Questions To Create a Powerful Dialogue in Your 1:1s with Your Reports

By: Courtney Templin

It’s one of my favorite times of year, not only because I adore the twinkle lights of the season. I love year-end 1:1s with my team as we look back on the year and lay the groundwork for the year ahead. I get energized seeing all the growth and development that can happen in just 12 months and the excitement of thinking through our next big goals. At JB, we are fortunate to have a high-performing and tenured team. With quarterly check-ins, I have to get creative to ensure we are generating new and fresh insights. It’s all about asking the right questions, and sadly, a simple “So, how are things going?” doesn’t get you very far.

I am guessing your plate is very FULL this time of year, so I pulled a few of my favorite check-in questions. Feel free to use them or share with your managers this December. Cheers to an energizing year-end!


• This quarter, what were some “flow” moments? What were “friction” moments?
• What has sustained you this quarter? What has drained you?


• What part of your role do you want to do more of but it’s hard to find the time?
• How do you learn best? What are 1-2 professional development ideas you have?
• What is on your short or long-term professional bucket list? (1 personal one too!)
• What story are you telling yourself that is holding you back?
• What is your superpower?


• What is one thing you think our team should prioritize? What about de-prioritize?
• You are part of my challenge network. What unpleasant truth should I know?
• What can I do more or less of as manager?
• Is there anything we need to “rethink” or “unlearn”?
• What was the last thing you complained about to a friend regarding your job?


• What motivates you? What demotivates you?
• What are your recommendations for making our meetings more effective?
• Create your own question here. (And then give your answer.)
• How do you think team members can support each other more?
• If you could change one thing about your job, what would it be?
• What is 1 self-care commitment you would like to make?
• Is there a team-care commitment we can focus on?