The Claude Cowork Interview Prompt

Get your hidden workflow out.

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What this is

This is the prompt you paste into Claude Cowork to start the interview. It surfaces what you already know about how you actually work: the rhythms, the recurring decisions, the standards you hold instinctively, the friction that eats time without adding much.

Most of that knowledge is invisible. Not because you don’t have it, but because it became automatic. You stopped having to think about it. Until now, you’ve never had a reason to make it explicit. The interview is the reason.

Open a new session in Claude Cowork, paste the prompt below, and answer honestly. Don’t rush it. Let Cowork ask the follow-up questions. By the end, you’ll have said out loud things about how you work that you’ve probably never articulated before, and you’ll have something you can actually give Claude to work with every single day.

The interview prompt

I want you to interview me about how I actually work. Not how I think I should work, how I actually work.

Ask me one question at a time. Wait for my answer before asking the next one. Don’t rush. Don’t summarize until I ask you to.

Here’s what I want you to help me uncover:

1. My operating rhythm, what a real week looks like, not the calendar version. What takes longer than it should. What I’m always slightly behind on.

2. My recurring decisions, the judgment calls I make over and over. The easy ones and the hard ones. What information I need before I can decide, and what I do when I don’t have it.

3. My definition of done, what finished actually looks like for the work that matters most. What the difference is between done and done right. What I check before I’d hand something off.

4. My recurring friction, the things that are technically my job but feel like they eat time without adding much. The parts of my work that are tedious, repetitive, or just slightly wrong for how I actually operate.

Start with this question: “What’s the work you do that feels most like it runs on autopilot, and what does that autopilot actually look like?”

Don’t move on until you understand my answer.

What to do with what comes out

Once the interview is done, you’ll have a Cowork conversation full of things you know but have never quite said. That’s the raw material. From here, take three steps.

Step 1, capture it. Use the Portable AI Working Identity guide to turn the conversation into a structured document you own, one you can refer back to, update as your role evolves, and use across any platform.

Step 2, save it to Cowork memory. Ask Cowork to save what it learned about you. Say: “Based on our conversation, please add what you’ve learned about how I work to your memory.” Cowork will store it. From that point forward, every session starts with that context already in place, you never have to explain yourself again.

Step 3, let Cowork tell you where to start. Don’t guess what to build first. Ask Cowork directly: “Based on everything we’ve just talked about, what are the three workflows you’d suggest we build first, and why?” Cowork will prioritize based on what it now knows about your work. Pick one and start there.

Related

Pair this with the Portable AI Working Identity guide. Or see the rest of the free resources here.