Have you ever received an email that seemed (obviously) intended for someone else? Have you ever sent an email to the wrong person, where it caused you embarassment because of what you sent?

No the mistake I often make is forget to use reply all in family mail, so only one person gets my reply, and nobody else knows what we are talking about.

I once tried to apply for several upwardly-mobile openings at the corporation where I worked. I tried using a template cover letter, with appropriate parts edited (Dear insert manager name: attached you will find my resume in response to your posting for insert position.)
I then went on to discuss my specific qualifications for the position in mind, with a polite close and request for an interview.

I applied for about five separate positions, and was not paying attention when I attached the letter for position a to the director/manager for position c, and just got them all mixed up.

Yes, both. In the workplace this has happened quite a few times. Ever seen the function that says ”—- wants to recall this message”? I always let them recall it, but of course I read it first.

A coworker of mine once clicked “reply all” when she meant to use “forward” and sent to our boss (instead of just to me) a scathing critique of a message we’d both received from the boss. I replied, “It’s been nice knowing you.”

Another coworker accidentally sent to the whole company of more than 400 people an extremely long, piteous message to his brother (written on company time) about his troubled relationship with their father.

I once did the reply-instead-of-forward thing and essentially called the facilities director an idiot for a new policy he’d instituted. As soon as I realized it, I sent a follow-up apologizing for my harsh language but standing by my opinion.

Another time I received a message crabbing about me, written by one coworker to another with a name similar to mine. I replied sweetly, “Did you intend this for me?”

I also fortuitously once sent to the wrong name in a list (to M instead of N) a message meant for a co-worker. It happened at a time when M was publicly questioning my integrity on account of a false statement made by someone else. My message to N, on a completely other subject in another setting, happened nicely to refute those questions through no intention of my own. At the time, I was not responding to anything said by N. But I couldn’t have done better if I’d planned it.

Once in a great while I reply to a whole list when I mean to forward an offlist PM to one person. Luckily none of those has been too awful. One outspoken coworker did this when he thought a project team had made a bad decision; he apologized for nothing and instead said, “Well, now you all know what I think.”

In those cases I always try to remember to add ”[Offlist]” to the subject line to avert heart attacks on the receiving end. And I double-triple-check the “to” address.

And when I’m writing anything sensitive, I don’t fill in the “to” line until the message is done, checked, edited, reedited, and sometimes left to cool overnight. A delay before sending has saved my life more than a few times.

I just got one this week from a client. The contents made no sense to me, and she immediately followed up with a “Sorry, that was a mistake” email.

I sent a message to the wrong kelly the day before yesterday.
When we first got email in my old office someone thought she was sending a message to her bf when she actually sent it to the boss.

And another facilities director accidentally sent a message out to the whole company that made him look ridiculous.

And then broadcast a plea to be excused for his fopah.

I laughed so hard that I thought someone was going to have to call 911.

Probably I’ll go to hell for that.

Years ago I learned the hard way how careful one has to be about hitting the SEND button when I accidentally sent a highly critical email about my manager to my manager. It was intended of course for someone else to read. When I immediately realized what I had done, I quickly went to her office and apologized. Turned out okay. We had a very good discussion.

Happens in large companies all the time. Too many John Millers and Jane Smiths.