Fill in the address last

How to remind yourself to pause before sending something contentious

Really bad or really good news shouldn’t arrive by email. It’s best to have these conversations in person or, at a minimum, over Zoom.

But let’s just say you’re sending an email that requires some serious thought. How can you guarantee that you won’t send it prematurely?

Simple — just fill in the address last.

This is easy enough if you’re starting an email from scratch. Don’t fill in the address line until you’re sure you’re done. If you rush and hit send (on purpose or accidentally) your email program will prompt you to fill in the address, which will give you another chance to think this through.

If you’re responding to someone else’s email, this is a little more tricky, but if you can see that your response is going to require some thought, go ahead and delete the person’s email address. You can always fill it in later after you ponder exactly what you’re going to say and how it might be interpreted.

When I have done this, I often find that I stop before sending and pick up the phone instead. But if nothing else, slowing down a little will decrease the chances that you say something that can’t easily be taken back.