Self-Inflicted Wounds with Microsoft Outlook

I sent out a Microsoft Office Outlook meeting invite yesterday for a call I was planning to have this morning—or so I thought. It occurred to me sometime late last night, as I was wondering why neither of the intended participants had responded, that in fact that was because I hadn’t included any invitees on the invite. Big Outlook fail on my part—although I’d like to go ahead and blame Outlook for letting me send an invite with no recipients.

OK, to be technically correct, Outlook didn't send an invite (and obviously, neither did I); because there were no recipients, I merely saved an appointment to my calendar instead of sending a meeting request. I had wondered why Outlook would allow me to send an invite with no attendees selected. What I learned after reviewing my process is that I typically set new meetings by double-clicking the time slot on the calendar, which defaults to an appointment, not a meeting request. You can switch it to a meeting request by clicking Invite Attendees on the Appointment tab of the Ribbon in Outlook 2007 (and I imagine it's quite similar in Outlook 2010). If you don't, your Send button isn't a Send button at all but merely a Save & Close button—which, in practice, looks pretty much the same as if it's sending and closing when you click it.

Obviously, I skipped a crucial step. This morning, when I explained what I'd done to Tony Redmond, one of the intended invitees, he suggested there might be an interesting story in discussing "the worst self-inflicted Outlook wounds." So, here I am. And thanks for the idea and the title, Tony!

This particular mistake certainly is one of the stupider ones I've made. But I'm sure we've all made this sort of glaring Outlook error from time to time—even beyond the unfathomable Reply All on the whole-company distribution list message just to say, "I agree!" I'll spill some of my dirty secrets, and then I hope you'll share with me some of yours.

Sticking on the calendar theme, I've put appointments and reminders on the wrong week, wrong month, and—yes—even wrong year. I've scheduled meetings for times I knew I wasn't going to be at work—but had obviously failed to put such information on my calendar. I've showed up for meetings at the wrong time simply because I failed to actually check my calendar and went with the time that was stuck in my head—not always the most reliable storage receptacle.

When it comes to email, sure, I've used Reply All a time or two that I wished I hadn't, but never on a global email list, and never with repercussions. So far. I've also replied to an individual when I intended to Reply All, and then sat wondering why no one was answering the question. I've replied to the wrong person. I recall one time when I was discussing an article by Paul Robichaux with another editor but in fact I sent my comments to Paul. He responded to me right away to let me know my message had gone astray. Fortunately, I didn't call him any bad names or anything; occasionally, I can maintain a professional demeanor, even if by accident.

Naturally, I've deleted messages that I wished I'd saved. Of course, I've got the Deleted Items folder as a backup, and it's even searchable. Works great—until I forget I'm already in the Deleted Items folder and hit Delete, resulting in the permanent delete. In the piler versus filer debate, I try to be a filer, so I have numerous folders in Outlook designated for saving certain topics. But then I'll drop something in the wrong folder, or forget which folder I decided something belonged in. Search to the rescue again.

More times than I can count, I've intended to send someone an attachment without attaching the attachment; I'm sure just about everyone has made this mistake. I don't think I've ever picked the wrong message recipient from Outlook's Autocomplete, but in a similar vein I have picked the wrong IM recipient from my Office Communicator contacts. Hey, she was the first green-jelly-bean Jill I came to, so I sent her my question. Too bad she had no way of answering it. And what's the big idea of having so many Jills anyway?

I could go on. But I think I won't. Outlook has features set up to prevent some of these problems. For instance, I know there's a warning you get when you try to delete a message from the Deleted Items folder—unless you've chosen to turn off said warning. With Outlook 2010 and Exchange 2010, the MailTips feature can help you avoid some of the message sending embarrassments that are all too common. But like all warnings, you have to actually pay attention to them for them to have any effect.

So I've showed you mine; now show me yours. That way we can all be embarrassed together. Leave a comment below with your personal Outlook self-inflicted wounds—or those of your end users. You might even trigger me to remember some more of my own that I've forgotten.

Follow B. K. Winstead on Twitter at @bkwins
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