The Horrors of the 'Send' Button

I quickly respond to an urgent email request from a client who has asked for a list of the company's service offerings. In excitement, my fingers fly over the keyboard wanting to prove the possibility of responding 'as soon as possible'. It's one of our selling points, anyway. Then I click send, and relax with a feeling of having achieved something. But as I relax, I open the sent folder just to gaze again upon my brilliant composition - and alas, the first thing I see is: "...we offered editorial and proofreading services to writers and corporate executives." Wait, what?! I begin to panic: did I actually send that? Oh, what will this client think of me? What a terrible first impression!

If you are like me, you must have experienced this over the years. Upon reflection, we regret having responded to that nasty email or text in like manner. Or we should have taken time to read over the email before clicking the send button. Well, there are ways to go about this. In the article written by Katie Smith Milway for the Harvard Business Review, she explains how to set a 2-minute send delay in your Outlook settings to give you that extra time required to recall, rewrite or cancel that email. Have a read...

Prevent Email Horror to a 2-Minute Send Delay

Marketing manager Grier was just plain tired of colleagues playing the expert in her domain. When a designer sent her an e-mail questioning her choice of quotes for a new product brochure, she snapped.

“How about you do your job, and I’ll do mine!” she typed back rapidly and punched “send.” A split second later, she wished she hadn’t. Her better self knew that a dose of circumspection would have saved her from the now face-to-face damage control she had to do with an offended colleague.

When was the last time you sent an email that seconds later you wished you hadn’t? Maybe you forgot an attachment? Maybe you forgot to check spelling or to delete the e-trail below your message that had personal comments — too personal. Or just maybe, like the fictitious (but realistic) person I’m calling Grier, you were irritated, and you realized you should have slept on your response before firing it off?

It’s for these sorts of reasons that several years ago I decided to put a two-minute delay on all of my office emails. It’s come to my rescue many a time, allowing me to pop into my outbox and fix inaccuracies; add the PowerPoint file I forgot to attach; or re-edit a sensitive message for nuance. I’d love to say it’s simple to get started, but if you use the version of Outlook that I use — Outlook 2013 — you’ll need to navigate a rabbit’s warren of clicks and commands. It’s worth it.

• Go to the “Home” tab and click on the “Rules” drop down
• Choose “Manage Rules and Alerts”
• Under “Email Rules” choose “New Rule” and under “Start from a blank rule” click on “Apply rule on messages I send.” Click “Next,” which will show conditions — you don’t need to choose any of these, just click “Next” again.
• On the final menu (the “Actions” page), check “Defer delivery by _ minutes” and fill in the blank. I choose two minutes, because it often takes me a minute to realize what I’ve forgotten!
• Click “Next,” and fill in any exceptions to your new rule.   Then, click “Next,” and “Finish” (Don’t forget this last step, or all your clicks will be for naught.)

(For info on different versions of Outlook go to: support.office.com and search for “Delay or Schedule Sending Messages.” One caveat: users report that it doesn’t work on Outlook for Macs.)

If you use Gmail, you’re in luck, as Google just added an “undo send” feature, which is much simpler. To enable it:

• Go to the little cog icon in the upper right-hand corner and select “Settings.”
• Look a third of the way down the page for the “Undo Send” section.
• Check “Enable Undo Send” and then choose between 5, 10, 20 and 30 second windows of unsendability. Again, I’d go for longest interval to give your mental red flags a chance to flutter.
• Make sure you hit “Save Changes” at the bottom.

Three Common Saves

Preventing a pickle like Grier’s is one way that a delayed send can save you from yourself. But it’s likely not the most common. In my experience, the top three rescues are from crossed messages, forgotten credits, and ingratitude.

Crossed messages occur when one reads e-mails out of order, answering a question that a subsequent email has rendered obsolete. Or, when one efficiently answers screens full of email offline during a flight — only to synch up hours later and find the criteria changed when you were somewhere over Nebraska. Then there’s the group e-mail, where replies cross in the ether, one carrying info that affects the other.

Exclusion can happen, unwittingly, in messages acknowledging broad-based teams. Darn it if one doesn’t realize, seconds after clicking send, that she forgot to acknowledge the social media associate, or the company founder!

My favorite save is from sounding ungrateful. No matter how much we appreciate the shoulders we stand on, too often our emails cut directly to the task at hand. Just as they sail away, we realize that we meant to open with thanks, and close with appreciation. Mercifully, a two-minute delay gives us a second chance to do just that.

Join the conversation: share your email/text horror stories in the comment section.