How to send emails to your boss: 10 easy-to-follow steps

John David Back
Apr 30 · 4 min read
This is a real email I may have sent

I am a passionate person. I get riled up by my work, and I tend to speak very directly about it. This can be a great trait to have when the passion is channeled positively. It can be absolutely detrimental to my career and my relationships when it is channeled negatively. Usually it’s the latter. I have spent 10 years learning how to write email better, particularly when it involves stakeholders, employees, colleagues, loved ones, and bosses.

Long story short — the way you come across in emails is important, particularly when directed at people who can have an impact on you. It’s your responsibility as the writer to make yourself clear, blunt your sharp edges, and articulate your message. It’s not your recipients fault if they don’t understand what you mean. Especially when this is your boss.

Here are my tips for writing emails to your boss. Pay close attention to these if you are upset, angry, or otherwise miffed.

Never, ever send in the heat of the moment

Once you click send and the email takes off, that’s it. Always take an hour and let an email cool off. I guarantee you that you’ll want to tone it down when you come back and have some perspective.

Don’t even put their email address in the To: field at first

This will help you from firing off the email prematurely. Just a trick of the trade. Always do that part last.

Have a conversation in person instead of sending an email

Usually a conversation in person is always better. Then follow it up with an email so you have something to agree to. Don’t just throw molotov cocktails through your boss’ window and expect not to get burned yourself. I know it’s easy to send email, much easier to have an in person or on the phone meeting, but that’s the point. You can so much more easily make a mistake in email than you can when you take the time to meet with your boss and deal with this directly.

If blame is due to you at all, own it immediately

The first thing you need to do in an email to your boss about a sticky situation is own what responsibility you have. You are an adult, you have some culpability in the events that surround you and their outcomes. Own that part of it. Even if it is vaguely your fault, if there was ambiguity it will help for you to own that, too.

Stress that you are seeking to gain understanding and to line up with

The point of the email is to get on the same page, right? That’s always the point of an email. A sore replacement for in-person communication, email exists to convey information and get agreement. You need to state that loud and clear. After you have agreed some of this is your fault (so you are also invested in a solution) you need to indicate how important it is to you to seek to learn, understand, and collaborate.

Stop using so many adverbs and adjectives

Don’t say things like “really” or “absolutely” or “literally” or “terrible” or “incompetent” or whatever else. Steer clear of hyperbole. “I am very disappointed” only makes you look very disappointing. No one gives a sh*t how disappointed you are. Those kinds of emails go DOWN the chain, not up.

Offer solutions to every single problem

Having solutions is an absolute must. You cannot just list problems and expect your boss to solve them. Do this without being too prescriptive — you’re not telling them how to do their job. “The communications haven’t been clear — would it help if I sent a template to so-and-so that they can copy and paste to make this easier?” Is a great way to make you look like you’re willing to put in the work and it solves your problem and it gets the point across that so-and-so is slipping up. Win-win-win.

Put yourself in their shoes

If you got this email from a subordinate, would you be pissed? If the answer is even remotely yes, then do not send it. Take a step back, recalibrate, and try again. This person is ostensibly more busy than you and is looking for work to get taken off their plate, not added. Are you doing that?

When in doubt, share with a trusted friend

Having someone proof your emails, especially ones that can be of a volatile nature, is a huge enabler. I often have my emails with sensitive content read by someone from HR. It just helps. Especially if I am defending the practice, expressing frustration, or calling someone out for a job not-so-well done.

Click send, and hold tight

Who knows, if you did a good job, you will get a good response. If you did a bad job, you’re screwed. Then it’s into firefighting mode.

So, there you have some easy to follow steps for how to write an email to your boss. At the end of the day you want to be seen as someone self-sufficient and capable. Actually, you don’t want to be just seen as that — you want to be that. So prove that you are.

John David Back

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