# Cs Onboard

> Structured C-suite onboarding via a founder interview that captures company context into a persistent file used by all advisory skills. Use when setting up advisory context, refreshing stale context, or onboarding a new executive.

- Skill: `majiayu000/cs-onboard` (Agent Skill, multi-file: 2 files)
- Install (CLI): `npx skillmds add majiayu000/cs-onboard`
- Raw SKILL.md: https://api.skillmd.com/api/skills/majiayu000/cs-onboard/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- License: MIT + Commons Clause
- Author: majiayu000 (https://skillmd.com/u/majiayu000)
- Updated: 2026-09-09
- Page: https://skillmd.com/skills/majiayu000/cs-onboard

---

# 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.

---

## 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 |

---

## 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.

---

## 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

---

## 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 lived]
**Aspirational values:** [Values that are work-in-progress]
**Key person risk:** [Who they cannot lose]
**Weakest link:** [Leadership gap]
**Last conflict:** [What happened and how resolved]

## 5. Market & Competition
**Winning competitor:** [Who and why]
**Real unfair advantage:** [Not the investor version]
**Kill-shot risk:** [Competitive move that could hurt them]
**Market position:** [Leader / Challenger / Niche / Emerging]

## 6. Current Challenges
**Priority #1:** [Top challenge area]
**Priority stack:** [Rank of product/growth/people/money/ops]
**Avoided decision:** [What they have been putting off]
**One-extra-day:** [What they would spend time on]

## 7. Goals & Ambition
**12-month target:** [Specific, measurable]
**36-month target:** [Directional]
**Orientation:** [Build to sell / Build forever / Undecided]
**Personal success:** [What success means for the founder personally]

## Notes
[Observations, inferred patterns, things to watch]
[CONTEXT UPDATE entries from subsequent sessions]
```

**Rules:**
- Write `[not captured]` for unknowns -- never leave blank
- Use their actual words when possible, not corporate paraphrasing
- Note confidence level for inferred information
- Never silently modify -- always confirm before updating

---

## Context Quality Scoring

### Completeness Score

| Dimensions Captured | Score | Label |
|--------------------|-------|-------|
| 7/7 | 100% | Complete |
| 5-6/7 | 70-85% | Good (identify gaps) |
| 3-4/7 | 40-55% | Partial (schedule follow-up) |
| 1-2/7 | 15-25% | Minimal (re-interview needed) |

### Freshness Score

| Age | Score | Label | Action |
|-----|-------|-------|--------|
| < 30 days | Fresh | High confidence | Use directly |
| 30-90 days | Aging | Medium confidence | Use, flag what may have changed |
| 90-180 days | Stale | Low confidence | Prompt for /cs:update |
| > 180 days | Expired | Very low confidence | Re-interview recommended |

### Quality Signals

| Signal | Confidence Impact |
|--------|------------------|
| Full interview completed | +High |
| Update done within 90 days | +Medium |
| Key fields populated with specifics | +High |
| Fields contain vague/generic answers | -Medium |
| Financial fields missing | -High (for CFO/CEO skills) |
| "Not captured" in 3+ fields | -High |

---

## Quarterly Refresh Protocol (`/cs:update`)

**Trigger:** Every 90 days or after a major event (fundraise, reorg, pivot, key hire/departure).

**Opening:** "It has been [X time] since we captured your company context. Let's do a quick refresh. What has changed?"

**Walk each dimension with a single "what changed?" question:**

| Dimension | Refresh Question |
|-----------|-----------------|
| Identity | "Still the same mission, or has it shifted?" |
| Stage & Scale | "Team size, revenue, and runway now?" |
| Founder | "Has your role changed? What is stretching you?" |
| Team | "Any leadership changes? New key players?" |
| Market | "Any competitive surprises? Market shifts?" |
| Challenges | "What is the #1 problem now vs 90 days ago?" |
| Goals | "Still on track for the 12-month target?" |

**After refresh:**
- Update relevant sections in context file
- Update `Last updated` timestamp
- Reset freshness to `Fresh`
- Note what changed in the Notes section

---

## Context Enrichment During Sessions

During advisory conversations, new information surfaces. Capture it without disrupting flow.

**Triggers for enrichment:**
- New metric or number shared
- Key person mentioned for the first time
- Priority shift expressed
- New constraint or risk surfaces
- Timeline or deadline revealed

**Protocol:**
1. Note internally during conversation
2. At session end: "I picked up a few things that would be useful to add to your context. Want me to update the file?"
3. If yes: append to relevant section, update timestamp
4. If no: respect the decision

**Never silently modify the context file.** Always confirm before changes.

---

## Privacy Rules

### Never Send Externally
- Specific revenue or burn rate figures
- Customer names (unless publicly known)
- Employee names (unless publicly known)
- Investor names (unless publicly announced)
- Specific runway months
- Watch list contents
- Avoided decisions

### Safe to Use Externally (Anonymized)
- Stage label (seed, Series A, etc.)
- Team size ranges (1-10, 10-50, 50-200+)
- Industry vertical
- Challenge category (not specifics)
- Market position descriptor

### Before Any External API Call
- Numbers become ranges or stage-relative descriptors
- Names become roles ("the CTO" not "Sarah")
- Revenue becomes stage labels ("early revenue" not "$800K ARR")
- Customers become "Customer A, B, C"

---

## Missing Context Handling

Handle gracefully -- never block the conversation.

| Missing | Approach |
|---------|----------|
| Stage | "Just to calibrate -- are you still finding PMF or scaling what works?" |
| Financials | Use stage + team size to infer. Note the inference. |
| Founder profile | Infer from conversation style. Mark as inferred. |
| Multiple founders | Context reflects interviewee. Note co-founder perspective may differ. |
| Recent context | "It's been a while since your last update. Should I assume things are roughly the same, or has something big changed?" |

---

## Integration with C-Suite Skills

The context file is loaded by every C-level advisory skill:

| Skill | Uses Context For |
|-------|-----------------|
| **ceo-advisor** | Strategic recommendations calibrated to stage and challenges |
| **cfo-advisor** | Financial guidance calibrated to runway and revenue |
| **cto-advisor** | Technical strategy calibrated to team and architecture |
| **coo-advisor** | Operations advice calibrated to scale and processes |
| **cmo-advisor** | Marketing strategy calibrated to stage and market position |
| **internal-narrative** | Narrative construction based on company truth |
| **scenario-war-room** | Risk variables calibrated to actual threats |

---

## Related Skills

| Skill | Use When |
|-------|----------|
| **ceo-advisor** | Using context for strategic decisions |
| **internal-narrative** | Building narratives from the captured context |
| **scenario-war-room** | Modeling risks based on company context |
| **context-engine** | Technical implementation of context management for AI agents |

---

## Troubleshooting

| Problem | Likely Cause | Resolution |
|---------|-------------|------------|
| Founder gives vague, marketing-speak answers | Interview not building trust; questions too formal | Reset with a personal question; follow a thread they care about; use reflection ("So what you're really saying is...") |
| Key dimensions left as "[not captured]" after interview | Founder avoided topic or interview ran out of time | Note which dimensions were skipped (avoidance signals importance); schedule targeted follow-up for missing areas |
| Context file feels generic, could apply to any company | Interviewer used the framework as a script, not a map | Re-interview with focus on specifics: names, numbers, stories; capture their actual words, not paraphrases |
| Advisory skills still giving textbook answers despite context | Context file too sparse or stale (>90 days) | Run /cs:score to assess completeness and freshness; schedule /cs:update if freshness is Stale or Expired |
| Quarterly refresh takes too long or feels redundant | Refresh covering all 7 dimensions instead of focusing on changes | Lead with "What changed?" per dimension; skip unchanged areas quickly; target 15 minutes total |
| Multiple founders give conflicting context | Different perspectives on stage, challenges, or priorities | Note the conflict explicitly in context file; mark which founder provided which data; flag for resolution |
| Context file modified without founder approval | AI agent or team member updated context silently | Enforce "never silently modify" rule; require explicit founder confirmation before any context update |

---

## Success Criteria

- Context completeness score reaches 7/7 dimensions within first session or first follow-up
- Context freshness maintained at "Fresh" (< 90 days old) through quarterly refresh protocol
- Advisory skills produce company-specific (not generic) recommendations when context is loaded
- Founder reports that AI advisory conversations feel "like talking to someone who knows my business"
- Time to complete full onboarding interview under 45 minutes
- Time to complete quarterly refresh under 15 minutes
- Zero instances of context file modified without founder approval

---

## Scope & Limitations

**In scope:** Structured founder interview across 7 dimensions (identity, stage, founder profile, team/culture, market/competition, challenges, goals), context file generation and maintenance, quarterly refresh protocol, context quality scoring (completeness and freshness), context enrichment during advisory sessions, privacy rules for external data handling, and missing context graceful handling.

**Out of scope:** Company financial modeling (use cfo-advisor), competitive intelligence gathering (use competitive-intel), team assessment or 360 reviews (use hr-operations/), product analytics (use cpo-advisor), and automated context capture from external data sources. This skill captures context through conversation, not data integration.

**Limitations:** Context quality depends entirely on founder candor; evasive or aspirational answers reduce advisory effectiveness. Single-founder interviews may miss co-founder perspectives. Context is a point-in-time snapshot; rapid company changes (pivot, reorg, fundraise) can make context stale before the 90-day refresh. Privacy rules prevent sharing specific context externally, which limits integration with external tools.

---

## Integration Points

- **ceo-advisor** -- Strategic recommendations calibrated to company stage, challenges, and founder archetype
- **cfo-advisor** -- Financial guidance calibrated to runway, revenue range, and growth stage
- **cto-advisor** -- Technical strategy calibrated to team size, architecture maturity, and founder technical depth
- **coo-advisor** -- Operations advice calibrated to scale, process maturity, and headcount
- **cmo-advisor** -- Marketing strategy calibrated to stage, market position, and competitive landscape
- **internal-narrative** -- Narrative construction uses company identity, values, and founder voice from context
- **scenario-war-room** -- Risk variables calibrated to actual competitive threats and company vulnerabilities