Sending a Difficult Email

Dear new developer,

Sometimes you have to send a difficult or awkward email.

But, before you send it, think about whether it should be an email or if an in-person conversation, phone call, or video call is best.

If it is an awkward topic, it’ll be an awkward conversation too, but the additional information bandwidth of seeing and hearing someone, the ability to converse and react and adjust, and the possibility of getting to a conclusion all make in-person/video calls worth considering.

But, if you need to do any of these:

• lay out a long and complicated situation
• let the other person have time to react
• keep a written record
• share the conversation with others for feedback
• communicate asynchronously for any reason
• have a long term record of the topic and decisions

Then an email is a good choice.

What is a difficult email

Examples of difficult or awkward emails I’ve sent include:

• Asking for a raise or role change
• Letting a job candidate know they aren’t being hired
• Informing a client that I won’t be working with them going forward
• Discussing a departure package from a job

How you do it

When I’m sending a difficult email, I like to compose it outside of my email client so there’s no way it could accidentally be sent. You can also have the recipient be yourself or blank.

I’ll start out by outlining what I want to cover at a high level, not even in sentences.

Then I’ll start to write the email, filling in the outline.

I’ll usually read it aloud a few times. I find that will often trigger new concepts or thoughts I want to explore further. At the least, it makes the email easier to read.

Sometimes I’ll ask someone else to read it, to make sure I’m conveying tone, the situation, and other information accurately.

Finally, I’ll schedule the email unless the topic is pressing. It’s easier to send when it isn’t going to be sent right away. If I rethink sending it or want to give it one more once-over, I can. (I usually don’t, but the knowledge that I could gives me confidence to send it.)

Sending awkward, difficult emails is a skill you can learn.

Sincerely,

Dan