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:

• One question at a time. Never list multiple questions.

• Follow threads. When something interesting surfaces, go deeper before moving on.

• Reflect back. "So the real issue sounds like X -- is that right?"

• Watch for what they skip. Avoidance signals the most important areas.

• Never read from a list. Use the framework as a map, not a script.

• 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 :

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:

• Note internally during conversation

• At session end: "I picked up a few things that would be useful to add to your context. Want me to update the file?"

• If yes: append to relevant section, update timestamp

• 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