What's the Worst E-Mail Mistake You Ever Made?

The other day, I received an e-mail that I shouldn’t have. While my name was indeed in the list of addressees, and while I knew some of the other addressees (as well as the sender), my name was plainly included by mistake. It took me about three seconds to figure this out, since the topic under discussion had nothing to do with me.

But not only did it have nothing to do with me: it was a confidential e-mail about an upcoming strategic move by a large American corporation, the news of which had the potential to move the market substantially.

The main purpose of this e-mail was to coordinate the announcement of this move without having any information leak to the public before the company could announce the move on its own.

Oops.

In this case, the sender got lucky: I don’t plan to use the information against the company, or to profit from the confidential message (unless you consider this blog post a profitable maneuver). But it could have easily worked out differently. And perhaps the erroneous inclusion of my name on this e-mail was a good indicator that, alas, this company’s news will indeed leak to the public before it is ready.

I have long prided myself on not making any such disastrous e-mail mistakes. Sure, I’ve sent things to the wrong person now and again, but the stakes were always low. A few months ago, however, I messed up, royally.

Oddly enough, my mess-up was directly related to someone else’s mess-up. Let me explain.

There was a team of academics who had done some interesting research that Levitt and I hoped to write about. However, the member of this team with whom I communicated — let’s call him William — was rather brusque in response to my inquiries.

As time would reveal, William had a fairly complicated political agenda that he feared would be ill-served if his research appeared in a Freakonomics article — so, while the other members of his team wanted us to write about their research, William was evasive and a bit rude in his replies to me.

Then I received another e-mail — this one from another member of the research team (we’ll call him Zachary), which was intended for William and the others, but not for me. It said, in part:

E-mail dramatization.

I thought the best thing to do in this situation was to write Zachary directly and let him know he’d inadvertently sent the e-mail to me. So here’s what I wrote:

E-mail dramatization.

His reply:

E-mail dramatization.

That seemed to break the ice, and communication got better. We were prepared to write about the team’s research, either on this blog or in our Times column. But then they got evasive again, and stopped communicating.

Then we got a surprise when a prominent article about their research suddenly turned up in a major publication. William had sandbagged us, and then Zachary had done the same.

It wasn’t a big deal — academics and journalists and politicians (and everyone else) are constantly competing over material — but if they had said from the outset that they were talking to another journalist, we would have happily left them alone.

Once I figured out what had happened, I dashed off an e-mail to Levitt:

E-mail dramatization.

The only problem is, I sent the e-mail not only to Levitt but also to Zachary!

In the end, I believe Zachary thought I couldn’t have been so foolish as to mistakenly send him a critical e-mail after he’d inadvertently sent me one. Zachary seemed to think I sent him this last e-mail in order to directly insult him.

To date, that is my worst e-mail mistake that I am aware of. Perhaps I have made worse mistakes that people had the good heart to not tell me about. I recently heard about a family whose child is having some trouble in school, and in an e-mail to his parents that discussed psychological counseling, etc., the school inadvertently cc’d the entire class list. Ugh.

What are your worst e-mail mistakes?