Catching up (10 – 15 minutes):

  • What are you most looking forward to this holiday season?

  • How has the workflow with the end of the year crunch been feeling?

Reflections on the past year (30 – 45 minutes):

  • When you consider this past year in full, how do you feel about the progress you personally made? How about to the progress your team made?

  • How did the pace of work, and the pace of progress feel across the year?

  • When did you feel most proud to be a part of the company this past year?

  • When did you feel most discouraged last year?

  • Who’s help or support on the team have you been most appreciative of?

  • What do you think has been the biggest area of growth for you? A time where you thought, “Woah, I really got better at this” or “I really learned something?”

  • Are there any ways that you’ve seen me grow as a leader?

  • In what ways has our work relationship changed over time? In what ways have we made positive progress? What are the areas we both need to work on how how we work together?

Looking ahead (30 minutes):

  • What can I do better in the upcoming year to be the best manager to you, as a possible?

  • In what ways do you want to stretch and grow in the upcoming year?

  • What about work, culture, or how the team is run do I need to pay closer attention to as a leader?

  • How can we better challenge and support each other in the upcoming year?

Takeaways and next steps (10 minutes):

  • What are we both taking away from this conversation?

  • Are there any next steps each of us need to take for the upcoming year?

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