Cs Onboard

What This Skill Does

The C-Suite Onboarding skill conducts a structured interview with founders to build a comprehensive company context file. This file provides persistent context for C-suite advisors, ensuring alignment and informed decision-making. It saves time and improves the quality of advice.

When to Use

Onboarding new C-suite advisors. Creating a shared understanding of the company. Quickly bringing new team members up to speed. Refreshing company context quarterly. Preparing for board meetings. Identifying key company values and priorities.

Key Features

Structured founder interview process. Captures company identity, stage, founder profile, team, market. Identifies potential red flags and areas of concern. Generates a persistent company context file. Offers commands for full onboarding and quarterly refresh. Focuses on conversational interviewing techniques.

Manual Installation

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 output references/interview-guide.md — deep interview craft: probes, red flags, handling reluctant founders C-Suite Onboarding

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