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Message an alum for a short informational call

Practice: Setting limits and rules. About 5 minutes.

About this exercise

You want a 20-minute call with an alum who works where you'd like to work. Write a LinkedIn message under 70 words, plain text: one specific reason you're writing to her (from her profile), a clear ask for a 20-minute call with two time options, and no attachments or job requests. Don't open with "I hope this finds you well." Write a prompt that gets you exactly that.

Common mistakes when you ask AI for this

  • Trusting the AI to count words. AI is bad at counting. Ask for "under 70 words" and it often lands well over. Try: Cap each part instead: "4 sentences, each under 16 words."
  • A generic opener. The AI starts with "I hope this message finds you well" and a long intro. Try: Add: "No pleasantries. Open with one specific reason from her profile."
  • A vague ask. "Would love to connect sometime!" gives her nothing to say yes to. Try: Add: "Ask for 20 minutes and offer Tue Nov 18 after 2 or Thu Nov 20 before noon."
  • Asking for a job. The AI mentions the open role or attaches a resume, which turns a chat into a favor. Try: Add: "Don't mention the open role or my resume."
  • Ignoring where it will be pasted. AI loves bold and headings, which show up as stray ** and # symbols in LinkedIn. Try: Name the place and the format: "For LinkedIn. Plain text, no bold or headings."

What a strong prompt includes

  • Gives a specific reason
  • Offers two times
  • Rules out job asks
  • Bans pleasantries
  • Sets a word limit

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