Can’t Believe I Just Sent That!!?

How to prevent embarrassing, misfired e-mails.

Michael Agger

Earlier in 2009, Google announced what one of its managers referred to as a “Gmail Embarrassment Reduction Pack.” The Web app will now give you a window of five seconds to cancel a sent e-mail. The “undo send” feature joins the little-used but funny “mail goggles,” which require you to answer math questions before sending late-night mail on the weekends, and the very useful “forgotten attachment detector.”

The final element of the embarrassment-reduction pack is the built-in Gmail feature that signals when the message thread that you’re reading has been updated. This theoretically prevents you from being the fourth person to drop the same witticism in an officewide e-mail jokefest.

Google, busy organizing all of the world’s knowledge, has apparently given itself a more difficult mission: saving us from our idiot selves. One of the leaders of this mission is Gmail product manager Keith Coleman, who explained the thinking behind “undo send”: “When we looked at the mistakes, we realized they were being discovered right after send. The user would see the wrong guy in the ‘To’ field and rush to close the browser window.”

Sending an e-mail, he said, has the paradoxical effect of clarifying what you actually meant to say: “When you hit send and the thing becomes real, that triggers people to realize what they were really thinking.” In our haste, we often don’t know what’s in an e-mail until it’s gone.

Is five seconds really enough? You can catch obvious mistakes, but, in my experience, the “I probably shouldn’t have written that” regret sets in around the two-minute mark. Coleman says other time options will be added, but more along the lines of 10 seconds than 10 minutes.

The problem with longer hold times is that people don’t like their e-mail to be “slow.” While “undo send” is undeniably useful, it’s not the ultimate face-saving tool. That would be “e-mail recall” (without anyone knowing that you recalled it). Let’s say you accidentally forward the details of your boring law internship at Skadden to half the partners in the firm. With “undo send,” you have five seconds.

The magical “recall” button would let you extract a misfired e-mail out of anyone’s inbox at any time. Coleman said that this was impossible to implement for mail sent to a non-Gmail address but that it could potentially be done for Gmail-to-Gmail communication, provided the recipients haven’t read the e-mail yet.

But don’t expect this anytime, ever, as it would create usability and server issues that are “nontrivial.” Not to mention the creepy, stalker-standing-outside-the house vibe of taking a message out of someone’s inbox rather than keeping it in a holding pattern in your own.



About Amr Badran

An Egyptian Business Consultant and Corporate Trainer since 1997. I've trained on Management, Leadership and Soft Skills to thousands of people from many nationalities, backgrounds and professions in more than 10 countries across the Middle and Far East. I've also provided my consultancy service for issues of Strategic Planning, Marketing, Sales and Capacity Building. Holder of an MBA and a Candidate for Doctorate in Business. Find more about my Management and Personal Skills Courses at and feel free contacting me at
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