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7 Tips for Successful Prospecting During the Holidays

Last updated November 22, 2022 Categories: Holiday Campaigns & Fun, Sales Prospecting

By Kendra Lee

Prospecting During the Holidays

December is a tricky time to prospect. You have year-end when people are trying to wrap up projects or close the books. Staff people of all levels are spontaneously out of the office, squeezing in their last vacation days before they lose them. Holiday parties and long lunches expand to Wednesday, Thursday and Friday. Companies (like ours) close between Christmas and New Year’s, or people just take the whole week anyway.

Reaching prospects is slow – sometimes painfully slow compared to other times during the year.

And yet, when you reach prospects, suddenly you find that they’re willing to chat longer. It doesn’t matter if they don’t know you yet and you cold-called. In December, they’ll open up and share their challenges, desires, decision criteria, upcoming projects, contract duration, budget, what they’re doing over the holiday, when the kids get out of school, how they can’t seem to find the perfect gift for their significant other, and why Sally can never make a decision.

If you can reach them, they’ll just talk. And talk. And share – a lot.

So, while December may be a difficult to time to reach people, don’t give up on prospecting. When you do reach contacts, you discover a treasure trove of information both business and personal. The conversations turn from five-minute prospecting calls to 20-minute relationship building.

Here are 7 tips to help you reach prospects, uncover last-minute sales in December and set you up for a fast start in January.

  1. Keep at it. Be persistent. Our research shows that with cold calling it can take at least 9 attempts to reach a new prospect. In December it’s going to take all 9 prospecting attempts. Call every few days. Send follow up emails. Stick with it. It’s going to be hard to catch prospects, so persistence and frequency are critical. Call, email, reach out through LinkedIn, call some more. If you learned our Bloodhound Follow-up Strategy in our Sales Prospecting for Profits training, follow it closely.
  2. Leave a voicemail with a promise to call back. December is a critical month to leave voicemails. With the light holiday spirit in the office, things drop through the cracks. Your call is easily forgotten even when it’s a priority. Leave a voicemail and include a promise to call back – then see #1 and do it.
  3. Use calendar invitations to request a quick 20-minute meeting. The closer you get to the holidays, the greater the likelihood that contacts’ calendars will be open if they aren’t taking time off. Your 20-minute conversation will extend well beyond that, and you’ll walk away with new opportunities. Remember, if prospects don’t decline or accept, call anyway. Your appointment may still be on their calendar. Even if it’s not, you may catch them at their desk
  4. Prospect with holiday spirit. This isn’t the month for a serious, dry voice. Of course, you don’t want to sound unprofessional, but this is a happy time of year no matter if you celebrate or not. People are lighter. Let your voice reflect this fun time of year. Is your value proposition different? Not really. It’s your delivery that’s different. Smile. Remember the tip to use a mirror so you can see your expression when you call? A mirror helps you be jovial this time of year.
  5. Drop by. If you work in an area where you can do drop-by cold calling, December is a perfect month to integrate it into your prospecting strategy. Receptionists will talk more freely. Bring holiday cookies to top prospects you haven’t been able to reach all year. If your contact is in the office, there is a greater chance they’ll come out to greet you than at any other time of the year. (Unless they’re heads down in year-end, and then you may have to settle for plying the receptionist or another staff person for some information.)
  6. Party it up. Prospects are going to all those holiday lunches and parties, so take yourself off to those parties when you’re invited. Local associations, Chambers, leads groups and membership organizations all seem to have some type of holiday event. Network with the intention of chatting and establishing more personal relationships with people. The treasure trove of information flows at holiday gatherings just as it does in one-on-one phone conversations.
  7. Prospect on Fridays. Don’t stop prospecting on Fridays or even the last week in December. A higher percentage of your prospects will take Fridays off, but those who are in the office often aren’t in meetings because of that. Set aside Friday mornings to prospect and maybe even some Friday early afternoons. You’ll reach a lot of voicemail – and be rewarded with quality conversations when you reach a decision-maker live.

While all other sales reps are sitting back to wait for the holidays to be over, it’s the perfect time for you to cold call and find more leads. Whether you do it over the phone or drop by offices, prospects are more relaxed and willing to have conversations. You’ll uncover last-minute sales for December and get January off to a fast start. Prospect all holiday long!

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