“I’ve told you a thousand times!”
If we’ve ever led a team — or parented a child — we’ve probably said that (or, at least, thought it).
And it’s often followed by something just as familiar: “Why can’t you just learn?”
But were they really ignoring us?
Being difficult?
Or are we relying on the wrong method to help ideas stick?
Maybe the issue isn’t resistance — it’s that we’re skipping the part where real learning happens.
Socrates seemed to understand this. He didn’t hand out answers.
No frameworks. No playbooks. He just asked questions — often to people who believed they already knew the answers.
He wasn’t trying to win arguments. He was planting seeds. And 2,400 years later, that still might be the most effective leadership move we can make.
Build the Web
Today, we often do the opposite of asking. We rush to explain, to prove we know, to sound certain. And it rarely works.
Because real learning doesn’t come from being told. It comes from building structure — our own framework that helps us connect and retain new ideas.
For me, that framework is like a web.
When I’m new to something, that web is thin — a few loose strands. Most ideas just pass through. But as I learn more, something catches. It connects. The web thickens. And as it does, it starts to catch more.
That’s how real understanding builds — not all at once, but strand by strand.
And what strengthens the web more than anything? A good question.
Good questions strengthen everything. The kind that forces us to stop, think, and rework what we thought we understood. Both the questions we ask — and, more importantly, the ones others ask us.
When Answers Fall Flat
That’s why I don’t lead with answers. I lead with questions.
It wasn’t always this way.
Earlier in my career, I saw a pattern: When I told someone what to do, they normally did it. But it didn’t stick. I’d get the same question again – or see the same mistake. They didn’t own it. It wasn’t theirs.
So, I tried something different. I started asking questions.
And over time, something shifted. People started thinking more critically. They built confidence. They made better decisions — without needing me in the room.
That’s when I realized I was using the Socratic method. Not to confuse or control — but to help people build their own framework instead of borrowing mine.
Questions Build Thinkers
Statements end conversations. Questions start them.
Telling someone what to do might feel efficient. But it rarely builds capability.
If we want people to grow — to become more confident and independent in their thinking — we have to stop answering for them.
It’s not about testing what they know. It’s about training how they think.
When we ask questions, we’re not quizzing. We’re creating space:
Space to pause.
To reflect.
To build judgment.
Here are a few I return to often:
- What do you think we should do?
- How did you arrive at that point of view?
- How have you thought about the risks?
- Have you considered ___________?
These aren’t tricks or gotchas. They’re invitations.
They help someone build the habit of thinking — and strengthen the web that’s ready to catch new insight when it comes.
That’s how people move from asking what to do… to knowing what to do.
Scaling Means Letting Go
Here’s the thing: the work still needs to get done.
But if every decision has to go through us — if we’re always the final step — we won’t move fast enough.
We don’t just slow things down.
We become the bottleneck.
Scaling isn’t just about adding headcount.
It’s about multiplying judgment in others — and trusting it.
So, I don’t give the answer (at least not immediately). I ask questions first.
Because the goal isn’t to be the smartest person in the room.
It’s to build a room full of people who can think for themselves.
Asking Ourselves First
Yet, we can also learn by asking ourselves questions first – especially when things don’t make sense.
Here’s an example.
We see something in the news that feels absurd. A story that seems completely out of step with how we see the world.
And our first instinct is to dismiss it.
We think, “Those people are just stupid.”
But I don’t buy that.
Rarely is the world black and white.
Instead, I try to ask myself:
- What led to this situation?
- What pressures or priorities shaped their actions?
- What assumptions might they be working from?
- What facts am I missing?
These kinds of questions help me get curious before I get conclusive.
And in a world where we’re constantly nudged toward quick takes and hot opinions, that kind of pause matters.
Asking other people questions helps them grow.
Asking ourselves questions helps us grow, too.
Ask First: A Simple Challenge
Next time you feel the urge to give a quick answer or judgment, pause.
Ask a question instead.
Not to delay. Not to test.
But to build the habit of thinking — together.
See what grows from it.
Key Takeaway (TL;DR)
If we’re always answering, we’re doing too much of the thinking.
To grow our teams — and grow ourselves — lead with questions.
They don’t just unlock better decisions.
Questions build better decision-makers.
Why I’ll Keep Asking
We often think of leadership as providing direction. Certainty. Answers.
But the best clarity isn’t something we hand over — it’s something people build for themselves.Socrates understood that. He didn’t push conclusions. He asked questions and let people wrestle.
That’s the kind of leadership we should strive to practice.
Not just to help others think — but to help ourselves think more clearly, too.
Because when we ask real questions — together or alone — we’re not just solving problems.
We’re learning how to think.
And what sticks — what grows — is never the answer we give.
It’s the question they carry with them.
