As we close out the year, I don’t know about you, but this is the time when many people feel like they’re running on fumes. Deadlines pile up, holiday plans pull us in every direction, and teams are juggling vacation schedules, customer needs, and end-of-year wrap-ups. And in the middle of all that…it’s easy to forget to check in with our people.
But here’s the thing:
The end of the year and the start of the year are two of the most important times for the engagement and retention of our people.
Over the last two decades working with leaders around the world, I’ve seen this pattern again and again. When things get busy, we rush to “check the box” on a holiday gathering or year-end celebration, but we miss the deeper opportunity — the moment to actually connect, reflect, and help people feel valued and supported before they head into the holidays.
And that moment matters more than we think.
Why December Is a Critical Retention Window
In my video Employee Retention Over the Holidays, I share three reasons this time of year carries so much career risk — and opportunity.
Here’s the short version:
1. People are burning out and need support now more than ever.
We’re sprinting toward the finish line. People need connection, appreciation, and space to reflect — not just another task.
2. This is when people start thinking about job changes.
A new year naturally triggers self-reflection:
“Do I want to be in the same job one year from now?”
And recruiters know that. January and February have the highest volume of new job postings because organizations finalize budgets in the fall.
3. Job search spikes when people are around family.
A Gartner study shows job search increases by 16% when people spend time with friends and family — second only to when someone has a management change.
Why?
They compare. They reflect. They dream a little.
And that’s why the conversations you have now matter.
The Retention Conversation Every Leader Should Have Before the Holidays
If possible, set aside 20–30 minutes with each person on your team. And if your team is large, hold a shared conversation that still covers the essentials.
Here’s the flow I teach:
1. Start by appreciating them for what they did this year.
Before the meeting, think about:
- What projects did they work on?
- How did they grow?
- What did you see in them this year that you’re grateful for?
Give them real examples — the things they specifically did that made a difference.
2. Invite them to reflect.
Ask:
- What are you most proud of this year?
- What did you learn?
- How have you grown?
You’d be amazed how many leaders forget to ask this — and how much people open up when you do.
3. Set up the January conversation.
This is the bridge that most leaders miss.
Before the holidays, say something like:
“Over the break, I’d love you to think about how you want to grow both personally and professionally in the year ahead.
What do you want to learn?
What kinds of projects do you want to be part of?
And how can the team and I support you to do that?”
Give them the three questions in writing:
- How do you want to grow professionally in the year ahead?
- How do you want to grow personally in the year ahead?
- How can the team and I support you in accomplishing your goals?
Then — and this part is key — schedule your January meeting now so they head into the holidays knowing they have a future-focused conversation already on the calendar.
Because when someone knows you care about their growth, when recruiters reach out in January, the answer becomes much easier.
And, if you want a simple structure for that new-year conversation, here’s another resource you can use. It’s a great companion to the retention video and pairs perfectly with a January reset.
A Bonus Resource to Support Those Conversations
If you want practical questions, exercises, and activities to support team connection heading into the new year, my book 75+ Team Building Activities for Remote Teams makes a great holiday gift — for yourself, another leader, or your whole management team.
It’s packed with plug-and-play activities you can use right away to strengthen communication, trust, and engagement with in-person, hybrid, and remote teams.
Planning Next Year’s Events? I’m Now Booking
If you’re looking for support in the new year — whether it’s a keynote, leadership workshop, or a program to help nurture culture appreciation in your organization — I’m now booking for this upcoming year. Reach out to me here.
Want more practical ways to recognize, engage, and grow your people?
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