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Holiday Emails 101: The Ultimate Holiday Email Outreach Survival Guide

Doing outreach can be difficult at the best of times. You never know how recipients are going to view your subject lines. Or your email templates. Or your actual offer.

Everyone who has ever done outreach, even on a smaller scale, has faced a month of little to no replies. And there have undoubtedly been months where handling the incoming onslaught of messages was difficult. However, what everyone dabbling in outreach dreads most is: Christmas.

While the rest of the office is counting presents in their minds, the outreach person is filled with mounting exasperation. How is he to run a campaign when no one is reading emails? Let alone replying to them.

To make life just a bit easier (and more festive), I’m sharing our tried and tested tips on doing holiday outreach. Trust me, they work. I am no longer dreading December. I have time to focus on the in-house Secret Santa ambush. And the sprinkles.

Know Your Calendar

The first thing you need to realize is that the frequency of out of office emails slowly starts to rise well before the final weeks of December. The period between Thanksgiving and New Year’s Day is practically dead. You can just about imagine the tumbleweed rolling across your screen.

However, you need to know what is happening in your specific niche. If you are marketing to students, for example, you should know your school calendar. If you are going international, not all of your prospects might be celebrating Christmas. If you are promoting a retail store, Christmas will be your time to shine.

Take the example of Samsung and their promo for their Galaxy and VR campaign (that’s not saying that gadgets and tech can’t be promoted at other times of the year). Rather than choosing to focus on a specific demographic, they cast a much wider net, and spun their entire campaign around gifting and gift wrapping (hence the name “Unwrap the Feels”). Their product was marketed as a gift everyone would like to find under their tree, and the campaign itself was hailed by Hubspot as a stellar example of getting it right.

If you can find a way to incorporate your product into such a campaign and promote that through your outreach campaigns, you will have a much better chance of reaching your desired targets.

Whichever niche you are targeting, make sure to explore it well in advance. Don’t just stick to your regular calendar – compile one specific to your campaign. Highlight all the dates that might be important for your audience. If you were a manufacturer of sweets, you’d know when National Jellybean Day was, wouldn’t you?

Start Outreach on Time

Depending on the habits of your prospects, you might want to start working on holiday outreach as early as late September. However, I personally have marked October the 5th as my starting point. (No particular reason for it being the fifth. It’s just after the initial monthly meetings and reporting, so it suits my schedule).

So, come October, the first thing I need to know is what the campaign goals are, what the targets are, and then start doing some research. I like to compile my prospect list for the rest of the year at this time. That way, I’ll have enough time to get to know them. I can also come up with plenty of email templates. The other marketing departments also start doing holiday planning at this time, so it works well.

You don’t need to work overtime though. Just try to re-organize your time a bit differently. As the year draws to a close, you will be sending less and less email. If you don’t start on time, you will not see the results you are looking for.

I tend to send the most emails in November. And that’s for my entire years’ worth of outreach. I have been burned badly once, and I don’t care to go through it again. Back in my first year on the job, I failed to look at the holiday season as an obstacle. Naturally, I knew it would get slow. I just didn’t expect it to come to a screeching halt. Luckily, I have learned a lot about blogger outreach since then.

The emails I now send in November need to make up for the ones I’d send in December. They need to both be better and there needs to be more of them. This is why prospecting goes into overdrive, and I also try to rework my approach a bit at this time of year. Which brings me to my next point.

Adapt Your Offer

The emails you send out in spring and summer need to change as winter is coming. They now need to reflect your holiday offer as well. Are you working on a special discount for different holidays? Do you have a new piece of holiday-themed content to promote? Or are you just building links?

No matter what the goal of the campaign is, your outreach needs to reflect it. This is when in-house communication starts to play a major role. You need to find out what exactly the company (or client) is doing for the holidays and reflect that in your emails. Sending out bland templates might work, but people are going to be showered with promotional emails at this point in time. Yours needs to stand out.

Remember that you are always competing for inbox space and attention with others. Your subject lines need to be catchy at all times. But as every advertiser breaks open the bank in the run-up to Christmas – the gloves are off.

Think in terms of catchy campaign slogans: like H&M’s “Come Together! You want people to remember you by something, and associate the email with a campaign already running, if at all possible.

Also, bear in mind that people will be more on the edge. Even though the holidays are supposed to be a time of joy, you can’t deny the stress levels. Attention spans are short already. Imagine just how short they are when a prospect is faced with 17 emails in their inbox. They will simply skip over the least enticing ones.

If you send too many follow-ups, you are likely to get on people’s nerves. I am by no means saying you should not send follow-ups. But don’t do more than two. Even one might be enough. Remember that these people will be prospects in the spring too. You don’t want to tick them off so badly now, trying to make one more sale or link, that they refuse to do business with you when the holiday rush is over.

Another very important point is to always stay calm. Your job is to juggle different tempers. Don’t ever be tempted to shout at someone over email. Or be the slightest bit rude or condescending. Of course, you are human yourself, but try to be forgiving during holiday campaigns. You don’t need to be adding to anyone’s stress levels.

Just Don’t do it

A couple of years ago, I would have told you not to do outreach during the holiday season. That is when I still believed “holiday season outreach” only referred to outreach on Christmas Eve and New Year’s Day.

Today, I would still advise you not to do outreach during the holidays. What’s with the lengthy intro then? Haven’t I already given you some decent advice?

The truth is, I would try to dissuade you from doing outreach a day before, on the day, and a day after any major holiday. You don’t want to stick in people’s minds as the person who pesters them while they are drinking eggnog and having dinner with their family. Because you do have to remember – people will not shut off their phones. You will still be reaching them. Their phones will still be pinging. Right in the middle of Hanukah.

The time between Christmas and New Year should be spent on following up on your positive responses, and nothing else. No fresh prospects. No initial emails. No hard selling. Just a friendly reminder. And a holiday card.

If you are short on results, you can only blame it on yourself. Don’t ever try to blame your prospects for not getting back to you on time. You now know better, and will be better organized for the coming year. Don’t try to dig yourself out of the hole by upping your outreach game way too late in the final quarter. It’s futile.

Human Touch

Finally, my most precious piece of advice for outreach during the holiday season would be to try and be as human as possible. Don’t be the human octopus sending out emails by the dozen. Don’t be a ruthless sales agent. Don’t chase the money, or the lead, or the conversion. I know it might sound a bit cheesy, but try to do some good with your power.

I got into marketing because I honestly believed every product has a buyer. You just have to find them. And when you make a sale that makes sense, everyone is happy. I don’t believe in mass emails and casting a wide net. I believe in finding just the people whose problems you can solve with your product. And then solving it for them.

This is why my holiday outreach is always warm, kind, personal and honest. I will thank every single prospect for getting back to me. (I actually do that for every email during the year) I will wish everyone a happy holiday. I will not push, I will not nudge. I will try to be as friendly as email will allow it.

Don’t push a bunch of random prospects from a prospecting tool into an email automation tool on December 20th and expect to get some value out of the exercise. Do your work on time, and tap into the human side of outreach.

After all, there is a human being sitting across that screen from you. With their very own Christmas wishes and New Year’s resolutions. They are not a number, an email address or a closed sale. God forbid a link. Approach them as such, and your holiday campaigns will never be a disaster again.

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