Q: What is the best thing to do it you send an e-mail to someone by mistake, and the e-mail contains some content that is not favorable toward that person?
A: First of all, don’t compound your error by sending an e-mail saying “disregard the e-mail I sent earlier.” All this will do is persuade your unintended recipient to read the earlier e-mail immediately. Instead, make a point of getting to the person before he comes looking for you. If you’re in luck, he won’t have seen the offending e-mail yet. But either way, a sincere apology is your best recourse: “Tom, have you read my e-mail? You haven’t? Good, because I want you to know that I said some things I’m embarrassed about, and I’m very sorry. I hope this can be water over the dam for us, because I truly value our friendship.” Second, vow to avoid the problem altogether from now on by hitting “Draft” or “Send Later” after typing your message. This lets you go back and double-check e-mails written in haste. With some distance, you’ll see where you should tone down the content, saving yourself the grief of having to correct a mistake after the fact.