How to Carry Sales Momentum Through the Holidays and Into the New Year (Ask Jeb)

Here’s the scenario that’s playing out in sales organizations everywhere right now: Your team fought through a brutal first half of the year, rallied momentum in the second half, crushed their numbers, and now they’re ready to coast through December.

That’s the exact situation Kyle Begbie, a regional sales director at Fuse HR Solutions in Ontario, Canada, brought to this week’s Ask Jeb. His team overcame massive market disruption, economic headwinds, and buyer hesitation to finish the year strong. Now he’s facing the most dangerous challenge of all: keeping that momentum alive through the holidays and into January.

If you’re nodding your head right now, you’re not alone. This is the point in the year where sales teams either set themselves up for a championship quarter or dig themselves into a hole that takes months to climb out of.

The Holiday Momentum Trap

Here’s what happened to Kyle’s team, and it’s probably happening to yours too: They worked incredibly hard through disruption and uncertainty. They pushed through discouragement when buyers were putting deals on hold. They ground it out for months to get back on track.

And now they’re exhausted.

The holidays are here. Christmas music is playing. Everyone wants to take their foot off the accelerator and coast a little bit. This is why December and January are the most dangerous months for sales professionals.

Here’s the deal: Nothing really changed in the market from the first half of the year to the second half. Kyle’s team faced the exact same headwinds, the same economic conditions, the same buyer concerns. The only thing that changed was what they believed.

Once they believed they could win, they kept winning. And once buyers realized nothing was going to change and all of this was permanent, they got on with business.

But here’s the problem: If you take your foot off the accelerator now, you’re going to pay for it in January and February. That’s not motivation speak. That’s math.

The 30-Day Rule Will Make or Break Your Q1

The 30-day rule is simple: The prospecting you do in any given 30-day period pays off over the next 90 days.

This is especially true in industries like staffing, but it applies to every sales role. If your team takes December off and doesn’t prospect, you’re going to have a catastrophic January and February. It’s that simple.

So the number one thing you need to do as a sales leader right now is get structure around prospecting. Every morning, your team needs to run their call blocks. They need to run their sequences. They need to go through the entire process, and that cannot stop.

The only way you’re going to lead this is from the front. Whether your team is dispersed or in the office, you need to be running prospecting blocks with them every single day all the way through the holidays. If you do that, you’re going to be golden.

Close What’s Closable Before January 1

The second critical action is closing every deal in your pipeline that’s actually closable right now.

Your customers are thinking they have time. Your salespeople are thinking they have time. Nobody’s pushing anybody. But here’s the reality: If those deals roll over past Christmas into the New Year, the likelihood of closing them is almost zero. You’re essentially starting all over again.

Sit down with all your salespeople right now and walk through their pipeline. Identify every single deal where everything is lined up. Fit, budget, need, authority. Everything’s qualified. The only thing keeping you from closing is they haven’t said yes yet.

Get in the middle of those deals and find a way to get them closed. That gives you momentum going into the new year. December feels great. And in staffing or any service business, those December closes become revenue in January, February, and March, which takes massive pressure off your team.

Set Your Team Up for Success in January

This is a critical time to start thinking about setting yourself up for success in the new year. While everyone else is checking out, you should be:

Building targeted prospect lists for Q1. Identify your ideal prospects for January, February, and March right now so you can hit the ground running.

Cleaning up your CRM. Get your data organized. Update records. Remove garbage. Make sure your team has clean, actionable information when they come back.

Revisiting close-lost deals from earlier in the year. Especially deals from the first half of 2025 where buyers were hesitating or went with a competitor. Maybe the grass wasn’t greener. Maybe they still have the same problems. Build those lists now so you can attack them hard in January.

Following up on qualified leads that stalled. There are good leads sitting in your system that were qualified but couldn’t move because of timing or market conditions. Gather those up and get lists together for your team.

What you’re doing here is acting like a coach getting your players in position to win. Because here’s what happens if you don’t: You come off the holidays, get into the first part of the year, and watch your sales team waste the first two weeks of January walking around in a daze, not knowing what to do.

You want to make sure that the first Monday of the new year, you’re running prospecting blocks, talking to customers, and working deals. Not figuring out what you should be doing.

The Power of Celebration and Storytelling

The last piece of maintaining momentum is taking time to celebrate what your team accomplished.

Sit down with your team and tell them the story of what they did this year. Make sure they understand the lesson: When they shifted their mindset, they changed their game. That’s what happened.

Tell them they did a great job. Make sure they’re taking time for their family and having fun. Help them manage their time so they can do both. But fill up their hearts with confidence and belief that they can do anything.

Because here’s the truth: Nothing changed this year except for them. And if that’s true, then nothing can stop them next year either. It doesn’t matter what happens in the marketplace. Even if we go into a recession, people are still hiring. The money is still there. It’s just that more people are chasing it.

Teach your team that it doesn’t make a difference what happens. The economy can fall apart, but they’re good enough to go find where the money is and take it. Because while everyone else is sitting around telling themselves what they can’t do, your team is telling themselves what they can do.

That’s how you carry momentum. That’s how you avoid the January hole. And that’s how you build a championship sales team.

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