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5 Sales Do’s and Don’ts During the Holidays

Some might be a little counterintuitive, some common sense, some you just may not have thought of..

Here are 5 do’s and don’t for the holiday season that I have either noticed work well for others, or have worked well for me in the past.

Some of them might be a little counterintuitive, some may be common sense to you and some you just may not have thought of yet in your professional sales career.


Most importantly do have a plan to make sure your clients feel special and valued over the holidays. This can be as simple as just sending a holiday card. What i like to do is a simple handwritten thanksgiving and christmas card sent to arrive at the clients office two business days before the holiday day. It can be a bigger investment such as some kind of christmas gift. I had a vendor of mine who i had a great relationship with come around to my office with small container’s of raw honey that he had harvested from his honey bee farm in his back yard, i was really grateful for that. It all depends on what your relationship is with your clients but at least show the effort of some sort of sentiment, even if it is just an email.


Get too personal with holiday names. In this day and age of political correctness, it is important not to get too specific on what holiday somebody might be celebrating. I did mention a ‘thanksgiving’ and ‘christmas’ card above, however, this depends on your relationship with the client. If you do not have a very strong relationship yet or are in a business that is more of a quick sales cycle, go with the ‘happy holidays’ saying. The idea here is for the client to keep you on their mind through the holidays, not to be offended by religious idea’s.


Plan ahead in your sales cycles in September, October and the beginning of November to account for a slower sales activity in late November and especially throughout December and the beginning of January (Flu Season), for most verticals. This accounts for forecasting your sales teams activity as well as your personal forecasting for your sales manager. Account for this in client conversations, “Let’s get this contract executed now as we don’t know what kind of hold ups we might run into in the holiday season, and we want to make sure we are hitting your deadline”.


Be too pushy with your sales around the holiday season. Don’t send to many emails or calls if you are not getting a response. Most likely the prospect or client is taking some time or very distracted and the last thing you want is for them to get back in the office and see too many messages from you. The consequence of this is they may feel a level of scarcity or neediness in your messaging and feel uncomfortable buying from your or reaching back out to you.


Put yourself in their shoes. Preface emails with “Happy Holiday’s” and ‘Hope your holiday preparation is going smoothly, I found X online store is doing X promotion”, again depends on your friendship with the client. Everybody has those last minute gifts they need to get. This is the time of year buyers will be paying the least attention to you.

About the author

Rick Middlemass has almost a decade of experience in Entrepreneurship, Business Development & Sales.

Rick began his sales and entrepreneurial career at 18 opening up a new territory for Student Painters creating over 100K in new business over the next 3 years. Rick also worked in various sales & marketing roles & internships throughout his time at Michigan State University.

In his first role out of school Rick joined NuWave Technology, a Cisco Systems Premier Partner in Michigan, and quickly worked his way up to be:

2014 Sales Person of the Year
2015 Sales Person of the Year
16 Time Sales Person of the Month

Rick Middlemass now works with the National Association of Sales Professionals helping salespeople and sales leaders reach their true potential and continue to grow through our behavioral conditioning programs.