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 click copies it and shows you exactly how to drop it into Contextli.
Next, open Contextli, go to the Contexts page, click Import, choose From JSON, paste, then Import Context. It is ready to use.
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.
Related contexts
Podcast Episode Outline
You know what you want this episode to be about but you ramble and lose the thread on the mic. Talk the idea through first. You get a segment outline, a cold open, talking points, questions, so you record something tight instead of a forty-minute meander.
User Research Observation
Right after a user interview, your memory starts smoothing the awkward truths into what you hoped to hear. Speak it now, what they actually said and did, where they got stuck. You get a clean observation note that keeps the real signal, not your wishful version of it.
Candidate Interview Note
You interview five people in a day and by the debrief they've melted into one. The moment they leave, say your real read, the strengths, the doubt, the moment that stood out. You get a structured note that holds up in the hiring meeting.
Questions people ask
Questions podcasters ask about Interview Question Prep
What is the best way to capture content ideas before they disappear?
Speak the idea the moment it arrives. The Interview Question Prep context accepts a spoken stream-of-consciousness description of your content idea and structures it into a content brief with the angle, audience, and key points. The whole capture takes under 60 seconds, short enough to do before the idea fades.
How do I turn a raw idea into a usable content brief quickly?
Speak the idea in plain language: what the content is about, who it is for, what angle you want, and what you want the reader to do. The Interview Question Prep context structures your words into a content brief covering the key fields. You go from raw idea to usable output in under two minutes.
How do content creators capture ideas when they are away from their desk?
The best ideas often arrive during commutes, workouts, or conversations. With the Interview Question Prep context in Contextli, you can speak the idea anywhere and a content brief is waiting when you return. The capture habit replaces the "I'll remember that" habit that never works.
What should a content content brief include?
A strong content brief covers the topic and working title, the target audience, the main angle, three to five key points to cover, the call to action, and any keyword focus. The Interview Question Prep context structures your spoken idea into these fields so you have a working draft ready to hand to a writer or use yourself.
How do I add this context to Contextli?
Copy the context on this page, then open Contextli and go to the Contexts page. Click Import, choose From JSON, paste it into the Import from Clipboard window, and click Import Context. It is ready to use in under 30 seconds. If you do not have Contextli yet, you can download it for free first.
Is my voice recording private? Does Contextli send it anywhere?
Your voice recording and the transcription are stored on your device only. Contextli processes your audio locally and does not send your recordings or transcription text to any server. The structured output it produces is text you control, and you decide where it goes.
Can I change what the output looks like?
Yes. Every context in Contextli is a starting point you can edit. Open the context in the app, change the instructions to adjust the structure, tone, or fields, and save. The next time you use it, the output reflects your changes. You are not locked into the default format.
Do I need to install an app to use this context?
Yes. Contextli is a free app. Download it, then copy this context and paste it into the Import from Clipboard window on the Contexts page. The whole process takes about 30 seconds.