5 Keys to Outselling the Holidays (Money Monday)

We are moving into the most dangerous time of year for sales professionals . . . the holidays. 

From now until the first week of January, you’re going to face a perfect storm of distractions, excuses, and temptations that can absolutely destroy your year end number and your first quarter production next year. Sadly, most salespeople don’t even see it coming. It’s not until the end of December that they realize they’re in trouble, but by then, it’s too late. 

The Trouble With the Holidays

The trouble typically starts Thanksgiving week in the United States and continues as we move into the first week of December. That’s when distractions start flooding in. You’ve got company parties, family obligations, shopping to do. All of which knock you off of your routine causing your daily prospecting and follow up activities to drop.

And let’s be honest, you’ve been grinding hard for the entire year and you’re ready to let your guard down and coast a bit before the end of the year. 

By the second and third week of December many of the opportunities in your pipeline that you were counting on closing start to ghost you or tell you that their pushing decisions off to next year. And by now you’re so mentally checked out that you’re barely doing any prospecting at all. 

Once we move into the Christmas and New Years weeks your office is a ghost town, the phones are silent, your pipeline is stalled, you’ve missed your forecast and you convince yourself there’s no point in even trying. 

And just like that, you’ve lost an entire month of selling.

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Holiday Sales Math

But here’s the brutal truth: You didn’t just lose a month. You lost three months. Because all of those prospects that pushed off decisions until the new year are not coming back; and that empty pipeline you’re staring at, as you move into January, is going to haunt you through March and potentially, through the entire year. 

Your average sales cycle is probably 60-90 days. That means deals you put into the pipeline over the next two to three weeks are crucial for a good January. Likewise, the ones you add in December are the key to delivering a solid February and March. 

But if you allow the Holidays to take you off of your game, you might not recover until April or May. Your entire first quarter is shot. 

This is the killer and how so many promising sales careers end prematurely. I’ve witnessed far too many salespeople get fired in March for pipeline problems that started in November when they let their discipline slip during the holidays.

Do Not Allow Active Deals Stall and Die

The deals currently in your pipeline are more vulnerable right now than at any other time of year. Your prospects have the perfect excuse to push decisions. 

When deals sit idle for a month, bad things happen. Stakeholders change. Budgets get reallocated. Priorities shift. Your champion gets distracted by seventeen other initiatives. Your competitors slip in while you’re eating fruitcake and drinking eggnog.

I’ve watched salespeople lose six-figure deals that they thought were “locked up” in November, simply because they took their foot off the gas during the holidays. 

I’ve said this before and I’ll say it again. Pipeline opportunities that push into the new year are not coming back. Do not count on them. Do not allow yourself to be delusional about them. If you don’t get forecasted opportunities closed by the end of the year, consider them dead!

For this reason, you must be vigilant with follow up, assertive with your communication and do whatever it takes to get those deals closed. 

The Holiday Discipline Advantage

When it comes to prospecting, the activity that keeps your pipeline healthy, the real reason you struggle during the holidays is because you give yourself permission to slack off. You tell yourself little lies to justify taking it easy. “Nobody’s making decisions right now anyway.” “Everyone’s on vacation.” “I’ll ramp back up in January.”

Yes, some prospects are on vacation. But not all of them. Yes, some decisions get pushed. But not all of them. Yes, it’s harder to get people on the phone. But not impossible.

The salespeople who crush it during the holidays understand something that everyone else forgets: Outselling the holidays is all about disciplined. It is discipline that transforms holiday impulsiveness into intention and a higher income. 

This is where mental toughness pays off and shows up in your bank account.During the holidays, more than ever, you need a concrete plan and the discipline to execute it.

5 Keys to Outselling the Holidays

Here’s what you need to do right now, and I mean this week:

Step One: Conduct a Pipeline Audit

Go through every deal in your pipeline. Assess the risk of each one stalling during the holidays. Then decide what needs to be done before year end to get them closed. 

For your most important opportunities, create a specific action plan. Don’t assume anything will “just keep moving forward” on its own. These deals will not close themselves. Nothing moves forward without your effort.

Step Two: Block Your Calendar

Pull up your calendar for the rest of this year. Block time for daily prospecting, deal advancement and follow-ups.

Yes, I know you have holiday parties and family obligations. Put those in too. The key is planning everything in advance so you don’t drop the ball.

You may have to get creative. Maybe you prospect for an hour before the rest of your family wakes up or make follow-up calls during your lunch break. Maybe you work a few hours on the weekend.

The point is, if it’s not on your calendar, it won’t happen. And if your calendar is blank for the next month, your pipeline will be blank in January.

Step Three: Set Non-Negotiable Activity Targets

This is critical. Decide right now what your daily minimums are going to be during the holiday season. Set the targets. Write them down. Commit to them. Then—and this is the important part—review your progress against these targets every single morning and every single afternoon to hold yourself accountable. Nobody else is going to do this for you. You have to be your own accountability partner.

Step Four: Front-Load December

We know that the last two weeks of the year are going to be a circus so double down and bank as much activity as possible at the end of November and into the early part of December. That way, by the time Santa comes down the chimney, you’ve already done the work to keep your pipeline healthy.

Step Five: Plan Your January

Don’t wait until January 2nd to start thinking about your first quarter. Plan it now. What’s your goal for Q1 revenue? How much pipeline do you need to hit that goal? What actions do you need to take now to start strong in January? Top performers don’t “get back into it” in January. They hit January running because they planned for it in November.

This isn’t about working 80-hour weeks. It’s about being strategic with your time so you can be productive AND enjoy time with your family. By maintaining discipline during the holidays, you actually feel less stressed and enjoy them more. 

Take Action Now

Now here’s your assignment: Block two hours on your calendar this week. Use that time to conduct your pipeline audit, build your holiday schedule, and set your activity targets.

Don’t wait. Don’t tell yourself you’ll get to it next week. Do it now.

The salespeople who take this seriously will end the year strong and start off next year even stronger. The salespeople who ignore this advice will spend the first quarter digging themselves out of a hole.

The only question that remains is which one of these salespeople are you going to be?

And remember, when it’s time to go home, especially during the holidays when you’re tempted to call it early, always stop and make one more call. That discipline is often the difference that will help you outsell the holidays.