Uncover the real problem with "What’s the biggest challenge here?"

The stated position is rarely the real problem — ask for the challenge behind it.

Why it works

Positions ("I need X") are surface-level; interests and constraints are what actually drive behavior. Asking "What’s the biggest challenge you’re facing here?" shifts the frame from positional bargaining to problem-solving. The listener tends to answer honestly because the question is about their difficulty, not a demand for concession — and the answer almost always reveals more leverage and creative options than the original position did.

How to do it

1. Instead of responding to a stated position, ask: "What’s the biggest challenge you’re facing with this?"
2. When they answer, probe deeper: "What else is making this hard?"
3. Resist the urge to immediately solve the problem they name — gather the full picture first.
4. Use their answer to reframe your offer as a solution to their real constraint, not a response to their position.

Evidence

Interest-based versus position-based negotiation is one of the most durable findings in negotiation research: surfacing interests rather than trading positions consistently produces better outcomes for both parties. The calibrated question is one vehicle for doing that. Pinkley, Neale and Bennett show experimentally that the underlying alternatives and constraints a party carries — the stuff this question surfaces — do more to shape the settlement than the stated position ever does. (mechanistic)

Interest-based negotiation has substantial practitioner and research support; the specific question phrasing is Voss-style craft layered on top of that framework.

Sources

• Fisher, Ury & Patton (1981/2011), Getting to Yes — separating positions from interests
• Pinkley, R. L., Neale, M. A., & Bennett, R. J. (1994). The Impact of Alternatives to Settlement in Dyadic Negotiation. Organizational Behavior and Human Decision Processes, 57(1), 97–116.

Common mistake

Jumping to solutions the moment the challenge is named, which signals you stopped listening — the question’s value is in what comes after it, not in the asking.