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Automation Squad
You run thisWritten for ChatGPT, Claude or Gemini (with calendar access)

Find the repeating task buried in my calendar

Robert MacKelfresh

By Robert MacKelfresh

Founder, Automation Squad

Everyone believes they know where their week goes, and almost nobody is right, because the expensive pattern is spread across entries with different names. Section 3 is the one that surprises people — the prep and follow-up around a meeting routinely costs more than the meeting, and it never appears on the calendar as anything at all.

The prompt

Look at my calendar for the last [HOW MANY] weeks — or if you can't reach it, I'll paste the list below.

I'm looking for what repeats, not what happened.

1. THE PATTERNS. Group my time into recurring shapes: the standing meetings, the ones that recur under different names, the blocks that always appear before or after something else. Give me hours per week for each.

2. THE MEETING THAT'S REALLY A DOCUMENT. Which recurring meetings look like status transfer rather than decision-making? Those are the ones where nobody would notice if they became a written update.

3. THE HIDDEN PREPARATION. What am I doing repeatedly that only exists to support something else — the prep, the follow-up, the chasing? That work rarely appears as its own calendar entry, so infer it from what surrounds each meeting.

4. THE ONE THING TO AUTOMATE FIRST. Given what you've found, name the single highest-frequency, lowest-judgement task in my week. Not the most annoying one — the most repetitive one. Then tell me what it would take to hand it off, and what would break if you got it wrong.

5. WHAT I'M NOT DOING. Look at what's absent. If there's no recurring block for the thing I say matters most, say so.

Be specific about hours. "You spend a lot of time in meetings" is not useful. "You spend 6.5 hours a week in recurring status meetings, 4 of which have the same four attendees" is.

[paste your calendar entries here if you're not connected]

One more thing: use anything you already know about me from our past chats and anything you're connected to. If you can find it yourself, don't make me look it up.

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

More for the same job

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