sense today.
“Today it’s about people.
Tomorrow it’s about results.
The day after, we’ll see what shows up.”
And it can pull you out of that exhausting pendulum swing away
from leadership driven mainly by impulse,
and closer to leadership guided by context.
The True Art of Paradoxical Leadership
Mature entrepreneurs don’t look for the perfect style.
They look for the right style for the right moment.
In a typical week, they might move through all of them:
On Monday, they help someone grow.
On Tuesday, they bring order.
On Wednesday, they introduce a new idea.
On Thursday, they ask for results.
On Friday, they ask themselves where there’s still room to simplify.
It’s not chaos.
It’s not confusion.
It’s the natural rhythm of a growing business.
Paradoxical leadership isn’t learned in a day.
It’s learned in practice.
In small decisions.
In fine adjustments.
In the courage to try something other than your natural reflex.
And, step by step, they become the kind of leader an organization follows
not out of obligation,
but out of trust.
That’s where mastery lives:
not in dominating a single style,
but in learning how to dance between styles.
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