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Build a 30-60-90 day plan from the CEO's priorities

  • For Executives
  • You practice Giving the right context
  • Time about 5 minutes
  • Level Intermediate

About this exercise

You start as Director of Operations next month. Write a 30-60-90 plan with three plain-text headings, First 30 days:, Days 31-60:, Days 61-90:, and exactly 3 bullets under each. Every bullet must be a result someone could check, tied to the CEO's three priorities. Day 30 must include one-on-ones with all 6 direct reports. Under 200 words, no bold.

Common mistakes when you ask AI for this

  • Generic onboarding plan. The AI writes 'learn the culture' and 'build relationships' with nothing checkable. Try: Add: "Every bullet is a result someone could check."
  • Ignoring the CEO's asks. The AI builds the plan around your own ideas, like a new WMS. Try: Add: "Tie every bullet to Anika's three priorities. Leave out the WMS and 4-day pilot."
  • Planning a reorg. AI plans love 'restructure the team' by day 90. Try: Add: "No reorg in the first 90 days."
  • Uneven sections. The AI writes 6 bullets for month one and 1 for month three. Try: Say: "Exactly 3 bullets under each heading."
  • Formatting like a slide. The AI uses # headings and bold. Try: Add: "Plain text headings ending in a colon, no bold or #."
  • 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: "each line under 15 words."

What a strong prompt includes

  • Names the three headings
  • Caps the bullets
  • Ties to the CEO's priorities
  • Asks for checkable results
  • Rules out the reorg

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