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What should you ask a new employee in a first one-on-one meeting?

You’ve got your first one-on-one meeting with a new employee scheduled. Here are the 15 questions you should put on the one-on-one meeting agenda.

New employee one-on-one meeting

The other week, I held a one-on-one meeting with a new employee – the first I’ve conducted in a while. (We don’t hire that often at Know Your Team, so it felt a bit of a momentous occasion!) As a part of our employee onboarding process, I’d set up weekly one-on-one meetings with our new hire with the purpose of having dedicated time set aside to talk through any potential issues, uncover feedback, and discuss her overall career direction.

As I sat down to prepare for the meeting, here’s the exact one-on-one meeting agenda I wrote out and asked for her input on…

Personal connection

  • How’s life?
  • What are you excited about lately?
  • Anything have you worried or down lately?


  • When have you felt frustrated in your first 2 weeks here?
  • What feels unclear? (E.g., Do you feel you have enough context about the company?)
  • How clear is “success” for you for the next 3 months, next 6 months, and next year?
  • Are there any decisions you’re hung up on?
  • Observations about the team and/or company culture?


  • Would you like more or less feedback on your work?
  • Would you like more or less direction from me?
  • How is the workload?
  • What aspect of your job you would like more help or coaching?
  • What about my management style can I improve?

Career direction

  • If you could be proud of one accomplishment between now and next year, what would it be?
  • What’s one thing we could do today to help you with your long term goals?

At the end of the one-on-one meeting, I then set aside 5 or so minutes to review takeaways and discuss next steps.

How’d the first meeting end up going? Unbelievably well. I was blown away by what I learned. (For example, I had no idea there was a personal outside-of-work issue that had been affecting our new hire!) And, I walked away with clear to-dos for myself to make certain projects more defined and to provide more support in other areas.

I’m curious: What might these 15 one-on-one meeting questions uncover for you and your new employee?

👊 Want a consistent system for preparing for ALL your one-on-one meetings (and not just ones with new hires)? Then you’ll want to peek at Know Your Team. Our One-on-Ones Tool makes it dead simple to prepare for one-on-one meetings. We give you hundreds of suggested one-on-one questions and agenda templates (just like this!) to make sure you get the most from your one-on-one meetings. Ready to try it out? Sign-up here to use the One-on-Ones Tool for free.

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Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.