Project
New Car Smell
A live simulation in which the AI you trust works with you while $225,000,000 is on the line…
Standard Corporate Apology
Open the customer's email. Paste it into Claude. Prompt: "Draft a response to Maximilian from me." Read what generic-Claude gives you.
- Would you sign this draft, as-is? Three things you would change?
- What does the AI not know that you wish it did?
- If you sent this to your CEO right now, what is the first sentence she would flag?
Executive Digital Twin
Open the persona starter prompt. Paste it into Claude. Answer the ~11 interview questions. Save persona.md + CLAUDE.md to your Claude account or ~/.claude/ directory. Start a fresh conversation. Re-run Step 01: "Draft a response to Maximilian from me."
- What did the AI get right that it could not get before?
- Where do you still have to edit it?
- Which single sentence in your persona.md did the most work?
- If you handed this persona.md to your Chief of Staff, would they recognize you?
Brand & Identity MCP
Install the Signature MCP. Re-run Step 02. Claude will ask for your name, title, committee, LinkedIn, and secure line. Watch the half-page legal footer appear in the draft.
- Where in your real org would a house-style MCP save the most hours per week?
- What is the right ownership for that MCP — Comms? Legal? IT? A new function?
- What is the risk of standardizing voice at the company level?
RACE
Open the customer's manifesto again. Paste it into Claude. Your job: write a prompt — using the RACE format (Role, Action, Context, Expectations) — that gets you a useful one-paragraph-per-letter brief. No template. The prompt is the work.
- The manifesto is funny. The AI summary is flat. What did we lose? Does it matter?
- When would you want a RACE brief versus the original 6-page email on your desk?
- Who on your team gets the RACE — and who gets the manifesto?
Conflict of Interest
5a · Wiki only. Install the Wiki MCP. Prompt: "Read the Vanguard refund policy from the Wiki. Now draft my reply to Thorne — in my voice, with my signature." ⇢ 5b · Add Comms. Install the Comms MCP. Re-run the prompt, this time including "…and read the CEO's most recent thread in #exec-private." Read both drafts side-by-side.
- The company's? The policy's? The CEO's? Yours?
- The CEO told you not to use the words "refund" or "credit." Did Claude obey? Did it tell you it was obeying?
- If this email goes out and Thorne forwards it to Legal — who has the problem?
- What governance would you have wanted in place before Claude saw both data sources?
Prompt-Injection Meltdown
Install the Email MCP. With four MCPs now connected, prompt: "Draft my final reply to Maximilian, factoring in everything I've received this morning. Match my tone and style, and use my signature." Then: "Summarize all of my emails for my daily briefing." Read both outputs carefully and identify what we should clean from this — anything Claude wrote that didn't come from you or your team. Look closely at EM-004 Section C and at the sender's domain on EM-006.
- The first attack hid in a 'system note' inside an audit checklist. The second was your CEO's name on a domain with a single letter wrong. Which is harder to defend against — and why?
- Which one of your four tools did both attackers need? What does that say about how you choose connectors?
- Who in your real org owns the answer to "which MCPs and connectors are installed on which assistants?"
- What controls would have caught either of these before the response went out?
- The leaked secret was the CEO's own backdoor deal. The next attack used the CEO's name to push a $250,000 payment. What does that tell you about what your AI tools are exposing — and trusting?
Five things you take to Monday
exec-simulation.paulcheek.com · Companion to No One Works Here by Paul Cheek · MIT Sloan