3 Coaching Questions for More Meaningful Year-End Conversations

Tomorrow marks the beginning of the final quarter of 2026, which also signals the launch of "performance review season" for many organizations.

Something I'm hearing more than ever this year is that leaders have struggled to hold meaningful development conversations throughout the year because their 1:1s have been largely tactical and focused on navigating rapid change.

In many cases, "did we achieve the goals we set?" is moot because those goals are no longer relevant today. If this rings true for you and you would like to adopt a coaching approach to your year-end review conversation to make learning front and center, consider these three questions as a starting place.

1) What are you most proud of when you look back on this year and your contributions?

2) What helped you move forward when facing setbacks?

3) What have you learned about yourself and your team that will help you navigate what comes next in 2027?

If you want your leaders to be more adaptive and resilient amidst uncertainty, celebrate the wins, identify what helps them overcome challenges, and encourage reflection on their growth.

The learning you help someone recognize today can shape how they lead through the next challenge.

What other coaching questions would you add to the list?