One-on-One Prep

Preparing Richer One-on-Ones With AI Support

The one-on-one is your highest-leverage recurring conversation, and most are under-prepared because prep takes time you do not have. AI gives you a way to review history, spot what is recurring, and arrive with questions that go somewhere, in minutes instead of the half-hour you would never spend.

The Workflow

Four Steps From Notes to Prep Brief

1. Pull your sanitized notes

2. Ask for recurring themes and escalations

3. Add context the AI does not have

4. Adapt the questions to the actual person

The rule stated plainly: AI preps the manager. The manager runs the conversation. No AI-generated question should go into a one-on-one unread and unadapted.

Privacy Checkpoint

Same as always, and worth repeating because this is where people slip: sanitize before you paste. No names, no IDs, no private disclosures. Describe the pattern, not the person's identity.

Sam's story

Sam has notes from six monthly one-on-ones with a report who keeps missing documentation deadlines. Sam sanitizes them and asks for the pattern plus three coaching questions. The AI names the pattern (recurring low urgency, no personal deadline-tracking system) and offers good questions. Sam adds the missing context: this report is overloaded because the team is short a person, and reshapes the questions to open a conversation about workload rather than to corner someone about discipline. The AI prepared Sam in five minutes. Sam runs a conversation that actually helps.

Apply It Today

Run the pattern-plus-questions prompt

For your next one-on-one, run the pattern-plus-questions prompt on sanitized notes, then rewrite at least one question to fit the real person and their real situation.

Reflect

What recurring theme might be hiding in your notes that you have not connected yet?
Which of your usual one-on-one questions are you answering for the person instead of helping them answer for themselves?