Category: Holiday Post

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.

Below 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 Follow-up Strategy in our  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!

Happy Selling,

David

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Tomorrow marks the final month of the year, and when we combine it with the holidays, it’s easy to simply pass on December and focus on January.

I can’t emphasize enough as to how much business you stand to do lose if you start focusing on January now.

Just because you’ve had a couple of customers or prospects tell you to check back with them after the first of the year doesn’t mean there’s no business out there.  

The closer we get to the end of the year, I’ll argue the more business there is to be had.

It starts with your competition throwing in the towel on the year and going into hibernation.   

Hey, I’ll encourage my competitors any time to do just that because it leaves me with more business. Go for it! Keep on pushing just as hard and you’ll find yourself taking customers away from your more lazy competitor.

Second is the end of the year spending blitz many companies are going through as they look to spend their remaining budget or accelerate buying decisions due to their year-end numbers.

Offer them Dual Pricing programs  and merchant cash advances and help them put thousands on the bottom line in the first quarter of the new year.

Either way it is easy business, but there’s no way you’ll get it unless you’re out there making it happen. 

What’s nice about this business is the customer is under the gun to get things done and that means many times you’ll have an accelerated buying process.

Nothing better than getting business to close quickly, especially from those companies that normally take forever to make a decision.

Final reason I like selling in December is it shows your prospects and customers alike that you’re working hard to make things happen. 

I’ll never forget the first year I was in sales walking into an account the day after Christmas at 8:30 AM. They were shocked to see a salesperson — so shocked that I walked out the door with a great account.

Make this December a big December by keeping on track making it happen. You’ll be thanking yourself come Dec. 31. Best of all, you’ll also wind up jumpstarting the New Year!

Happy Selling,

David

What would the holiday season be without the “It’s the Holidays blog…?

It’s that time of year. Time for a reality check.

How many salespeople do you know that go on cruise control between Thanksgiving & New Year’s Day?

How many companies do you know that will actually admit to winding things down right about now?

It happens every year. So common. We could call it an epidemic at some companies & an easy way out for many salespeople.

Saying things like,

 “Nah… they don’t want to see salespeople… it’s the holidays. Or,

 “I’m sure they don’t want to see us over the holidays”. Or, “Nobody’s even there, they’re all off, it’s the holidays”. 

That’s Total B.S. !

Here’s an idea: Get out of the office. Go see some clients, customers & prospects between now & the start of 2024? Make it a point to capitalize on your competition’s weakness – laziness! Epidemic laziness!

It’s time to buckle down & do the one thing that you actually control in your daily selling lives. Pick up the phone, get in the car and go see prospects & customers. Yes, you control that activity. Nobody else will be doing it so you will stand out automatically. Nobody else thinks anyone is “IN” – so I like your chances.

Strong salespeople don’t go on cruise control – ever.  Successful companies don’t wind down during the holidays. They make things happen.

The holidays are great times to see prospects & current clients & customers.  

Here are 5 reasons to keep prospecting for new business & keep seeing current clients during the holidays:

1.  It’s your job
2. Companies review current year incumbent products & services & decide what to do for the next year
3. Prospects will see you – it’s their job
4. It’s a great time to plan new programs for 2024 with current clients (your competitors won’t be there)
5. As my mother always says, a Thank You is never inappropriate – thank your clients for their business

Business does not stop between Thanksgiving & New Year’s Day. 

Some salespeople do. Don’t be one of them!

Happy Selling.

David

The period from Thanksgiving to New Year’s can be a tough time in sales. You still have goals and quotas, but instead of workplaces abuzz with activity, you encounter busy business owners vacationing decision-makers, and an overall atmosphere of wanting to take time off. 
The holiday season is huge for retailers, representing up to 40 percent of annual sales, but sales departments in some verticals tend not to expect much from this time of year. It can be a self-fulfilling prophecy — some teams find that their close rates in December plummet by 10–20%. It doesn’t have to be this way.

Over our years of selling, I have identified five quick tips that contribute to prospecting success during the end of the year. As a result, our clients’ sales funnels continue to fill consistently — even while wading through an influx of out-of-office responses. These techniques may not work for every business, but they could work out for you. Test them out and do a little bit of tweaking. See if you can customize them for your outbound prospecting. Here they are… 5 holiday prospecting tips you can put to work today.

Tip #1: Focus more on nurturing current leads. The holiday season is all about spending time with those who matter most. So why not extend that philosophy to your sales funnel?

Look at your sequence touchpoints and identify those who have engaged with you in the past but have fallen by the wayside in favor of higher priorities. Set a goal to identify an X number of those prospects who you would like to put into an end-of-year re-nurturing campaign. 

If possible, set up a multi-touch sequence that involves email, phone, and LinkedIn ot text messaging. Since they have communicated with you before, these are all warm channels for you to reach out again. Connect over something that connects the holidays and your business relationship. 

How to Do It? Bring 

up something that’s both timely and relevant.  Personalize your message with the recipient’s name, and reference a prior conversation. Allude to something they’ve expressed interest in previously — hopefully you took some good notes during initial conversations. Settle on a next-step based on their timeline, whether that’s a sale before end-of-year or a meeting in 2022. 

How NOT to Do It Don’t

 send the same message out to everyone. Not segmenting and personalizing your messaging never gets you anywhere in outbound prospecting — during the Holidays or any other time of year. Don’t include language like “we know you’re probably busy” or “when you have time.” Assume they’re in business mode just like you are.
Tip #2: Emphasize End-of-Year BudgetingWe’ve mentioned end-of-year budgeting several times, and that’s not an accident. Just like the retail shoppers who are racing around town and surfing the internet to get the most gifts for the least amount of money.  Lets make the most by focusing on offering dual pricing. Let your competitors take the end-of-year slump as an excuse to knock off early. Get focused, look at those touchpoints again, and follow up with promising leads. When you make contact, ask about the prospect’s how they feel about putting thousands of dollars on the bottom line in 2023. Have options for different budget levels prepared, so when they give you a number, you can show them how your product or service fits perfectly. How to Do It Do your homework. Have a couple of suggestions ready so you can make your offering work with their budget. Ask multiple questions. Focus on budget, but also ask what they’re hoping to accomplish in the coming year. The more you know, the more you can tailor your pitch. Talk about pricing and onboarding. Can you be flexible about billing so you make the sale and they get the perfect closure for their fiscal year? Guide them into a purchasing mindset. Use words like “this month” and “this year.” How NOT to Do It Don’t pitch too soon. Wait until you’ve figured out the right angle. Don’t pigeonhole a solution where it doesn’t belong. If your product or service would work best for them now, go with that.

Tip #3: Schedule your 2024 Appointments Now Appointment scheduling is a time-consuming part of the sales professional’s day. At times, it can cut significantly into your client contact time, which inevitably reduces your revenue. Take advantage of the downtime in early December to schedule meetings for early 2024. Of course, between office parties and people trying to use up their expiring vacation time, it may be harder to reach your prospects during the holiday season. Instead of letting that slow you down, consider using an online scheduling tool that lets contacts choose a mutually convenient appointment when they’re at work and in that mindset.Alternatively, think about engaging an outbound sales agency to get your early 2023 calendar booked.  

How to Do It 

Include a touchpoint in your current sequence that focuses solely on messaging for 2023 planning, identifying this might be a slow time to connect, and schedule a meeting for after the new year. If you catch them on a phone call, try to schedule right away over the phone. If you can’t, arrange another way of choosing a time. If you get an out-of-office message, make a note in your CRM of the date that the person will be returning. Follow up a day or two after they get back and get the ball rolling. 

How NOT to Do It 

Don’t push a meeting back into 2023 if the prospect wants to meet with you now. They might be hoping you can help them now. Don’t get stuck in your process. If a client wants to set up the meeting later or use a particular tool to do it, be willing.

Tip #4: Pick up the phone & Make the Calls 

Not all decision-makers hop on a plane out of town in December. 

Many are in their offices, taking advantage of the relative quiet to plan for next year. Businesses like auto repair, tire shops, dry cleaners, storage places are just a few great places to hit this time of year. 

These are the people you want to talk to. They’re thinking about how to grow their businesses, they understand the value of thinking ahead, and they’re probably considering the rest of this year as well as next.

 In sales development we can become shackled to our email sequences sometimes and forget that we are all just humans who communicate best 1:1 in verbal conversations. During Holidays, there is a general feeling of openness, and you might find that a call converts quicker to a demo or sales appointment. 

How to Do It 

Approach this cold call like any other. Ask your questions, make your pitch points, and connect where your product or service meets their needs. Meet them where they are. Some will be focused on their 2022 finances; some will be thinking primarily about next year. 

Offer them solutions accordingly. Work with their schedules. If they want you to call back after the new year, get them to suggest a particular day and time. 

How NOT to Do It 

Don’t come across like you’re interrupting someone’s holiday. You’re not. You’re helping the prospect do what they’re already doing, which is preparing for next year. Don’t leave a message if your call reaches a machine. They might be on vacation and come back to so many messages that yours falls through the cracks.

Tip #5: Launch an end-of-year specific outbound sequence. 

When business slows down for the holidays, decision-makers have more time to do what they couldn’t do in busier periods. 

That includes reading emails, and it’s particularly applicable to longer prospecting emails. As we discussed earlier, the holidays are when many decision-makers take deep dives into how they do things. 

They’re already thinking about changing certain approaches, so an email could engage a prospect at just the right time. 

 How to Do It Use an email automation tool like constant contact, get response or mail chimp to create a multi-touch end-of-year sequence that incorporates themes we have already touched on: end-of-year budget, 2024 plans, and holiday-specific messaging. Create a sense of urgency. Offer a special deal for those who take action before the new year. Perhaps a free consultation?

Craft subject lines and pre-headers that are personable, inviting, and communicate your unique offer. 

How NOT to Do It 

Don’t send out something too general. Make it relevant to the time of year and the new fiscal year coming up. 

Don’t be cute. People are already getting enough snowman and Santa references. Avoid images or sparkly gifs — honestly, those hurt your deliverability rates anyways. 

Don’t overdo the urgency. Everyone is asking people to “buy now” during the holidays. 

Holiday Prospecting Tips: 

Wrapping Up Here are your key takeaways for prospecting in the holiday season…

 ➜ The holidays are notorious for being slow in many verticals, Identify those and attack. If you don’t accept this assumption as a given, you’ll have many opportunities that others miss. 

➜ Take advantage of the slower holiday pace to touch base with current leads and work on lead generation by cold-calling new prospects. Not everyone is doing business, so you’ll have a captive audience. 

➜ In December, merchants are looking for ways to put money on the bottom line. offer up Dual pricing. 

➜ Some prospects will be making decisions for 2023, some will be thinking about 2024. Listen to where their thoughts are and pitch accordingly. 

Do you rev up prospecting at year’s end?

What’s your favorite holiday prospecting tip?

Happy Selling,

David 

(In the tone of It was the Night Before Christmas)

It was the night of Thanksgiving and all through the town black Friday deals come early like never before.

Stores opened early, disrupting family time, “Farewell to dinners,” they said in a chime.

Children in tents, freezing and cramped, Outside Best Buy, where bargains were camped. Ma with her coupons, Pa with a rant, Don’t you cut in line, was his rant.

At the mall, all was a clatter, doors flung wide, People running wild, cash savings as their guide. Hair pulling, elbows thrown in the rush, Like animals hunting, a frenzied hush.

A lady fell, in the chaotic crush, A fear she stayed down, in the mad rush. Fighting for deals, a fervent zeal, Discounts so deep, a shopping steal.

Two ladies tussled at the clothing rack, Over a sweater, a sleeve they attack. Flat screens, laptops, appliances galore, Discounts, sales, and even more. Shelves ransacked, as shoppers do, “Go to hell!” they yelled, a chaotic crew. Three microwaves bought, just because, At 40 percent off, applause.

One lady with iPads, a Walmart spree, Gift cards galore, how rad is she? An employee whispered of TVs in the back, Duck and cover, stay off the pallet jacks.

Stores emptied out, doorbusters done, A second wave came, shopping for fun. No dawn lines, too good for that crap, Vultures descended, scavenging the gap. Bins searched for finds, Black Friday’s plight, Everything bought, a desperate night. From deep in the store, a joyous shout, “Norbit for two bucks!” bought without doubt.

People left, broke and nearly dead, Passing a jolly man, all dressed in red. He exclaimed, as I drove out of sight, “Shop online, my friends, it’s the new modern delight!”

Have a Great Weekend everyone,

David