If you’re a manager, you’ve probably heard this advice: “Make sure you do a year-end reflection!” “Take time to reset before next year.” “Be intentional about how you want to lead.”

All of that sounds reasonable. It’s just not very helpful.

Because no one really explains how to do a year-end check-in in a way that feels honest and useful, instead of like another thing to put on your to-do list (and never actually do) before the holidays.

That’s why in this week’s video, I walk through a manager roleplay of a year-end self check-in. I talk through the questions out loud the way a real manager might when they finally slow down enough to think about the year.

I've also made the same self check-in tool I use in the video available for free, so you can try it yourself. You can get it right here. 

Don’t Start With “What Happened.” Start With What You Expected.

Most people jump straight to listing everything that went wrong or right this year. A better place to start is asking what you thought the year would look like back in January.

Questions like:
- What did I think my work would look like this year?
- What did I expect to spend most of my time on?

These matter because so much frustration comes from a mismatch between expectations and reality. Maybe you thought you’d be hiring, focusing on strategy or finally getting ahead, and instead you spent the year managing change, doing more with less or just trying to get through each day.

That’s not failure. That’s context.

Look at What Actually Took Up Your Time and Energy

Once you’ve thought about expectations, then look at what really happened.

- What surprised you?
- What took way more time or energy than you expected?
- What actually went better than you thought it would?

This step helps you stop lumping everything together as “a hard year” and start identifying specific issues and patterns. Many managers realize that if they struggled this year, it wasn't because they weren’t capable, but because the year asked something different of you than you planned for.

Pay Attention to How You Responded When Things Got Hard

One of the most useful parts of a year-end check-in is noticing how you responded when plans changed or work piled up.

- Did you take on more yourself instead of asking for help?
- Did you push conversations off that would have helped sooner?

Most managers don’t do this intentionally. You often do it because it feels faster in the moment, or you want to "protect" your team. Looking back helps you see where that approach helped, and where it made things harder than they needed to be.

Think About How You Showed Up for Your Team

This isn’t about judging your leadership. It’s about noticing patterns.

- If you were on your team, how would you describe the way you showed up this year?
- When were you thoughtful and steady?
- When were you rushed or reacting?

These questions matter because your team experiences your leadership in moments, not in job descriptions. If you're only going to ask yourself one of these questions in the whole check-in guide, I'd choose the first one here. Pausing to think about how your team perceives you makes you an even stronger leader in the future.

Think of Your Team Members as Individuals

It’s easy to think about your team as a group. It’s harder to slow down and think about people one by one.

- Who really stepped up this year, and how do you know?
- Who might be doing “fine” (or even well) on paper but carrying more than they should?

This reflection often changes how managers approach one-on-ones going into the new year. Instead of generic check-ins, you come in with better awareness of what each person might need.

Separate What You Could Control From What You Couldn’t

Some things that shaped your year were out of your hands. Hiring decisions, budgets, organizational changes - those aren’t yours to fix.

Other things were in your control. How early and often you communicated, whether you asked questions instead of making assumptions, and how clearly you set expectations and gave feedback.

A good year-end check-in helps you let go of the first category and focus on the second, instead of carrying everything forward as your responsibility.

Use the Reflection to Decide What You’ll Do Differently

The goal isn’t a long list of goals. It’s picking a few things that actually matter.

- What’s one thing you need to stop doing yourself?
- What’s one habit you want to be more consistent about?
- What’s one conversation you don’t want to avoid next year?

Those answers are far more useful than big resolutions you won’t realistically revisit.

Think About Yourself

Managers spend a lot of time thinking about their teams and very little time thinking clearly about their own role.

- What do you want more of next year?
- What do you want less of?
- Have you actually said that out loud to anyone who needs to know, or could help you get there?

This part of the check-in isn't always comfortable (because it can feel easier to think about your team than yourself) - and also the one people are most glad they didn’t skip.

Get the Free Year-End Manager Self Check-In

If this sounds helpful, don’t stop at reading or watching. Download the free Year-End Manager Self Check-In. 

Take 10-15 minutes to go through this. Write it down. Use this to close out the year, then come back to it as you head into the next one. Because reflection should give you something to carry forward, not just something to cross off.

Want help putting this reflection into action?
Manager 101 is our foundational leadership course built for real, day-to-day management. It gives you practical tools for things like setting expectations, giving feedback and leading your team with more confidence. It’s a great way to start January with habits you can actually use.