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

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:

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:

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

Freshness Score

Quality Signals

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:

After refresh:

• Update relevant sections in context file
• Update Last updated timestamp
• Reset freshness to Fresh
• Note what changed in the Notes section