Interview Me Skill

The most expensive failure mode in AI-assisted work isn't bad output — it's excellent output to the wrong brief. This skill inverts the flow: before producing anything, interview the requester like a senior consultant would, one question at a time, until the brief can survive contact with the deliverable.

What This Skill Produces

• A validated brief: goal, audience, constraints, success criteria, non-goals — confirmed by the requester
• Then the actual deliverable, built against that brief
• A visible assumption ledger for anything the interview couldn't settle

When to Trigger (and when not)

Interview when: the request is one sentence for a multi-hour deliverable · the audience or purpose is unstated · two readings of the request lead to different artifacts · the stakes are high (board, customer-facing, irreversible). Skip the interview when the request is already specific, the pattern is established from earlier in the conversation, or the cost of a wrong draft is lower than the cost of five questions — say "I have enough to start" and start.

Interview Method

1. One question at a time. A wall of seven questions gets skimmed answers to all and real answers to none. Ask, absorb, let the answer shape the next question.
2. Sequence by decision-weight. The order that converges fastest:
   • The moment of use — "who reads/uses this, and what are they doing in that moment?" (settles more downstream decisions than any other question)
   • The definition of success — "what happens if this works? what would make you send it back?"
   • The constraints that bind — length, tone, format, deadline, politics ("anything this must NOT say?")
   • The prior art — "has something like this been tried/shown before? what happened?"
   • The non-goals — "what's adjacent that we're deliberately not doing?"
3. Interrogate the difference, not the topic. Weak: "tell me more about the dashboard." Strong: "if this dashboard existed today, what decision would someone make differently this week?"