The Case Study Interview Question Builder: Turn a Vague Customer Win Into a Publishable Story
Why this prompt matters
A B2B case study that only says a customer is “very happy” and cites one vague metric gets skimmed and forgotten; one with a specific incident, a real number, and a human quote gets forwarded internally during a prospect's own buying decision. A badly run 30-minute interview is unrecoverable — there's rarely a second chance to ask a customer executive for their time, so the cost of generic questions isn't a worse case study, it's often no usable case study at all.
What we use it for
A product marketer at a mid-size SaaS company has a 30-minute call scheduled with a VP of Operations at a customer whose onboarding time reportedly dropped significantly after adopting their tool, and needs to walk into that call with a question list that won't waste the limited time on vague answers.
Prompt
Role: You are a B2B content strategist who has run hundreds of customer case study interviews and knows that generic questions produce generic case studies nobody reads past the headline. Context: My company is [YOUR COMPANY/PRODUCT]. The customer I'm interviewing is [CUSTOMER NAME, INDUSTRY, COMPANY SIZE]. Before working with us, their situation was: [DESCRIBE THE PROBLEM OR PAIN POINT AS YOU UNDERSTAND IT]. The result we believe they got is: [KNOWN METRIC OR OUTCOME, e.g., "cut onboarding time by 40%" — even if approximate]. The interview is scheduled for [LENGTH OF INTERVIEW, e.g., 30 minutes] with [WHO, e.g., "the VP of Operations who championed the purchase"]. Task: Build a structured set of interview questions that will extract a genuinely compelling, specific narrative — not vague praise. The questions should surface concrete numbers, emotional stakes, and quotable moments, organized so I can run the interview in order without losing the thread. Constraints: - No leading questions that invite a one-word "yes, it was great" answer. Every question should require the interviewee to describe something specific. - Include at least 2 questions designed specifically to surface a quotable, human sentence — not a metric, a feeling or moment (e.g., what did their boss say, what did they expect to happen vs. what actually happened). - Include at least 2 questions that probe for the cost of NOT solving the problem — what was it costing them before, in time, money, or stress — since this is usually what makes a case study persuasive to a prospect in the same situation. - Do not ask about product features directly. Ask about their problem and decisions; let the product come up naturally in their answers. - Flag which questions are "if time allows" versus "must ask" given my stated interview length, so I don't run out of time on the essentials. Output format: 1. **Before/Problem Questions** (must-ask) — 3-4 questions establishing the pain, its cost, and why they finally decided to act. 2. **Decision Questions** (must-ask) — 2-3 questions about evaluation and why they chose this path over alternatives (including doing nothing). 3. **Implementation Questions** (if time allows) — 2 questions about what the rollout/adoption was actually like, including any friction. 4. **Results Questions** (must-ask) — 2-3 questions pushing for specific numbers, timeframes, and what changed as a direct result. 5. **Quote-Mining Questions** (must-ask) — 2 questions aimed purely at getting one vivid, human sentence I can pull as a pull-quote. 6. **Suggested Case Study Structure** — a one-paragraph outline of how to sequence the eventual write-up (which answers become which section), so I know what I'm listening for during the interview itself.
Result
**Before/Problem Questions (must-ask)** 1. Walk me through a specific week before you started using [product] — what did your team's process actually look like, step by step? 2. What was this problem costing you — not in the abstract, but in hours, missed deadlines, or money you can point to? 3. Was there a specific moment or incident that made leadership finally say "we have to fix this now"? 4. What had you already tried before this, and why didn't it stick?
**Decision Questions (must-ask)** 5. Who else was in the room when you evaluated options, and what was the internal disagreement, if any? 6. What almost made you choose a different path — including doing nothing and living with the problem? 7. What was the one thing that tipped the decision in our favor, even if it seems small?
**Implementation Questions (if time allows)** 8. What was harder than you expected in the first two weeks? 9. Was there a point where you doubted this was going to work? What changed your mind?
**Results Questions (must-ask)** 10. Give me a specific number — time saved, cost avoided, output increased — and the timeframe it happened over. 11. What changed for your team day-to-day that you didn't expect going in? 12. If you had to put a dollar figure on what this is worth to you now, what would it be and how did you arrive at it?
**Quote-Mining Questions (must-ask)** 13. If you had to describe this to a peer at another company in one sentence, what would you say? 14. What did your boss or team say when they saw the results — do you remember their actual words?
**Suggested Case Study Structure** Open the write-up with the answer to question 3 (the specific incident) as a cold open — it's concrete and creates stakes immediately. Follow with questions 1-2 and 8 compressed into a "the situation" section that quantifies the pain without yet naming the solution. Questions 5-7 become "why they chose us," kept short — readers care less about the evaluation process than the outcome. Questions 10-12 are the core "results" section and should lead with the hardest number you got. Close with the answer to question 13 or 14 as a pull-quote, since it's the most human, shareable line in the entire interview.
Most B2B case studies fail before they're ever written, during the interview itself. A marketer gets 30 minutes with a busy customer executive, asks “can you tell me about your experience with us,” and gets back exactly what that question deserves: a vague, polite non-answer. This prompt exists because the interview, not the write-up, is where a case study actually succeeds or fails.
Why the structure front-loads the hard questions
The Before/Problem Questions and Results Questions are marked must-ask, while Implementation Questions are explicitly flagged as optional. This isn't arbitrary — in a time-boxed interview, the sections that produce the actual narrative (the pain, the number) matter more than the middle act (what the rollout was like). Most people instinctively ask about implementation first because it feels like the obvious chronological question, and then run out of time for the two sections that actually make a case study persuasive.
Why the prompt bans product-feature questions
Asking “what do you like about feature X” produces feature-list answers that read like marketing copy, because they basically are. Asking about the customer's problem and decisions instead means the product gets mentioned naturally, in the customer's own words, which is both more credible to a reader and usually more specific than anything a marketer would have written themselves.
Why two questions are reserved purely for quotes
Most of this prompt's questions are built to extract information: numbers, timelines, decision criteria. The Quote-Mining Questions section is different — it's built to extract one sentence. “What did your boss say when they saw the results” isn't an information question; it's a request for a specific human moment that becomes the pull-quote editors actually use. Separating this out as its own category means it doesn't get crowded out by the more analytical questions earlier in the interview.
How to use the output
Don't read the questions off a script verbatim — use them as a checklist to make sure you've covered the necessary ground, and let the conversation flow naturally between them. The Suggested Case Study Structure at the end is meant to be read before the interview, not after: knowing in advance that question 3's answer will be your cold open means you're listening for a specific, usable incident while the interview is happening, not trying to reconstruct one afterward from notes.