THE MANAGEMENT TIP OF THE DAY: Harvard Business Review

April 26, 2024

Ask Smarter Strategic Questions


With organizations facing increased urgency and unpredictability, being able to ask smart questions has become a key leadership skill—especially when setting strategy. Here are five types of questions to ask that can boost strategic decision-making.

Investigative: What’s Known? When facing a problem or opportunity, the best decision-makers start by clarifying their purpose, asking themselves what they want to achieve and what they need to learn to do so.

Speculative: What If? These questions help you consider the situation at hand more broadly, reframing the problem and exploring outside-the-box solutions.

Productive: Now What? Assessing the availability of talent, capabilities, time, and other resources ultimately helps you determine a course of action.

Interpretive: So, What? This natural follow-up can push you to continually redefine the core issue—to go beneath the surface and draw out the implications of an observation or idea.

Subjective: What’s Unsaid? This final question deals with the personal reservations, frustrations, tensions, and hidden agendas that can push decision-making off course.

This tip is adapted from “The Art of Asking Smarter Questions,” by Arnaud Chevallier et al.




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