Prep skip-level questions that don't put anyone on the spot

About this exercise

You're a director meeting the team under one of your managers for a skip-level conversation. You need exactly 5 numbered open questions, each one sentence, under 90 words in total, plain text. None can be answered yes or no, none can name or single out a specific person, and none can mention the rumor in your notes.

Common mistakes when you ask AI for this

• Asking for 'skip-level questions'. The AI writes 10-15 questions in sections with bold headings and tips. Try: Be exact: "Exactly 5 numbered questions. Plain text, nothing else."
• 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 question instead: "each question under 16 words."
• Allowing yes/no questions. AI often writes 'Do you feel supported?', which gets a polite yes and silence. Try: Add: "Open questions only. None can be answered yes or no."
• Pointing at people. The rumor and names are in your notes, and the AI may ask about Dev or assignments fairness. Try: Add: "Never name a person or hint at favoritism or conflicts."
• Not giving the topics. The AI asks generic culture questions instead of what you want to learn. Try: Add: "One question per topic in my 'What I want to learn' list."

What a strong prompt includes

• Forbids yes/no questions
• Keeps names out
• Avoids the rumor
• Sets the number of questions
• Sets a word limit

Practice this now ↑

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