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.

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

• "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?"

• 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

• "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?"

• "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?"

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

• "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?"

• "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

• "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."

• "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

• "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?"

• 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

• "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?"

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

• Update relevant sections in context file
• Update

  Last updated

  timestamp
• Reset freshness to

  Fresh

• Note what changed in the Notes section

• New metric or number shared
• Key person mentioned for the first time
• Priority shift expressed
• New constraint or risk surfaces
• Timeline or deadline revealed

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

• 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

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

• 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"