The First Leader Who Taught Me What Leadership Feels Like

Most of us can remember our first boss.

But very few of us remember the first leader who made us feel human at work.

I do.

Before I learned anything about leadership theories, performance goals, or organizational charts, I learned what it felt like to be seen.

I was new to nonprofit work. Nervous. Eager. Still trying to prove that I belonged.

I expected instructions and expectations. What I didn’t expect was a question that stopped me in my tracks:

“How are you… really?”

She didn’t rush past it.

She didn’t multitask.

She waited.

And in that moment, something shifted in me. I realized leadership could be more than direction. It could be connection.

She Learned Our Stories, Not Just Our Skills

She was the founder and executive director of the organization, yet she made time for each of us as if we were the most important part of the mission.

She remembered our families.

Our children.

Our parents.

The pieces of our lives we carried quietly into work each day.

“How is your son doing?”

“How is your daughter?”

“How is your mom?”

“How is your dad?”

Those questions weren’t small. They told us:

You are not invisible here.

And when you are not invisible, you work differently.

You care differently.

You believe differently.

Years Later, I Found the Language for What She Practiced

Years later, I read The Inspirational Leader by Gifford Thomas, and one passage felt like it was written about her:

“A simple thing like asking how are you going, how’s your son or your daughter, how’s your mother or your father going. These simple things add tons of value to your leadership and develop a healthy bond between the leader and their team. One of the best places to begin leading with love is exhibiting patience and kindness toward other people (without forgoing accountability and expectations).”

She lived this before I ever read it.

She proved that love does not weaken leadership.

It deepens it.

A Question for You

Think about the leaders you’ve worked for.

How many knew your job description?

And how many knew your story?

How many asked for your results?

And how many asked about your heart?

We spend so much time teaching people how to manage.

We spend so little time teaching people how to care.

Yet the leaders we remember most are not the ones who gave us the most direction.

They are the ones who gave us the most dignity.

Why the First Leader Matters

There is something sacred about your first true leader. They shape the way you believe leadership is supposed to feel.

Because of her, I learned that leadership is not about distance or control.

It is about presence and trust.

About seeing people as whole human beings, not tools for productivity.

She taught me that when people feel known, they don’t just work harder.

They work with heart.

Coming Thursday: The Lessons She Left Me

On Thursday, I’ll share the lessons she planted in me—lessons that still guide the way I lead today:

• How to lead with love without lowering expectations

• Why small questions build strong teams

• How patience becomes power

• Why kindness creates culture

• 
  

For now, I’ll leave you with the question that changed me:

What kind of leader are you becoming—the one who knows the work,

or the one who knows the people?