The fourth quarter isn’t the time to bury your head in spreadsheets and hope momentum magically carries you across the finish line. And if you’re leading a team, the way you close out the year matters just as much as how you start the next one. This requires meaningful conversations that recalibrate, celebrate and spark momentum.
Here are the five conversations every stable leader should be having before the year winds down.
1. Celebrating Wins (Big and Small)
Highlight what your team accomplished in 2025, including headline achievements and the smaller, often-overlooked moments. Recognition isn’t just about applause. It’s about building morale, reinforcing positive behaviors and showing your people they matter.
It’s important to remember that if you only celebrate the flashy wins, you miss the heartbeat of the team. The everyday efforts that keep the team running. The late-night troubleshooting. The customer who left happy. The behind-the-scenes fixes that no one notices. Recognize these moments, and your people will head into the holidays with pride instead of burnout.
2. Clarifying Priorities for the Remainder of the Year
Reality check: The closer the holidays get, the more motivation wanes. Narrow down your team’s must-do tasks between now and December and clear away any distractions. When everything feels urgent, nothing truly gets done. Your team needs focus, not chaos. This conversation is about answering one simple question: What absolutely needs to get finished before year-end, and what can wait?
It’s tempting to try to cram in everything you didn’t tackle earlier in the year. Instead, get ruthless. Help your team hone in on what will truly move the needle. Clarity reduces overwhelm and gives people the satisfaction of finishing strong, rather than drowning in a list of half-completed tasks.
3. Surfacing Challenges Honestly
Engage in a safe, judgment-free and direct conversation about what didn’t work well this year. Too many teams sweep problems under the rug to stay positive during Q4. But avoiding challenges doesn’t make them disappear. Acknowledging them without blame creates trust and signals maturity.
Have the team be honest about missteps and mistakes that they don’t want to repeat in 2026. The goal isn’t to point fingers but to learn and improve. Teams that can talk openly about their struggles build resilience. They’re better prepared to adapt and innovate when the next curveball rolls in.
4. Revisiting Individual Growth and Development Goals
Check in with each person on their professional aspirations, skills they want to build and how they feel about their current role. People aren’t robots, and they don’t just want tasks. They want progress. Ending the year with a one-on-one that focuses on how they’re doing shows employees they’re more than a cog in the machine.
Go into this conversation with an open heart. What do your people want for themselves? Where do they see themselves making the most impactful contribution? What do they want to learn? Maybe someone wants to sharpen their leadership skills so they can grow with the company. Maybe another wants to become a subject matter expert so they can be the go-to expert at the office then be off the clock with their family. When you acknowledge these ambitions and talk about what’s possible in 2026, you create loyalty and motivation. Your team walks into the new year knowing you’ve got their back.
5. Resetting Team Norms and Ways of Working
Talk about how the team works together, focusing on meeting rhythms, communication habits and collaboration styles. Check in about whether those norms still serve the group. What worked in January might be dragging you down come Q4. Is the team drowning in too many status meetings? Has Slack turned into a noisy distraction? Do remote work routines need a refresh?
This is the time to reset. Address the daily mechanics of teamwork, and you’ll eliminate friction and enter 2026 with smoother, more efficient workflows. Plus, involving everyone in the process builds a team culture where everyone feels heard.
Why These Workplace Conversations Matter
Most employees don’t quit because the work is too hard. They quit because they don’t feel seen or clear on what they’re doing. These conversations are your antidote. They’re simple, but they pay massive dividends.
Leaders who skip these conversations often end up in firefighting mode. The team starts the new year tired, disconnected and unclear. Don’t be that kind of leader to your people. Be the one who chooses to pause, connect and set the stage for real momentum.
Kick Off Your Year-End Conversations
So, how do you put this into practice before the calendar flips?
- Schedule time now. If you wait until December, everyone will be scrambling. Start these conversations early in Q4 while people still have bandwidth.
- Mix group and one-on-one discussions. Some conversations, like celebrating wins or clarifying priorities, work well in team settings. Others, like development check-ins, need intimacy.
- Listen more than you talk. The magic isn’t in delivering a perfect speech. It’s in asking the right questions and letting people share.
- Close the loop. Don’t just nod and move on. Capture what you hear, act where you can and follow up in January to show you meant it.
Lead with Confidence Through 2025
The way you close out 2025 will shape how you start 2026. Make these conversations count, and your team will walk into the new year clear, aligned and ready to make progress —together.
