20 questions to self-reflect on for 2024
What to ask yourself as a leader, looking back on 2024 – and ahead to 2025.
Reflection is an oddly difficult act.
I consider myself a naturally reflective person (I’ve kept a journal since I was in the fifth grade, believe it or not!) — yet taking the time to reflect on 2024 as a leader is something I find myself postponing, every single day this week.
I keep telling myself, “Oh I’ll do it tomorrow…”
I told myself this a couple days ago.
Today is Friday.
An inconvenient truth seems to be revealing itself to me…
I haven’t just been putting off reflection – I’ve been flat-out avoiding it.
Why? I’m exhausted. The kind of bone-deep tiredness that is an accumulation of having the privilege of doing too many things, and simultaneously overestimating how much capacity you have to do all things. (Sound familiar to anyone? 😅 )
Reflection takes time and effort – things we feel in short supply of when we’re tired.
Reflection can also feel like pressure. As though some magical epiphany should present itself at the end of a reflection: A through-line of “dots that connect themselves while looking back” à la Steve Jobs.
But here’s what I wasn’t fully appreciating…
Reflection isn’t about deducing insights or neatly pinpointing the lessons.
Reflection is about giving yourself space as a leader to step away. To purposefully extract yourself from the day-to-day — and look out from a different vantage point.
To see things again, but from an alternate perspective.
When you look at something more than once, there is often a tendency to see it differently.
So don’t force the lessons. Let the insight show itself to you, on its own.
You simply have to give yourself the space to see things differently, first.
In particular, here are the 20 questions I’ll be asking myself today as I self-reflect.
(I won’t be putting it off any longer 😉)
Think back to this time last year. In what ways do you feel different, as a leader? In what ways do you feel the same? What do you think accounts for those differences and consistencies?
When was a time this past year you made the harder decision, rather than a more popular or easier one? Knowing everything you know now, would you make the same decision, or a different one? Why or why not?
What was energizing? When did you feel most energized in the past year? Why was that?
What felt like your “crucible” this year? A moment where you felt tested, and put through the fires? What surprised you about that experience? What changed in you or around, from that experience?
What work relationship do you think you strengthened and/or you are satisfied with how you’ve oriented toward? Why is that?
What work relationship did you find yourself struggling with and/or you are dissatisfied with, and hoping changes for the better in 2025? Why is that?
What’s something you originally said you wanted to focus on in 2024 – and the completed? How content are you with that experience? Why or why not?
What occurred in the past year at work that pleasantly surprised you? What might’ve laid the path for that pleasant surprise?
What occurred in the past year at work that was a rude shock? What might’ve laid the path for the unexpectedly unsavory outcome?
What is the best piece of feedback that you received in the past year? Why? Who did it come from? (P.S.: If you can’t think of any meaningful feedback you received in the past year, why do you think that might be?)
When did you choose to confront a hard truth in the past year and take action – rather than ignore it? What did you learn, if anything, from that experience?
When did you feel most “in flow” and loving the work itself, this past year?
When did you feel most discouraged or beaten down, this past year?
When did you feel a deep sense of gratitude, this past year? Was it toward specific people? Specific moments or actions?
When did you notice yourself acting out of fear, anger or anxiety, this past year? What was happening in those moments? What may have triggered those sentiments?
When did you notice yourself acting out of courage, compassion, or calm, this past year? What was happening in those moments? What might be helped enable those operating states?
What do you think has been the biggest area of growth for you this past year? A time where you thought, “Woah, I really got better at this” or “I really learned something?”
What about work, culture, or how the team is run do you want to pay closer attention to as a leader?
In what ways are you craving to stretch and grow in the upcoming year?
What this past year at work has given you a dash of renewal, a spark of a flame, a sense of hope for in the year ahead?
Here’s to seeing 2024 from a different perspective. I hope these questions help.
And, if you’d like to work together in 2025 on leadership training, 1:1 executive coaching, team keynotes or workshops, or using Canopy in your day-to-day as a leader, I’d be honored to chat! Feel free to reach out to me directly here 💚
-Claire