How to Help Your Team Hit Quota During the Holiday Season

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Sunny Sandhu
Sunny Sandhu


Many sales teams struggle to hit quota during the holiday season — and this issue comes from a lot of different angles, including:

Team hitting quote during the holidays
  • 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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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.;

Generating the end-of-year motivation reps need can be tough. That said, I personally;love;the holidays. They were always some of my highest-generating months as a sales rep, and I almost always see my teams outshine others during this time of year.;

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. 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

1. 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.;

It goes like this: 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, we do a raffle and send two winners home with additional prizes. These gifts are fun and low-cost, ranging from Mini Zen desk gardens (my personal favorite) to Bluetooth speakers and phone holders.;

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?

2. Encourage reps to send holiday gifts to prospects.

Reciprocity is a staple of productive, mutually beneficial sales relationships. 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 working on for months.

Develop a strategy with your team regarding companies they should include in the gift-giving. 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.;

The more personalized and thoughtful the gift, the better. For example, if your rep notices a prospect always has a half-full cup of coffee on their desk, 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? Have reps reach out to prospects and let them decide for themselves.

Before your team hits the ground running, it's essential to identify gifts and an appropriate budget;before;the holidays to ensure you have everything you need to succeed in this strategy.

3. 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 discuss how your reps communicate the offer and when in the sale process to give the news to your prospect.

This strategy can be a little finicky. Tell a prospect too soon, and the discussion becomes about price instead of 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 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, it doesn't work if prospects think these offers are indefinite — so make sure your reps communicate that the deals won't last forever!

4. Break down goals into achievable targets.

Relentlessly focusing on hitting targets and closing targets can wear down any sales rep. Sales leaders can take the pressure off by breaking down goals into smaller targets.

For example, a smaller target could include calling a certain number of prospects each day, or moving a deal down the pipeline.;

Whatever the target, make sure it's reasonable and achievable. This is a great way to boost your team's confidence while keeping them motivated in the process.;

5. Recognize your reps for their great work.

Recognition is a powerful motivator, yet many sales leaders only acknowledge bigger wins. This can lead to trouble, especially when your team is grinding to meet quotas, but their effort isn't recognized.

As a sales leader, calling out every single win is essential. Make your reps feel like every achievement is significant because that mindset pays off long-term.
For instance, take notice when someone hits a smaller goal, contributes a great idea, or nails a task.

Acknowledging these smaller moments affects how reps feel when they come to work and keeps them motivated in the long run.

6. Implement holiday talk track revisions.

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

For instance, sales teams should 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 arise 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.

Back to 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. Instead, 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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