If you’re new here, welcome! Every week, we unpack leadership, mindset, and personal growth into something real and doable. Expect research-backed insights, a little storytelling, and practical ideas that actually fit into your life (even the messy parts).

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Early in my leadership journey, I thought I had a pretty solid grip on what I was doing.

I could read people well.

I’d studied every book I could find on management, motivation, and organizational behavior.

I believed if I treated everyone on the team with equal respect and autonomy, everything would fall into place.

And for a while, it did.

Then I hired someone new. A recent college grad, full of energy and bright ideas. She showed up curious, attentive, and engaged in every team meeting.

At first, it felt like a perfect fit.

But over time, something shifted.

Her voice got quieter. Her contributions started to fade. One-on-ones became short status check-ins. The spark I saw in week one? Gone.

Eventually, I started to wonder: Is she going to quit?

So I asked her a simple question in our next 1:1:

“How are you doing?”

She answered: “Fine.”

Then I asked again, more intentionally:

“How are you really doing?”

That changed everything.

She told me, honestly and vulnerably, that she was struggling.

She didn’t feel like she had the structure she needed. She felt adrift, unsure of what “good” looked like in her role.

She needed more feedback. More guidance. More clarity.

And in that moment, I realized something important:

I’d been leading my idea of a team—not the individuals on it.

I thought I was being fair by treating everyone the same. But fairness isn’t sameness.

Leadership isn’t a one-size-fits-all formula.

It’s about adapting.
To people.
To needs.
To context.

That conversation changed the way I lead.

I began asking better questions. I started observing more closely. I paid attention to not just how people work, but what they need to thrive.

And I stopped trying to be the leader with all the answers.

Instead, I started becoming the leader who listens.

And adapts.

Sure, generational frameworks are helpful.

They give you a place to start.

But if you rely on them too rigidly, they stop being useful.

That’s what happened to me.
I thought I was being thoughtful. Strategic, even.

But the more I leaned on generational trends, the more I missed the people in front of me.

I wasn’t adapting.

I was applying assumptions, albeit with good intentions.

That’s when I started learning about adaptive leadership.

Adaptive leadership is a framework developed by Harvard scholars Ronald Heifetz and Marty Linsky.

It’s not a trend. It’s a research-backed approach built around a simple truth:

Most real leadership challenges aren’t technical. They’re human.

A technical challenge is about execution.

An adaptive challenge is about:

People. 
Emotion.
Behavior. 
Belief.

I learned that to lead across generations, you can start with the frameworks.
But then you have to move beyond them.

Because people don’t want to be led like a category.
Sorted by date, like groceries in your fridge.

They want to be led like a person.

That means shifting from leadership as a formula to leadership as a relationship.

From what “people need” to what this person needs.

That’s when leadership starts to feel real, for everyone.

So, how do you take this from concept to practice?

Here are two simple tools I use daily (at work and at home) to stay focused on my people, rather than their personas.

Ask 4 Human-Centered Questions

These work in 1:1s, onboarding, team check-ins, and even the car ride home after soccer practice.

• When do you feel most energized or capable?

• How do you like to receive feedback or input?

• What kind of communication helps you feel supported?

• Where do you want freedom, and where do you want guidance?

The goal isn’t to collect preferences like a quiz.
It’s to start conversations that reveal how people thrive.

Use the Adaptation Loop

This is how personalization becomes a leadership habit:

1. Observe – Notice how they show up

2. Ask – Get curious about what’s working and what’s not

3. Adapt – Make small shifts based on what you hear

4. Align – Revisit regularly. People grow, and your leadership should too

This isn’t about over-customizing your style.
It’s about showing people you see them.

Want to keep exploring? Here are a few standout resources:

🎧 The Knowledge Project – Ep. 117: Jennifer Garvey Berger on Leading in Complexity
A brilliant look at how leaders can navigate messy, adaptive challenges with curiosity and connection.
Listen on Apple Podcasts

🎤 Simon Sinek – “Why Good Leaders Make You Feel Safe”
A compelling case for relational leadership and trust as the core driver of performance.
Watch the talk

📘 Leadership on the Line by Ronald Heifetz & Marty Linsky
The foundational guide to adaptive leadership.
Check out the book

🎧 Brené Brown with Esther Perel – “Building Connection Across Difference”
A conversation that blends leadership, psychology, and humanity, perfect for understanding how trust really gets built across generations.
Listen on Apple Podcasts

I used to think great leadership meant finding the right strategy and applying it universally.

Now I know better.

Because no two people thrive in exactly the same way.

And no one wants to be managed like a checklist.

People want to be seen.

They want to be understood.

They want to be led like the one-of-a-kind humans they are.

Adaptive leadership isn’t about having all the answers.

It’s about noticing, adjusting, and meeting people where they are.

So this week, try this:

Ask one person:

“What kind of support helps you do your best work?”

Then pause.

Don’t fix.
Don’t rush to interpret.
Just listen.

Because the best leadership doesn’t come from a playbook.

It comes from paying attention.

—

Warmly,
Justin