LISTEN the LOUDEST

The Best Leaders Don’t Know Everything. But They Do Ask.

I used to think being a leader meant having the answers.

You know the type - head high, voice steady, slides polished. I played that part for years. Every meeting was a performance, every question a threat. I thought admitting “I don’t know,” would unravel the illusion of competence I worked so hard to build.

But the illusion cracked anyway. And oddly enough, that’s when the real leadership began.

When Pretending Breaks, Curiosity Builds!

I remember standing in front of my team after a quarter had tanked. They were waiting for a fix, a plan, a confident speech. I had none of it. All I had was this question:

“What do you think we should do?”

Not rhetorical. Not a trap. Just a genuine reach across the silence.

And in that moment, when I stopped pretending and started asking, something shifted. Ownership showed up. Ideas flowed. We became a team instead of a stage and an audience.

John Maxwell was right: Good leaders ask great questions. But I’d argue this - Damaged leaders ask the bravest ones.

Control is Comfortable. Curiosity Isn’t.

If you're clinging to control, questions feel dangerous. Because asking “What’s not working?” might lead to answers that hurt. Asking “How are you really doing?” might open a floodgate. Asking “What do I need to change?” might flip your whole identity. But if your leadership can’t handle hard answers, it’s built on sand.

Will Wise, in Ask Powerful Questions, says questions invite people into safety, but only if you're brave enough to sit in the silence afterward. Only if you can take their truth and not flinch.

Damaged Leaders Ask From the Dirt

You don’t need a title to ask bold questions. You don’t need permission to ask better ones.

You just need the guts to say:

• “Why do we keep doing it this way?”

• “What are we afraid to admit?”

• “What’s it costing us to stay silent?”

• "Can you tell me more?"

Damaged leaders don’t ask because it’s strategic. We ask because it’s survival. Because we’ve been burned by silence. We’ve faked the answers before. And we know what it feels like to sit in a room full of yes-men while the truth is dying in the corner.

Inquiry Is What Unlocks Healing

The best question I’ve ever asked myself: “What am I pretending not to know?”

That one hurt. Still does. But it cracked open everything. My perfectionism, my fear, my obsession with control.

Now, questions are my go-to tool. Not polished statements. Not three-point speeches. Just real, raw, maybe-even-wobbly questions that say: “I’m listening. Not performing. Not posturing. Just… listening.”

Let’s Be Leaders Who Listen Loudly

The world doesn’t need more leaders with perfect answers. It needs more leaders with the courage to ask the right questions and the humility to hear the messy replies.

At The Damaged Leader, we’re not chasing polish. We’re chasing presence. We’re not demanding perfection. We’re asking better questions.

So here’s yours:

What’s one question you’ve been afraid to ask lately? Ask it. Write it down. Whisper it if you must. But start there.

Because the leaders we admire most? They aren’t flawless. They’re curious.

And curiosity might just be the strongest form of courage there is.

Keep questioning, keep listening. 

Chris

Natalie's Notes:

As some of you know, Chris is also the author of Alphabet Town: The ABCs of Raising Successful Kids. Each week in the Alphabet Town world, Ms. Grandma Reads brings a new letter to life, offering a deep dive into how to grow, nurture, and practice that trait in both our kiddos and parenting. As a new parent, I’ve found her background in early childhood education and insight incredibly grounding.

Last week  the letter was "Q is for Questions." As the mom of a toddler just finding his voice, this was a "heads up" that I needed. My son is starting to ask “why?” and I know the floodgates are coming. We joke about it as parents, get frustrated in the moment, wonder why our kids aren’t ever satisfied with our answers. But last week, I saw it differently.

When a child asks “why,” they’re not just curious, they’re building neural bridges to understanding. Every repetition wires their brain toward connection and meaning. When we pause to answer, the answers become the mortar that holds that bridge together.

It struck me how true that is in leadership.

When your team asks questions, they’re doing the same thing - trying to close the gaps, trying to build understanding. But by the time we reach adulthood, many of us have been conditioned by classrooms, boardrooms, or bad bosses, to believe our questions are interruptions, or worse, signs of incompetence.

Ms. Grandma Reads pointed out that by third grade, most children already start to internalize the belief that questions are a waste of time. Think about that. That’s not just a classroom issue, it’s the root system of a “yes-man” culture.

So next time your team brings you their questions, don’t get frustrated. See it for what it is: a sign they trust you enough to ask. That they want to understand more deeply. That they’re trying to build a bridge, and you, as their leader, are the mortar that makes it strong.

Imagine a culture where no one has to say, “I’m sorry if this is dumb, but…”

Imagine one where people don’t need permission to be confused. And don’t need to feel embarrassed if they are.

That’s the kind of leadership that doesn’t just tolerate questions, but welcomes them.

TDL Library: click here for The Damaged Leader takeaways from John Maxwell's, Good Leaders Ask Great Questions, and Will Wise's, Ask Powerful Questions.