For those of you who are intimidated by writing long professional emails or wonder how recipients feel about your emails (in the professional world). Enjoy! You need not worry anymore!

How Spelling Mistakes and Bad E-mail Etiquette Can Help You Get Ahead

Imagine that you’re the 22-year-old co-founder of a small but growing tech start-up. One day, you get an unexpected e-mail from Mark Zuckerberg, the billionaire founder of Facebook. In a short e-mail sent to your personal address, Zuckerberg praises your company, calls himself a “big fan,” and says he’d love to meet with you one-on-one at Facebook’s headquarters.

How do you respond? Most experienced professionals would probably advise you to calm down, take a deep breath, and write a courteous e-mail back, perhaps one that starts “Dear Mr. Zuckerberg,” and praises the CEO (he is, after all, one of your heroes) before saying that yes, you’d absolutely love to meet with him at his earliest opportunity, and sure, you’ll hop the next flight to San Francisco if he wants to meet today.

But that’s not what Snapchat’s Evan Spiegel did when Zuckerberg e-mailed him in November of 2012. Instead of flattering the Facebook CEO or expressing his eagerness to meet, Spiegel (whose disappearing-photo app hadn’t yet become a household word) tapped out a shockingly casual e-mail on his iPhone:

“Thanks 🙂 would be happy to meet – I’ll let you know when I make it up to the Bay Area”

That’s it – no “Dear” or “Sincerely,” no effusive praise, just a smiley-face emoticon, a sentence fragment, and a vague, unpunctuated offer to meet at some indeterminate point in the future. It’s the kind of e-mail you’d write to an annoying high school classmate, not a billionaire tech mogul who could acquire your company and make you rich.

Spiegel’s e-mail, which he released earlier this week after a Forbes profile characterized the exchange in a way he didn’t appreciate, has been called cocky and arrogant. And it was. But it was also brilliant. By one-upping Zuckerberg’s breezy, informal style in his reply, Spiegel positioned himself as the CEO’s equal. Most people in Spiegel’s position would have conveyed shock and breathless excitement over being approached by someone like Zuckerberg. And I’d bet that Facebook’s subsequent pursuit of Snapchat – the social network offered $3 billion for the app last year, an offer Snapchat refused – is partially related to the fact that Spiegel played hard to get, and dialed down his enthusiasm from the start.

In most business situations, it’s helpful to abide by the time-tested rules of communication – proper spelling and grammar, courtesy and professionalism, and all of that. But, as Siegel’s e-mail shows, there’s another approach that can be even better when you’re trying to impress someone.

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 whyMichael Bloomberg can reply to e-mails with “tx” instead of spelling out “thanks,” and why many of Amazon CEO Jeff Bezos’s e-mails to his subordinates consist of only a single question mark, appended to the top of a customer’s e-mail. 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.

But in certain, very rare instances, non-CEOs can also benefit from bending the rules.

For example: Like every blogger who writes about tech start-ups, I get barraged by press releases and pitches from PR firms touting the latest apps and gadgets. And 90 percent of the time, I delete these e-mails without looking. But the 10 percent I respond to are often the ones that depart from the formula. I can still remember the PR guy who introduced himself with an e-mail that read “what things can i send you that you’ll actually give a crap about.” It was direct, puzzlingly sparse, and shockingly informal. I loved it, and e-mailed him back.

For another example: Here’s a cover letter that got passed around Wall Street last year. In it, the writer, a kid applying for an internship at an investment bank, took a brutally honest turn halfway through: “I won’t waste your time inflating my credentials, throwing around exaggerated job titles, or feeding you a line of crapp [sic],” he wrote. “The truth is I have no unbelievably special skills or genius eccentricities, but I do have a near perfect GPA and will work hard for you.” The blunt, unpolished letter was a huge gamble, but it paid off – by breaking the rules, the kid stood out from every other applicant with a “To Whom It May Concern” form letter. He got several interviews.

Now, some caveats:

• Strategic sloppiness isn’t right for every situation. In my experience, the ultra-casual approach works best when the person you’re e-mailing 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 e-mail I send.” Twelve grammar mistakes says “I did not pass remedial English.”

Professional communication is extremely dicey territory with high stakes. So if you don’t feel comfortable using strategic sloppiness at your job, forget it. (If you’re uncomfortable, your e-mails will come off as forced anyway, which kind of defeats the purpose.)

But if you, like Snapchat’s Evan Siegel, want to show a powerful person that you’re important enough to be feared and respected, you might want to try playing fast and loose with your communication from time to time. If pulled off correctly, strategic sloppiness can be a great playing-field leveler. Just, please, no winky emoticons.