As the year winds down, it’s easy to get caught up in the chaos of wrapping up projects and planning for what’s next. But before rushing into 2025, take time with your team to pause, reflect, and celebrate. We’re big reflection fans at transform.forward and believe an “End of Year Reflection” session can be a meaningful way to acknowledge growth, process challenges, and set the tone for the year ahead.

Whether it’s a formal meeting, an extended coffee chat, or a quick addition to your holiday gathering, this exercise can foster connection and clarity. Use these 20 questions (pick as few or as many as you like!) to spark thoughtful conversations. The questions are designed to honor the highs, the lessons learned, and the aspirations waiting just around the corner. We’ve organized the questions into four strategic categories to help you guide your team through a meaningful and impactful activity:

Celebrating Accomplishments and Growth

Encourage your team to think about the highlights that made this year memorable and meaningful. These questions are great for setting a celebratory tone and emphasizing collective and individual growth.

1. Identify your biggest accomplishment. What about the team’s biggest accomplishment?

2. Which goal or milestone was the most rewarding to achieve?

3. What’s a “small win” from this year that deserves recognition?

4. What teammate or colleague have you developed a stronger working relationship with this year?

5. What moment this year made you laugh the hardest at work?

6. What do you think our clients/students/partners would say was our biggest success this year?

Reflecting on Challenges and Lessons Learned

Encourage honesty and vulnerability when reflecting on challenges. Reassure your team that discussing setbacks is about learning and growth, not dwelling on mistakes. These questions create space for shared problem-solving and continuous improvement.

7. What didn’t go as planned, and you’re looking forward to getting it right next time?

8. Was there a project or task that felt impossible at first but turned out to be a win?

9. What is one piece of feedback or recognition you received that stuck with you?

10. What did you notice about how the team navigated challenges or setbacks?

11. What is something you learned this year that surprised you?

Fostering Team Connection and Culture

These questions focus on team relationships and creating a strong, shared culture moving forward.

12. What’s one thing you’re proud of the team for handling, even though it was tough?

13. What is a habit, ritual, or tradition you’d like to see the team continue next year?

14. If we could do one thing to make work more enjoyable in 2025, what would it be?

15. What word or phrase would you use to sum up this year?

16. Who had the biggest professional impact on you this year?

Looking Ahead and Building Momentum

Encourage optimism and creative thinking as the team considers what they want to achieve and improve upon in the year ahead.

17. What is a process or practice that has been updated that you’d never want to go back to the old way?

18. What puzzle or problem needs dedicated time to solve?

19. Are there quick fixes or low-hanging fruit you hope to address early in 2025?

20. What is one hope or aspiration you have for the team in 2025?

Tips for Successful Facilitation

Start Light, Then Go Deep: Begin with lighthearted questions, like “What made you laugh the hardest this year?” to warm up the discussion. Transition into deeper topics, such as challenges and lessons learned.

Encourage Participation: Give everyone a chance to answer at least one question in each category to ensure balanced input and diverse perspectives.

Allow Flexibility: Choose which categories resonate most with your team, tailoring the session to fit your unique dynamics.

Close on a High Note: End the session with forward-looking questions to leave everyone feeling inspired and motivated for the year ahead.

Ending the year with reflection isn’t just about looking back—it’s about building momentum for what’s next. Taking time to celebrate wins, acknowledge challenges, and envision the future creates a stronger sense of purpose and connection. So carve out some time to reflect with your team, whether through these questions or your own twist on them. 

Here’s to a meaningful close to 2024 and an exciting start to 2025!