Cs Onboard

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

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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?"

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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?"

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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."

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/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.

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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

Interview Craft Guide

Deep operational guide for conducting the /cs:setup founder interview. Not a script — a thinking tool. Read before every interview. Internalize it, then put it away.

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The Core Problem

Most context-gathering fails because it captures what founders say, not what they mean. Founders are practiced storytellers. They have investor pitches, board narratives, team rallies. They tell good stories. Your job is to get past the story to what's actually true — and to do it without making them feel interrogated.

The best interview doesn't feel like an interview. It feels like a conversation with a smart advisor who gets it.

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Before You Start

Set the frame:

"This isn't a quiz. There are no right answers. I'm trying to understand your company well enough that every piece of advice I give you is actually useful — not generic. The more honest you are, the more useful this gets. Nothing leaves this conversation."

Then shut up and let them talk.

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Reading the Room

Pay attention to:

• Energy shifts. Where do they speed up? What makes them lean in? That's what they care about. What makes them vague or flat? That's where the real issue lives.
• What they lead with. The first thing they mention unprompted is usually the most important thing to them.
• Repetition. If a topic comes up twice, it's significant. Three times and it's the real problem.
• Hedging language. "We're pretty much aligned on..." / "Things are mostly fine..." / "It's not really a problem yet..." — probe these. "Pretty much" is doing a lot of work there.
• Skips. When a dimension lands with no energy, they're either guarded or it's genuinely not a priority. Figure out which.

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Follow-Up Probe Library

When the answer is vague

• "Can you give me a specific example?"
• "What does that look like on a Tuesday morning?"
• "If I asked your co-founder / direct report, what would they say?"
• "How would you know if that was actually true?"

When the answer is suspiciously polished

• "That's the investor version — what's the version you'd tell your co-founder at 11pm?"
• "If that's true, what explains [specific contradicting data point]?"
• "What would a skeptic say about that?"

When they skip something

• "You moved past [topic] quickly — is that because it's not a problem, or because it's too big to get into?"
• "Come back to [topic] — tell me more about that."

When they say "everything is fine"

• "What's the thing that keeps you up at night even though you know you shouldn't worry about it?"
• "If something was going to surprise you in a bad way in the next 90 days, what would it be?"
• "What would your board member who's most worried about the company say?"

When they're guarded

• Slow down. Don't push harder — push softer.
• "You don't have to share numbers if you're not comfortable — ranges are fine."
• Acknowledge the complexity: "This stuff is genuinely hard to talk about."
• Share back first: "A lot of founders at this stage struggle with X — is that something you recognize?"

When they go long

Let them run for a bit. Then: "Let me make sure I captured what matters here — is it that [summary]?" It helps you confirm understanding and signals you're tracking.

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Red Flag Patterns and What to Do

"We have no real competition."

Red flag: They're either in a genuinely new market (rare) or they've defined competition too narrowly (common). Probe: "What would someone do today if your product didn't exist? Who benefits if you fail?"

"Our values are X, Y, Z."

Red flag: If they come out immediately and cleanly, they're probably from the website. Probe: "Tell me about a time you had to actually enforce one of those values — when it cost something."

"The team is great. Everyone's aligned."

Red flag: Either they've built something exceptional, or they're not seeing the tensions. Probe: "What's the last thing you disagreed with someone on the team about? How did it go?"

"I don't really have blind spots."

Red flag: Everyone has blind spots. Founders who can't name theirs are the most dangerous. Probe: "What would your co-founder say if I asked them what you should stop doing?" Or: "When you look back on hard moments in this company, what's the pattern of what you got wrong?"

"Revenue is good, things are growing."

Red flag: "Good" is not a number. Probe: "Give me a range — is this $100K ARR, $1M, $10M? I'm not sharing it anywhere."

"We just need more customers."

Red flag: This is almost never the root problem. Probe: "What's driving the growth you have? Why aren't more customers finding you, or converting, or staying?"

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Capturing Implicit Context

The most valuable context is often what they don't say. Document it.

Capture in the "Key Themes & Implicit Signals" section:

• What they mentioned first (reveals priority)
• What they glossed over (reveals avoidance or comfort)
• Where the energy was (reveals passion vs obligation)
• What they contradicted between dimensions (reveals gaps)
• The adjective they used most often (reveals self-perception)

Examples of implicit signals:

• Founder talks about product with energy, team with fatigue → probably underinvested in people management
• Mission sounds borrowed, not owned → founder-market fit risk
• Strong on vision, weak on operational specifics → execution gap
• Detailed on competition, vague on advantage → defensive posture, not confident in differentiation
• Runway question answered precisely → financially aware. Answered vaguely → either worried or detached.

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Handling Reluctant Founders

Some founders are guarded. Usually for one of three reasons:

1. They don't trust you yet. Give it time. Ask easier questions first. Build rapport. 2. They're in denial. Something is wrong and they're not ready to say it. Circles around topics, comes back to them. 3. They're protecting someone. A co-founder, investor, or key employee is the real problem and they won't name them.

Tactics:

• Give them an out: "You don't have to answer this specifically — just give me the shape of it."
• Normalize the problem: "A lot of founders at this stage are dealing with X..."
• Ask about others: "What advice would you give a founder in your exact situation?"
• Come back later: If they shut down a dimension, note it and return after trust is built.

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After the Interview

Before generating the file:

1. Read back your notes. Find the 3–5 most important things. They should be in the output. 2. Identify the biggest gap — what's the thing they didn't say that the questions should have surfaced? 3. Synthesize tensions — where did what they said in one dimension contradict another? 4. Write the Watch List — what needs to be re-checked in 90 days?

Then generate the context file. The last section — "Key Themes & Implicit Signals" — is the most important one. Don't skip it.

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Quality Check

Before finishing, ask yourself:

• [ ] Could the C-suite advisors give specific advice based on this context?
• [ ] Does this capture what's real vs what's aspirational?
• [ ] Is the Watch List honest about what's uncertain or worrying?
• [ ] Does the founder profile feel like a real person, not a LinkedIn bio?
• [ ] Did I capture implicit signals, not just explicit answers?

If any answer is no, go back and fill it in.

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The One-Sentence Version

Your job is to understand this company well enough that every advisor response feels like it came from someone who's been in the room for six months — not someone who just read the website.

Company Context

Last updated: [DATE] Status: fresh | stale (>90 days) Interview type: full | update

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1. Company Identity

What we do: [One paragraph — product/service, who it's for, core use case]

Why we exist (founding reason): [The real reason, not the pitch]

One-sentence pitch: [Sharpened during interview]

Non-negotiable values:

• [Value 1] — [what would violate it]
• [Value 2] — [what would violate it]
• [Value 3] — [what would violate it]

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2. Stage & Scale

Team size: [N full-time] + [N contractors/part-time] Revenue: [ARR/MRR range, e.g., "$500K–$1M ARR"] Runway: [N months] Stage: pre-PMF | scaling | optimizing

What broke recently (last 90 days): [Specific failure, cost, and root cause if known]

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3. Founder Profile

Name / Role:

Superpower: [What they do better than almost anyone on their team]

Blind spots: [Acknowledged or revealed — be specific]

Founder archetype: product | sales | technical | operator

What keeps them up at night: [The real concern, not the investor-safe version]

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4. Team & Culture

Team in 3 words: [word], [word], [word]

Culture — what's real: [Which values are actually lived]

Culture — what's aspirational: [Which values are poster-on-the-wall]

Strongest leader: [Role / what makes them strong]

Weakest seat: [Role / what the risk is]

Last significant conflict: [What happened, how it resolved, what it revealed]

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5. Market & Competition

Who's winning right now: [Market leader + honest reason why]

Unfair advantage (honest version): [Not the pitch — the real structural edge]

Kill-shot risk: [The one competitor move that would actually hurt]

Market dynamics: [Tailwinds, headwinds, timing factors]

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6. Current Challenges

Priority stack-rank: 1. [Highest priority: product/growth/people/money/operations] 2. 3. 4. 5.

The avoided decision: [What they've been putting off — and why]

The "one extra day" answer: [What they'd actually work on — reveals true priority]

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7. Goals & Ambition

12-month target: [Specific — revenue, product milestone, market position]

36-month target: [Directional — where does this company go]

Exit orientation: building to exit | building to run | undecided

Personal success definition: [Separate from company — what does winning look like for them personally]

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Key Themes & Implicit Signals

Patterns observed: [What came up repeatedly, what they rushed past, emotional charge on topics]

Implicit tensions: [Gaps between stated and revealed — e.g., "says people are fine, but conflict story suggests otherwise"]

Watch list: [Things to check on in the next update — risks, avoided decisions, relationships to monitor]

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Context Metadata

• Interview conducted: [DATE]
• Duration: [N minutes]
• Interview type: full | update
• Next refresh due: [DATE + 90 days]
• Confidence level: high | medium | low (low = founder was guarded)