Asking Better Questions
How to ask open-ended questions
Ask the question that gets you a story, not a yes or a shrug.
Why it matters
A closed question hands you a dead end: one word, and now you're guessing at everything underneath. An open question hands you the real story, unprompted, in their words.
What it sounds like
Closed questions start with is, did, can, will, and get you a fact or a shrug. Open questions start with what, how, tell me about, and get you the reasons. Open first to explore, closed later to confirm.
The closed question
“Is the rollout going okay? (Answer: Yeah, mostly. And now you know nothing you didn't already.)”
The open question
“How's the rollout actually landing with the team? (Answer: Honestly, rough. Support's drowning and two people have stopped using it.)”
Practise it
Marcus Feld, prospect on a discovery call
“We're evaluating a few tools. Yours is on the list, but we haven't decided anything.”
Ask two open questions that surface what's behind their search. Nothing answerable with yes or no, and aim at motivation, not logistics.
A strong answer: “What's pushing you to look now, after living with the current setup this long? And what would have to be true for a switch to feel worth it?”
Free in your browser. Speak for 60 seconds and get feedback.
The short version
Open first to explore, closed later to confirm. The question shape decides the answer shape.
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.