Prospecting Through the Holidays

It is a misconception that work doesn’t get done through the holiday season. I’m workingYou’re working. And after a pandemic that shut down all our companies for an extended period of time, I can’t imagine that business owners will be taking lengthy holiday trips this year. 

However, here at Managed Sales Pros, we never onboard new clients during a holiday break. Why? 

When you begin your first outbound prospecting campaign, most of your data will be inaccurate. It may take up to 17 dials just to verify decision– maker names and number of computers.  All lists are at least thirty percent inaccurate at time of purchase, and the longer you let them stagnate, the less accurate they become. Throw a few holiday weeks into the beginning of your sales program, and suddenly at least 50% of your dials are going nowhere – people are out of the office, receptionists have PTO. It is a lot of work for very little return. 

That doesn’t mean you shouldn’t be prospecting through the holidaysIt means you shouldn’t start prospecting through the holidays.  You want your dials to be as meaningful as possible.  As a cold calling company making hundreds of calls a day, even on our worst day we are going to get a few people on the phone.  As an MSP business owner making ten calls a day, you’re burning an hour or two that could be better used elsewhere. 

Calling campaigns require a steady build

For example: 

Day One:  20 dials, 2 conversations, 1 follow up carried forward to a later date. 

Day Two: 20 dials, 0 conversations 

Day Three: 20 dials, 3 conversations, 2 follow ups carried forward to a later date. 

Day Four:  20 dials, 2 conversations, no interest, 2 annual check in calls scheduled  

Day Five: 20 dials, 1 conversation, no interest 

That’s one week of activity for a business owner committing two hour per day to outbound calling. Scale that up X5 for a fulltime outbound caller, and you can see that there is still plenty to do at the holidays providing your outbound teams is asking for those follow up calls. 

You see there have been no appointments scheduled, but there has been some interest generated, and together, you and your prospect have determined a follow up schedule that makes sense for you. 

Likely, you both realized a holiday was coming up, and you scheduled your follow up conversation at a time when both you and the prospect were going to be in the office. 

Start calling early

If you had started calling a month ago, you would have a few dozen of those followup calls scheduled. You would already have them scheduled around holiday days or adjusted office hours. You need not worry about having “nothing to do” through the holiday week – your prospects have already told you when they will be available for follow up discussions. 

If we start a cold calling campaign a month before Thanksgiving, our callers are well-positioned to have a productive calling week through the holiday week. If we start brand-new calling campaign the week before, we just don’t have the opportunity to create the same amount of impact. I would always rather start a client campaign when I know we can make a great first impression – the holiday week doesn’t show off our numbers the way launching a few weeks later would – we’d rather push the start date, save our client’s investment, and put our best foot forward 

But we never stop calling through a holiday for a client who is already active on our roster. 

There is no wrong time to cold call (except maybe accounting firms in April, I’d avoid those) – and your calling team should not blame inactivity on holidays. They have the same number of hours in their day on the Tuesday before Thanksgiving as they do on September 14th. 

Skipping weeks that you believe to be “dead” weeks for calling adversely affects your pipeline. Every day you don’t cold call means a week of no follow up activity.  Every week you skip leads to a month of no follow up activity. And every quarter you put off starting cold calling leads to a full year of missed follow up opportunity.  You can’t afford to skip business development on holiday weeks.  We don’t work on the statutory holidays, but we work all the rest of them. 

How to keep your sales team motivated

Here are three ways you can keep you or your team motivated through the weeks where it seems like everyone but them is on vacation: 

1. Incentivize for activity, not outcome

Reward your team for gathering data on your prospects, or your competitors, or both.  We use a competitor “bingo” card. Anyone getting a full line of competitors on their bingo card gets a cash prize. To find out who your prospects are doing business with right now, you need to ask the question. Reward people for doing so. 

2. Offer some continuous training through the holiday season

Is your team struggling to get through gatekeepers? Are they having trouble getting past a specific objection? This is a wonderful time to offer some coaching and training. Random call audits are a great way to improve your quality control. If you have trained something on Monday, make sure that when you are auditing calls, anyone who is clearly practicing and utilizing the trained skill is acknowledged and rewarded. This doesn’t need to be cash – we offer the agent who demonstrated the best improvement the opportunity to choose our catered lunches, a gift card, our Friday team party theme…there are a lot of things that leadership chooses for the team, giving someone the chance to choose the things that are meaningful to them is a great way to keep people motivated.  

3. When all else fails, money has a remarkable way of motivating people

If you have variable compensation tied to a certain behavior, increase that amount at the holidays. This allows for fair and equitable bonuses at the holiday (should your top performer and your least productive agent get the same holiday bonus?) and clearly delineates the reason for the larger bonus – we do this at the holidays, no other time – it removes the expectation that your variable compensation rates are going to increase permanently.

If you are doing your own cold calling, do not let your motivation for business development activities wane during the holidays. It’s hard to get back into a habit that you ignore. Think about it like going to the gym – every time you stop going daily, it gets much harder to get yourself back through those doors. This is no differentGood prospecting requires commitment – no matter what time of the year it is. 

If you don’t want to do your own cold calling, Managed Sales Pros is happy to helpEmail them at to choose the right start date. 

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