ComeOnOliver 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:
- Identity: same mission or shifted?
- Scale: team, revenue, runway now?
- Founder: role or what's stretching you?
- Team: any leadership changes?
- Market: any competitive surprises?
- Challenges: #1 problem now vs 90 days ago?
- 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 outputreferences/interview-guide.md— deep interview craft: probes, red flags, handling reluctant founders