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Ask Your Direct Reports These 5 Questions in Your Next Check In

Susan Peppercorn


January 21, 2022




If you’re worried that your employees are eyeing the door, it’s time to start having some important, career-defining conversations. Here are five key questions to ask your direct reports at your next one-on-one to ensure that they feel seen and valued — before it’s too late.


  1. How would you like to grow within this organization? Identify the career development opportunities they need — whether that’s coaching, mentoring, increased visibility, or more challenging projects. They’re more likely to stay if they feel like they’re growing.

  2. Do you feel a sense of purpose in your job? Tap into what’s meaningful to them — and connect it with the values of the organization.

  3. What do you need from me to do your best work? Be prepared to devote more time and resources to help your employee feel fulfilled.

  4. What are we currently not doing as a company that you feel we should do? Asking what they feel the company could be doing better — what market opportunities it might be overlooking, how to leverage resources more effectively, etc. — conveys that their thoughts and opinions matter.

  5. Are you able to do your best work every day? This allows you to determine whether they’re optimizing their strengths. You might follow up with, “What part of your job would you eliminate if you could?” Don’t make promises but knowing which aspects of their job are least and most enjoyable will help you make any necessary changes to ensure they stick around.

hbr.org