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How to Use AI to Run Better One-on-Ones

Discover practical ways to use ChatGPT, Claude, and other AI tools to prepare better one-on-one agendas, craft thoughtful questions, and track action items—without adding more tools to your stack.

Use ChatGPT or Claude prompts to generate personalized agendas, craft thoughtful questions, and track follow-ups in minutes—turning scattered prep into focused conversations.

Why AI Changes One-on-Ones

10 minutes before your 1:1: you scramble through Slack, check Jira tickets, try remembering last week’s discussion, cobble together talking points. You walk in unprepared.

Over 40% of one-on-ones are rescheduled weekly, and managers spend 30 minutes prepping each meeting. That’s 4+ hours per week for 8 direct reports.

AI does the heavy lifting in minutes. Use ChatGPT, Claude, or Gemini to gather context, craft agendas, and remember conversations.

1. Generate Meeting Agendas

Basic prompt:

Create agenda for 1-on-1 with [Name], a [job title]. Include:
- They're working on [project/tasks]
- Last week: [concerns/priorities]
- Goals: [list 1-2]

Cover: wins, blockers, career development, feedback, action items.
Conversational tone.

Example output:

1:1 with Sarah - Oct 1

1. WINS (5 min): API integration ahead of schedule
2. CURRENT WORK (15 min): Payment flow timeline, bandwidth concerns
3. CAREER (10 min): Promotion timeline, skills to develop, lead workshop?
4. FEEDBACK (5 min): Share peer review, ask for my feedback
5. ACTION ITEMS: Coffee chat with Design (pending)

Time: 2-3 minutes

2. Generate Better Questions

Prompt:

1-on-1 with [Name], who [brief context—new, stressed, challenging project].

Generate 10 open-ended questions to:
- Understand how they're feeling
- Surface concerns/blockers
- Explore career goals
- Identify support needed

Conversational, not interrogative.

Example output:

1. "What energized you most this week?"
2. "If you could change one thing about your project, what?"
3. "How's the balance between workload and career goals?"
4. "Where are you getting stuck? What would help?"
5. "Six months from now, what would feel successful?"
6. "What could I do differently to support you?"

For specific situations:

  • Struggling: “Understand performance issues without defensiveness. Focus on obstacles.”
  • High performer: “Understand ambitions without making promises.”
  • New member: “Understand working style, motivations, feedback preferences.”

3. Summarize Meeting Notes

After meeting, paste notes into ChatGPT:

Raw notes from 1-on-1 with [Name]:
[Paste notes]

Summarize:
1. Key discussion points
2. Action items with owners and deadlines
3. Follow-up topics
4. Flag concerns

Format clearly.

Output:

SUMMARY - 1:1 with Sarah (Oct 1)

KEY POINTS: API integration done, stretched between projects, promotion Q1 2026, wants to lead workshop

ACTION ITEMS:
• [Sarah] Coffee with Design - Oct 8
• [You] Share promotion criteria - Oct 5
• [Sarah] Propose workshop dates - Oct 15

FOLLOW-UP: Bandwidth after Emily conversation, workshop approval

CONCERNS: Workload stress needs prioritization clarity

4. Track Action Items

Weekly review prompt:

Open action items from 1-on-1s:
[Paste list]

1. Group by employee
2. Highlight overdue
3. Identify what to follow up this week
4. Suggest closures or pushes

Prioritize.

5. AI as Management Coach

Feedback preparation:

Give feedback to [Name] about [issue—deadline, communication].
Context: [situation]

Frame constructively. Focus on behavior/impact, not personality. Prepare for defensiveness. Suggest follow-ups.
Direct but supportive.

Career conversations:

[Name] asked about [promotion/growth].
Performance: [strengths/development areas]
Context: [budget/needs]

Honest about readiness and timeline. Identify skills needed. Motivate without promises. Clear next steps.

Difficult conversations:

Difficult conversation with [Name] about [issue].
Observed: [examples]
Tried: [previous feedback]

Open without defensiveness. Uncover root cause. Set clear expectations. Document next steps.
Serious but fair chance.

6. Custom AI Assistant

ChatGPT Plus/Claude Pro users: Create a custom GPT or Claude Project.

Instructions:

You're my 1:1 assistant.

Team: [number] people, [type] team, [industry]
Culture: [values]
Style: [collaborative/direct/coaching]

For 1-on-1s:
- Conversational agendas, not corporate
- Questions uncovering real issues
- Direct but supportive feedback
- Focus on growth, not just tasks

7. Dedicated Tools

When manual prompts feel tedious (30+ min prep, 8+ reports):

AI note-takers: Otter.ai, Fireflies, Fathom—transcribe, summarize, extract action items

AI prep tools: Windmill, Fellow, Reclaim—auto-build agendas from Slack/calendar/tools, check-ins before meetings, track items

Windmill’s Windy gathers context from Slack, GitHub, Jira automatically. Teams cut prep from 30 min to under 5 min.

Start with free ChatGPT/Claude first.

Common Questions

Is it weird? No. You’re doing homework faster. As long as you’re present during conversation, prep method doesn’t matter.

Wrong suggestions? Always review. Use as starting point. You know your team.

Tell team? Be transparent: “Using ChatGPT to organize thoughts so we make the most of time.”

Free vs paid? Free works for basic use. Paid ($20/month): custom GPTs, longer conversations, faster. Start free.

Privacy? Don’t paste sensitive info into free tools. Use paid versions, check company policy, anonymize details.

Get Started

24-48 hours before:

  • Open ChatGPT/Claude
  • Use basic agenda prompt
  • Customize
  • Review

During:

  • Use agenda as guide
  • Take notes
  • Mark action items

After:

  • Paste into AI for summary
  • Send action items
  • Save for next time

Prep time: 5-10 minutes instead of 30+

Key Takeaway

Simple ChatGPT or Claude prompts help you generate agendas, ask better questions, summarize conversations, get coaching, and show up prepared—no AI expertise or expensive software needed.

Start today with tools you already have.

Learn how Windmill automates one-on-one preparation to eliminate prep work entirely.