10 Powerful Prompts to Spark Year-end Reflection and Meaningful Conversations
My favorite prompts to spark meaningful conversation and reflection as the year winds to a close. These are great to do on your own, or with a group of colleagues or friends.
If you like reading this article, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏
As we near the end of the year, I’m reminded of something I believe deeply: one of the simplest and most powerful ways to create the future we want… is to inspect the past.
This is not just a transition on the calendar—it’s a natural pause point. A moment to inspect where we’ve been, uncover the lessons we’ve learned, and set the stage for what’s next.
Best of all, reflection is not just for individuals; it’s a valuable opportunity for leaders to bring their teams, communities, and families together, to unify the conversation and connect on a deeper level.
Reflections are most powerful when shared.
When we intentionally deepen the conversation with the people around us, we cultivate a growth-mindset that is grounded in meaningful connection. EOY provides a built-in opportunity to do just that. People are naturally open to reflection, and by asking the right questions, we can help people to celebrate their progress, process their challenges, and build deeper bonds.
If you have a company holiday party or a final in-person meeting, consider sharing a few of these prompts with your team. If you are going on an end-of-year trip with family and friends, bring these up at the dinner table.
My favorite reflection prompts / conversation starters:
What were your biggest wins this year?
Take time to fully celebrate what went right. Don’t rush past your victories—soak them in. This is especially helpful when we can give the people around us time to celebrate what went right. Not a time to be humble!
What were the most important challenges you faced, and what lessons did you learn?
Challenges are the birthplace of growth. Reflect on what tested you and how those moments shaped you.
What were your most prevalent fears this year? Did they come true?
Fear has a way of distorting reality. Inspecting it can reveal insights about how you face uncertainty and build courage. What were you worried about, and how did things actually shake out? Do you need to worry about this thing in the new year?
What were some of the biggest risks you took this year? How did they work out?
Growth often lives just outside our comfort zones. Reflecting on risks can help you see where boldness paid off—or where you found unexpected lessons.
What am I most proud of from the year behind me?
Take a moment to name the accomplishments, growth, or moments that brought you pride. Ask yourself what personal values were being expressed in those moments.
What were my biggest missteps or mistakes from the year behind me? What lessons do I want to learn from them?
Mistakes aren’t failures if they teach us something valuable. Use this prompt to turn missteps into growth opportunities.
What am I letting go of from last year?
Reflect on what no longer serves you—habits, mindsets, relationships, or fears—and consciously release them. You can also do a fun ritual around these things: write them down on a piece of paper and burn them with a group of coworkers or friends.
Who are the people you are most grateful for from the year behind you? Who showed up for you or impacted you in meaningful ways?
Bonus points: take a few minutes to share your appreciation with these people. Record a voice note and tell them WHY you appreciate them. If we have anything kind to say, we should share it. Full stop.
What were the pieces of art, content, and literature that impacted you this year? Were there any books, movies, or podcasts you want to remember?
At the end of every year, I like to share the most impactful content I’ve consumed as an homage to the creators and as a way to contribute to my community. This year I was especially grateful for discovering sci-fi as a genre (Three Body, Red Rising) and new podcasts like The Free Press and All-in.
What are my biggest goals in the year ahead?
Be specific about what you want to achieve and distinguish between your personal and professional goals. I think goal setting is most powerful when we focus on three core things that we’d like to achieve for our personal and professional lives.
Closing thoughts, choose gratitude
As we wrap up the year, I encourage you to revel as much as you reflect.
Take a long moment to pause and sit in gratitude for the people, experiences, challenges, and opportunities that came your way last year.
If you are with people, here is one of my favorite gratitude meditations that always helps to put things in perspective.
Looking back has this profound way of compressing so much life into our present moment awareness. It always reminds me of the most important thing there is to get….
Holy shit we’re alive.
Let’s make the most of it!
P.S. Are there any prompts that you would add to this list? Let me know!