claude-skills-reference/c-level-advisor/cs-onboard/references/interview-guide.md

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.