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10 most embarrassing moments in business

COMMENTARY For politicians, embarrassing moments are usually seen live or caught on video, providing endless fodder for comedians, late night talk show hosts and YouTube users. Who can forget Howard Dean's primal scream, Sarah Palin's Katie Couric interview or President George Bush throwing up on the Japanese Prime Minister?

And Rick Perry forgetting the third government agency he'd get rid of? Priceless.

Corporate executives have the same sort of embarrassing moments, but critical customer meetings and big presentations are almost always held in private, and participants are usually pretty discreet about that sort of thing. Until now, that is.

When I look back over a long and eventful career, what stands out are the underdog victories, the unexpected defeats, and yes, those all-too-common embarrassing moments. They're not caught on video, but they may as well have been, since I'll never forget the times when I felt most fallible, humble...and human.

How not to impress a VC

As CEO of a startup desperate to raise a second round of funding, I was pitching to a prominent Silicon Valley venture capital firm. Finally, the moment came to reveal our brand new beta sample, a small technical marvel of silicon and fiber optics. It looked very impressive as I pulled it out of it's box and held it out for the VCs to see. Then it shattered in my hand.

Don't take your cell phone to the bathroom

I'd been sitting in a conference drinking coffee all morning, so when my cell phone buzzed, I stepped out of the room, took the call and made a beeline for the bathroom. Everything was fine until I flushed. There was silence on the line as my ad director -- a woman -- processed what she'd just heard and I realized what I'd done. And yes, when I got back to the office, I got a good talking to from HR.

Stay awake when the CEO is talking

It was a meeting between two very big companies in Japan. The participants were me, my CEO and our Japanese counterparts. While my boss was presenting, the other CEO fell sound asleep. He wasn't just dozing; he was out like a light and his VP did nothing but motion for us to continue. My CEO was presenting, my customer was snoozing, and I couldn't believe this was happening.

Don't make Bill Gates angry

I once let my guard down with a reporter and said something I shouldn't have said about one of my company's most important partners, Microsoft. Of course, the reporter quoted me. The next day I got an angry email from my Microsoft liaison that included a forwarded email from Bill Gates. In short, the message was more or less "muzzle that guy."

In Japan, you've got to sing

If you do business in Asia, you know that karaoke is a really big deal. It's like playing a round of golf or having dinner to celebrate a business deal, except after hours. Well, I've got the worst voice you've ever heard and somehow, over the years, I've managed to avoid having to get up and sing, until my counterpart from a key Japanese customer just about dragged me up on stage to do a duet. I couldn't refuse. The only thing worse than the way I felt was seeing the horror in everyone's eyes when they heard me.

Don't give your boss the finger

One day at work I ran out for a sandwich, stopped at the gas station, and somehow slammed the car door on my middle finger. Don't ask how I did that, but I did it. After a trip to the emergency room, my hand was bandaged and the finger was in a splint. That afternoon, at our quarterly company-wide communication meeting, I got up on stage to do my presentation, gestured to the CEO who'd just introduced me, and half the auditorium burst into laughter. My offhand gesture looked just like I was giving him the finger.

Whatever you do, don't forget the pitch

Back in the day we used to give presentations with plastic transparencies on overhead projectors. I was sitting in a relatively high-level customer meeting, waiting patiently as the sales manager introduced me -- the product line executive and featured speaker. I calmly reached into my briefcase to grab my presentation slides and realized in horror that they weren't there; I'd somehow forgotten them.

Remember your board director's name

Responding to a director's question during a board conference call, our new VP mistakenly called him by the wrong name. Our CEO didn't correct him -- probably figuring it was a one-shot deal -- and neither did the director or anyone else. But as the meeting went on, it turned into a dialog between the two, and the VP just kept repeating the wrong name over and over again. By then it was too late. I never told him, but I'm sure somebody did after the fact.

You can't always look your best

As a young manager at Texas Instruments, I had a serious car accident and although I was okay, half my face, which had hit the windshield, looked like a mask from a horror movie. The following Monday I had to give a big presentation and I was really self-conscious about the way I looked. When I stood up, people actually gasped. To break the tension, I told them I'd cut myself shaving that morning. It worked, but still.

Don't drink and blab to the press

Back in the heyday of the PC industry, I was a relatively high-profile marketing chief for a microprocessor company that competed with archrival Intel. Chatting with a friendly reporter at a party during a Las Vegas tradeshow, I casually mentioned having all sorts of Intel paraphernalia from my prior job, including T-shirts I could never wear in public. The following week an article appeared that said I wore "Intel Inside" T-shirts to bed at night. I never lived it down.

Hey, if you can't laugh at yourself, you have no business laughing at anyone else. Share your most embarrassing moment in the comment section. Try it; it's cathartic.

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