One-on-one Meetings

Career Development Questions for One-on-Ones

Kate O'Neil
October 4, 2021

A How-to guide for starting career development conversations in your one-on-one meetings.

Opening a one-on-one conversation with a team member about their career development doesn’t have to be hard. Below are a few tips for getting the conversation going.

First, it’s important to know that this conversation will come up, and it’s a lot more effective if you, the manager, initiates the one-on-one conversation because it shows you care about their career development. Studies have shown that a clear plan for career development improves employee engagement and performance. So, it’s also never too late to start having these conversations. It’s ideal to start them whenever you start managing a new team member, but even if you didn’t set up these conversations from the beginning, now is a great time to start.

To open the one-on-one conversation, start by asking about how their current role is going:

  1. What has energized you in your role [over a period of time]?
  2. What has challenged you [over a period of time]?
  3. What has gone well/not so well for you [over a period of time]?
  4. What’s one thing (or a few) you learned [this year / quarter]?
  5. Was there any project you wished you could be a part of? Why?

Then, ask about the future:

  1. How would you like to see your role evolve [next year]?
  2. What would you like to do more of? Less of [next year]?
  3. I hope it’s not anytime soon, but if/when you leave the company, what new role would you love to have?
  4. If you could wave a magic wand and be an expert in a new skill, what would it be?
  5. Is there anyone you look at and think, ‘I want to be him/her someday?

Next, create an action plan together for what to do next. After this initial one-on-one conversation, some team members will have a very clear picture of where they want their career to go next, some won’t and that’s okay. A good action plan for all team members has short-term and longer-term goals that are measurable.

To learn more about creating measurable goals, check out Teaming's Team Leadership playbook.

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