How to Use the Holidays to Win Deals

Collette Parker

So much of sales comes down to relationships. But even great relationships can grow a little cold over time. This is even more true with new relationships, which tend to need lots of attention.

So, at the risk of sounding insincere, how can we leverage this magical holiday time to win some deals? Or, at the very least, pump some life into those waning relationships?

The truth is, some points of interaction between seller and prospects are natural – those first few calls and meetings. In the early relationship stages, meetings come easy as both sides are learning about one another. But as time moves along, deals can get stuck. The prospect returns your calls and emails a little more slowly, and maybe then, not at all.

At this point, the play is to engineer a point of interaction. The holidays provide many opportunities for an engineered interaction.

There’s no shame in it; it’s good selling. Many sales people – and even sales leaders – believe the client is in control of the relationship or deal process. We don’t want to bug the buyer, so we let weeks go by while waiting for a response. Today’s noisy and over-scheduled world only compounds matters. Yet, our research shows many senior buyers actually appreciate follow-ups by sellers. Certain buyers want someone to help drive the process forward. The best reps don’t focus on selling, but instead guide the buyer through the decision journey. This guiding in complex sales can't be passive. 

Unless you’re cold calling or have been explicitly told not to call, consider leveraging the holiday period to warm up a relationship. There a number of ways to intentionally engage with buyers to get things moving again.

Below are three ways to engineer a reconnection that can help reignite a stalled deal or relationship:

1. Keep clients in the loop. Holidays are conveniently scheduled at the end of the year. And this a great time to reach out for a call about what’s happened in the last year and what’s on the horizon for next. Not just from your perspective – where it’s pertinent or helpful to share (who wants to agree to a call that ends up being a lecture or a verbal Family Christmas Letter?). Keep your situational awareness high, adapt to what the client is saying, and focus the conversation on the challenges they’re facing now or could face in 2019. 

2. Offer resources. While people often tune out during the holidays, somewhere in their mind they know the cold, hard truth of January is coming. That means some level of planning needs to start now. What content or strategic insight do you have to help your prospect or client plan for their next year? Is there a way to help share the burden of planning or at least help them focus on the top priorities? The holidays also signal the end of budgeting cycle. You might be surprised how many reps we know have secured deals from an unscheduled call at the end of the year. In more than a few cases, the client happened to have "left over" budget from the current year - money that would be "lost", if not put to use.

3. Thank your clients. Now is the perfect time to show appreciation to your current clients for their business. Giving thanks should extends to your prospects as well. Thank them for their time and effort in the interactions you did have. Expressing gratitude has a little magic of its own – you’re acknowledging that a particular person is busy and you sincerely value the time they’ve given to you (even if you’re writhing in frustration). Send a card or gift if appropriate, invite someone out to breakfast or lunch, or just send an email or give a call.

One key point to sales leaders. Thanksgiving has evolved into a week-long holiday for many. And we certainly encourage everyone to take the time to recharge with family and friends. But this time also represents an important window for hitting your number in ’18 , not to mention starting ’19 strong. Find the right balance with your teams: Don’t forget to thank them for their hard work, but also make sure they’re executing intentional reach-outs to customers and prospects in the coming days.

Happy Thanksgiving from The Brevet Group! We’re especially thankful for you, one of our more than 30,000 readers.

Collette Parker

Collette Parker

Experienced consultant with a focus on sales training and content development. Collette uses her background in journalism to uncover underlying business drivers and shape tailored solutions for clients. She has authored numerous sales research studies, articles and books.