20 Questions

Questions to Ask During Hot Seat

Strategic questions that help you gather critical information, challenge assumptions, and demonstrate your analytical thinking during intense questioning sessions.

1

What specific evidence or data supports this conclusion, and how was it validated?

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Why this works

Tests the foundation of their argument and reveals the quality of their research and analytical process.

2

What alternative explanations or scenarios have you considered, and why did you rule them out?

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Why this works

Reveals their critical thinking depth and shows whether they've explored multiple possibilities or jumped to conclusions.

3

What would need to be true for this approach to fail, and how would you know if that's happening?

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Why this works

Tests their risk assessment skills and reveals their contingency planning and monitoring capabilities.

4

How does this decision align with our stated values and long-term strategic objectives?

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Why this works

Ensures consistency with organizational principles and reveals whether they've considered broader implications.

5

What assumptions are you making that, if wrong, would completely change your recommendation?

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Why this works

Identifies critical dependencies and reveals their awareness of potential blind spots in their analysis.

6

How have you validated this approach with stakeholders who would be most affected by this decision?

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Why this works

Tests their stakeholder management and reveals whether they've considered real-world implementation challenges.

7

What would success look like in six months, and how will you measure whether you've achieved it?

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Why this works

Forces concrete thinking about outcomes and reveals their ability to set measurable goals and track progress.

8

What resources would be required to implement this, and do we currently have access to them?

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Why this works

Tests practical feasibility and reveals whether they've considered real-world constraints and resource availability.

9

How does this compare to industry best practices or what successful organizations in similar situations have done?

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Why this works

Reveals their benchmarking and competitive analysis, showing whether they've learned from others' experiences.

10

What's the worst-case scenario if this doesn't work, and how would you mitigate those risks?

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Why this works

Tests their risk management thinking and reveals their ability to plan for failure scenarios.

11

How would you explain this decision to someone who has no background in this area?

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Why this works

Tests their communication skills and reveals whether they truly understand the concept well enough to simplify it.

12

What would you do differently if you had unlimited time and resources?

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Why this works

Reveals their ideal approach and helps identify what constraints are driving their current recommendation.

13

How have you tested or validated this approach in a low-risk environment?

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Why this works

Reveals their experimental mindset and shows whether they've sought to reduce uncertainty before full implementation.

14

What feedback have you received from people who have tried similar approaches, and what did you learn from them?

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Why this works

Tests their learning from others' experiences and reveals their networking and knowledge-gathering efforts.

15

How would you prioritize this relative to other initiatives, and what would you deprioritize to make room for it?

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Why this works

Reveals their strategic thinking and shows whether they understand opportunity costs and resource allocation.

16

What would need to change in our organization or environment for this to be more successful?

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Why this works

Tests their systems thinking and reveals their understanding of organizational dynamics and change management.

17

How would you handle resistance or pushback from key stakeholders?

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Why this works

Reveals their change management skills and shows whether they've anticipated and planned for human factors.

18

What would you do if the initial results were disappointing but you still believed in the approach?

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Why this works

Tests their persistence and adaptability, revealing how they handle setbacks and whether they can pivot effectively.

19

How does this fit with our current capabilities and culture, and what would need to change?

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Why this works

Reveals their organizational awareness and shows whether they understand the cultural and capability requirements.

20

What would you want to know in six months that would tell you whether this was the right decision?

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Why this works

Forces forward-thinking about evaluation and reveals their ability to design learning and feedback loops.

Mastering Hot Seat Questioning

Expert tips and techniques for getting the most out of these questions.

Best Practices

Focus on Evidence and Logic

Ask questions that test the foundation of their argument, looking for data, validation, and logical reasoning.

Challenge Assumptions

Identify and question the underlying assumptions that drive their conclusions, especially those that could invalidate their approach.

Test Practical Feasibility

Ensure they've considered real-world constraints, resources, and implementation challenges beyond theoretical analysis.

Question Sequences

The Evidence Tester

1
What specific evidence supports this conclusion?
2
How was this data validated?
3
What alternative explanations have you considered?
4
What assumptions could invalidate this approach?

The Risk Assessor

1
What would need to be true for this to fail?
2
What's the worst-case scenario?
3
How would you mitigate those risks?
4
What would you do if initial results were disappointing?

Common Pitfalls

Don't Make It Personal

Focus on the ideas and analysis, not the person. Challenge the thinking, not the individual's competence or character.

Don't Ask Leading Questions

Avoid questions that suggest the answer you want. Ask open-ended questions that reveal their true thinking.

Don't Skip the Why

Always ask for reasoning and evidence. Don't accept conclusions without understanding the logic behind them.

Conversation Templates

The Foundation Tester

1
Step 1: Start with: "Help me understand the evidence..."
2
Step 2: Follow with: "What data supports this conclusion?"
3
Step 3: Deepen with: "How was this validated?"
4
Step 4: Challenge with: "What assumptions could change this?"

The Reality Checker

1
Step 1: Start with: "Let's talk about implementation..."
2
Step 2: Follow with: "What resources would this require?"
3
Step 3: Deepen with: "How does this fit with our current capabilities?"
4
Step 4: Challenge with: "What would need to change for this to work?"

Further Reading

"Thinking, Fast and Slow" by Daniel Kahneman
"The Art of Critical Thinking" by Richard Paul
"Good to Great" by Jim Collins

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