Manager Resources

Manager tools: ChatGPT for One-on-One Meetings

MMonday SimonNovember 8, 20252 min read

Key takeaways

👉 Try my ChatGPT one-on-one meetings

Screenshot of the ChatGPT for One-on-One Meetings tool by Monday Simon showing coaching prompts for managers to prepare one-on-one discussions.

One-on-ones are the single most important mechanism you have forperformance managementand developing talent. They should be laser-focused on roadblocks, growth, and feedback.

That’s why I built a specific tool: ChatGPT for One-on-One Meetings. It’s a prep assistant that helps you translate the noise of the last week into two or three specific, high-impact coaching questions. This custom ChatGPT tool is part of myManager Toolscollection for busy managers.

Why you need ChatGPT for one-on-one meetings

A recurring conclusion from my coaching sessions with managers is that managers want to coach, but they don’t have time to “plan coaching sessions.” They’re juggling deadlines and crises instead.

The ChatGPT for One-on-One Meetings changes that because it acts as your backstage prep coach.

You tell it:

And it instantly helps you structure the conversation:

How ChatGPT helps you prepare for a meaningful one-on-one

Here’s what it does: 15 minutes of thoughtful preparation.

Start by telling ChatGPT for One-on-One Meetings three things:

From that, it helps you build a simple three-part meeting flow:

RELATED RESOURCES

You may also find our team development resources useful.

Monday Morning Action Plan: Prepare for Coaching with the GROW Model

Here’s a brief Monday Morning Action Plan using the ChatGPT for One-on-One Meetings framework:

Before opening the GPT, identify the one key focus area for that employee this week: it could be a developmental feedback point, a career conversation, or a performance challenge. Feed the GPT with the employee’s role, their top goal, and the key focus area first.

Use thisGROW coaching modelto guide the conversation from problem to action:

G: Goal - Define the specific objective for the session or the near future.Question:“What specifically do you want to accomplish or resolve?”

R: Reality - Explore the current situation and obstacles without judgment.Question:“What have you tried so far, and what were the results?”

O: Options - Encourage brainstorming multiple solutions, pushing past the first easy answer.Question:“If anything were possible, what are three ways you could approach this?”

W: Will (or Way Forward) - Commit to concrete action steps with clear deadlines.Question:“What is the very first step you will take, and when will you have it done?”