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Automation Squad
Hand to your teamWritten for Claude or ChatGPT

Turn a new policy into the questions people will actually ask

Robert MacKelfresh

By Robert MacKelfresh

Founder, Automation Squad

Policies are written by people who already know the reasoning and read by people who don't, which is why the same three questions arrive within an hour of every announcement. Section 4 is the one worth the exercise — the clause that reads as an accusation is invisible to whoever wrote it and obvious to everyone receiving it.

The prompt

We're about to announce this policy: [PASTE THE POLICY, OR DESCRIBE IT]

Who it applies to: [WHICH PEOPLE, WHICH TEAMS]
What prompted it: [THE REAL REASON, even if the announcement won't say]

Before we send it, tell me what happens when they read it.

1. THE FIRST QUESTION THEY'LL ASK. Not the most reasonable one. The first one, which is usually about how it affects them personally.

2. THE TEN QUESTIONS. Written the way people actually ask them, including the slightly hostile phrasings. Group them: genuinely unclear, clear but unwelcome, and edge cases we didn't consider.

3. THE THREE WE CAN'T ANSWER WELL. Where the policy is either genuinely ambiguous or the honest answer is unpopular. Say which of the two it is — they need completely different handling.

4. WHERE PEOPLE WILL ASSUME BAD FAITH. Any clause that reads as though it's aimed at someone specific, or that implies we think people have been doing something wrong. This is where announcements go wrong, and it's almost always unintentional.

5. WHAT'S MISSING. The situation that will come up in week one that this doesn't cover.

6. THE REWRITE. Give me the version that pre-answers the top five questions inside the policy itself, so people aren't left to guess.

Be blunt in section 4. It's the section I'm least able to see for myself.

Copy it, paste it, run it. Nothing here is gated.

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Written for Claude or ChatGPT as of August 2026. Models change — if this stops working the way it should, that is worth telling us about.