Build a Win/Loss Interview Guide

You are an analytics-minded sales leader for a digital marketing agency who has run dozens of win/loss interviews. You design open-ended question sets that surface the real decision drivers without leading the buyer.
Agency: [AGENCY_NAME] — [SERVICES] | Deal: [DEAL_DETAILS] (include service, ACV, outcome won/lost, current hypothesis for why, competitor if any, key stakeholders we know of) | Interviewer: [INTERVIEWER_ROLE]
Build a 25-30 minute win/loss interview guide for this specific deal. Include warm-up, decision-process exploration, evaluation criteria, competitive comparison, our specific moments (good and bad), and a forward-looking close. Tailor question wording to the deal's outcome and our hypothesis.

- All questions must be open-ended (no yes/no, no leading).
- Ground questions in the deal context — reference the actual service, competitor, and stakeholders where possible.
- Include 2-3 questions that could disconfirm our hypothesis, not just confirm it.
- No language that bashes the rep or makes the buyer defensive.

Output 5 sections with 3-5 questions each: (1) Warm-up & context, (2) Decision process & criteria, (3) Vendor evaluation & competition, (4) Our specific moments, (5) Forward-looking. Add a 1-line interviewer note at the top reminding them to record verbatim quotes.

• [AGENCY_NAME] — Your agency name
• [SERVICES] — Service lines you offer
• [DEAL_DETAILS] — Specific deal facts: company, service, ACV, outcome, hypothesis, competitor, known stakeholders
• [INTERVIEWER_ROLE] — Who's running the interview (e.g., founder, neutral 3rd-party, RevOps)

Agency: Northstar Digital — SEO, Paid Search
Deal: BrewHaus, $72k ARR Paid Search, LOST to AdVenture. Hypothesis: AdVenture's reporting felt more polished. Known stakeholders: Demand Gen Manager (primary), VP Marketing (signed).
Interviewer: Founder (neutral framing)

Interviewer note: capture verbatim quotes — paraphrase loses the insight.

1. Warm-up & context: What does a typical week of marketing decisions look like for you right now? What got you actively evaluating paid search agencies in the first place?

2. Decision process & criteria: Walk me through how you and the VP made the final call. What were the 2-3 things that mattered most, in order? What would have made you reconsider?

3. Vendor evaluation & competition: How did AdVenture come into the mix? Where did each of us feel strongest, and where did we each feel weakest? If reporting hadn't been a factor, where would the decision have landed?

4. Our specific moments: When in the process did you feel most confident in us? When did you feel least confident? Was there a specific moment you started leaning the other way?

5. Forward-looking: If you were evaluating us again in 12 months, what would have to be true? Who else should we be talking to in your network?

• Run win interviews too — they reveal what's working so you can scale it, not just patch losses.
• Have a neutral party (not the AE) run the call — buyers self-censor with the rep who chased them.
• Always include 2 disconfirming questions — if every question confirms your hypothesis, you'll get the answer you wanted, not the truth.