Hey Devin — I’ve got two questions this month, not one, so bear with me. First: how do you put together a holiday card at the end of the year that doesn’t take a ton of time to make but still feels genuine, not like something you grabbed off a template site? And second: we just launched a new company-wide newsletter for our 1,200 employees, and I want to make sure it’s actually engaging and useful, not just another email people skim past. Any advice on either front would help.

Love these questions! And goodness, I can’t believe how quickly the end of the year is approaching!

First up, for the holiday card — the tension you’re describing (authentic and low-effort) is super valid, and I’d actually say it’s less of a trade off than you think! The biggest lever for authenticity in this case isn’t more time, it’s the voice you use. If your company has brand voice/tone guidelines lying around, try popping them into an AI tool (like ChatGPT, Copilot, or Claude) and ask for a few holiday card variations in that voice. You’ll get something that sounds more like your company instead of a generic template, and it takes just a few minutes!

The second lever is who it’s coming from. A card signed (a digital signature is fine!) by your CEO/someone from your executive leadership team… or even better, sent by managers to their own teams, reads as way more personal than a company-wide send. Now, that can be a bigger ask for capacity, so it’s worth being honest with yourself about what’s realistic this time around. Starting with a company-wide send is more than okay!!

I’d also build in both a digital and a printed version if you can — I’d safely assume some if your employees are remote, some on-site, and meeting people through more than one channel tends to land better than picking just one. And on design: loop in someone who can make sure the imagery reflects the diversity of your company. It’s worth keeping in mind that not everyone celebrates the same holidays (or any holidays at all), so I’d lean toward something warm and seasonal rather than specifically religious or culturally specific unless you know your audience wants that.

Now, for the newsletter — with 1,200 employees reading, I wouldn’t spend too much time guessing on what they want. Instead, ask! That could be a short pulse survey on what they actually want in there, i.e. company-wide updates, department news, deadlines, events, etc. that will save you from guessing and finding out six months in that nobody’s opening it.

Once you know what’s going in, the format matters almost as much as the content. Email is not the place for a wall of text — break things up with images, video, or even a short Loom if you’ve got the tool for it. I’d also add a TL;DR or “main points” section near the top so someone who has thirty seconds still walks away knowing what they need to know.

Last thing, and this one takes more setup but pays off: think about segmentation. Not every one of your 1,200 employees needs every piece of news — a company-wide newsletter that’s actually relevant to each reader will get opened a lot more consistently than one that tries to be everything to everyone.

Neither of these needs to be perfect on the first try. Ship a version, see what lands, adjust. That’s basically the whole job.

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Devin Owens

Hey there, I'm Devin!

Most of the time you can catch me deep in the world of internal comms at Workshop (yes, the Happy Mondays folks!), and while I love AI, there are just some comms questions that need a human who really gets it… that’s me!