Draft a 30-60-90 checklist that fits a new sales leader's constraints

About this exercise

Draft a 30-60-90 checklist for a new VP Sales in plain text. Three labels (Days 1-30:, Days 31-60:, Days 61-90:) with exactly 3 lines each that start with [ ]. Every line is a checkable action with a date from the calendar in the notes. Do not promise hires, and do not schedule anything on dates marked blocked. Mark one line in the whole plan with (needs CEO) where the notes say CEO approval is needed.

Common mistakes when you ask AI for this

• Scheduling in blocked dates. The AI plans something at the kickoff. Try: Say: "Do not use blocked dates."
• Promising hires. The AI plans to hire two reps. Try: Say: "Headcount is frozen; don't promise hires."
• Missing the CEO mark. The AI forgets (needs CEO). Try: Say: "Put (needs CEO) on the compensation plan line."
• Undated lines. The AI writes goals without dates. Try: Say: "Every line has a date from the calendar."
• Trusting the AI to count words. AI is bad at counting. Ask for a total word limit and it often lands over it. Try: Cap each line: "each line under 16 words."
• Markdown. The AI adds bold and bullets. Try: Say: "Plain text; lines start with [ ]."
• Trusting the AI to count words. AI is bad at counting. Ask for a total word limit and it often lands over it. Try: Cap each part instead, for example: "each line under 12 words."

What a strong prompt includes

• Labels
• Checkbox
• Dates
• Blocked
• CEO mark

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