Adding humor to your presentations can give you edge

Part I of two-part series


I had the privilege of hearing you speak recently at a SCORE presentation in southern Connecticut, and I’ve become a big fan of your small business lecture series on YouTube.

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 reread this totally unsolicited email I received this week. You would be amazed how often I receive emails 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 his 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 also shows my complete confidence, if not fearlessness, in my abilities. If someone can be lighthearted in times of great stress, he must really know what he is doing. Hawkeye Pierce from the TV show “M.A.S.H.” was not a great surgeon, but his persistent wisecracking and 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, 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, “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 1990s murder trial. That whole business of waving the bloody glove around while 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 to life in prison, not because the evidence doesn’t add up but because they could never live with themselves if they were to do so.

You cannot hate someone who makes you laugh. This is why dramatic actors are referred to as “great” but 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 lighthearted 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, Jonathan Winters, Buddy Hackett, 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 mic 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.

Watch for conclusion of the story next week.•

Cliff Ennico ( is a syndicated columnist, author, and former host of the PBS television series “Money Hunt.” Opinions expressed are those of the author.

© 2019 Clifford R. Ennico

Distributed by