“A bad email reputation is like a hangover: hard to get rid of and it makes everything else hurt.” – Chris Marriott

When the story first broke by the Wall Street Journal about controversial email exchanges between Las Vegas Raiders coach Jon Gruden’s and former Washington Football Team president Bruce Allen, I let out a long sigh. The trove of email, uncovered as part of a workplace misconduct investigation, painted a particularly ugly image of the longtime coach. The initial story barely scratched the surface of the entirety of the exchange, which went from bad to worse about as fast as a typical season for fans of some football teams. I pushed back from my desk while pondering the wisdom of a former boss.

“Never write anything in an email that you don’t want to see on the front page of the New York Times.”

To be fair, this was The Wall Street Journal, but the outcome was the same. As the release of the emails gained steam, Gruden was forced to resign, stripped from the ring of honor in Tampa Bay’s Raymond James Stadium, and became the impetus behind a much deeper probe into the conduct of team executives across the league. The Gruden effect is going to be felt around the National Football League for a while, and there are more than a few people today who have good reason to be worried.


Email has been around now for a while, so stories like this no longer have that cautionary feel to them. Most people should know better than to commit to digital record the kinds of things Gruden wrote in his emails. But not a day goes by when we’re not reading a similar tale of woe. When the Guardians of Peace hacked Sony Pictures’ systems and accessed company email servers, they found a culture of entitled intolerance that left the filmmaker reeling from public outrage. And I wouldn’t be surprised to learn that Hillary Clinton never wants to hear the term “email” again. Ever.

Like the internet, email is forever. Once it’s out there, it’s out there. If you’re someone who has a tendency to bare their soul in email, you stand a good chance of everyone discovering what really goes on inside your head. If you’re the kind of person who leans toward ad hominem attacks in your emails to others, you might wake up one day to find that the wrong person knows exactly how you feel about them. Or, if you like to use racist, sexist, or other -ist language when safely perched behind your keyboard, there’s a strong likelihood that the day will come when that bad Karma comes home to roost. And that’s going to be a really bad day when it happens.

But it doesn’t have to be that way. You don’t have to experience the Gruden effect or impose it on others. While Gruden couldn’t exactly unsend his own emails, you have a choice. You can choose not to be “that guy” in your email exchanges. You have an opportunity to rethink the language you use in your message traffic. You don’t have to hit “send.” It was too late for Gruden; it doesn’t have to be too late for you.

How to Not be on the Front Page of the New York Times

A quick check of Google will reveal any number of listicles concerning email etiquette. Those include everything from including a clear subject line, stating your “ask” up front, and not sending an email when you’re compromised (drunk, distracted, emotional, etc.). What they don’t always include is advice on how not to become the subject line of your own email. Or how to avoid ending up on the front page of the New York Times.

1. Someone else is looking.

Assume your email will have unintended readers. This applies in both the case of the New York Times or the office genius who forwards emails without thinking. Don’t include content you don’t want widely shared, ad hominem attack on others, or language that might leave you on the unemployment line.

2. Brevity is next to godliness.

Keep things clear, simple, and direct. The longer your email, the more likely you are to ramble or write something that just isn’t necessary.

3. You’re not as funny as you think.

Humor in an email is often misunderstood and easily misinterpreted. You’re not Dave Chappelle. If you find yourself giggling over your own email, don’t send it.

4. Your personality is showing.

Personal comments, emojis, and over-familiarity are also often misunderstood and easily misinterpreted. Keep things professional. You won’t have as much explaining to do when you inadvertently send your boss an email signed with robot and fist emojis.

5. Email is not a fire-and-forget system.

Long after you’ve moved on, the emails you sent will still be on a server somewhere. If you’re not smart, these can become modern day skeletons in your closet. And there’s nothing quite as embarrassing as having someone open the closet and start asking questions. Remember that when you’re thinking about hitting “send” on an email. Do you want to be answering questions about that email in ten years?

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Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a senior fellow at the Modern War Institute; the co-founder of the national security blog, Divergent Options, and the podcast, The Smell of Victory; co-founder and former board member of the Military Writers Guild; and a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal. He is the author of five books, numerous professional articles, countless blog posts, and is a prolific military cartoonist.