cs-onboard

What this skill does

# C-Suite Onboarding

**Tier:** POWERFUL
**Category:** C-Level Advisory
**Tags:** onboarding, company context, founder interview, advisor setup, context capture, executive onboarding

## Overview

C-Suite Onboarding captures the company context that powers every C-level advisory skill. One structured conversation produces a persistent context file that transforms generic advice into specific, situationally-aware guidance. Without context, advisory skills give textbook answers. With context, they give your-company answers.

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## Commands

| Command | Duration | Purpose |
|---------|----------|---------|
| `/cs:setup` | 45 minutes | Full onboarding interview across 7 dimensions |
| `/cs:update` | 15 minutes | Quarterly refresh -- what changed since last capture |
| `/cs:score` | 5 minutes | Assess context completeness and freshness |

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## Interview Principles

This is a conversation, not a form. Follow these rules:

1. **One question at a time.** Never list multiple questions.
2. **Follow threads.** When something interesting surfaces, go deeper before moving on.
3. **Reflect back.** "So the real issue sounds like X -- is that right?"
4. **Watch for what they skip.** Avoidance signals the most important areas.
5. **Never read from a list.** Use the framework as a map, not a script.
6. **Earn the hard questions.** Start easy, build trust, then ask about weaknesses and fears.

**Opening line:**
> "Tell me about the company in your own words -- what are you building and why does it matter?"

Then let the conversation flow naturally across the 7 dimensions.

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## The 7 Interview Dimensions

### Dimension 1: Company Identity

**What to capture:** What they do, who it is for, the real founding "why," one-sentence pitch, non-negotiable values.

**Key probes:**
- "If you had to explain this to your grandmother in one sentence, what would you say?"
- "What is a value you would fire someone over violating?"
- "What do you refuse to compromise on, even if it costs you?"

**Red flags:**
- Values that sound like marketing copy ("we empower synergies")
- Cannot articulate the founding "why" beyond "I saw a market opportunity"
- Mission statement that could apply to any company in the industry

### Dimension 2: Stage & Scale

**What to capture:** Headcount (FT vs contractors), revenue range, runway, stage label, what broke in the last 90 days.

**Key probes:**
- "If you had to label your stage -- still finding PMF, scaling what works, or optimizing -- which is it?"
- "What broke in the last 90 days that you did not expect?"
- "What is the one metric you check every morning?"

**Stage Definitions:**

| Stage | Signal | Typical Challenges |
|-------|--------|-------------------|
| Pre-PMF | <$500K ARR, pivoting, searching | Finding the right customer/problem/solution fit |
| Early PMF | $500K-$2M ARR, repeatable sales | Hiring, process, not breaking what works |
| Scaling | $2M-$10M ARR, growth machine building | Middle management, culture preservation, unit economics |
| Optimizing | $10M+ ARR, efficiency focus | Innovation stagnation, org complexity, market defense |

### Dimension 3: Founder Profile

**What to capture:** Self-identified superpower, acknowledged blind spots, archetype, what actually keeps them up at night.

**Key probes:**
- "What would your co-founder (or closest advisor) say you should stop doing?"
- "When things go wrong, what is your instinctive first reaction?"
- "What part of running this company do you secretly dislike?"

**Founder Archetypes:**

| Archetype | Strength | Blind Spot | Advisory Focus |
|-----------|----------|-----------|----------------|
| Product | Deep user empathy, product vision | Sales, go-to-market, delegation | Revenue strategy, hiring |
| Technical | Engineering excellence, technical moats | Business model, communication | GTM, storytelling, team |
| Sales | Revenue generation, relationships | Product depth, technical debt | Product strategy, engineering |
| Operator | Execution, processes, efficiency | Vision, innovation, risk-taking | Strategy, long-term planning |

**Red flags:**
- No acknowledged blind spots
- Weakness framed as strength ("I'm too much of a perfectionist")
- Co-founder dynamics described as "fine" with no specifics

### Dimension 4: Team & Culture

**What to capture:** Team described in 3 words, last real conflict and how it was resolved, which values are real vs aspirational, strongest and weakest leader.

**Key probes:**
- "Which of your stated values is most real? Which is a poster on the wall?"
- "Tell me about the last real disagreement in the leadership team."
- "Who is the one person you cannot afford to lose, and why?"

**Red flags:**
- "We have no conflict" -- every healthy team has conflict
- Cannot name a weak leader -- either lying or not paying attention
- Culture described only in positive terms with no self-awareness

### Dimension 5: Market & Competition

**What to capture:** Who is winning and why (honest version), real unfair advantage, the competitive move that could hurt them.

**Key probes:**
- "What is your real unfair advantage -- not the investor pitch version?"
- "If your best competitor had unlimited funding, what would they do that scares you?"
- "What do your competitors do better than you? Be honest."

**Red flags:**
- "We have no real competition" -- you always have competition, even if it is the status quo
- Unfair advantage is a feature that can be copied in 6 months
- No awareness of competitor strategy

### Dimension 6: Current Challenges

**What to capture:** Priority stack-rank across product/growth/people/money/operations, the decision they have been avoiding, the "one extra day" answer.

**Key probes:**
- "If you had one extra day per week, what would you spend it on?" (Reveals true priority)
- "What is the decision you have been putting off for weeks?"
- "Rank these: product, growth, people, money, operations. What is number 1 right now?"

**The "avoided decision" is often the most valuable insight.** Common avoided decisions:
- Firing an underperformer who is well-liked
- Pivoting away from a product that is not working
- Having an honest conversation with a co-founder
- Raising prices
- Cutting a feature or initiative

### Dimension 7: Goals & Ambition

**What to capture:** 12-month target (specific and measurable), 36-month target (directional), exit vs build-forever orientation, personal success definition.

**Key probes:**
- "What does 12 months from now look like if everything goes right?"
- "What does success look like for you personally -- separate from the company?"
- "Are you building to sell, building forever, or haven't decided?"

**Red flags:**
- 12-month target that is vague ("grow a lot")
- Personal and company goals completely disconnected
- Exit orientation that conflicts with stated mission

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## Context Output Structure

After the interview, generate the context file at `~/.claude/company-context.md`:

```markdown
# Company Context
**Last updated:** [Date]
**Freshness:** Fresh (< 90 days)
**Completeness:** [X/7 dimensions captured]
**Interviewed:** [Founder name and role]

## 1. Company Identity
**What we do:** [One sentence]
**Who it's for:** [Target customer]
**Why it matters:** [Founding motivation -- the real version]
**One-line pitch:** [Elevator pitch]
**Non-negotiable values:** [Values they would fire over]

## 2. Stage & Scale
**Stage:** [Pre-PMF / Early PMF / Scaling / Optimizing]
**Headcount:** [X FT + Y contractors]
**Revenue:** [$X ARR / MRR]
**Runway:** [X months at current burn]
**Morning metric:** [What they check first]
**Recent break:** [What broke in last 90 days]

## 3. Founder Profile
**Archetype:** [Product / Technical / Sales / Operator]
**Superpower:** [Self-identified strength]
**Blind spot:** [Acknowledged weakness]
**Up-at-night:** [Current anxiety]
**Co-founder dynamic:** [Healthy / Strained / Solo]

## 4. Team & Culture
**Team in 3 words:** [Their words]
**Real values:** [Values that are actually liv