I'll preface these tips by mentioning that many sales teams struggle to hit quota during the holiday season — and those issues come from a lot of different angles, including:

  • It's a shorter quarter with weeks-long holidays for prospects.
  • Prospects take additional PTO during the holidays, in addition to company-wide holidays.
  • Company-wide freezes — like code, website, purchasing, and budgeting freezes — tend to occur during the holidays.
  • The last thing a company wants to do is break their systems during the biggest sale of the year.

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All told, I generally find that the anxiety that stems from those factors can cause reps to push their contacts too hard — causing an endless cycle of increased pressure and no way to alleviate it. But while generating the kind of end-of-year motivation reps need to tackle those problems can be tough, I personally love the holidays.

They were always up there with my highest generating months as a sales rep, and I almost always see my teams consistently outshine others when that time of year comes around. So what's the secret? Well, it's pretty straightforward — instead of pushing, pull.

Break the cycle of pressure to hit quota by playing into the holiday season and spreading the cheer! The holiday season is prime time to hit quota and set your team up to smash their numbers for months to come — but only if you play your cards right.

Here are some key tips and tricks you can leverage to make sure you and your reps thrive this holiday season.

How to Help Your Team Hit Quotas During the Holiday Season

Stage holiday competitions.

Every December, I ran a holiday competition for my team — a strategy passed on to me from my manager when I was a sales rep. If a rep sets a meeting, they get a raffle ticket. If they set two in one day, they get two tickets and can pick a gift-wrapped present from under a tree you put up in the office.

At the end of the week, do a raffle and send two winners home with additional prizes. These gifts should be fun and low-cost, and they'll have everyone driving towards finding that next lead — as opposed to throwing in the towel due to the holidays.

Gifts ranged from Mini Zen desk gardens (my personal favorite) to Bluetooth speakers to phone holders. There are tons of knick-knacks you can find on Amazon, and over my time in management, I've saved a list of favorites for every year.

Since many of us are working with remote teams this season, this competition can still be leveraged using virtual raffles, randomizing and numbering each gift, and delivering them to your team members' homes.

This is guaranteed to get your reps fired up to hit quota while putting your team in the right frame of mind to spread positivity during the holidays. Who doesn't want to take a prize home with them?

Encourage reps to send holiday gifts to prospects.

Reciprocity is a staple of productive, mutually beneficial sales efforts. To that end, gifts are a fantastic way of moving a deal along — or getting your foot in the door with a contact you've been trying to break into for months.

Develop a strategy with your team regarding companies they want to send gifts to. Make a list of hard to break into accounts, leads that have gone radio-silent, and other prospects who could use a gift to keep a deal moving forward. Identify gifts and an appropriate budget before the holidays hit to ensure you have everything you need to make this strategy a success.

The more personalized and thoughtful, the better the chances for the outcome your reps want — whether that be a generated lead, a closed deal, or any other productive endgame they might be eyeing.

For example, if your rep noticed your prospect has a half-full coffee mug on their desk all day long, consider sending a coffee mug that keeps drinks hot throughout the day.

Gift baskets, headphones, handwritten notes — the possibilities are endless. Don't know what to send? If your team selects a few gift options, try having reps reach out to prospects and let them decide for themselves.

Put deals, discounts, and limited-time offers (LTOs) in effect.

The concepts of scarcity and FOMO can be applied to the extreme during the holidays — especially if your company is offering LTOs to prospects who sign up during this time.

Before the holidays, host a training session to orient your team on selling LTOs effectively. You'll want to index on the structure of how your reps communicate the offer and exactly when in the sale process to give the news to your prospect.

This strategy can be a little finicky. Tell them too soon, and the discussion then becomes about price as opposed to the value of your offer. Tell them too late, and you may lose out on the momentum you've built with your prospect. No matter what, make sure your prospect is bought-in on the value of your solution before communicating changes in pricing or deal structure.

When done effectively, prospects will be both excited about leveraging your solution (which creates long-term retention) and ready to take advantage of the holiday LTO. But while this strategy is effective within an appropriate window, it doesn't work if prospects think these offers are indefinite — so make sure your reps communicate that the deals won't last forever!

Implement holiday talk track revisions.

No matter which of the previous tips your team implements, everyone has to remain focused on value — every sales rep needs to prioritize communicating the value of your offering and why it's important to buy now.

While this is the case month over month, sales teams can revise their talk tracks to include more holiday-oriented language — putting prospects in a good mood while effectively tailoring the value of your company's solution to the time of the year.

Ensure your sales team is ready for the typical objections that come up during the holidays — such as pricing, budgeting, or pushing conversations into the New Year. Your team needs to understand both why prospects are looking for a solution and how delaying conversations will hinder a potential customer's ability to solve problems with your offering.

When such objections come up, your team can leverage what they understand about a prospect's needs to drive urgency and move the deal forward.

They have to stay on top of questions like:

  • What are the prospect's goals for next year?
  • How would getting started now set them up to accomplish those goals?
  • Why is it important they get started now to ensure success for those goals?
  • What risks did the prospect uncover that they are working on now?
  • How would your offering mitigate that risk?
  • What do they stand to lose if they don't get started now?

It's all about creating urgency and communicating why now is the perfect time for them to start with you.

The holidays often get a bad rap among sales reps — but that shouldn't be the case. This time of year provides excellent opportunities for your team to create urgency and capitalize on the spirit of the season.

It's also a time for reps to thrive and set themselves up for future success — even if prospects can't meet right away due to time or company constraints, they become hot follow-ups your team can tap into right at the beginning of the new year.

One way or another, you, as a manager, can always find effective ways to motivate your reps and help them crush it come holiday season. Though the list of tips and tricks I've mentioned here isn't exhaustive, it'll prove incredibly useful when this time of year comes around.

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Originally published Nov 8, 2021 8:00:00 AM, updated November 08 2021