Calibrated How/What Questions
Open-ended questions starting with "how" or "what" that hand the buyer control while you steer the conversation.
How it sounds
- You What about this is most important to you?
- Buyer Explains their priorities without feeling pushed
- You How would we know if this were working, six months in?
- Result They talk themselves into defining the problem on your terms
The full entry
Calibrated questions are open-ended questions that start with “how” or “what,” described by former FBI hostage negotiator Chris Voss in Never Split the Difference (2016). Unlike a “why” question, which tends to sound accusatory, or a closed question, which invites a one-word answer, a “how” or “what” question gives the other person the feeling of being in control while quietly steering them toward the information you actually need.
To use it, replace direct asks with calibrated ones. Instead of “is budget a problem?” try “what about this is most important to you?” Instead of “will this work for your team?” ask “how would we know if this were working, six months in?” Voss suggests preparing several of these in advance so they come out naturally instead of sounding rehearsed.
They work anywhere you need real information but a direct question would put the other person on the defensive, which covers most of discovery. The common mistake is starting a question with “why,” which almost always reads as a challenge to justify themselves rather than an invitation to explain.