Who this is for
Podcasters, journalists, and researchers preparing to interview someone, who want questions that go deeper than the obvious.
The moment this saves you
I show up to interview someone interesting with a list of obvious questions they've answered a hundred times, the conversation stays shallow, and I waste a rare chance to ask what I'm actually curious about.
See it work
Messy spoken thought in. A clean, structured artifact out.
Prepping questions for my interview with the founder who sold her company and then started a totally different one. What I'm really curious about, the emotional whiplash of going from huge exit to scrappy beginner again, nobody asks about that. I want to know what she misses about being small, and whether the money changed how she takes risks now, does she play it safer or bolder. I also want to dig into why she didn't just retire, what's driving her. And a sharper one, what did the first company teach her that she's deliberately doing differently this time. Save the personal stuff for the middle once she's warmed up.
Interview questions, June 5, 2026
Opening
- Why didn't you just retire? What's actually driving you to start again?
Middle (once warmed up)
- What was the emotional whiplash like, going from a huge exit back to scrappy beginner?
- What do you miss about being small?
- Did the money change how you take risks now, do you play it safer or bolder?
Sharper / deeper
- What did the first company teach you that you're deliberately doing differently this time?
The workflow
Record a voice note
Hit the hotkey and talk, no formatting, no typing.
Tag it with this context
Contextli shapes your words into the structured output above.
Find it later
Everything's searchable and organised by context.
Pull it into Claude or ChatGPT
Bring your contexts straight into your AI tools with the Contextli MCP.
Your raw recording and transcription stay on your device, so you can always go back to the original.
The prompt behind this context
I'm going to talk through what I'm curious about for an upcoming interview. Turn it into an ordered question list grouped under bold headings by flow: **Opening** (easy entry), **Middle** (the substance, once warmed up), and **Sharper / deeper** (the harder, most interesting questions). Phrase each as a real, specific question in a conversational voice, drawn only from the curiosities I mention. Honor any sequencing I specify (e.g. "save the personal stuff for the middle"). Don't invent questions about topics I didn't raise. Output only the question list.
Make it your own. This is a starting point. Once it's in Contextli, tweak the instructions so the output comes out exactly how you like it.
Use this context
One tap adds it to your clipboard. Open Contextli and paste to add it.
Next, open Contextli, Contexts, Import, paste.
Make it your own. This is a starting point. Once it's in Contextli, tweak the instructions so the output comes out exactly how you like it.
Your raw recording and transcription stay on your device, so you can always go back to the original.
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