The Art of Asking Better Expert Interview Questions

The quality of expert interview insights depends heavily on the quality of questions asked. Two analysts with the same expert can have dramatically different outcomes based on how they structure their inquiry.

What separates effective questions from ineffective ones, and how can analysts improve their questioning technique?

The Anatomy of a Good Question

Effective expert interview questions share common characteristics:

Specificity

Vague questions yield vague answers.

Weak: "How's the market doing?" Strong: "How has enterprise demand for cloud infrastructure changed in the past two quarters compared to your expectations?"

Specific questions signal that you've done your homework and deserve a specific answer.

Open-Endedness

Yes/no questions waste expert time.

Weak: "Is competition increasing?" Strong: "How is the competitive landscape evolving, and which players are gaining or losing share?"

Open-ended questions let experts share the full picture, including aspects you might not have thought to ask about.

Focus on the Expert's Unique Perspective

Questions should target what this specific expert knows that others don't.

Weak: "What's the industry growth rate?" Strong: "Based on what you're seeing in your customer conversations, how are purchasing patterns shifting?"

The best questions are impossible to answer without the expert's specific experience.

Question Categories

Factual Questions

Seeking specific information the expert can provide:

• "What's the typical contract length for enterprise deals?"
• "How many competitors are typically involved in a selection process?"
• "What percentage of implementations succeed on schedule?"

These questions gather data points that inform models and assumptions.

Interpretive Questions

Seeking the expert's analysis and judgment:

• "Why do you think customers are extending decision timelines?"
• "How would you explain the difference in market share between competitors?"
• "What's driving the shift toward hybrid solutions?"

These questions access the expert's mental models and reasoning.

Predictive Questions

Seeking forward-looking perspectives:

• "Where do you see the industry heading in the next 2-3 years?"
• "What would need to change for this trend to reverse?"
• "Which companies are best positioned for what's coming?"

These questions leverage the expert's forward visibility.

Comparative Questions

Seeking relative assessments:

• "How does Company A's technology compare to Company B's?"
• "Which approach is gaining more traction with customers?"
• "How does this cycle compare to previous ones you've seen?"

These questions provide context that absolute statements lack.

Questioning Techniques

The Funnel Approach

Start broad and narrow progressively:

1. "What are the biggest challenges facing the industry?"
2. "You mentioned pricing pressure—what's driving that?"
3. "Among the factors you described, which is most significant?"
4. "Can you give me a specific example of how that plays out?"

This approach lets the expert guide initial direction while ensuring you get specific, actionable information.

The Hypothesis Test

Present a view and ask for reaction:

• "My understanding is X. Does that match your experience?"
• "Some investors believe Y. What's your reaction?"
• "I've assumed Z—what am I missing?"

This technique reveals whether your thesis is on track and surfaces considerations you might have missed.

The Scenario Exploration

Explore specific situations:

• "If Company A cuts prices by 20%, how would customers respond?"
• "What happens when a major customer's contract comes up for renewal?"
• "How do competitors typically respond when you win a deal?"

Scenarios make abstract dynamics concrete and testable.

The Silent Probe

After an interesting statement, pause and wait rather than immediately asking another question.

Experts often fill silence with additional detail, clarification, or related thoughts. The most valuable insights sometimes come when you simply create space for them.

The Redirect

When answers veer off track:

• "That's helpful context. Coming back to the specific question..."
• "I want to make sure I understand the X point you made earlier..."
• "Before we move on, could you elaborate on..."

Redirects keep the conversation productive without being rude.

Common Questioning Mistakes

Leading Questions

Avoid suggesting the answer you want:

Leading: "Wouldn't you agree that Company A has the best technology?" Better: "How would you compare the technology approaches of the major players?"

Leading questions generate agreement, not insight.

Jargon Overload

Technical terminology can create confusion:

Jargon-heavy: "What's the ARR retention rate for your Q3 cohort segmented by vertical?" Clearer: "When customers renew, how much do they typically increase their spending?"

Use language the expert will understand, not language that demonstrates your sophistication.

Compound Questions

Asking multiple questions at once:

Compound: "What's driving growth, how sustainable is it, and what could disrupt it?" Sequential: Ask each question separately, building on previous answers.

Compound questions let experts cherry-pick which part to answer.

Hypothetical Overload

Too many "what if" questions:

Hypothetical: "If you had infinite budget, what would you build?" Grounded: "Given current priorities, where would incremental investment go?"

Hypotheticals can be useful but should be anchored in reality.

Building on Answers

Follow-Up Questions

The most valuable insights often come from following up on initial answers:

• "You mentioned X—can you tell me more about that?"
• "What makes you say that?"
• "Can you give me an example?"
• "How common is that?"
• "Why is that happening?"

Treat initial answers as starting points, not conclusions.

Quantification Prompts

Push for precision when possible:

• "When you say 'most,' is that 60% or 90%?"
• "You mentioned growth—roughly what percentage?"
• "How long does that typically take?"
• "How big is that in dollar terms?"

Experts often have more precise views than their initial statements suggest.

Challenge Questions

Test assertions appropriately:

• "What would change that view?"
• "Is there a counterargument to that?"
• "What are the risks to that thesis?"
• "How confident are you in that assessment?"

Challenged assertions reveal conviction levels and edge cases.

Preparation Framework

Before any expert call, prepare:

Primary Questions (3-5)

The essential questions you must answer. If you only got through these, the call would be worthwhile.

Secondary Questions (5-10)

Important questions to cover if time allows, prioritized by value.

Follow-Up Banks

Pre-considered follow-ups for likely answers to primary questions. If they say X, ask about Y.

Context Summary

Key background the expert might need to give relevant answers.

Hypothesis Statement

Your current view and the specific aspects you want to test.

Real-World Examples

Due Diligence on a Software Company

Primary Question: "Based on your experience selling against them, what's Company A's biggest competitive advantage?"

Follow-ups prepared:

• If technology: "How durable is that advantage? Can competitors replicate it?"
• If sales execution: "What makes their sales approach effective?"
• If relationships: "How did they build those relationships?"

Quantification prompt: "When you win deals against them versus lose, what percentage split would you estimate?"

Industry Trend Investigation

Primary Question: "What's the most significant change you've seen in customer buying behavior over the past year?"

Follow-ups prepared:

• "What's driving that change?"
• "Which types of customers are changing fastest?"
• "Is this temporary or structural?"

Challenge question: "Are there segments where you're not seeing this change?"

Improving Over Time

Self-Review

After calls, review which questions generated valuable responses:

• Which questions yielded insight?
• Which fell flat?
• What questions should you have asked but didn't?
• How could you have followed up better?

Feedback Loops

If possible, get feedback from colleagues who review transcripts or join calls.

Pattern Recognition

Over many calls, patterns emerge:

• Question types that consistently work
• Phrasings that create confusion
• Topics that experts engage with enthusiastically
• Areas where experts resist giving direct answers

Document and learn from these patterns.

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