There are ads on TV featuring Santa at the beach; carols are piping through shopping centres (and actually have been since mid-October!); last week I already saw someone wearing a pair of those crazy reindeer antlers in the street; and it's finally starting to warm up a bit outside. 

It’s beginning to look a lot like Christmas … 

This Friday I’m even going to my first Christmas party for 2022. Seriously … In the middle of November! 

I’ve already started receiving emails that are signed off “All the best for the festive season”, “If we don’t speak before the end of the year, see you in 2023!”, “Happy Holidays”, and “Merry Christmas”! 

I’m sure I have surprised a few people in the last few weeks by sending an email straight back in response to their jovial holiday sign-off. 

“Let’s make sure we catch up before the end of the year. We’ve still got about six weeks to go. I’m working until Friday December 16th. When’s good for you?” 

And guess what? I’ve already been able to lock in a few meetings. 

I can assure you I’m no ‘Scrooge’, but I have always felt that from a salesperson’s perspective anyway, having a flat or ghostly quiet Christmas or summer can often become a self-fulfilling prophecy. It’s a mindset thing. 

It’s only “dead out there” (as I’ve already heard a lot of people tell me) if you allow it to be. 

The holidays are meant to be fun. Right? Technically yes. But for anyone running a sales team, summertime or Christmas time (however you choose to define it) can be pretty stressful if you’re staring at a revenue goal you may have set perhaps even 6 – 12 months earlier. 

Your prospective clients may already be taking time out; your sales team may be getting bombarded with ‘out of office’ replies to many of their automated emails; sales appointments may be down; and there may just be an imminent sense of gloom and frustration settling in amongst the team. 

Even at a quiet time of the year, it is definitely possible to keep your sales team motivated. 

As someone who has led sales teams through more holidays than I can actually remember, I’ve prevented many sales folks from falling into the proverbial ‘downward spiral’. But I can recall closing one of my own biggest ever deals on Christmas Eve one year. So, it can definitely pay off to be part of the ‘skeleton staff’ working in the lead-up to the holidays. 

What makes a tenacious, driven, and ambitious individual tick at this time of the year? 

There will usually be a gap between an individual salesperson’s motivations and the company’s motivations. As a sales leader it’s your job to balance the goals of the individual and the needs of the business. 

Motivate your individual team members 

You know that you have different personality types making up your sales team. It’s during a holiday season or quiet time that you have to focus on these individual personalities more than any other time during the year. 

Has your “money machine” suddenly lost all confidence in her ability to close a record number of deals consistently? How can you support her through this time? 

What about the “prima donna” whose ego is huge at the best of times? Is he suddenly in a complete panic and blaming everyone else around him for the fact nobody is returning his calls or replying to his emails? 

And then there’s ‘the hopeful’ who even on December 31st will desperately hold on to the belief that the deal of the year will miraculously appear before close of business. 

It’s up to you to motivate them individually and help them maintain at least some level of ‘holiday cheer’. 

My final piece of advice here is to have daily catch ups with everyone at this time of the year. 

Motivate the team as a whole 

Of course, you then have the responsibility to keep the team focused and up-beat as a group. 

During the ‘festive season’ it’s important to shift your focus away from specific KPIs around revenue and focus more on morale, attitude and energy. You might also want to shift the strategy away from new client wins to perhaps trying to re-connect with customers you may not have worked with for a while. 

Encourage your team to get out and about (now that they can!). Rather than staring at prospecting lists, spreadsheets, pipelines or dashboards all day literally counting the hours passing by, at least they’ll be out of the office building relationships face-to-face. 

If your team is back in the office every day, having your weekly team meeting offsite will also help prevent the team falling into a slump as will running group coaching and training sessions. If the team is operating remotely, having team members joining each other’s sales calls and de-briefing together might also help keep everyone energised. 

Create an element of healthy competition 

Salespeople are competitive by nature. Right? 

So why not create some additional healthy competition while it’s quiet? You can initiate competitions within individual teams (eg the SDRs, Account Executives etc), or within your entire team. 

However, it’s critical that everyone knows exactly what the goals are; when the competition kicks off and when it runs through to? What’s the reward? And who’s invited to play along? Remember, though, not to shift the goal posts once the competition is underway. 

You could run a competition for a day, a week or a month. Just make sure that if you have a prize up for grabs (whether it’s a gift voucher or something else tangible) that you can give or send it straight to the winner as soon as the deadline has passed. 

Winners hate waiting for their prize. (I’m sure you can relate!) 

Embrace the ‘coach / cheerleader’ double act 

Throughout the year you’re probably able to separate the times that you spend in your role as coach from that of the cheerleader. 

But at this time of the year, it’s as if you need to be wearing both hats all the time. 

You’re rolling up your sleeves and getting down and dirty with the team – leading by example; getting on the phone yourself; running spontaneous training sessions etc. But you’re also carefully watching over everyone – anticipating the denial and preventing the despair from setting in.  

You’re revving up the team and celebrating every win – no matter how small. You’re keeping the wolves from the door and preventing the ‘Negative Nellies’ from dragging down the rest of the team (please excuse all the clichés here!). 

Remember that sometimes it’s the small perks that matter 

As a sales leader, I used to personally let all my team take a half day off for Christmas shopping at this time of the year. Of course, it’s a bit different now with so many people working remotely (not to mention the fact that online shopping has taken over the need to hit the stores and battle the crowds), but just giving the team some extra time out can help them stay upbeat. 

I can also remember one particularly hot summer when every Friday during that December I had several tubs of ice cream delivered to the office since it was honestly too hot to go outside. Again, if your team is remote, a few scoops of Messina delivered by Uber Eats could do the trick! 

Ask your team what they’d like. It’s not always related to the dollars. 

A few hours out shopping or the chance to sit around as a team with a few scoops of ice cream can have a huge impact on someone’s motivation. A fun culture and a positive employee experience are key in any work environment. But energy and excitement can really help a sales team stay focused … especially around the holidays. 

Remember, Hellomonday can provide support to everyone in the organisation, reinforcing habits through curated learning and impactful coaching, and ideally helping sales leaders navigate the challenges of keeping their team members upbeat over the next few weeks.