Career Development Questions for One-on-Ones

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 the Team Leadership playbook.