How to win “Let’s Circle Back” season ❄️
Ah, “Let’s Circle Back” season. The pre-holiday period when everyone has mentally checked out and visions of whiskey-infused eggnog dance in their heads.
BUT NOT IF YOU’RE IN SALES.
Raise your hand if you’re still clawing and scratching your way into people’s inboxes right now to close the last deals you need to meet Q4 goals. (I’m just going to assume your hand is raised.)
I’ve already shared a few email/voicemail templates for the Thanksgiving holiday lull. Those can be tweaked for the Christmas season and work just as well, like:
“Hey [Name], figured you might be clearing your inbox before the holiday — wanted to see if I can help you make a decision on [our solution]. I’ll be around this week for a call if you want to hammer out any details! If not, just wanted to wish you a happy holiday! Talk soon.”
If your inbox is truly a dead zone, what else can you do so that December isn’t a total loss?
Here are two tactical ways to use the holiday lull to level up your sales strategy so you can hit the ground running in 2026 — and leave your 2025 sales numbers in the dust.
1. Run a sales retro
This is the single most overlooked thing reps and founders don’t do in December: reflect with purpose. Don’t wait until January planning meetings!
Take this time to conduct a brutally honest review of what worked, what didn’t, and what needs to change.
Here’s how to do it in 60 minutes or less:
📉 Start with your losing patterns
- What kind of deals consistently didn’t close?
- What red flags did you ignore?
- Where did deals stall — and why? (Bad handoffs? No urgency? Wrong buyer?)
- What leads looked promising but turned out to be time-wasters?
Example: “We kept chasing mid-sized agencies, but they all wanted customization we can’t support.” Great — stop targeting them.
📈 Then look at your winning patterns
- What deals closed fast — and why?
- Where did you win despite being the underdog?
- Which segments or lead sources had the highest close rate?
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What objections were easy to overcome? Which ones consistently killed momentum?
Example: “Our fastest closes came from founder-led teams who were switching from HubSpot after hitting scale pain.” Cool — double down there.
💡 Ask: “What would I never do again?”
- Chasing unqualified inbounds for 6 weeks?
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Sending long proposals without commitment?
- Giving a product tour before understanding the problem?
Make a list. Burn it into your brain. Tattoo it on your sales dashboard.
💥 Turn lessons into action
Write down 3-5 tactical changes you’ll make starting January:
- “I’ll push harder for budget clarity during discovery."
- “I’m retiring this dead segment.”
- “Follow-up will be weekly until a deal’s closed or lost. No more passive checking in.”
If you manage a team, do this with them. Run the session. Get the insights. Commit to being a fully-aligned sales team full of A-players in 2026.
2. Use the Sales Playmaker to dial in your sales process
We work with thousands of small, scaling businesses and the number 1 problem we see: they don’t have a formal sales process.
Maybe you’re a founder who’s been winging it at sales. Or maybe you’re a seller who just operates with your gut instinct.
But if you really want to level up your sales motion in 2026, you need to operationalize your best tactics.
Take 2 minutes to use The Sales Playmaker, a strategy tool we built to help you turn what’s in your head into a clear, repeatable sales process. It asks you a few focused questions, identifies your sales motion, and then shows you:
- What your ideal sales process should look like, step-by-step
- How to structure your pipeline and stages
- How to set up your CRM to support how you sell
Do this in December so that in January, you’ll have a solidified process you can run, refine, and scale.
Clarity now saves you months of pain later.
Have a happy holiday season—and make 2026 your best year yet. 💪
