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Want a Motivated Team? Ask and You Shall Receive

6 powerful but simple end-of-year questions to ask your direct reports

It’s the end of the year and you’ve got a lot to do: end-of-period and end-of-year reporting, team reviews, customer follow-ups, virtual holiday gatherings to maintain key relationships, not to mention whatever you’ve got going on personally during this holiday season, even in this off- the-rails whack job of a year. Even in the midst of all the to do’s—if you also have direct reports—you also have a tremendous opportunity to do some relationship-building with members of your team as the year winds up and a new one is set to begin. And the good news is that it’s relatively easy to do and can pay dividends throughout the coming year. (And if you have to wait to schedule it for right after the New Year, that’s ok, but don’t wait much beyond that timeframe.)

Okay, This sounds possibly good. What do I have to do?

This isn’t hard, although it may take a little practice to feel confident with it. What we’re talking about is creating an opportunity to ask each of your direct reports some powerful open-ended questions designed to give you useful insight into some important areas relating to your direct report’s motivation and performance. Taking the time to have this year-end wrap-up conversation—whether part of a standard review process or just a standalone conversation—will reveal what your team members see as their biggest accomplishments (which may differ from what you think they are), and show you the areas where they are motivated to grow. Knowing these things can be tremendously useful as you look to make task assignments, fill openings, and generally try to get the right people into the right roles where they can thrive and help your organization reach its goals.

Besides the insight that you gain, another key benefit of asking your people these questions--and listening carefully to their answers—is that doing so will have them feeling seen, understood and cared about, all of which has been shown time and again to help build and maintain employee motivation and loyalty.

So what are the questions?

Feel free to lightly edit the questions below to fit the way you usually communicate, but DO NOT ask simple yes-or-no questions. What you want to do here is gain some insight into what your people are thinking in some important areas relevant to their performance and therefore to your team’s success. So, here are the questions. I suggest you send them out ahead of time and then schedule 25 minutes with each direct report to allow you both to discuss their responses.

  1. What’s one accomplishment that you feel ownership of or made a strong contribution to that you are especially pleased with this year?  What is it about this accomplishment that has it rise to the top?
  2. What personal and professional qualities have helped you get through this challenging year and have contributed to your success?
  3. What’s an obstacle—either at work or in your personal life--you overcame this year that you are proud of?
  4. What’s an area you’d like to grow in next year; i.e., a skill you’d like to improve or a quality in yourself you’d like to use more, and why? What might the benefits be of doing so, to you and to our organization?
  5. How might I (as your supervisor) and/or the organization support you in growing in this area?
  6. BONUS QUESTION:  Of the changes we’ve had to implement this year, are there any that you would like to see continued once we are no longer required to work remotely?  If so, which ones? (Okay, it's a yes or no question, but could yield useful information and lets your direct report feel part of the planning process.)

During the conversation, be sure to practice active listening. This means you make eye contact (if it’s a virtual meeting—and it likely will be—look into the camera as opposed to looking at the person’s image on your screen), nod in understanding as your direct report is talking, and offer feedback and encouragement as warranted.

As a way to up-level the experience, come to the meeting with at least one example of where you have seen this person step up and the positive impact of that on the organization (and on you, if relevant). Consider also adding the following the sentence to the conversation: “One thing I especially appreciate about you is…”

Got it. Let’s wrap this up

Asking these questions and taking the time to listen to your team members’ answers is not only a smart leadership move, but also a way that to let your team know you care about them as individuals. And if you want a more hard core reason, here’s a thing to consider: According to a 10-year study conducted by Rainmaker Thinking, Inc. (based on interviews with over 10,000 employees and executives at more than 700 organizations), “the day-to-day communication between supervisory managers and direct reports has more impact than any other single factor on employee productivity, quality, morale, and retention.” This conversation will likely stand out in your team member’s mind as a memorable (and positive) example of communicating with you.

Give it a try and let me know how it goes!

Alan Roby is a Leadership Coach who’s passionate about using a people-first, personal approach to leading others. Find him online at

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