Best Questions to Ask Leaders
High-impact questions that surface strategy, culture, decision-making, and how leaders enable people to do their best work.
1What few metrics matter most to you right now, and why?
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What few metrics matter most to you right now, and why?
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Why this works
Reveals the leader’s current focus and the causal story behind priorities.
2When you changed your mind on a major decision, what triggered the shift?
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When you changed your mind on a major decision, what triggered the shift?
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Why this works
Shows intellectual humility and what evidence persuades them.
3What trade-offs are you consciously making this quarter?
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What trade-offs are you consciously making this quarter?
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Why this works
Every strategy involves costs—this uncovers honest constraints and risks.
4Where do you see the biggest execution bottleneck today?
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Where do you see the biggest execution bottleneck today?
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Why this works
Pinpoints operational reality beyond slideware and OKRs.
5What is a behavior you celebrate that outsiders might miss?
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What is a behavior you celebrate that outsiders might miss?
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Why this works
Exposes cultural markers that drive outcomes but aren’t obvious on paper.
6How do you prefer people disagree with you?
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How do you prefer people disagree with you?
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Why this works
Clarifies psychological safety norms and the mechanics of upward candor.
7Which risks do we accept, monitor, and only act on if tripped?
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Which risks do we accept, monitor, and only act on if tripped?
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Why this works
Surfaces a practical risk policy rather than a vague risk appetite statement.
8What would you stop doing today if you had to cut 20% of effort?
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What would you stop doing today if you had to cut 20% of effort?
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Why this works
Forces ruthless prioritization and reveals sacred cows.
9What does ‘good’ look like for this team six months from now?
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What does ‘good’ look like for this team six months from now?
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Why this works
Anchors expectations in observable outcomes rather than slogans.
10What feedback most changed how you lead?
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What feedback most changed how you lead?
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Why this works
Signals coachability and models a learning loop for the organization.
11Where do you want more bad news, faster?
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Where do you want more bad news, faster?
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Why this works
Invites early signal escalation and reduces surprise failures.
12How will we know our strategy failed early enough to course-correct?
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How will we know our strategy failed early enough to course-correct?
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Why this works
Defines falsification criteria and triggers for contingency plans.
Getting Real Insights from Leaders
Expert tips and techniques for getting the most out of these questions.
Approach
Be Specific
Tie questions to timeframes, metrics, and decisions to avoid platitudes.
Invite Trade-offs
Ask what they won’t do—constraints reveal real strategy.