Tough questions don’t always produce revealing answers. If someone can anticipate what you’ll ask, they can prepare a polished response and steer the conversation. To learn how they really think, ask questions that are relevant but difficult to predict. Here’s how.

Work from their narrative. Listen closely to the claims and assumptions they’re making. Instead of simply pressing harder, probe a connection or dependency they haven’t addressed.

Ask for connections. Move beyond requests for more facts or details. Ask how two ideas relate, where priorities might conflict, or what one decision implies for another.

Change one key assumption. Stress-test their reasoning with a plausible counterfactual. Ask what would change if an important assumption proved wrong, or what evidence would cause them to reconsider.

Use surprise judiciously. Your goal should be learning, not embarrassment. Give the other person room to think through an unexpected question without creating unnecessary pressure.

Time it well. Ask your curveball while it directly relates to what was just said, making it harder to dismiss or redirect.

Keep changing your approach. Once questions become predictable, they lose their value. Avoid relying on a permanent script.

Adapted from Research: How Curveball Questions Can Surface the Insight You’re Looking For by Wei Cai, et al.

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