10 Questions Every Leader Should Ask Themselves Before the Year Ends

By James Fleming, Managing Director of The Power Within Training

 

If you’re reading this, there’s a good chance your to-do list is longer than Santa’s, your inbox is plotting against you, and you’ve already been to at least one “festive” networking event that should’ve been an email.

Welcome to December.

It’s the time of year when everyone tells you to slow down, reflect, and plan for the year ahead… right after you’ve somehow managed to close projects, finalise budgets, and attend seventeen Christmas lunches.

But reflection doesn’t need to be some long, drawn-out process involving scented candles and motivational playlists (though if that’s your thing, crack on). It’s about asking yourself the right questions; the kind that make you pause, take a breath, and look at the bigger picture.

So, before you switch off for the year (mentally or physically), here are 10 questions every leader should ask themselves before the year ends.

 

1. What am I most proud of this year?

Start here, because we’re usually rubbish at it. Too many leaders finish the year fixated on what didn’t happen, rather than what did. Take a moment to give yourself credit for the wins, the tough calls, and the times you held it together when you could’ve walked away.

 

2. What drained me the most?

This is where honesty matters. Was it endless firefighting? A lack of boundaries? Or maybe certain meetings that could’ve been an email (we’ve all been there). Recognising what’s been draining your energy helps you protect it next year.

 

3. Who made the biggest difference to me this year?

Think of the person who had your back, challenged you, or lifted you up when you needed it. Leadership can be lonely, but you’re never doing it alone. Who deserves a thank you before the year ends?

 

4. Did I actually grow as a leader, or just stay busy?

Busy doesn’t mean progress. It’s easy to get caught up doing rather than developing. Did you challenge yourself? Learn anything new? Take a risk? If not, that’s your cue for next year.

 

5. How did I make my team feel this year?

This one’s uncomfortable but powerful. Did your team feel valued, trusted, and supported… or just managed? People don’t remember every task you assigned, but they do remember how you made them feel.

 

6. Where did I avoid change?

If you’re being honest, there’s probably an area you’ve resisted shaking up; that “we’ll deal with it next year” project or that tricky conversation you’ve avoided. Spoiler alert: it won’t fix itself.

 

7. What’s one mistake I can laugh about now?

Leadership’s messy. If you can’t find humour in the chaos, you’ll burn out fast. Whether it’s a presentation gone wrong or a wild idea that flopped, find the funny side. It’s a sign you’re learning.

 

8. What am I pretending not to know?

We all do this. Pretending that certain team dynamics aren’t an issue. Pretending someone’s “just having a bad month” when you know it’s a pattern. Pretending you’re fine when you’re exhausted. Honesty is where real leadership starts.

 

9. Have I been leading by example, or by habit?

Are you modelling the behaviour you want to see, or are you just running on autopilot? Think about what your team sees from you daily. Consistency is powerful, but authenticity is what builds trust.

 

10. What’s my focus for next year, and what am I leaving behind?

You don’t need a ten-page strategy. Just clarity. What’s your theme for next year? Maybe it’s growth, balance, boundaries, or courage. Choose one focus that anchors your actions, and one thing you’re ready to let go of.

 

The Power of Reflection

Most leaders don’t take time to do this. They hit “go” again in January without ever stepping back to understand what’s actually working (or not).

But those who do lead differently.
They’re calmer, clearer, and more intentional.
They build teams that think, act, and take ownership, because they’ve built those habits in themselves first.

This is exactly what we teach through Motivational Intelligence (MQ), the science behind how people respond to challenges, change, and setbacks. High-MQ leaders don’t just set goals; they understand the mindset that makes goals possible.

 

James’ Take

If I’m honest, these are the same questions I ask myself every year too. Running a business, being a husband, a dad, and trying to keep all the plates spinning, it’s easy to lose sight of why you started in the first place.

For me, reflection is about realignment. It’s the moment I stop and ask, “Am I building the business I actually want to run? Am I being the leader I’d want to work for?”

And if the answer is “not quite,” that’s okay. That’s what the new year’s for.

 

Before You Go…

Take 20 minutes this week to answer these ten questions.
You don’t need a journal or a fancy worksheet (though we can sort you out with one if you’d like). Just take time for yourself.

And if you want to start 2026 with more clarity, confidence, and purpose, not just another to-do list, we can help.

Our Leadership Development Programmes are designed to help leaders at every level shift their mindset, lead with purpose, and create lasting change, both in their teams and in themselves.

Get in touch with us here to find out more.

Here’s to ending the year strong, and starting the next one with focus, balance, and a bit more breathing room.

 

James Fleming
The Power Within Training,
The Motivational Intelligence Company
james@tpwtd.com