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. (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

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.