Asking Better Questions
How to ask follow-up questions without interrogating
Go deeper without making the other person feel like a suspect.
Why it matters
Too soft and you never get past the surface, so you leave with nothing. Too hard and they brace, give you clipped answers to end it, and stop volunteering anything real. The middle is curiosity, and it's where the insight actually lives.
How to do it
Match the emotional tone, not just the information need. An echo probe ("The timing?") or a soft "Say more about that" invites them to expand. Rapid-fire why, who, when reads as an audit. Curious keeps them talking.
Vague
You nod and let it slide, so you never reach the real thing. Polite, but empty.
Curious
One soft probe at a time. "Say more about that." Low pressure, and they open up on their own.
Interrogating
Four hard questions back to back. They feel cross-examined and start answering just to get free.
What it sounds like
Prospect
“We tried something similar last year and it didn't really work out.”
You
“Didn't work out how? ... Say more about that, I'm curious what actually got in the way.”
Practise it
Priyanka Nair, prospect
“We actually bought a tool like this before. It sat unused and we quietly killed it.”
Two soft probes that uncover what really happened. Curious, not grilling. Give her space to tell it instead of forcing her to defend it.
A strong answer: “It sat unused, huh? That's frustrating. What do you think got in the way of it actually sticking?”
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The short version
One soft probe at a time. Curiosity opens people, cross-examination closes them.
Practise it every day
This is one lesson from the Asking Better Questions course in the Insight7 app, with a roleplay to rehearse the real conversation.