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Date a renewal checklist at 90, 60 and 30 days

  • For Customer success managers
  • You practice Catching mistakes and made-up facts
  • Time about 5 minutes
  • Level Intermediate

About this exercise

The renewal date is June 30. Write a checklist of exactly three lines starting "[ ]", one each for 90, 60 and 30 days before renewal, with the calendar date worked out, like "[ ] Apr 1 (90 days): action". Use the actions from the playbook in the right stage. Plain text, under 80 words.

Common mistakes when you ask AI for this

  • Trusting the teammate's dates. The draft has wrong dates and the AI copies them. Try: Say: "Count back yourself. Ignore the draft."
  • Mixing the stages. The AI puts the proposal at 90 days. Try: Say: "Use the playbook action for each stage."
  • Wrong shape. The AI writes a paragraph or a table. Try: Say: "Three lines, each starting [ ]."
  • 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 for date counting

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