Why Smart People Make Dumb Email Mistakes (And How To Stop Them)

Email mistakes
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The Bank of England employs some of the United Kingdom’s smartest and most accomplished professionals. Senior executives frequently hold advanced degrees from Oxford or Cambridge and are recruited from positions at top investment banks.

But sterling credentials did not help one senior banker who in 2015 accidentally emailed a highly confidential study of the economic implications of Brexit to an editor at the Guardian newspaper. The mistake made headlines around England and as a result the bank banned its elite workforce from using the autofill feature in their email.



Lawyers, like bankers, suffer when emailing goes awry. The legal insurer ALAS reported that in 2014 alone, it reserved more than $60 million against claims related to harmful emails.

So why are professionals who stake their reputations on exercising good judgment laid low by email mistakes? Though it is cold comfort to the lawyer who has just accidentally forwarded confidential information to opposing counsel, intelligence and expertise themselves might be culprits. A growing body of research suggests that smart people and experts are more likely to make certain kinds of mistakes. They take mental shortcuts in order to focus their attention on their highest priority tasks and may skim over rote or uninteresting details, unconsciously relying on their background knowledge and reasoning skills to fill in gaps in evidence or attention.

To the lawyer who is preoccupied mentally composing a trenchant rebuttal or juggling several time-sensitive deadlines, typing in the addresses to an email may be the rote or uninteresting part of a larger process. And while a high-profile snafu might temporarily cause the lawyer to pay more attention to addressing emails, such mistakes are rare enough for any given individual that in the course of sending dozens of emails per day, she is likely to soon drift back to her old habits.

It is notoriously difficult to train people to overcome their own biases, as psychologist Daniel Kahneman argued in his book, “Thinking, Fast and Slow.” But better designed email programs might help. Existing email applications typically give users only two options for addressing their emails. The first option, typing in all email addresses manually, as the Bank of England now requires, is a long and cumbersome process that might itself create errors by encouraging users to mentally fill in gaps rather than think through each address. The alternative, using traditional shortcut features like the replyall button and autofill, clearly fails to help users make accurate selections or give them feedback about possible problems.

Is there a third way for email, a set of tools that improve on reply-all and autofill and allow users to address emails both more quickly and more accurately? In full disclosure, this is exactly what my company has attempted to build with our ReplyTo- Some application.

In the meantime, there are certain strategies to help protect against errors that you can use with your existing email program. One is to develop the habit of addressing your email last, aft er draft ing the body. This has a couple of advantages. First, it protects against accidentally sending out an email before it has been fully written and reviewed. Second, thinking through the content first helps to focus the mind on the separate task of deciding who it should go to.

Another strategy is to set a delay timer that will hold messages in your outbox for a certain period of time aft er you press send, allowing you to take advantage of the common tendency to be a better writer and editor aft er sending the email. The delay timer will allow you to reopen the email and edit or even delete it before it is sent out. The set-up process is a bit involved, but a Harvard Business Review article, “Prevent Email Horror with a 2-Minute Send Delay” sets out step-by-step instructions.


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If legal geniuses are more susceptible to email mistakes, the good news is that they can use their smarts to develop strategies for shoring up their weaknesses. Good email safety strategies can ensure that the quality of your expertise and not a second of distraction defines your reputation. Peter Norman

Peter Norman

Peter Norman co-founded Winnieware LLC, a software company that develops user-centered solutions to problems. Previously, Peter was a lawyer at Arent Fox and Milbank Tweed, and in-house at Sunedison. Learn more about his team’s flagship application at www.replytosome.com.

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