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What Looks Like Bad Email Etiquette Could Actually Be 'Strategic Sloppiness'

What Looks Like Bad Email Etiquette Could Actually Be 'Strategic Sloppiness'
Strategy2 min read

Evan Spiegel Snapchat

Video screengrab/AllThingsD

Evan Spiegel, CEO of Snapchat

As email is the preferred form of communication between professionals today, following email etiquette rules is especially important.

But since everyone is following the same rules, ignoring them completely will definitely make you stand out.

This is what happened in late 2012 when Snapchat's CEO Evan Spiegel responded to an email from Mark Zuckerberg. In his email, Spiegel didn't have a proper greeting, failed to follow proper punctuation rules, and even included an emoticon.

Here's his response: "Thanks :) would be happy to meet - I'll let you know when I make it up to the Bay Area"

Although Spiegel's email has been called "cocky and arrogant," New York magazine writer Kevin Roose writes on LinkedIn that the email was also "brilliant."

"By one-upping Zuckerberg's breezy, informal style in his reply, Spiegel positioned himself as the CEO's equal," says Roose.

"Call it 'strategic sloppiness.' We've known for years that the higher you are on the food chain, the more license you're allowed to take with the rules of professional communication. It's why Michael Bloomberg can reply to emails with "tx" instead of spelling out "thanks," and why many of Amazon CEO Jeff Bezos's emails to his subordinates consist of only a single question mark, appended to the top of a customer's email. As the boss, you can make as many mistakes as you want. Cutting corners is a time-saving mechanism that doubles as a display of dominance."

Although this is a power play, there are definitely some caveats and at the end of the day, unless you're a tech genius being pursued, you should probably take it down a notch. The best strategy is to sound informal and casual in your email while still using proper grammar and spelling rules.

Here are some other caveats Roose says to take into account:

  • Strategic sloppiness isn't right for every situation. In my experience, the ultra-casual approach works best when the person you're emailing is already familiar with you and your work, and interested in you for a job or a new project. It's risky with strangers, whose communication styles you don't know, and riskier yet with bosses, who tend to be older and more conservative, and might take your casual tone as a sign of disrespect.

  • It's probably best not to try sloppiness in formal job applications (especially if you're applying to be a copy editor).

  • Don't be sloppy in a way that will cast doubt on your intelligence and/or language skills. Typing "tx" instead of "thanks" is much different than mixing up "your" and "you're."

  • Strategic sloppiness doesn't work at every organization. The brash, misspelled cover letter that might get you noticed on a Wall Street trading floor might get you laughed out of an arts non-profit or a law firm.

  • Don't go overboard. The goal here is to appear important, not incompetent. One grammar mistake says "I'm too busy to proofread every email I send." Twelve grammar mistakes says "I did not pass remedial English."

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