Thinking Outside the Box This Holiday Season

Santa Claus may be coming to town, but as a sales professional, it is difficult to get into the holiday season until you meet your sales numbers. For the few who exceed their quota before Thanksgiving, everything is merry. For the rest of us, it’s time to make a list and check it twice and qualify the prospects that are naughty or nice. In this article, we will outline a few tactics you can deploy to ensure you end the year with a bonus in your stocking and not a lump of coal.

The only thing more exciting than a Christmas tree piled with presents is closing the final deals of the year to earn your bonus. The best company holiday parties are when the sales team hits their numbers. The parties are always a little more festive than those off years when the numbers are missed. It seems it always comes down to a handful of deals that make the difference. If you are in that situation now and reading this article, maybe this is the Christmas story you are looking for.

The first thing to remember is to not be a Scrooge during the holiday season. Mindset during the holidays can make or break a sales professional, because it is the only thing you have 100% control over this time of year. I’ve worked with teams who say, “It’s always slow this time of year.” Or they believe, “You can’t get ahold of anyone. Everyone is on vacation.” If this is how you are talking to yourself, you can bet you won’t find the energy to accomplish your goals.

I get it, it’s harder to connect and it’s tempting to slow down. But you can choose to look at the glass half full. Your competitors are likely slowing down too. They are taking time off, they have the “You can’t get ahold of anyone attitude.” Don’t follow the herd. Take the path less traveled and double down on your outbound efforts. Keep leaving creative messages like, “I hope I’m not the only one still working this holiday season.” Sure, some prospects might say, “Get back with me at the first of the year,” but others who are still putting in the work (like you), will see you as hard-working and appreciate your hustle.

One of the biggest benefits of prospecting during the holiday season is fewer gatekeepers. In our experience, many decision-makers work through the holidays. This can give you easier access with fewer distractions. Another benefit is while these decision-makers are in the office during the holidays, they often have more free time to talk with you. They’re not holding staff meetings, putting out the daily fires, or dealing with the daily company interruptions. Plus, their phone likely isn’t ringing off the hook so you have an opportunity to connect and have a quality call. 

Now with the right positive mental attitude, you are ready to create your holiday prospect plan. This requires you to think about your old prospects and what they are dealing with right now. Look for prospects in your CRM that went dark and are now missing in action. If you changed the lead to “not interested” or “lost deal” these are prime prospects to reconnect with during the holidays. These prospects still have awareness of your offerings, and are still dealing with daily challenges to get better. 

To reconnect with MIA prospects during the holidays requires a different approach. Everyone is sending out emails with the subject line Happy Holidays. You need to be different. For example, say you review your MIA prospects and sort out the top 50 prospects you’d like to do business with. Purchase holiday cards and take the time to write a personal note. Hopefully, you added good notes in the CRM so that you can personalize the card. Don’t be pushy or salesy. Let your prospect know you are thinking of them. It’s a good way to stay top of mind and stand out from the competition.  

Don’t expect to get a call or email from everyone you send a card to. But better be prepared to receive a few calls and emails. Nothing worse than having the prospect call you to thank you for the card, and you don’t remember sending it to them. That’s awkward and self-defeating. When you do talk to the prospect let them know you are looking forward to earning your way onto their holiday card list next year. 

I know what you are thinking, “Sending handwritten personal Christmas cards to prospects? That’s corny.” But people still buy from people and as more and more companies go to “digital automation,” the personal touch stands out. The holiday season is about gratitude and taking the time to write your prospects a note, shows you are different than 99% of the sales reps out there.  I challenge you if you’ve never tried it, to try it this year. The worst case is you’re out $100. In the best case, you win a few new high-value clients for life.

Now we aren’t going to just send out a few cards and think Santa Clause is going to drop our dream client down our chimney. That’s for amateurs. We are going full-on Clark Griswold this holiday season. Plan to use a variety of outreach channels, like video and LinkedIn. Understand, everyone else is reaching out to your prospects with emails and phone calls. If you want different results this year, you have to think outside the box. In your message, bring up something that is timely and interesting. Don’t be that sales rep who’s “just checking in.” 

December is a time when decision-makers take the time to review and assess how they are currently running their company or department. They’re already thinking about making changes, cutting costs, or fine-tuning their operation. 

Let’s have a jolly holiday season this year and avoid the ho-humbug. The key to success while prospecting in December is to keep a positive mental attitude, use your time wisely prospecting with high-value opportunities, and be different in your outreach. Contacting prospects during the holidays at just the right time could lead to something great, a new deal, or at the very least create a new relationship to give your pipeline a jumpstart come January.

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