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Advice / Succeeding at Work / Work Relationships

Confronting an Employee Over Email? 5 Tips for Doing it Right

Confrontation (especially work confrontation) is never fun for anyone. But even more uncomfortable than trying to say something unpleasant to someone’s face is trying to express those feelings over email.

As the co-founder of a completely virtual organization that has more than 120 contributors all over the world, I’ve had my fair share of awkward confrontation emails. So, what should you do if you find yourself in an emailing predicament? Here are a few tips.

1. Don’t Resort to Email Unless You Have To

This should go without saying, but it’s important: Email should never before your first choice for confrontation communication. In fact, it should only be used as a last resort.

Don’t send a confrontation email to someone unless you’ve tried to get in touch with him or her every other possible way with no success, or if the problem is so urgent that he or she needs to be told immediately and the only available option is email. Additionally, confrontation emails should only be used for smaller issues, not large, life-changing events (like firing someone; ideally, that’d at least be done on Skype or a platform where you can see someone’s face).

There are two main reasons for this rationale. First, face-to-face interaction (even if it’s through Skype or Google Hangout) allows for the other person to pick up on facial cues and body language to some degree, which can help you better get your point across. Second, words in an email can be taken out of context very easily (as can the context of the email itself), and you don’t want a situation blowing up in your face (cue the other person going to your boss to complain about your email).

However, there are definitely going to be times when you’ll have to use email, and trust me, in those situations, it’s better to communicate via email than not at all.

2. Be as Straightforward and Specific as Possible

The most important part of writing an email is to just say what you want to say. Take your commentary or other side thoughts out of it (this isn’t supposed to be a novel), and just get straight to the point. Your entire confrontation email should only be a couple of sentences, and the goal should be to move communication offline and into real life as quickly as possible.

What does that mean? Don’t beat around the bush, don’t word vomit everything that comes to mind, and definitely don’t apologize for what you’re saying. You can still do this without being mean—as an example, check out the email below that I sent to one of my contributing writers.

Hi [name],

I saw on the editorial calendar that you failed to turn in your article for this week, and it’s the second time you’ve missed an article this month. As you know, we have a three strikes policy at The Prospect, and I just wanted to check in and see if everything is okay. If you’re having any trouble with deadlines or if something is going on and you need more time between deadlines, we can definitely talk about those options.

Let me know if you’d like to hop on Google Hangout or the phone to chat about it.


Also, if you feel like you can’t explain your case in six sentences or fewer, perhaps the subject is too big and hairy for email. After all, you don’t want to minimize a delicate situation. A short email addressing missed deadlines, assignment quality, absence, or progress is fine—but you can only imagine how terrible it’d be to send an email that said, “Hey so-and-so, just wanted to let you know you’re being written up. Cool.”

3. Offer to Be Available to Chat

Another problem that arises when you confront someone via email is that online communication is very one-sided. Someone else cannot immediately disagree with you; instead, they receive your email, read it, respond, and so on. Thus, it can take a while for both parties to get their points across, and typically not a lot is accomplished.

Even though you sent the confrontation via email, you should give the other person the option to respond through a different medium. Ending a letter with something like, “Definitely let me know if you have any questions, and if you would like to discuss this further, we can absolutely grab lunch or hop on Skype.”

4. Think Before You Send

Before you send your email whizzing through cyberspace, think to yourself, If my superiors saw this, what would they think of what I said? Doing so can keep you from sending an email that’s too harsh or that gives off a different vibe than you were hoping for. If you think your boss would get the wrong message looking at your email with no context, then it’s time to go back to the drawing board.

If possible, try and write your email a day (or at least a couple of hours) before you send it. If you’re writing your correspondence in the midst of anger, you’re going to want some time to cool down before that other person sees your message. Not many great decisions are made in the heat of rage, and you certainly don’t want your reputation to be put in jeopardy because you sent one not-so-carefully-worded email.

5. Be Prepared For the Reply (Or Not)

Of course, emails are a two-way street; make sure you’re ready for any and all reactions when you send out any sort of confrontation. Additionally, take some time to think about what you’re going to do in different scenarios, like if the person on the other end doesn’t respond or if he or she blows up at you 10 minutes later.

For example, if the writer I sent that email above to doesn’t respond within three or four days, I’ll send a follow up email with a deadline or ultimatum (something like, “If I don’t hear back from you by [DATE], I will assume you’re no longer interested in writing for The Prospect”). This puts a little more pressure on the other person to respond.

And in the case that you receive a rude or angry response, take some time (at least a few hours) before responding. It can be tempting to fire back and also very easy for one message to turn into an email war zone. And again, your primary goal should be to get out from behind the shield of email and to talk things out face to face.

Photo of woman writing email courtesy of Shutterstock.