By Cliff Ennico

“I had the privilege of hearing you speak at last year’s eBay Radio Party, and again this year at the Sellers’ Conference of Online Entrepreneurs (SCOE) conference in Philadelphia.

You seem like a pretty smart lawyer, and you’ve got lots of good information, but the best thing about you is your ability to make the audience laugh. Seriously, until I heard you I didn’t think it was possible for anyone to make me laugh talking about income taxes, sales taxes, and tax accounting.

You have an amazing gift. When you have a moment, could you please share how you developed this talent?”

If there are any conference organizers or event planners reading this column, please re-read this totally unsolicited e-mail I received this week. You would be amazed how often I receive e-mails like this. Quite a few reviewers and bloggers have referred to me as a “stand-up comedian with a law degree,” and I don’t mind that at all. What they’re trying to say is that I’m not just a “typical” lawyer. Let’s face it, most lawyers aren’t funny. Nor are they expected to be. Nor do you hire them to be.

But my sense of humor is probably my biggest competitive advantage in the legal marketplace: I think I’m the only person on LinkedIn with “legal services” and “entertainment” selected as their two most relevant business categories. And when I sense a client is on the fence about retaining me for a legal matter, I always make a point of saying “and, you know, I can make a warranty about my services that I don’t think any other lawyer in the country will give you, at least in writing: at some point in our relationship, I will make you laugh.”

That statement not only humanizes me (the respondent almost always laughs at that moment), but shows my complete confidence if not fearlessness in my abilities. If someone can be lighthearted in times of great stress, they must really know what they are doing. Hawkeye Pierce, from the TV show “M.A.S.H.”, was not a great surgeon, but his persistent wisecracking irreverent humor held his combat medical team together during the depths of the Korean War.

So much of business and legal communication consists of “psyching out” people in a positive way. I can’t tell you how many times I have successfully defused a tension-filled negotiating session, or scraped a client off the ceiling after some bad news, or gently talked a client out of taking a legally disastrous course of action, by simply pointing out how ridiculous the whole situation was and putting it in perspective.

Criminal trial lawyers have always said that “a laughing jury never convicts.” And it’s true. Probably the master practitioner of this art was the late Johnnie Cochrane, the criminal defense lawyer who represented O.J. Simpson in his 1990’s murder trial. That whole business of waving the bloody glove around chanting “if the glove don’t fit, you must acquit!” over and over again was a brilliant piece of theater – a jury who sees how totally ridiculous the prosecution’s case is will never send a defendant to the gas chamber, or life in prison. Not because the evidence doesn’t add up, but because they could never live with themselves if they did.

You cannot hate someone who makes you laugh. This is why, while dramatic actors are referred to as “great,” successful comedians are referred to as “beloved.” You remember the comedians long after you forget the dramatic actors.

So how do you build humor and light-hearted banter into your sales pitches, your business negotiations, and so forth?

Well, of course, it helps if you’re naturally funny. In my case, I had no choice. My father – the hero of my childhood – constantly commented on the human comedy he saw at work every day, and taught me to respond in kind. As a young boy, perennially overweight and picked on by grade-school bullies, I learned that the best way to avoid a beating was to make your tormentors laugh. I memorized the best routines of Bill Cosby, Flip Wilson, Pat Cooper, Jackie Vernon and, ahem, Totie Fields (hey, I needed fat jokes) and performed them “live” for the acne-scarred multitudes in the hallways, the gym and the lunchroom. As a teenager in the late 1960s who bore a striking physical resemblance to Richard Nixon while wearing a pocket protector and carrying a briefcase everywhere he went, I learned that the only ways to attract girls were (a) play a varsity sport, (b) play the guitar, or (c) make them laugh. Guess which way I went?

As a young lawyer, I moonlighted by volunteering for “open mike nights” at New York City comedy clubs (I used a stage name and insisted on cash payment so my bosses wouldn’t find out). I also started including humorous stories from my life in bar association programs and professional meetings. Even when they fell flat, I never got bad reviews.

More next week . . .

Cliff Ennico (, a leading expert on small business law and taxes, is the author of Small Business Survival GuideThe eBay Seller’s Tax and Legal Answer Book and 15 other books. Follow him at @cliffennico.