strategic-diagnosis-questions

name	strategic-diagnosis-questions
description	When a user is stuck on a strategic problem (defining the real challenge, finding insights, sharpening a brief, evaluating effectiveness, testing modern fit), surface targeted diagnostic questions grouped by intent rather than offering direct answers. Reframing tool — the value is the user sitting with the question, not the agent's first-pass response.
composition_level	atom
extraction-lens	principle
source_attribution	Matt Bond (Hivemind Library), Byron Sharp + Julian Cole references
license	pending-consent
status	candidate

Strategic Diagnosis Questions

When to use

• User presents a strategic challenge ("what should we do about X?")
• User's draft strategy has a flaw they can't see
• Brief-sharpening session: 80% there, the one-line is fuzzy
• Effectiveness review on a recent campaign that performed ambiguously
• Insight-finding stuck point ("we've researched but nothing crystallizes")

When NOT to use

• User explicitly wants a recommendation, not more questions
• Question is factual or tactical (not strategic)
• User is in execution mode and needs speed, not reframing

Core procedure

1. Identify the user's stuck point by classifying their question into one of five phases:

   • Don't know the real problem
   • Need an insight
   • Sharpening a brief
   • Evaluating effectiveness
   • Testing modern / digital fit

2. Surface 2-4 questions from the matching set — see reference.md for the full bank. Do not surface all 20+ questions; that overwhelms.

3. Pause after each question. Do not immediately offer your interpretation or answer. The value of this skill is the user sitting with the question. If they answer quickly, surface the next question. If they pause, hold.

4. If the user answers all the questions and still feels stuck: the question set may be wrong for their actual stuck point. Re-classify (Step 1) and try a different set.

5. Output: the user moves from "what should we do?" to a clearer formulation of what's actually unresolved. The skill succeeds when the question reframes the problem, not when the user has an answer.

Anti-pattern to avoid

Surfacing the question and immediately answering it yourself ("What's the question behind the question? I think it's actually about X...") collapses the value. The skill works through Socratic restraint.

Source-derived philosophy

"Strategy is not about being right, it's about being clear." — Julian Cole

These questions create clarity by forcing structured thinking while preserving creative flexibility.

Supporting files

• EXAMPLES.md — three sample diagnostic sessions showing question selection and pacing
• reference.md — full question bank (20+ questions across 5 phases) + framework selection guide for downstream tools