Thought-Provoking Questions to Prompt Your End-of-Year Reflection
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As we get to the end of the year, it’s natural for us to want to spend some time reflecting. What went well for us in the past year? What were some areas where we’d like to improve in the future?
And while you may naturally spend time doing this for yourself, if you’re a leader, it’s especially important for you to model this type of self-reflection and encourage it on your team.
Personally, I find Stephan’s list of 40 questions very helpful. I’ve been using them since 2016 to help me get into reflection mode. I don’t necessarily need to answer all 40 of them every year, but returning to the same list annually helps bring things to mind that I might have otherwise overlooked.
I’m sharing them here in case you find them equally valuable. And remember: You don’t have to wait until December 31st to look at these questions. It can be just as helpful if you take time to reflect on a quarterly or six-month basis. What’s most important is making time and space for reflection in a way that works for you.
What did you do this year that you’d never done before?
Did you keep your new year’s resolutions?
Did anyone close to you give birth?
Did anyone close to you die?
What cities/states/countries did you visit?
What would you like to have next year that you lacked this year?
What date(s) from this year will remain etched upon your memory, and why?
What was your biggest achievement of the year?
What was your biggest failure?
What other hardships did you face?
Did you suffer illness or injury?
What was the best thing you bought?
Whose behavior merited celebration?
Whose behavior made you appalled?
Where did most of your money go?
What did you get really, really, really excited about?
What song will always remind you of this year?
Compared to this time last year, are you: happier or sadder? Thinner or fatter? Richer or poorer?
What do you wish you’d done more of?
What do you wish you’d done less of?
How are you spending Christmas?
Did you fall in love this year?
Do you hate anyone now that you didn’t hate this time last year?
What was your favorite show?
What was the best book you read?
What was your greatest musical discovery of the year?
What was your favorite film?
What was your favorite meal?
What did you want and get?
What did you want and not get?
What did you do on your birthday?
What one thing would have made your year immeasurably more satisfying?
How would you describe your personal fashion this year?
What kept you sane?
Which celebrity/public figure did you admire the most?
What political issue stirred you the most?
Who did you miss?
Who was the best new person you met?
What valuable life lesson did you learn this year?
What is a quote that sums up your year?
And if you want to do more—if you want to reflect on your professional life—here are some additional questions tailored for product managers and product leaders. But please start with the personal ones above, as they’ll help you put everything into perspective!
On Leadership and Team Development
How has your leadership style evolved this year?
What’s one leadership behavior you started or stopped doing this year?
Did you make time for 1:1s with your direct reports consistently? How effective were they?
How well did you provide feedback to your team? What’s one thing you could improve in your feedback delivery?
What steps did you take to develop the skills and growth of your team members?
Did you create a culture where feedback flowed in all directions (team to leader, peer to peer, etc.)?
Who on your team surprised you this year with their growth or contributions?
Did your calendar reflect your top priorities as a leader?
Were you able to timebox critical tasks like strategic planning or team development?
How well did you manage distractions and protect your time for deep work?
Were there recurring meetings or tasks that should have been delegated or eliminated?
Did you set and maintain clear boundaries to ensure you could focus on what matters most?
How effective were your quarterly or annual planning sessions?
Did your product roadmap align with your company’s overarching goals?
What steps did you take to involve your stakeholders and ensure alignment?
Were your team’s goals clear and achievable?
How well did you track and communicate progress on these goals?
What product decisions are you most proud of this year?
What customer insights had the biggest influence on your product direction?
Did you deliver measurable value to your customers and business? If so, how?
How well did you balance building new features with optimizing existing ones?
What metrics or feedback would you point to as evidence of your success this year?
What was your biggest professional achievement this year?
What’s one mistake you made, and how did you grow from it?
Did you focus on your own personal development as a leader?
What’s one skill or area you’d like to improve on in the coming year?
If you could go back to the beginning of the year, what advice would you give yourself?
Take your time with these, and remember: the goal isn’t to answer every question perfectly—it’s to create a clearer picture of where you’ve been and where you want to go.