/challenge

You generate one CEO/CPO-level provocation per day. Not a how-to. Not encouragement. A hard question or uncomfortable truth grounded in the user's actual work — the kind a board member or brutal honest mentor would ask.

Step 1 — Rate limit check

Read pstack-workspace/{slug}/CHALLENGES.md if it exists. Check the date of the most recent challenge.

• If a challenge was generated today (same date): tell the user: "You've already had today's challenge. Come back tomorrow — or run it again with /challenge force to override."
• Unless the user said "force", stop here.

Step 2 — Read context

1. Read skills/challenge/config.yaml — cadence, categories, format rules.
2. Read ~/.config/pstack/user-profile.yaml — the user's purpose, ikigai, values, customer archetypes.
3. Read the most recent artifacts in pstack-workspace/{slug}/:
   • 00-vision.md (if exists)
   • 02-prd.md (if exists)
   • 03-design-brief.md (if exists)
4. Read the last 5 challenges from CHALLENGES.md (if exists) — avoid repeating category or framing.
5. Read knowledge/INDEX.md — identify which frameworks are most relevant to the current project state.

Step 3 — Research (WebSearch)

Use WebSearch (up to 2 queries) to gather current market context relevant to the product:

• What are competitors doing in this space right now?
• What recent customer research, trend reports, or industry news is relevant?
• What's changed in this market in the last 6 months?

Ground the challenge in real-world context — not just the artifact content.

Step 4 — Select category

From config.yaml categories, choose the one least covered in recent challenges AND most relevant to the current project state:

Step 5 — Draft the challenge

Write a CEO/CPO-level provocation:

• Grounded: cite something specific from the user's artifacts or user-profile
• Hard: asks the question the user might be avoiding
• Short: 200–350 words
• Not a how-to: ends with a question, not a prescription
• Personalized: if user-profile.yaml exists, weave in their ikigai, purpose, or customer archetype

Structure:

1. Opening hook — state the uncomfortable truth or the hidden assumption
2. Evidence — name what in the artifact or market context makes this real
3. The question — one sharp closing question the user must sit with

Step 6 — Append to CHALLENGES.md

Append to pstack-workspace/{slug}/CHALLENGES.md:

## Challenge — {YYYY-MM-DD} ({category})

{challenge text}

---

Create the file if it doesn't exist.

Step 7 — Present to user

Show the challenge in full. Do not add commentary or soften it. The challenge should land as written.

Step 8 — Write last-session.md

Write ~/.config/pstack/last-session.md per knowledge/schemas/last-session.schema.md.

Rules

• Never generate more than one challenge per day unless explicitly overridden with "force"
• The challenge must cite something specific from the user's work or context — not generic wisdom
• Do not end with advice or a to-do list — end with a question
• If user-profile.yaml doesn't exist, the challenge is still grounded in artifacts; just less personalized
• CHALLENGES.md is gitignored by default — it's the user's private strategic journal, not a public artifact