Holiday Selling Tips to Survive the Seasonal Sales Slump

This season can be very jolly, but for B2B sales professionals, December isn't known for its festive sales funnel. The holiday months can wreak havoc on your commission and your confidence. In this post, we share some holiday selling tips to help you make it through to the new year, merry and bright.

a blueprint showing how selling tips can get your business out of a sales slump

10 min. read

It is (or, can be) the most wonderful time of year – the first snowfall, fantastic food, spending time with friends and family, and the constant holiday hustle and bustle in all our favourite shops.

It’s also the time of year a desperate parent (not naming any names) will happily pay a 400% markup on what's essentially a glorified Kinder Surprise, without the chocolate. 

But when you’re in sales, December can feel very different. As a sales professional, you may experience a whole new level of stress as you struggle to get hold of clients to close the deals you need to make your Christmas bonus so you can buy said overpriced 'surprise' for your child and more of life’s necessities.

Welcome to the official seasonal sales slump!

Any of these December challenges ring a holiday bell for you?

  1. Client budget and decisions are on hold until January.
  2. Everyone is out of the office most of the month.
  3. Clients would prefer to drink rum and eggnog than hear your incredible sales pitch (go figure).
  4. You’re struggling to keep sales momentum and would also prefer to be drinking rum and eggnog. But rum and eggnog aren't going to get you to your Christmas bonus.

Having worked in B2B sales for over 11 years – eight in a fortune 500 company and three in a medium-sized company before I joined the wonderful world of Proposify – I have a few December sales slumps under my belt, and I used to DREAD this season.

After a few years of succumbing to December sales hell, I couldn’t do it anymore. My bank account and sanity relied on maintaining momentum through to the end of the year.

Fortunately, after more than a few trials and tribulations, I made peace with December and now know how to make it a great month. Or at least one I can live with.

I rarely see my old friend desperation in December anymore, so in the spirit of giving I’m going to share my 'Seasonal Sales Slump Survival Plan' and holiday selling tips with you.

Control your controllables

The first key to Seasonal Sales Slump Survival is an important one that you can also apply in many situations: control your controllables. Salespeople like to be in control of every aspect of the sales cycle, but at this time of year, there are many outside variables that we just can’t control.

So what can you do?

It may sound glib, but all you can do is control what you can control and be proactive as early as possible.

So let’s revisit that list of things we think we can’t control and see what we can do:

Client budget on hold until January/Everyone is out of the office most of the month.

This took me awhile to figure out, but the big change I made was to set up as many meetings as I could in November or early January so I could prep for the new year, or at least get some face time before everyone goes merry M.I.A.

Typically, there’s a sense of urgency in November because everyone knows the holidays are fast approaching, so use this to your advantage. You may be able to close a few quick deals and avoid the purgatory of out-of-office replies.

Everyone would rather be drinking rum and eggnog (including you)

Overcoming this particular December obstacle was the hardest and most painful one for me to figure out. The worst side effect of being in a sales slump is it can start to negatively affect your motivation and sense of urgency.

It’s not an easy feeling to shake. Salespeople thrive on life being fast-paced, so when we lose that drive, we feel like crawling under our desks until Groundhog Day.

The lesson here is, don't take December personally. There are lots of things at play during this season that have nothing to do with how great your sales technique is or how awesome your product is.

Sulking and being lazy isn’t going to help your bank account now or in the year ahead.

Time to brainstorm

When I finally reached my sales slump-breaking point, I decided to do an old-fashioned brainstorm on an actual piece of paper (also old fashioned, I know) and wrote out whatever came to mind.

I wish I still had that paper as it was pivotal to creating the sales process I follow to this day. It even had some pretty kick-ass dinosaur drawings on it for creative inspiration.

I started with a list of questions:

1. What makes me want to buy from someone?

Easy! I am sold by any sales person who asks the right questions and remembers who I am even when they’re not trying to sell me.

2. What drives me crazy about salespeople?

PUSHY salespeople, anyone who feature-sells to the max (don’t sell the steak, sell the sizzle!), anyone who doesn't follow through, and, of course, greasy salespeople. I am the first person to not sell something unless it’s the right fit for my client.

3. What can I do NOW that I can control?

This was tricky; all I came up with was to try to think of creative ideas to build my sales pipeline – but how?

4. How can I make sure I am memorable?

I like to think I'm memorable, but I took a step back and thought about what made my partners, both external and internal, stand out.

As I read over my list of questions, I started to notice a recurring theme.

It’s not enough to survive. You want to THRIVE.

Download our free ebook “The Full Scale Agency” and start taking action.

Relationships, duh.

I buy from, and remember, salespeople I trust and have a good relationship with. This made even more sense for December since the holiday season is all about relationships - family, friends, colleagues, and clients.

It was my ‘a-ha!’ moment. This was what my focus was going to be from now on: building better relationships. Not just for the sake of a sale, but to make long-term and genuine connections.

Maybe you were expecting something more earth-shattering?

It’s probably not the first time you’ve heard about relationships being at the heart of sales. But it’s surprising how no matter how prevalent the concept is, people still don’t get it. Or they don’t get how to authentically build relationships. And they don’t do it.

All the right people

Before I figured out how I was going to connect with people, I needed to think about who I wanted to connect with.

I thought about who was important to me. Who did I truly want to say “thank you” to?

Current clients - Who did I work with over the past year?

Top potential clients - Who do I want to work with in the coming year?

Internal partners and coworkers – You may be surprised that I included coworkers to help my December slump, but I’m a big believer that it’s extremely important to thank the people you sit with every day.

My favourite part of working at Proposify is the endless support everyone gives – even if it is the same question 100 times, or a moment of panic when you break your work email (was totally my fault), everyone will drop what they're doing to help each other out.

Beyond the animated elf email

So, the question now was, how could I try to make a genuine connection with the groups on my list without looking like a typical salesperson sending out the typical generic and impersonal holiday email?

Current Clients

I decided to go back to basics with this group.

While the big company I worked for sent out ecards to all our clients, I wanted to be more personal.

I bought some appropriately themed holiday cards and a big roll of stamps. People glaze over emails but notice a nice hand addressed card.

Whether your cards say, Merry ChristmasHappy HanukkahHappy Kwanzaa, or Season’s Greetings is up to you. I like to be as inclusive as possible while still communicating the happy collective spirit of the season.

Then, I wrote each of my clients a note and tried to make it as personal as possible to demonstrate that I was specifically writing to, and thinking of, them. A good salesperson remembers the details, so include your client's pet’s name in the card, for example.

Depending on your budget and the size of your client list, it’s not always realistic to send a fancy gift basket, but you may want to send a few key clients a small token of appreciation. I have sent movie passes, coffee cards, and some random things like dog treats before. Again, I try to match the gift with what I know about the client.

Top potential clients

Trying too hard and looking tacky is the sales kiss of death. With this group, I didn’t necessarily have the same kind of relationship yet as I did with my existing clients. So I kept my interaction simple with a handwritten card saying I was looking forward to working with them in the coming year, without being pushy or presumptive. It’s a good way to keep yourself top of mind even if you haven’t quite closed the deal.

Internal partners and co-workers

Remember this whole exercise is all about genuinely saying thank you. Bring in homemade or store-bought treats for everyone and take the time to write a nice card to truly show your appreciation (I am ruining my Christmas surprises with my Proposify coworkers now). If you have the means, take a few people who really saved your ass this year out for lunch.

Don’t underestimate the role your team members play in your success. Their support and resources have no doubt made your job easier or helped you close a deal. We salespeople can be highly competitive by nature, but it’s important to remember that no one is an island - we’re all in this together.

Rules of the road

I established a few rules when I hatched my holiday plan. But, as the saying goes, rules are made to be broken. You know your own business best, so do what feels right for each client and your business.

  1. Avoid emails as much as possible. ‘Tis the season for snail mail.
  2. Do not include business cards but still, make sure they know who you are.
  3. No trinkets and trash! A company I worked with decided to buy little bags of jellybeans to send to clients, and it was a disaster. Do NOT mail people jelly beans, trust me on this one.
  4. NO GLITTER – This may sound silly but lots of holiday cards come with glitter. You and your clients will annoyingly have glitter everywhere for months. That’s not how you want to be memorable.
  5. Most importantly, BE GENUINE. You need to be genuine with any interaction and personalize your messages. If you can’t, you’re better off sending a boring generic email.

The result

That first year I decided to send personal cards, the big corporation I was working for sent out generic ecards to all our clients and partners, as they did every year.

That year though, the people I sent real cards to CALLED ME ON THE PHONE to say thank you, or they at least sent me an email. I didn’t get responses about the generic corporate ecard. I only received reactions from the personal holiday card.

And what was really remarkable was that some of those people had been difficult to get on the phone in the first place and now here we were, chatting. All thanks to a card with an adorable snowman on it. That opened the door for us to connect in January and it helped revive my sales mojo!

You probably thought that I had some secret weapon to keep my Seasonal Sales Slump at bay, but it is really that simple – it’s all about showing real gratitude. And that shouldn't be season specific. You should be building connections all year round.

When you’re genuine with and truly grateful for your clients, or anyone you cross paths with, you'll be remembered. And the effect is more impactful than a few quick sales in December.

Full disclosure: Sometimes I still have lower sales in December, but my gratitude approach helps me manage my anxiety about it, knowing I am ready to hit the ground running for a lucrative January, and that I’m sowing long-term seeds for fruitful relationships.

Holiday Selling Tips to Survive the Seasonal Sales Slump

    Proposify's mascot, P, in a blue suit. Coffee is for closers

    It’s about more than just proposals—it’s about world domination.

    Get a demo and start your team's total takeover.