As someone who works remotely, I mostly communicate over email.
And because email’s (obviously) in writing, I feel added pressure to get the tone just right. That’s because conversations others might have in person, be it in the break room or a closed-door meeting, live in my inbox. And, if I cross the line, I can’t just walk over to someone’s desk and clear it up. So, whether I’m giving critical feedback or using humor to show warmth or be congratulatory, I do my best to make sure that everything’s coming across the way I want it to.
And I do that by asking the following questions:
1. Who Am I Emailing?
One of the most important things to consider is the person you’re writing to. For example, you’d speak differently to your best friend than you would your boss—even if you were telling the same story. Similarly, a joke that’ll be a hit with your office BFF may be misinterpreted by that new client you don’t know well.
Which isn’t to say you have to avoid humor entirely, unless you’ve known the recipient for years. While it can be risky, if you do your research, it can pay off.
For example, Muse columnist Abby Wolfe wrote about how including a GIF in her cover letter helped her get hired at The Muse. As she explained, “One of the tasks The Muse listed for the editorial internship was ‘Trolling the interwebs for the best videos, infographics, stories, and memes to share with our audience.’”
Both the task—and how it was explained—suggested a light-hearted, internet-savvy approach would be well-received.
2. Would This Person Send Me a Similar Message?
The answer should be a resounding yes.
3. Does This Cross the Line?
Scary, but true: Getting it wrong could cost you your job.
Sure, telling a bad joke won’t always lead to the most extreme consequences. It could be that you write something that’s not funny—and all that happens is the other person rolls their eyes and feels slightly awkward.
However, if you say something inappropriate—even while striving to be funny—it can get you fired. It’s important to understand this in no uncertain terms. Any “jokes” that make fun of or put down another person’s gender, race, religion, ethnicity, background, or citizenship have no place in the office (or anywhere else for that matter).
It doesn’t matter if you think the intended recipient would laugh. As you know, private messages can be forwarded. Imagine it printed out on your manager’s (or HR’s) desk. Imagine it going to the wrong person—or even to the person you intended, but deeply offending them.
4. Would My Boss Be Disappointed in Me if They Discovered This Email?
The answer should be a clear no.
5. Does This Person Send Jokes Over Email?
Unlike the last question, the answer to this one should be yes.
6. Am I Glossing Over a Serious Subject?
Giving feedback in writing isn’t easy. I’ve rewritten critical messages five times over to make sure I’m crystal clear without being harsh. So, it can be tempting to use humor because of how it can both defuse and illuminate tough topics in face-to-face conversations.
However, this rarely translates well, because the other person can’t hear your tone of voice or see your body language. The end result is often similar to making someone up who just happens to be in the same situation as your friend, so you can give them unsolicited advice. They’re still getting criticized—and they feel a bit mocked, as well.
So, your best bet is to keep the jokes out of tough conversations, so people know you’re taking them—and the matter at hand—seriously.
Part of creating strong relationships with your colleagues is discussing more than work all the time (and in a serious tone). So don’t let these questions scare you away from making a joke, sending a quality GIF, or writing a funny birthday message. Rather let them steer your humor in the right direction—so that both you and the recipient can walk away feeling good—and not into HR’s office.