The 11 Best Business Etiquette Tips of the Millennium?

My friend and colleague Ross McCammon recently gave me a scolding over email.

I was in the middle of writing him a note when I prematurely hit "send." So I immediately sent him another email with the subject line "Oops," and explained my mistake in the text of the note.

Ross wrote back: "Oops is the worst subject line. The worst. It’s unsettling. Could mean nothing, but it could also mean 'I just torpedo'd your career' or 'I lost your dog' or something. I don't know why you did the oops." 

Maybe I should have been insulted, but I wasn’t. I loved the tough love.

First, he's right. Second, he speaks from a place of authority.

Ross is an editor at Esquire, but he's also the etiquette columnist at Entrepreneur magazine. And he's written a new book called  Works Well With Others: An Outsider's Guide to Shaking Hands, Shutting Up, Handling Jerks, and Other Crucial Skills in Business No One ever Teaches You. 

It's hilarious and massively useful, and one of my favorite business books ever, with advice about interviews, speeches, collaborations, clothes and the art of not being the office jerk.

I've known Ross for a long time — he took over my Esquire magazine office when I began working from home. I don't remember this, but Ross tells me that I left him just one welcome gift: An all-Braille version of Playboy magazine that I’d been sent for reasons that remain mysterious (this was when Playboy still published nudes). But I honestly believe I would rave about Ross’s book even if he was a total stranger who had never smacked me down for writing 'oops.' 

Here's a sampling of my favorite advice from Works Well With Others:

1. EMAIL LIKE DE NIRO

Ross writes, "I propose an emailing approach that amounts to a single question: 'What would Robert De Niro type?' You get an email. You read that email. You respond to the email as if you were Robert De Niro. You will find that your email responses will involve messages like: 'Sure' and 'great' and 'Yes' and 'No' and 'Perfect' and 'Sorry.'" 

(Ross adds an additional wise email rule: "Not only should you assume that every email you send will get forwarded to someone else; you should assume that every email you send will someday be read aloud in a court of law").

 2. EMBRACE IGNORANCE

Ross tells the story of going to a dinner his first week at Esquire, and the conversation turned to an assessment of documentary director Werner Herzog. Someone asked Ross his opinion of Herzog. Ross spouted some rubbish about how Herzog's later work was derivative. "I should have said, 'I have no idea who that is.' When we have no idea what’s going on, we should always say, 'I have no idea what you’re talking about.' I love it when people enthusiastically admit ignorance. If a job candidate says, 'I'm sorry. I have no idea what you’re asking. Can you please explain?' during an interview, I consider that a positive – they seem honest, curious and exacting." 

3. SMILE

"Smile 20 percent wider than feels comfortable. You want to give it the ol' Julia Roberts. If you’re not feeling a little stupid, then the smile’s not working." 

 4. MAKE MISTAKES   

"The main failure of my first couple of years in New York was the shame I felt at making mistakes…I was too caught up in the fear of making mistakes. I sometimes acted timidly. In the short term, I probably did 'better' work, but in the long term I did worse work because I didn’t allow myself to get my mistakes over with early."

 5. MAKE EYE CONTACT IN THE JOB INTERVIEW

 "Do not look down, to the side, through them, at their chest, into their souls. Look everyone in the eye. Studies show that interview candidates who maintain a high level of eye contact are judged much more favorably than those who don’t." 

Ross adds this other tip for interviews:

"At some point, toward the end of the interview, consider saying, 'If you throw me out of here right now, this will have been the greatest thing that’s ever happened to me.' It works. As long as you believe it."

 6. DON'T GET BORED

"As you're pitching, ask yourself one crucial question: Are you bored? Because if you're bored, then whoever you’re pitching to is going to be REALLY bored. And if you're bored, you’re probably bored because you’ve buried the point." 

7. WHEN SHAKING HANDS, GET UP IN THERE

"With handshakes, the key part of your anatomy is not the palm, but the weblike area between the thumb and forefinger. That’s the adductor pollicis muscle. The way to firmly shake a hand is to perform a meeting of your adductor pollicis muscle with the other person’s adductor pollicis muscle…You want to 'get up in there.' You want to rock the other adductor pollicis’s world. But only for a second." 

 8. OPEN YOUR MOUTH WHEN MAKING A SPEECH

"Open your mouth wider than normal. Like the opera singers do. Wider. Speak louder. Louder." 

 9. BE DELUSIONALLY CONFIDENT

"In business, you must assume that everyone is rooting for you." 

10. WEAR DECENT CLOTHES.

Ross writes about Columbia University researchers who studied the phenomenon of "enclothed cognition." Which means clothes affect your thinking.  "Among other things, the Columbia researchers found that people who wore a doctor's coat showed higher attention to detail during a task than those in street clothes. The conclusion: Clothes can actually put you in a different psychological state. Think of your favorite shirt or dress. Its power doesn’t lie so much in how it looks but how it makes you feel.”" 

11. BE INTENTIONALLY IMPERFECT

Ross takes some wisdom from 16th  entury Italian courtier Baldassare Castiglione, who wrote his own etiquette guide. Baldassare said: "Practice in all things a certain sprezzatura [nonchalance] so as to conceal all art and make whatever is done or said to appear to be without effort and almost without any thought about it." Ross points out Esquire's style editors are great at sprezzatura. They always make sure "the photos aren't perfect – just a little bit 'off.' In one photo a collar was a little askew. In another, the subject wasn’t wearing a belt.' Your work should not be perfect. Your work should be wrinkled. It should show wear, and it should indicate that you’re trying new things and taking chances." 

And one final bonus piece of advice from me:

12. AVOID RIDICULOUS SUPERLATIVES SUCH AS "THE GREATEST X OF THE MILLENNIUM." Sorry. I know I broke my own rule with the headline, but I really did want you guys to read Ross's wisdom. Blame it on sprezzatura! 

A.J. Jacobs is the author of several bestselling books including The Year of Living Biblically and Drop Dead Healthy. He is also founder of the Global Family Reunion.

Ross McCammon 

Credit: Spencer E. Cohen