5 Ways to Successfully Engage Prospects and Customers During the Holidays

Authored by Kayla Brehm

Published on December 16, 2015

As of today, you realistically have, at best, 8 days left to hit what’s left of your monthly sales number- whether that’s in terms of closed revenue, number of demos scheduled, or amount of pipeline opportunities generated, we’re coming up to the end of the productive period. Christmas Day and New Year’s day are federal holidays, and Christmas Eve and New Year’s Eve you can chalk up as a loss in most cases. Even worse, it’s become more popular to work from home just before the holidays, limiting your options for direct contact.

Realistically, the 14th-18th is the last full week you’ll have along with a few days at the tail end of the year (these days are huge depending on your industry). The vast majority of your prospects will still be in the office along with their colleagues who may need to sign off on that last minute deal of yours. In many cases most companies won’t be at full strength until the second week of January. If you’re behind on the number of demos you need to set for the month it’s time to get creative.

Below are a few specific, tactical ways that I’ve used to help finish the year strong.


1. If you’re trying to close a deal, make sure you’re staying in contact with your prospects daily. If possible, set meetings the same day or the following day to condense the timeline as much as possible.

Assume there are four other vendors vying for your contact’s attention. Call your contact first (leave a voicemail if they don’t answer), email second. Then do it again in the afternoon if no response. That meeting with your contact’s boss for final sign off? Ask if there’s room this afternoon to talk, and if the answer is “no,” then ask if she’ll be free tomorrow. Simply asking to move up the timeline gives you a better chance that unexpected delays won’t derail the deal. Odds are that an unexpected delay will occur, but it’s your job to ensure that if one does occur that it happens early enough to recover from.


2. If you’re working with an existing customer and you’re trying to sell a few extra licenses to take advantage of end of year budget, you need to be talking to them about this now.

Look at your existing customers and figure out which ones could benefit the most from that extra user license or that memory upgrade on the server. Focus on them. Don’t just call or email everyone on your list–you’ll lose credibility.

One of my favorite quotes is “you cannot prove you are better unless you first prove you are different.” Don’t be the hack salesperson that hits up everyone. Be the one who does their research, presents a plan and what your customer has to gain, and offer a reason to do it now (end of year discounts, products going end of life, etc.). If you do, you have a better chance of being one of those people who sneaks a deal in last minute.


3. If you’re an SDR and you need to set up demos, try calling out the obvious: the next two weeks are a terrible time to start a discussion so it’s better if you’d reach back out in January BUT that you’d like to put a placeholder on their calendar as a reminder.

Say something like this (a personal template):

Hi ,

I know the odds are stacked against me to get your attention mid-December, but I’m wondering whether potentially switching [describe business] is something you’ve considered in the past or have on the roadmap for 2016?  

[Describe your platform/ service in more detail in this paragraph]

Again, not likely that this will catch your attention to make a move now or take a call tomorrow. Correct me if I’m wrong. If you see the value in having a quick call in January I’d be happy to send you a meeting invite that will act as a placeholder and I can follow up a few days before to confirm day and time.

If not, I’d appreciate if you could say so or let me know if there’s someone else on your team that would be better for me to have this conversation with in January.

Happy Holidays,


The great thing about this is that you can use it for most holidays as an excuse to reach out. Again, “you cannot prove you are better unless you first prove you are different.” Most hacky salespeople are desperate to hit their numbers and trying to sell sell sell. Be cool, calm and collected.

This message lets your prospects know that you respect their time, that you have perspective, and that you have patience. I cannot emphasize this enough. This will pay dividends when 2016 starts and all the new salespeople with new territories will start emailing and calling your contact. When you follow up, she’ll already have made a mental note of you and take your call at a later date.


4. Send them some love with company swag, holiday treats from their local bakery, or a handwritten note.

People are in a giving mood this time of year, and receiving a package of some sort has the best chance of succeeding now. Sending handwritten cards thanking them for their business is also a great way to get people to respond to your calls and emails. If you have an expansion opportunity, this can help since they already work with you.  Just make sure you write a personalized note that is clearly about the individual customer and sounds genuine.


5. If you’re really in dire straits, or just want to keep pushing ahead, call Christmas Eve and New Year’s Eve in the morning.

Have a casual tone and make a joke how you’re counting down until your boss leaves for the half day–something that makes it clear that you, just like them, are looking forward to leaving work and spending time with family and friends. Then, ask if it’s ok to follow up with them in January since no matter what you say at that moment they’ll still probably completely forget about you and your product.

During the holidays, there is no silver bullet. Using all or a combination of these tactics alongside side your normal prospecting efforts can yield better than average results.

I’ll wrap it up with a quick story that I think illustrates the points I mentioned above.

When I was starting out at Oracle, I worked in a call center. At the time, this State Farm commercial was on TV and was a somewhat of a pop culture hit. Since I was just one of what seemed like a billion other sales reps, I really struggled to find a way to standout. I’ve had a few friends call me ‘Jake from State Farm’ before so one day I just had an idea to say on cold calls that my name was Jake from State Farm. The length of awkward silence between that moment and their response (because you can NEVER be the first to speak during an awkward silence) was dumbfounding.

After they said something in complete confusion, I would quickly mention something along the lines of “hey man just kidding, my name actually is Jake but I don’t work for State Farm–I work for Oracle, I hope you don’t mind.” 75% of the time, they either broke down laughing or just with a heavy sigh, in a sign of surrender, ask me what product I worked with and we’d actually talk for a few minutes. Sometimes they were totally lost or disinterested, but I scheduled a lot of follow up conversations as a result and gained insight I didn’t have before in terms of future projects and decision makers.

Aside from the laughs it got around the office, the more important takeaway is that you just have to find a way to be different.

It doesn’t truly matter if it’s humor or sending a care package. Inject your personality into as many situations as possible. Tactics I’ve mentioned above are a spin off of that lesson. Accept the reality that you are one of many sales reps and  need to say something that stands out but isn’t off putting. During the holidays is the worst time for you to do cold outreach, so craft your message accordingly. People like people who have perspective and care more about others than they do themselves. Recognize that for them, this time of year is tough. Finally, call out that reality to them and get something scheduled for January. I promise you that you’re in the minority if you do that, and they’ll respect you for it.

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