By the fall of 2013, I had gotten myself into a pretty difficult place.

Some of my closest relationships at work had fractured, and I was carrying a lot of hurt. I felt betrayed. I felt misunderstood. And, if I’m being truthful, I had built a pretty convincing story in which I was the victim.

Then, in October of that year, Chris Halter came into my life as a coach.

What followed was not particularly comfortable.

Chris began helping me examine the stories I was telling myself, take responsibility for my own life, and recognize how often fear was shaping the way I led, loved, and related to the people around me.

It was an awakening—and I didn’t particularly enjoy being awakened.

At times, Chris’s coaching felt like having a bucket of ice water thrown on me, day after day. Just when I wanted to settle back into the comfortable sleep of my old narratives—I’m the victim, they’re the problem, this isn’t my responsibility—another conversation would wake me up.

And I really wanted to go back to sleep.

But slowly, I began learning to take responsibility for my own life. I had to learn some things about leadership. I had to learn some things about love. I had to learn to walk out my faith differently.

And perhaps hardest of all, I had to learn some things about myself that I would rather not have seen.

Early in that journey, Chris gave me a definition that landed hard and has stayed with me ever since:

“Humility is seeing myself in the correct estimation.”

I understood the sentence.

More than a decade later, I’m still learning how to live it.

Humility sometimes gets a bad rap. We can picture the humble person as passive or timid—the person who doesn’t speak up, doesn’t stand his ground, and lets other people walk over him.

I don’t think that’s humility at all.

In fact, I have come to believe that humility is the most compelling attribute of any leader.

And I think humility begins with having the courage to see ourselves accurately.

For me, that means holding two truths about myself at the same time.

The first isn’t particularly flattering:

I am capable of getting it wrong.

I can be selfish. I can protect myself. I can misunderstand someone’s motives. I can speak too quickly. I can become convinced that my way is obviously the best way. There are tendencies within me that can cause me to hurt other people—sometimes knowingly and sometimes without even realizing it.

Scripture calls this sin.

“For all have sinned and fall short of the glory of God.”

That includes me.

One way I experience the effects of sin is relationally. It damages my relationship with God, with other people, and even with myself.

So part of seeing myself in the correct estimation is recognizing that I am not always right.

My motives are not always pure.

My perspective is not always complete.

But that is only half of the correct estimation.

The other half is almost too wonderful for me to comprehend:

I am unfathomably loved.

I am known. I am wanted. I am cared for. I am a child of God.

I don’t have to perform my way into His affection.

I can’t make Him love me more.

And I can’t make Him love me less.

Humility, then, asks me to hold two truths together:

I am more capable of getting it wrong than I like to admit.
And I am more deeply loved than I can possibly comprehend.

Not thinking more highly of myself than I should.

But not thinking less of myself than God does either.

Seeing myself in the correct estimation.

And I think that changes the way we lead.

For many years, I believed the leader was supposed to know.

The leader had the answers.

The leader brought clarity.

The leader had the insight.

If I’m being candid, I think I believed the leader was supposed to be the smartest person in the room.

That posture did not serve me well.

And it certainly did not serve my business partner, who often found himself on the receiving end of my need to be the smartest person in the room.

These days, some of my favorite words as a leader are:

“I’m not sure.”

I’m not exactly sure what we should do here.

I have some ideas.

What are you seeing?

Let’s huddle up and figure this out together.

There was a time when I might have considered that weak leadership.

Today, I think it sounds a lot like humble leadership.

Humility seeks understanding

Years ago, I learned another phrase that has become important in the way I try to relate to people:

Quality Interaction: an open exchange that seeks understanding.

There is a lot of humility packed into those few words.

An open exchange means I am willing to hear something I may not want to hear.

Seeking understanding means I haven’t already decided what you think, why you did what you did, or what is wrong with you.

I ask.

I listen.

I get curious.

“Help me understand.”

“What am I missing?”

“Tell me what you’re seeing.”

“Is there something I’m doing that is contributing to this?”

That doesn’t mean I have to surrender my ideas, my discernment, or my responsibility as a leader.

I can listen carefully to another person, genuinely remain open to what they see, and still come to the same conclusion.

Humility does not mean indecision.

It simply recognizes that the person sitting across from me may see something I don’t.

Humility asks, “What am I defending?”

There is another place I have learned to look for humility—or its absence.

Defensiveness.

I can remember plenty of conversations when someone questioned me and I could almost feel myself brace.

I would explain.

Justify.

Correct the record.

Make sure the other person understood why I was right.

Over time, I’ve learned to listen for a question when I feel that defensiveness starting to rise:

“Tom, what are you defending?”

It can be a surprisingly revealing question.

Sometimes I really am defending an idea that matters. Sometimes something important is at stake.

But other times, if I’m willing to look a little deeper, I discover that I’m defending something inside of me.

My competence.

My intelligence.

My reputation.

My worth.

For several decades of my life, I unknowingly carried around an equation that looked something like this:

Being right = being smart.
Being smart = being worthy.
Therefore, being right = being worthy.

If A equals B, and B equals C, then A must equal C.

Except this equation wasn’t true.

Being right does not make me worthy.

And being wrong does not make me less worthy.

That seems embarrassingly obvious when I put it on paper.

But I didn’t always live as though it were true.

When someone challenged my idea, it could feel as though they were challenging my intelligence.

And somewhere deeper still, if my intelligence was being challenged, my worthiness felt as though it were, too.

So I defended.

At the time, I probably would have told you I was defending my position.

Looking back, there were plenty of times I was defending myself.

My insecurity was trying to protect something that didn’t actually need protecting.

And this is where that second half of humility—the part about being unfathomably loved—becomes so important.

If I already know I am loved, your disagreement doesn’t have to threaten me.

If I know my identity is secure, I can hear:

“I think you got this wrong.”

without translating it into:

“You are less than.”

I can apologize without collapsing.

I can change my mind without feeling diminished.

I can allow someone else to have the better idea.

I can be corrected.

I can even fail.

Maybe that is one of the great freedoms humility gives a leader:

I no longer have to win the conversation in order to be okay.

We see the opposite posture all around us.

In business.

In families.

In churches.

And certainly in public life.

People attack rather than listen. Questions become accusations. Disagreement becomes contempt. Painful one-liners are used to discredit another person rather than understand them.

It can look like strength.

But sometimes I wonder if we are actually witnessing insecurity trying desperately to protect itself.

Humble leadership looks different.

It can be confident without being arrogant.

Convicted without being closed.

Strong without being defensive.

Curious without being indecisive.

A humble leader can say:

I know some things.
I don’t know everything.
I am capable of being wrong.
I am willing to learn.
And my worth is not on trial.

Maybe that is why humility is so compelling.

When I no longer need the people around me to confirm my worth, I become much freer to actually see them.

I can listen instead of preparing my defense.

I can ask instead of assuming.

I can seek understanding instead of victory.

I can lead without constantly needing to prove that I deserve to lead.

I still don’t live this perfectly.

That may be part of the correct estimation too.

But I keep coming back to the words Chris gave me more than a decade ago:

Humility is seeing myself in the correct estimation.

Not more than I am.

Not less than I am.

A flawed, unfinished person who is capable of getting it wrong—

and who, at the very same time,

is unfathomably loved.