What do you call a deal stipulation that must be agreed upon contractually prior to the new year?

A Santa clause!

Thank you folks, we’ll be here all night!

For all you other readers who haven’t left after seeing that cringe-worthy joke, you know that selling during the holiday season is no laughing matter. Whether your prospects are celebrating Christmas, Hanukkah, Kwanzaa or just taking time off for their annual vacation, it can be tough to reach people on the phone, or get decision makers to stop dragging their feet.

But all is not lost! There are steps that sales reps and account executives alike can take to work on closing deals, or simply remain productive with sales activities in other areas. Here are 10 tips for working and selling through the holiday season:

Don’t make assumptions

The first step to take is to not make assumptions about what your prospects are doing. The common industry assumption is that buyers are busy or out of the office, and won’t deal with buying decisions at this time…but who’s to say that your specific prospects won’t buck the trend? It’s entirely possible the prospects you’re working with are actually more ready to buy – the end of the year can spark urgency in buyers, as they line up the tools they need for next year, or have to spend their remaining 2014 budget.

The concept of spending budget can actually be a huge leverage boost for you. Many companies and departments have budgets that don’t carry over year-over-year, behooving them to spend any surplus, lest it goes to waste. If your prospect admits such an end-of-year scenario to you (admittedly unlikely), that can really strengthen your negotiation position.

Lean on the bottom line

Another good trigger to use around the holidays and end of the year is if a prospect has been struggling to meet his or her goals, either around sales numbers, marketing leads generated or some other metric. Appealing to that struggle – a very real pain that is being felt immediately – can help hold your product up in a stronger light, especially if your product is positioned as the solution. For instance, a Sales Manager who struggled with pipeline visibility all through Q4 will find our sales pipeline management software even more relevant when reached out to at this time.

Learn More About Sales Pipeline Management»

Connect with past customers just to check in 

Struggling to sell to new customers? Don’t worry, you can just focus more of your efforts on your existing customers, which is especially important if you’re selling a Software-as-a-Service product. Even if this is Account Management’s primary role, it wouldn’t hurt for you to check up on how some of your customers are doing; they will appreciate you going that extra mile. Showing that you care about your customers’ engagement with your product can help you reduce your churn rate. Now is the perfect time to check in and just let them know you’re thinking of them.

Set up meetings for after the holidays

Of course, you still want to generate new business, which means getting prospects on the phone for meetings and demos. Can’t carve out enough time in their calendars during the holiday season? No big deal; just make sure you get the meaningful time you need with them immediately after the holidays. Figure out exactly when they will be back in the office – factoring in the week or so they will need to dig themselves out from emails – and schedule your meeting then, to ensure that you remain a top-of-mind priority immediately upon their return.

Gather triggers for ice-breakers

A great way to break the ice on that post-holiday meeting call is to talk about the holiday that your prospect just went on. This means knowing what they did on that vacation, so be sure to ask – and remember! – before they leave for the holidays. Asking them about that trip to St. Thomas, or their kids’ first holiday with the grandparents, or some other similar personal trigger can be an effective way to break the ice.

Marketing emails

This is a lot more relevant to your counterparts in marketing, but the point remains that this relatively quiet time should not be construed as opportunity for unproductivity. Some marketing departments might hold off on email volume during the holiday season, assuming that nobody reads emails during this time, but let’s be real; with cell phones and international roaming, nobody ever takes a real off-the-grid vacation these days. This might be a good time to take advantage of the vacuum and silence left by other marketing departments who aren’t sending emails, making your emails stand out and giving them a higher chance of being read.

Prospect creatively

A great deal of prospecting takes place on the phones, which isn’t great if everyone’s on vacation and nobody’s picking up. Time to get creative! Take a day to scour the newswire or sites like TechCrunch and VentureBeat to find companies who have raised funds or hired in droves recently – those companies might be in need of your products. Search around LinkedIn groups or Quora forums to see who’s talking about a pain that you solve. Just because the phones are down doesn’t mean prospecting has to grind to a halt.


Some other ways to remain productive don’t necessarily have to do with active selling or prospecting either. Check out these three tips to stay productive even when not selling.

Read a book

The “offseason” is when professional athletes add elements to their game, to come back next season an even better player. Sales reps should adopt that same mindset during the relative offseason of the holidays. Just as an axe needs a whetstone to keep sharp, so does a mind need books. Interested in improving your sales management? We got you covered! Want to broaden your mind in helpful ways, but tired of reading about sales? We can help you out there too!


Sales reps who are agile and operate with an experimental mindset are more successful. Now would be the perfect time to experiment with that new talk track, or that new sales process that you’ve been meaning to implement. This is a low-risk, low-pressure time that is the perfect environment to experiment a little bit and get creative.

Humble yourself

As a successful sales rep, you can be resistant to sales coaching and improving, especially when you’re so busy trying to close deals. If it’s a quiet time for deal-closing, maybe now’s the right time to humble yourself and take your sales manager up on those extra sales coaching sessions he’s been offering. Those might actually make a huge difference in your sales performance in 2015, so put in the offseason work now and see the results pay off on the field.

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