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Date a new CSM's 30-day checklist from the start date

  • For Managers and team leads
  • You practice Catching mistakes and made-up facts
  • Time about 5 minutes
  • Level Intermediate

About this exercise

The new CSM starts Monday Nov 16. Write a checklist of exactly four lines starting "[ ]" for Day 1, Day 7, Day 14 and Day 30, formatted "[ ] Mon D (Day N): action". Day N means N days after Nov 16. Use the playbook actions. Plain text, under 60 words.

Common mistakes when you ask AI for this

  • Copying the team draft. The draft counted from Nov 15 and has wrong dates. Try: Say: "Count from Nov 16 yourself; ignore the draft."
  • Mixing the actions. The AI assigns actions to the wrong days. Try: Say: "Use the playbook action for each day."
  • Wrong format. The AI writes a table or paragraphs. Try: Show the line: [ ] Nov 17 (Day 1): action.
  • Getting markdown back. AI adds bold and headings by default, which show up as stray symbols where this is pasted. Try: Say "plain text, no bold, no headings, no asterisks".
  • Trusting the AI to count words. AI is bad at counting and usually runs long, so a vague "keep it short" lands well over the limit. Try: Cap each part instead of the total, for example "each line under 15 words".

What a strong prompt includes

  • Asks for plain text
  • Sets a length limit
  • Shows the line format
  • Asks to count from the start

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