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How to use this page. Find the section for the person you are about to sit across from, or the situation you are walking into. Take two questions, not ten. Every question has a line under it saying what it actually gets you, because the follow-up work is the part that counts.
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Both are from Chris Voss, Never Split the Difference. They change the answers you get more than the questions do.
1. Open with a question that invites a no.
"Is now a bad time?" gets you further than "Do you have 30 minutes?" Yes is a commitment people brace against. No costs them nothing to hand over, and it makes them feel safe enough to keep talking. Voss's position is that no is the start of the conversation, not the end of it.
Same move in writing, after three ignored follow-ups: "Have you given up on this project?" A no is a cheap, face-saving reply, and most people would rather send one than keep ignoring you.
2. Ask how and what. Never why.
"Why did your team push back on that?" reads as an accusation in every language on earth. "What made that the right call at the time?" is the same question with the charge taken out, and it gets you a real answer.
"How am I supposed to do that?" is Voss's workhorse. It is a refusal delivered as a request for help, and in answering it people often talk themselves into your constraint.
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One follow-up move, and it is the whole of listening. When they say something loaded, name it back flat: "It seems like the timeline is the part that worries you." Then stop for about four seconds. "It seems like" is a statement about the world they can correct. "I think you're worried about the timeline" is a statement about you they now have to manage. One invites correction. The other invites defense.
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These are the anchor examples from the piece this page came from. Both are real questions, aimed at a named role.
To the Sales SME that holds the keys to the CEO's heart, about your big rock feature for next quarter: do you think this product solves the core problem we need to?
Gets you: whether the person who narrates your product to the CEO believes in it. If the answer is soft, you have a positioning problem before you have a shipping problem.
To your design partner: what did you think of the PM artifacts you saw from me last quarter, and how can I improve them next quarter?
Gets you: the quality bar of your own output, judged by the person who has to build on it. Almost nobody asks this, so almost nobody hears the answer.
Book 30 minutes with each person in the inner rings of your stakeholder map and run it the way you'd run a customer interview.