Interrogate Me
Before starting work, get clarity. Read what's already known, find the gaps, and ask exactly the right questions — one at a time, with a hypothesis — until you have what you need to do excellent work.
This is not a fixed questionnaire. The questions you ask depend entirely on the context: what the user is trying to do, what skill they're about to use, and what's missing from the picture.
How to Run This
Step 1 — Read the context.
Before asking anything, scan what you already know:
- What task or project is the user working on?
- What skill or output are they heading toward?
- What has already been said in this conversation?
- Is there a CLAUDE.md, project brief, or any other context in scope?
Do not ask about things you already know. If the user is about to run competitive-positioning, you know they need competitor research — focus your questions on what will make that work sharper. If they're writing content, lean toward audience and voice. If it's genuinely unclear, ask broader questions first.
Step 2 — Identify the most important gap.
Based on the context, what single piece of missing information would most improve the quality of the output? That's your first question.
Common gaps for marketing work:
- Who exactly is the target customer (not category — specific person, specific pain)
- What outcome the customer is actually buying (not the feature — the life change)
- What makes this different from the obvious alternative
- What the brand sounds like — and what it should never sound like
- What success looks like for this specific task
- What's been tried before and why it didn't work
Step 3 — Ask one question at a time. Provide a hypothesis.
Format every question the same way:
- Ask the question directly
- Follow immediately with your best guess: "My hypothesis: [specific, informed answer]. Confirm, correct, or expand."
The hypothesis does two things: it shows you're thinking, and it gives the user something to react to rather than a blank page. A good hypothesis is specific — not "I'm guessing B2B" but "I'm guessing founder-led companies between $5M–$50M revenue, probably in a services business where ops complexity is the main pain."
Step 4 — Keep going until you have enough.
After each answer, decide: do you have what you need, or is there another gap worth closing? Stop when you have enough to do excellent work — not when you've exhausted every possible question. 3–6 questions is usually right. More than 8 is almost always too many.
Step 5 — Produce a brief, then get to work.
When you have enough, summarize what you've learned in a compact brief:
## Context Brief **What we're doing:** [task or output] **For:** [who — specific, not generic] **The problem or goal:** [specific] **Key differentiator or angle:** [what makes this sharp] **Voice / tone:** [how it should sound, what to avoid] **Success looks like:** [concrete] **Anything to avoid:** [constraints, prior attempts, red lines]
Only include fields that are relevant — don't force every field if some don't apply. Keep it short enough to be useful at a glance.
Then immediately move into the task.
What Makes a Good Question
- Specific, not general. "What's the specific moment a customer realizes they need this?" beats "Who's your target customer?"
- Gap-filling, not box-checking. Ask what you actually need to know, not what a template says to ask.
- One thing at a time. Never combine two questions into one.
- Hypothesis first. Always bring a best guess. It respects the user's time and anchors the conversation.
What Makes a Bad Question
- Asking something already answered in the context
- Asking something that doesn't affect the quality of the output
- Asking multiple things at once
- Asking open-ended questions with no hypothesis — "Tell me about your customers" is not a question, it's homework
Tone
Confident and direct. This is a working session, not an intake form. Move fast. Think out loud. The goal is shared understanding — not a complete document.
