As someone who runs a large organization with dozens of virtual employees, I’ve seen my fair share of emails. And, as with all other things in life, some messages are better than others.

In the world of email correspondence, “ugh” is probably the last thing you want your boss to say when reading your message. So, what types of messages should you avoid sending, and how can you make them better? Below are three prime examples.

1. Unnecessary Follow-up Emails

Follow-up emails come in all shapes and forms, so what makes one unnecessary? If all your message does is ask for your boss to email you, it becomes more of a nuisance than an important correspondence.

A lot of people send these emails out of paranoia that they’ve done something wrong or missed something, but I can tell you from a boss’ perspective that it’s aggravating to receive several follow-up emails when someone hasn’t given me a chance to breathe.

One example: A long time ago, I had an employee who would panic if I didn’t respond to her emails within an hour, thinking that it meant she’d done something wrong (when, in reality, I just hadn’t gotten to her email). I can think of one particular instance when I came home from a long day to find six (yes, six!) emails from her asking if I’d received her message.


What to Send Instead

While most people wouldn’t be so paranoid as to send six follow-up emails in a day, even just one ill-timed follow-up email can leave your boss annoyed.

Unless the contents of your email need to be dealt with today (in which case, you should probably talk to you boss in person instead of emailing), I suggest waiting at least 24 hours, then sending what I like to call a “faux follow-up” message.

This entails sending your follow-up (“Just checking to make sure you received the quarter reports I sent you two days ago”), but you’ll also include some other tidbit of information, whether that’s a question about an upcoming presentation or an update on a current project (“Oh, and we just got the latest numbers in on the X account, and sales are up 30%!”). This allows you to sneakily ask your boss for an update while also giving him or her some information that will add some value, making it feel less like you’re just bugging him or her.

2. Emails With New Ideas

I absolutely love enthusiastic members of the team, but something that does get a little overwhelming is when employees send me all of their new ideas—in separate emails. I once received 10 different emails over the span of 24 hours because someone on the marketing team hit an inspiration stride and kept sending me new ideas.

While having so many new things to try was awesome, it was also extremely confusing trying to catalogue everything and keep track of every single email and idea that was coming in. Even when just one email comes in with new ideas or concepts, it’s so easy to lose it in the black hole that is my inbox.

What to Send Instead

First, I would recommend waiting for a more opportune time to bring up ideas. In the case of the marketing team employee, I would’ve waited until the Google Hangout meeting we had scheduled for the following week to bring all of this up.

If you’re not sure when the right time is—or email is the only option for some reason—I’d recommend emailing your boss to say that you have some new ideas and you’d like to know what the best way to share them would be. If my employee had asked me that, I would’ve told her to send me one email with a Word doc filled with everything she wanted to. It would’ve been much more streamlined and easy to save for later. Your boss may suggest a quick call to talk through them or ask that you stockpile the ideas and then email them en-masse on a certain day of the week.

3. Emails Where Your Boss is CCed for No Reason

Any professional would get annoyed with being CCed on email threads they aren’t really a part of: It just adds to the growing pile of emails, and you end up wasting time reading something that you probably don’t need to be.

From the employee’s perspective, I get it: You want to make sure your boss knows you’re doing your job and that you’re trying to keep the line of communication open. But most of the time, all this really does is clog your boss’ inbox.

What to Send Instead

Unless your boss absolutely needs to be in the loop, take him or her out of the CC line and, once the interaction is over, send a very short summary of relevant information that came up during the conversation (“FYI, Company Y will be featured in that story on Z date”). It keeps your manager informed about what’s going on, without keeping him or her constantly in the loop as you figure out the details. One email definitely trumps 42!

Overall, the name of the game with emailing your boss is to streamline your messages and be more selective about what you send. It might sound counterintuitive, but if I’m receiving fewer emails from an employee, but all of them are meaningful, I probably think that person is doing a better job than someone I hear from all the time.

Photo of woman checking mailbox courtesy of Shutterstock.

Updated 6/19/2020