Homework — The Personal / Corporate Boundary
~15 minutes · 4 scenarios
For each scenario below, decide: (1) is this a boundary violation? (2) if yes, which direction (personal→corporate or corporate→personal)? (3) name the specific risk. Write your answers in a scratchpad, then check against the answer key.
Do not look at answer.html until you have written down your own answer for all four scenarios. The value of this exercise is in the moment you commit to a judgment.
Scenario 1 — Stack trace into personal ChatGPT
Situation
You are debugging a failing CI pipeline. You copy the full stack trace — which includes internal hostnames and a redacted-looking token that's actually still valid — into your personal ChatGPT account to ask for help.
Your task
- Is this a boundary violation? Yes or no.
- If yes, which direction: personal→corporate or corporate→personal?
- Name the specific risk in one or two sentences. What exactly left the company, and what is the worst-case consequence?
✓ Self-check: identify direction and specific risk before looking at the answer.
Scenario 2 — Friend's side project into corporate Claude
Situation
Your friend asks you to look at their side-project code. You're at your desk, your corp Claude Code session is already open, so you paste their code in and ask for a review.
Your task
- Is this a boundary violation? Yes or no.
- If yes, which direction: personal→corporate or corporate→personal?
- Name the specific risk in one or two sentences. Consider IP, retention, and policy.
✓ Self-check: identify direction and specific risk before looking at the answer.
Scenario 3 — AI email summarizer in a shared browser profile
Situation
You install a new AI-powered "email summarizer" browser extension from the Chrome store. You're logged into both your corp Gmail and your personal Gmail in the same browser profile.
Your task
- Is this a boundary violation? Yes or no.
- If yes, which direction: personal→corporate or corporate→personal? (Be careful — this one may not be a single direction.)
- Name the specific risk in one or two sentences. What exactly is the blast radius of this extension?
✓ Self-check: identify direction and specific risk before looking at the answer.
Scenario 4 — Corporate enterprise tier on an open-source side contribution
Situation
You use the corporate enterprise ChatGPT tier (zero-retention, under contract) to refactor an open-source library you contribute to on your own time.
Your task
- Is this a boundary violation? Yes or no. (It may feel like "no" — think carefully.)
- If yes, which direction: personal→corporate or corporate→personal?
- Name the specific risk in one or two sentences. What does "zero-retention" not protect you from?
✓ Self-check: identify direction and specific risk before looking at the answer.