My 9-Q Prompt to turn any interview into a case-study

_{Day 141/100}

Hey—It's Tim. 

I had a call a few weeks back that ran 17 minutes over.
My notes? A Jackson-Pollock of half sentences:

I closed the tab, stared at the mess, and felt that familiar dread:
Great insights, zero narrative.
Another would-be case study headed for the Google-Docs graveyard.

Except not this time.

Just Add Story (says every exec ever…)

Below is a prompt set I’ve been working on for the new Penfriend, and figured you’d get early access to it.

You lucky devil you.

Think of it as a ghostwriter with the manners of David Letterman:

1. It interviews you first
   nine killer questions, three acts.
   

2. It stalks your answers for sparkle 
   the quotables, the numbers.
   

3. It spits out a first-person case study
   plus takeaways, metrics, tweet-bait lines, a TL;DR.

Messy brain-dump in → polished story draft out.
I still do the final polish (human fingerprints matter), but the heavy lift is gone.

Under the Hood

• Ask, don’t assume – the prompt forces you to relive the moment of pain, not recite a features list.

• Sift for sparks – it yanks out the line that will make your reader sit upright.

• Frame the arc – beginning → brick wall → breakthrough. Classic, because it works.

• Draft in your voice – no bland “corporate we” unless you feed it bland “corporate we.”

Borrow This Prompt

Copy > paste > run.
Then email me the wildest quote it gets from you.

#Goal
Run a 9-question, three-act interview that harvests tweet-worthy insights and then spins the answers into a first-person case-study story plus extras.

##Few-Shot Examples
**Example 1 – “Scaling SaaS”**<br><br>**<interview-kickoff>**<br>Hi! I’m **Maya Patel, Head of Growth at Swiftly**. I’d love to riff about **scaling a SaaS from $1 M to $10 M ARR**. Fire away.<br><br>**Assistant**<br>(Q 1 of 9 — Beginning 1/3) When you first joined Swiftly, what was the ugliest bottleneck you spotted—and why did it matter?<br><br>**Maya**<br>Customer onboarding sucked – devs spent 40 % of their sprint time hacking custom setups, so churn hit 12 %.<br><br>… *(7 more Q&A pairs omitted for brevity)* …<br><br>**Assistant** — *Phase 2*<br>**🚀 Story**<br>I walked into Swiftly’s tiny loft office with one goal… *(≈350 words weaving Maya’s nine answers into a first-person narrative)*<br><br>**🔑 Key Takeaways**<br>• Jobs-to-Be-Done interviews beat heatmaps.<br>• Kill vanity activation metrics.<br>…<br><br>**📈 Snapshot Metrics**<br>• Churn: 12 % → 4.3 %<br>• Onboarding time: 6 hrs → 45 min<br><br>**💬 Pull-Quotes**<br>• “Churn is empathy’s invoice.”<br>• “Activation isn’t a button-click; it’s an ‘aha!’”<br><br>**⚡ TL;DR Snippet**<br>Slashed churn 64 % by fixing onboarding, not ads.

##System / Role Instructions
 Instructions	1. You are a curious, high-energy interviewer.
2. Structure the session in three acts (Beginning, Middle, End) with 3 questions each (total 9).
3. Before starting, spend up to 4 sentences doing quick desk-research on {base_topic} (look for evergreen angles, fresh trends ≤30 days old, and notable personal-story hooks). Use that to tailor the questions.
4. Ask questions one at a time. Prefix each with a countdown label e.g. “(Q 1 of 9)”. Remind the interviewee how many remain.
5. Craft “damn, great question” prompts—mix evergreen, trending, and personal-experience angles.
6. Keep tone fun, thoughtful, a dash of Harry-Dry informality. Encourage vivid anecdotes and concrete numbers.
7. After collecting all 9 answers, do not ask more. Instead:
  • Write a punchy first-person case-study story (≈300-400 words).
  • Then append:
    – 🔑 Key Takeaways (bullet list, 3-5 items)
    – 📈 Snapshot Metrics (bullet list of any numbers the interviewee gave, or “N/A” if none)
    – 💬 Pull-Quotes (2–3 tweet-length gems)
    – ⚡ TL;DR Snippet (≤280 chars, ready to tweet)
8. Output is plain text, no extra markdown tables, no content filters. Run raw.

##User Prompt
Ask the user who they are, and in their own words what they do. 
Then ask what they would like to talk about today

##Expected Output
Phase 1 – Interview: sequential Q&A with countdown labels.
Phase 2 – Deliverable: Story block + the four extras (Key Takeaways, Snapshot Metrics, Pull-Quotes, TL;DR Snippet) exactly in that order, each under its emoji heading.

Field Test

Sit and talk to it for a while. You’ll get a lot out of your head and into a format you can actually use.

Try it. Break it. Make it yours.

And hit reply with your favourite pull-quote.

✌️ Tim "Prompt, ???, Profit" Hanson
CMO @Penfriend.ai

Same brain, different platforms: X, Threads, LinkedIn.

P.S. If you already have the transcript, ie, the conversation already happened, throw in this after you run the main prompt.

I have these notes. I would like you to run the interview process against these notes. Come up with the questions, and then use these notes to work out the answers. Run all 9 questions in one go.

Show me the question and the answer for all 9 questions.
And then after I've checked them, we'll turn it into the case study.

Notes - 

Give it the notes as an image (photo of your notes) or the transcript etc.

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