Coaching 100: Question the Question

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Question the Question

Teams stall when they accept the first version of a problem without challenging it. Leaders rush into action plans, only to discover they solved the wrong issue, invested in low-leverage work, or misread the real constraint. Cross-functional partners feel the consequences through churn, unclear direction, and last-minute resets. Customers experience delays caused by teams chasing the wrong target. “Question the Question” is the antidote. It stops teams from blindly accepting the initial ask and instead pushes them to clarify intent, desired outcomes, and the real problem underneath. When leaders apply this discipline, direction becomes sharper, execution accelerates, and buy-in strengthens because people understand why the work matters.

Imperative Explained

Question the Question means interrogating the initial request until the true need becomes visible. “Good” looks like slowing down long enough to ask: What problem are we solving? Why now? Who benefits? What’s the opportunity cost? Leaders who question the question prevent teams from climbing the wrong hill.
This imperative drives two outcomes: clearer, more motivating direction and faster buy-in that accelerates execution. When leaders clarify the true objective, alignment sticks, and teams spend far less time reworking unclear goals.

Five Behaviors

  • Ask the core need — “What are we really trying to accomplish?”

  • Clarify constraints — Time, resources, non-negotiables.

  • Surface assumptions — Challenge what’s taken for granted.

  • Map stakeholders — Who wins or loses with this direction?

  • Translate into outcomes — Anchor work to measurable impact.

If You Don’t

Teams chase vague or misframed goals. Work expands without direction. Rework spikes as hidden misunderstandings surface late. Cross-functional partners grow frustrated by shifting targets. Customers feel delays caused by teams solving the wrong problem.

If You Do

Direction sharpens and momentum builds. KPIs improve: strategic clarity ratings rise, rally speed increases, and adoption rates strengthen. Teams commit faster because the purpose behind the work is transparent and motivating.

Mini-Case

A GM inherited a stalled initiative. Instead of pushing harder, she questioned the question: Why does this matter now? What outcome are we driving? The team realized the original problem was misframed. They rewrote the brief, cut two low-value components, and delivered a tighter, more impactful solution in half the expected time.

Try It This Week

  1. Ask “What problem are we solving?” once per meeting.

  2. Clarify one hidden assumption.

  3. Identify the real beneficiary of a task.

  4. Rewrite one vague request into a clear outcome.

  5. Pause one project to question its purpose.

Learn More

For deeper reframing discipline, explore Decision Making 300: Refresh on Repeat. To strengthen clarity of direction, see Purpose 100: Name Your Why and Who. For surfacing hidden issues early, check Alignment 100: Model the Mess.