Ask Better Questions. Live a Better Life.

It came out more like a statement than a question. But it ended with a word I wasn’t expecting: “Why?”

My friend David had said to me, “It doesn’t seem like you love yourself very much. Why?”

There was no response from me.
I was speechless—which, for me, is rare.

I’d never even considered that possibility. Was it true?
If it wasn’t, why did David think that? And if it was true, why had I never been asked?

Maybe I had—but not like that.
Not that directly.
Leave it to David.

We all need friends who are willing to ask the tough questions.

The Questions That Open Us

That one question led to more. And those led to even more.

It’s been years, and I’ve realized: It can take a lifetime to become the kind of person who understands the questions.

Especially the ones about what it looks like to love yourself.

Loving others? Easier. Caring for others? Forgiving others? Even that feels more natural sometimes than turning that same kindness inward.

But this is true: the quality of our questions often shapes the quality of our lives.

The Core of Growth and Leadership

The courage to ask better questions is at the heart of every great leader, creator, or seeker.

Not to control. Not to impress.
But to understand. To discover.

“The important thing is not to stop questioning. Curiosity has its own reason for existing.”
— Albert Einstein

Being curious is a key part of developing a strong sense of Self.
In every moment, every conversation, curiosity allows us to go deeper.
To discover more about the world, our neighbors, our families, and most importantly… ourselves.

It’s not about finding the right answer.
It’s about not being afraid to ask the next question.

Trading Answers for Insight

This goes against a part of me I know well—my “need to know” part.
The one that wants to figure things out. To make sense of it all. To give it meaning.

But I’ve been learning to let that part step back and let curiosity take the lead.

Because when I approach life from a posture of questioning instead of solving—
My behavior shifts.
So do my relationships.
So does my understanding.

Leadership Requires Questions

In my career, I’ve seen leaders who operated from ego.
They were certain.
They didn’t ask much.
They didn’t invite feedback; in time, they surrounded themselves with yes-people in echo chambers.

It never ended well.
Frustration.
Isolation.
Failure.

The best leaders—the most respected, the ones people trusted—did something else:
They asked.
They invited others in.
They were curious, not just correct.

“Judge a man by his questions
rather than by his answers.”
— Voltaire

Lincoln’s Quiet Strength

Abraham Lincoln was known for gathering input from all sides—even those who fiercely disagreed with him.

He famously appointed political rivals to his Cabinet—people who had challenged him, doubted him, even disliked him.

But he valued their perspectives. He listened.

Because he understood that strong leadership isn’t built on certainty—it’s built on curiosity and courage.

He didn’t need to be the smartest person in the room.
He needed to ask the right questions and intensely listen to the answers.

Reflect a Minute

So here’s a question for you:
Are you still asking questions?
Or have you settled into answers that feel safe?

This week, pause to consider:

• What question are you avoiding right now?
• What’s something you’ve never thought to ask yourself?
• Who in your life needs you to ask, not assume?

Closing Thoughts

There’s wisdom in wondering.
Curiosity doesn’t just keep us engaged—it keeps us growing.

And asking better questions?
That’s not just the path forward—it’s part of the whole trip.