The Craft of
Asking Better
Questions.
Most of us ask questions to get answers. The best coaches, teachers, and leaders ask them to create movement — to open a door the other person didn't know was there. This is that craft, taught patiently.
Nine slides · about fifteen minutes · bring a notebook.
A bad question closes a door.
A good one builds the room.
Most of the questions people get asked in a workday are transactional. Did you finish it? How long will it take? Is the client happy? Accurate, necessary — and almost entirely useless for helping anyone grow, decide, or see themselves clearly.
Better questions are rarer because they are harder to ask. They require the asker to slow down, to tolerate not-knowing, and to resist the quiet arrogance of having ready answers. But when someone asks you a good question — really asks — you remember it years later.
Every question lives in one of four places.
Two axes do most of the work. The first: open (invites any answer) vs closed (expects a specific one). The second: functional (gathers information) vs generative (creates new thinking). Four quadrants, each with a job.
A note in the margin: most of us over-use the Confirming quadrant and under-use the Opening one. That's the shift.
Which quadrant is each?
Tap the label you think fits.
The hardest part of a good question
comes after you ask it.
In 1972, a researcher named Mary Budd Rowe timed classroom questions. The average teacher paused about 0.9 seconds after asking one. When she coached them to wait a full three seconds, three things happened:
- Student responses got longer, richer, more nuanced.
- More students volunteered — not just the same three.
- Teachers started asking fewer, better questions.
The silence after a good question is not a failure of the conversation. It is the conversation.— Rowe, 1972
A conversation with Jordan.
In your 1:1, Jordan says, "I think I'm burned out." Four possible next moves. Pick the one that does the most work — both for Jordan and for your own understanding.
Getting better at this is mostly about getting smaller.
Asking better questions is less about learning new techniques and more about unlearning three quiet habits:
Most of us, hearing a problem, reach immediately for a solution. The better move is to ask one more question about the problem before you ever discuss the answer.
"Don't you think we should…" isn't a question — it's a sentence in disguise. Watch for the shape of your own voice. If the answer is already implied, you're teaching, not asking.
Three seconds feels like ten. Sit in it anyway. The person you asked is doing the most important work of the conversation — out loud, in their own head — and you are not invited yet.
Write down one question you'll hold this week.
Not a list. Not a system. One question — specific enough that you'd know when to use it, generative enough that it opens a door. Write it here. We'll send it back to you, quietly, on the other end of the course.
Carry it for seven days. Use it at least three times. Notice what happens — in the other person, and in yourself.
Every good teacher
is, at bottom, a person
who has learned how to ask.
Your question is safe with us.— the question you held —
Thanks for giving this its full attention.