Have You Ever Emailed The Wrong Person?

After 20 years of using email, my personal and professional email address books have grown into the thousands. Maybe that's a lot for some people, and a little for others.

But one thing is certain: My address book has reached a critical mass whereby a significant percentage of the names are similar, and some are the same.

Why does that matter?

My propensity to select the wrong person and email address has gone up significantly in the past year. I’ve even noticed it among colleagues, industry peers and friends -- and people I don’t even know.

Such user error is usually harmless and inconvenient. But sometimes it is potentially damaging, such as when communicating confidential or sensitive information in either work or professional settings. Indeed, I’ve been accidentally sent emails detailing not-yet-public M&A activity, juicy office gossip of other companies, and more. That’s why I triple-check my recipients when emailing anything of great consequence.



But for the massive volume of email we’re all expected to process, mistakes become more likely. Email services play a huge role here. I use Gmail, and this user error happens with Gmail's Web browser interface while working on my various laptops.

I love Gmail's auto-populate email feature for the Web browser interface when I type in an address or a name. I type in a few letters and it does a great job guessing my intended contact -- but it’s not perfect. When working fast or distracted, I’m more likely to select the wrong person and hit send without realizing the mistake.

I also love Gmail's auto-populate email feature on my Android Phone (an Evo). But given the imprecise nature of touch-typing on the go, my propensity for selecting the wrong email recipients is even greater.

Moreover, my Android address book merges all of my professional and personal contacts into one database that is accessed from the Gmail app, making the possibility of selecting wrong email recipients even higher.

What to do?

Gmail is most certainly the best email service out there. I love how it integrates seamlessly with my Android phone and Google's other productivity services like documents, spreadsheets and calendar. It also has great spam filtering.

But it could use better controls and management for large email address books, where there is greater propensity to mistakenly email the wrong person.

Google has invested heavily to come up with an algorithm that recommends email recipients. That feature is seldom useful. Instead, I wish Google would detect email recipients with a high probability of being incorrect, and then alert me before it’s too late.

It’s important to be diligent about whom you fire emails to -- and whom you don’t. But amidst an avalanche of email volume, it would be great to have a little more help from tools and automation.

Hey Google, is this feature coming?

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