Guide any conversation with How and What questions that create control
A consultant sat in a cramped conference room with a client who’d missed every deadline for paying invoices. The urge to scold was strong. Instead, she said, “What’s making cash tight this month?” and waited. The controller explained a new system rollout. Then the consultant asked, “How am I supposed to keep delivering this month without payments clearing?” The tone stayed calm, but the question forced the other side to think.
They offered a new accounting contact and a split payment by Friday, which showed there was room to move. The consultant resisted the urge to fill the silence and followed with, “How will we handle next month if the rollout is still rocky?” They proposed an interim schedule and both sides left with a clearer plan than any lecture could have produced.
A week later, the same consultant visited her nephew’s school. The principal described a plan to cut art time. She asked, “What problem are we solving by reducing art?” The principal named reading scores. “How would you protect reading time without eliminating art?” The question shifted the frame from complaint to design. They found a small scheduling tweak that preserved both.
These questions work because they lower defensiveness and recruit the other person’s problem‑solving brain. How and What give the feeling of control while quietly aiming the spotlight at constraints, trade‑offs, and implementation. Use Why sparingly, only when it invites them to defend a goal that also supports your outcome.
Before your next tough talk, sketch a small funnel: one discovery What, one constraint How, and two implementation How questions. Open with the discovery question and listen fully. When a demand appears, use the constraint How—“How am I supposed to do that with the current staff?”—delivered calmly. Close with implementation: “How will we know we’re on track?” and “How will we handle drift?” Keep Why in your pocket unless it helps them defend a good goal. Try this once tomorrow and watch people volunteer the plan you needed.
What You'll Achieve
Internally, you’ll feel less reactive and more curious under pressure. Externally, you’ll get clearer plans, fairer scopes, and real ownership from others.
Design your question funnel
Start with discovery What
Open with, “What’s the biggest challenge here?” or “What problem are we trying to solve?” Let them educate you.
Shift to constraint How
Ask, “How would we do that with our current resources?” or “How am I supposed to make that timeline work?”
Avoid Why unless it supports them
Use Why only to defend a goal that helps you both: “Why change vendors if your current one meets every requirement?”
End with implementation How
Close with, “How will we know we’re on track?” and “How will we handle it if we drift?”
Reflection Questions
- Which question will reveal the biggest unknown right now?
- Where can a constraint How replace a blunt refusal?
- What implementation questions will prevent future surprises?
- When is a supportive Why actually helpful?
Personalization Tips
- IT project: “What’s the one risk that could sink this?” then “How do we design around it without new headcount?”
- Home repair: “What’s the earliest safe fix?” then “How will we know it stays fixed after the first rain?”
Never Split the Difference: Negotiating As If Your Life Depended On It
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