How To Ask Good Questions

When my daughters were young, we had a small Post-it note taped to the wall in our kitchen. It said:

Every afternoon after school, we’d talk about their day—but I always came back to that question.

Not "Did you get the right answer?’" Not "Did you do well on the quiz?"

But:

Did you ask a good question?

That was the question I cared about most.

I wasn't that interested in a question just asked for clarification of facts. That's important too. Or a question that really was just a way to show off what they know. That's a waste of everyone's time. What I had in mind was a question that showed they understood the lesson—and wanted to explore further.

That’s my definition of a good question. And it's something we still talk about today.

Because here's the truth: you learn more when you ask better questions. Not just about the world—but about how others think, what they value, and how they see the problem.

That’s what I wanted my daughters to learn. And it's what the best leaders I know practice every day. They don’t rush to the answer. They dig deeper with the next question—a good question.

Answers Are Easy. Insight Is Not.

AI can generate answers—quickly and fluently. What it can’t do is pause, connect dots, or reframe the premise.

That’s still OUR job. That’s the job of a founder. A leader. A strategist.

Especially if you're leading, advising, selling, or building something new. The most powerful person in the room isn’t the one with the answer. It’s the one asking the question no one else thought to ask.

One of My Favorite Questions

One of the best clarifying questions I’ve ever learned came from my longtime mentor Mike Ross:

It sounds simple, but it’s powerful. It forces alignment before action.

You can't move forward with confidence if you don’t know what you're aiming for—or how you’ll know when you get there.

I explored this in People Like Bad Pizza, where I wrote:

It’s not just about defining what success means for you. It’s about defining what it means for them.

These aren’t trick questions or clever soundbites. They’re the ones that drive clarity, shift perspective, spark action, and open new ground.

Four Questions That Move the Conversation Forward

I’ve found that when conversations stall—or worse, go in circles—it’s usually because we’re not asking the right kind of question.

Over time, I’ve come to rely on four types that consistently move things forward.

1. Clarifying Questions

Cut through noise. Make sure everyone’s solving the same problem.

“What problem are we actually solving?” “What does success look like—for them?”

2. Framing Questions

Shift the lens. Reorient priorities.

“What would this look like if it were easy?” “What’s the real cost of doing nothing?”

3. Commitment Questions

Move people from ideas to action.

“What would make this worth doing now?” “Who else needs to believe in this?”

4. Expansive Questions

Open new ground. Invite reflection and exploration.

“What aren’t we seeing yet?” “Where else could this apply?” “What would change if we flipped the premise?”

These are the questions that surface when curiosity replaces certainty. They don’t close loops or end conversations. They open up the conversation to further exploration.

Good Leaders Ask Better Questions

Back in Real Thought Leadership Helps People Decide, I wrote:

Helping someone by asking a good question creates more value than giving them a fast answer. It builds trust. It changes the shape of the conversation. It encourages exploration and collaboration. It’s how you move people forward—whether they’re your team, your customer, or anyone you're trying to help.

The Bottom Line

If you want better outcomes, start with better questions. If you’re leading a company, a team, or even just a conversation, try this:

• Don’t just look for the answer.

• Ask if you’re even solving the right problem.

• And then ask: What are we missing? What would move this forward?

It works in business. It works in life. It worked in my kitchen.

Berkson's Bits

What business are you in?

I ask that question a LOT.

And tell me without talking about your product or your job description. 

What is driving you so much that you are going to spend years of your life building this business?

What I'm Reading

Chicago Sun-Times prints summer reading list full of fake books

This caught my attention. Yes, it was in a special supplement. Yes, it was syndicated content shared nationally. And yes, whoever created it took some shortcuts. I'm not calling out editorial malpractice. This is just a symptom of how poorly we know how to deal with the impacts of AI. It will get better. Until then, good luck out there. Caveat lector.

I don't have the original Post-it note, but I have a picture of it. And I remember what it stood for. If you’re trying to get clear on what YOU stand for, what your customers care about, and how to tell that story—let’s talk.

That’s what I do. I help founders and exec teams build strategic narratives that cut through noise and create momentum. It starts by asking good questions.

What questions do you like to ask? I want to hear how you help move conversations forward and promote exploration and collaboration.

If you need some help with good questions, let me know. I'm here to help.

Looking forward to continuing the conversation...

Alan