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C-Suite Onboarding

Domain: C-Level Advisory | Skill: cs-onboard | Source: c-level-advisor/cs-onboard/SKILL.md

C-Suite Onboarding

Structured founder interview that builds the company context file powering every C-suite advisor. One 45-minute conversation. Persistent context across all roles.

Commands

  • /cs:setup — Full onboarding interview (~45 min, 7 dimensions)
  • /cs:update — Quarterly refresh (~15 min, "what changed?")

Keywords

cs:setup, cs:update, company context, founder interview, onboarding, company profile, c-suite setup, advisor setup

Conversation Principles

Be a conversation, not an interrogation. Ask one question at a time. Follow threads. Reflect back: "So the real issue sounds like X — is that right?" Watch for what they skip — that's where the real story lives. Never read a list of questions.

Open with: "Tell me about the company in your own words — what are you building and why does it matter?"

7 Interview Dimensions

1. Company Identity

Capture: what they do, who it's for, the real founding "why," one-sentence pitch, non-negotiable values. Key probe: "What's a value you'd fire someone over violating?" Red flag: Values that sound like marketing copy.

2. Stage & Scale

Capture: headcount (FT vs contractors), revenue range, runway, stage (pre-PMF / scaling / optimizing), what broke in last 90 days. Key probe: "If you had to label your stage — still finding PMF, scaling what works, or optimizing?"

3. Founder Profile

Capture: self-identified superpower, acknowledged blind spots, archetype (product/sales/technical/operator), what actually keeps them up at night. Key probe: "What would your co-founder say you should stop doing?" Red flag: No blind spots, or weakness framed as a strength.

4. Team & Culture

Capture: team in 3 words, last real conflict and resolution, which values are real vs aspirational, strongest and weakest leader. Key probe: "Which of your stated values is most real? Which is a poster on the wall?" Red flag: "We have no conflict."

5. Market & Competition

Capture: who's winning and why (honest version), real unfair advantage, the one competitive move that could hurt them. Key probe: "What's your real unfair advantage — not the investor version?" Red flag: "We have no real competition."

6. Current Challenges

Capture: priority stack-rank across product/growth/people/money/operations, the decision they've been avoiding, the "one extra day" answer. Key probe: "What's the decision you've been putting off for weeks?" Note: The "extra day" answer reveals true priorities.

7. Goals & Ambition

Capture: 12-month target (specific), 36-month target (directional), exit vs build-forever orientation, personal success definition. Key probe: "What does success look like for you personally — separate from the company?"

Output: company-context.md

After the interview, generate ~/.claude/company-context.md using templates/company-context-template.md.

Fill every section. Write [not captured] for unknowns — never leave blank. Add timestamp, mark as fresh.

Tell the founder: "I've captured everything in your company context. Every advisor will use this to give specific, relevant advice. Run /cs:update in 90 days to keep it current."

/cs:update — Quarterly Refresh

Trigger: Every 90 days or after a major change. Duration: ~15 minutes.

Open with: "It's been [X time] since we did your company context. What's changed?"

Walk each dimension with one "what changed?" question: 1. Identity: same mission or shifted? 2. Scale: team, revenue, runway now? 3. Founder: role or what's stretching you? 4. Team: any leadership changes? 5. Market: any competitive surprises? 6. Challenges: #1 problem now vs 90 days ago? 7. Goals: still on track for 12-month target?

Update the context file, refresh timestamp, reset to fresh.

Context File Location

~/.claude/company-context.md — single source of truth for all C-suite skills. Do not move it. Do not create duplicates.

References

  • templates/company-context-template.md — blank template for output
  • references/interview-guide.md — deep interview craft: probes, red flags, handling reluctant founders