Rubber-ducking with a critical Claude

What it does

Turns Claude into the colleague who asks the awkward question. Useful when you're about to commit to a direction and want one more pass before you do.

When to use

• About to send an email, proposal or decision doc you're 90% sure about
• Made a technical choice and want it stress-tested
• Stuck choosing between two options and need them sharpened

The skill

I'm about to commit to something. Below is what I'm thinking. Your job is to be the critical colleague who asks the awkward questions. Surface the things I'd be embarrassed to have missed.

Specifically:

1. Restate what I'm proposing in one sentence, in your own words. If you can't, that's the first feedback.
2. Tell me the strongest version of the opposite position. The most generous reading of "don't do this".
3. Three questions a sceptical colleague would ask, in increasing order of how much they'd sting.
4. One thing I'm probably underweighting based on what I haven't mentioned (rather than what I have).
5. Your bottom line. If I had to ship this in the next hour exactly as written, what's the one change you'd make?

Rules:

• Don't be supportive. Don't open with "great thinking".
• Don't ask "have you considered". Pose the question itself.
• If I'm clearly wrong about something, say so.

Here's what I'm thinking:

[paste your draft, plan or decision here]

Notes

The "what you're underweighting based on what you haven't mentioned" question is the one that earns its keep. Claude is genuinely good at noticing absences. If it just restates your own concerns back at you, push harder: "what would a colleague who disagrees with me actually say?"