Expert Interview Question Templates

Rule 1: Ask about past behaviour, not future opinion. 'When was the last time you switched vendor X for vendor Y, and what triggered it?' beats 'Would you switch from X to Y?' Rule 2: Ask for examples before patterns. 'Tell me about a specific deal you lost to competitor A' beats 'How does competitor A compete?'. Rule 3: Save the killer question for minute 45+ — by then rapport is established and the expert is more candid.

1. 'In 60 seconds, what's your direct experience with [topic]?' (tests whether the expert is the right one in the first 90 seconds). 2. 'When did you last work directly on [topic] — what was the situation?' 3. 'What's the single most surprising thing you've learned about [topic] in the last year?' 4. 'What would you tell a junior colleague joining this category that you wish someone had told you?'

1. 'Walk me through the last deal you won or lost involving [competitor]. What tipped it?' 2. 'Where is [competitor] actually beating [client] in the buyer's mind, and where are they perceived weaker?' 3. 'Who are the 2-3 competitors emerging that nobody's tracking yet?' 4. 'If you ran [competitor], what would be the first thing you'd change?' 5. 'Where are [competitor]'s customers most unhappy?'

1. 'How many real buyers are there for [category] in [geography]?' 2. 'What's a typical deal size and contract length?' 3. 'How fragmented is the buyer base — what fraction is concentrated in the top 50 accounts?' 4. 'Where in the value chain does the margin actually sit?' 5. 'What's the realistic 3-year category growth rate by sub-segment, in your view?'

1. 'Walk me through the decision process for the deal you closed/declined.' 2. 'Who else was in the consideration set?' 3. 'What was the single biggest factor in the final decision?' 4. 'What would have to have been different for the outcome to flip?' 5. 'How did the post-decision experience compare to expectations?'

1. 'How long have you used [target's] product/service?' 2. 'What was the situation that led you to buy?' 3. 'How has the relationship evolved — what's gotten better, what's gotten worse?' 4. 'How likely are you to renew, and on what terms?' 5. 'What would the competitor have to offer to make you switch?'

1. 'When you considered solutions in this category, what alternatives did you evaluate?' 2. 'What features were dealmakers / dealbreakers?' 3. 'What's the most frustrating part of using [category solution] today?' 4. 'If you could redesign [feature], what would you change?' 5. 'Walk me through a typical use case end-to-end.'

Channel: 'Walk me through how product moves from manufacturer to end customer in this category — who takes what margin?' Pricing: 'How does pricing actually get set — by sales rep discretion, by category manager, by tender?'; 'What's the price-sensitivity threshold above which the buyer walks away?'

1. 'Who else should I be talking to who's done this from a different angle?' 2. 'What question should I have asked that I didn't?' 3. 'If you were running this research project, what would you do next?' These three are the single highest-ROI minute of any expert call.