There are two things you need to know about income taxes. The IRS has extended the deadline to April 18, and when you write your check, just make it out to “China.”

Sure, David Letterman might get away with a joke like that, and by no means should advisors start new client meetings with a monolog. But successful advisors know that targeted humor in moderation can serve an important communications purpose.

READ "TWO FINANCIAL ADVISORS WALKED INTO A BAR..." FOR SOME FUNNY - OR NOT SO FUNNY - FINANCIAL ADVISOR JOKES

At its best, humor can disarm clients. Very little value gets added when clients are tense or embarrassed. In the right hands, humor helps establish rapport or underscores a point in a memorable way. A humorous anecdote can disarm a prospect or client, especially when the subject is difficult, such as life insurance or long-term care.   

“We think humor is a huge differentiator when used properly,” says Steve Cody, managing partner of Peppercomm, a New York-based strategic communications and marketing firm that specializes in cultivating the tools of standup comedy to foster better professional communications. “Listening skills, handling difficult conversations, the ability to deal with silence; all of these strengths are honed by the tools of comedy.”

“It’s not about jokes, but telling authentic stories,” says Clayton Fletcher, Peppercomm’s chief comedy officer. “The more difficult something is to say, the more important it is to have a sense of humor and to acknowledge the tension of the actual situation.” 

One approach to a conversation about life insurance, for example, might go: “Today I wanted to talk to you about something that is easy for everyone to talk about, which is death.” It’s all in the timing.

Breaking the Ice

“I use humor as a way to bond with clients and to also break the ice on difficult topics, says Jason T. Wheeler, CEO of Pathfinder Wealth Consulting in Wilmington, N.C. “I have yet to run into a situation when a client reacted negatively.”

Wheeler often introduces humor as a way to talk about scenarios that many clients find uncomfortable. He tends to introduce such topics in a joking way and then shifts to a more serious tone. For example, when tackling the subject of life insurance and the specific amount that a client needs to protect his or her partner—always a fraught topic as it references the client’s demise—Wheeler has been known to say:

This is what I call a “Spousal Replacement Protection Plan.” You’ll need to have enough money in life insurance that will create a lifetime income stream for your spouse so that she doesn’t have to replace you with another spouse!”

Wheeler usually gets a good laugh, and the tension of the moment is broken.

Candace Sallale, founder of Sallale Financial Strategies, a Raymond James Financial Services practice in Plainville, Mass., also broaches the subject of life insurance with a joke. If she believes the client will be receptive, she says, “OK, make believe you’re dead. What’s the first thing your wife needs to do?”  The client will attempt to say something and she’ll interrupt, “Hold it. You can’t speak up. You’re dead.” The point is made: The client doesn’t have a say when he’s dead, so plans have to be made now. 

The physiological research about humor backs them up. When people are tense, their ability to listen, empathize, and communicate is compromised. A well-timed laugh releases endorphins that relaxes muscles, lowers blood pressure, and encodes for memory. That’s why you can’t remember what you had for lunch, yet you can still remember knock-knock jokes from elementary school.  

Risky Business

Although Christopher Tasik, managing director and CFPR at Tasik Financial Strategies in Stamford, Conn., has a good sense of humor, he generally saves any attempts at humor for the third date and avoids joking about money, finance, or politics. Tasik knows how difficult humor is to pull off. At one point, he inserted some humor into a presentation and had it fall flat. “Nothing fatal,” he says, “but it made me more generous as an audience member when I go to a comedy club.”

Humor is tricky stuff. For that reason, Tasik will generally use humor when he’s convinced that he’s established good rapport with the client and has identified some common interests to joke about. “I take the view that the planning/investment relationship is just too serious of a topic and I would never want to risk a client or prospect interpreting something I say the wrong way,” he says.

Invoking Spider Man

Based in Rochester, N.Y., Westminster Consulting provides fiduciary advice, research, and counsel to institutional fiduciaries. To make the heavy material a little easier to digest, the company is known for referencing popular culture—The Simpsons, and popular movies like Spider Man—in its blog and in-house magazine, Confero.

“We know the principles of fiduciary responsibility and modern portfolio theory are often dry topics,” says Senior Researcher Gabriel Potter. “To compensate, our monthly newsletters and weekly blog posts actively try to engage our audience with humor.”

For example, an article on properly conducting due diligence on investment managers lifted lessons straight from The Simpsons.

As for sharing actual jokes with setups and punchlines, tread carefully. People these days are on edge, often manufacturing insults and grievances when none are intended. Still, sometimes the right joke or one-liner can defuse a situation or underscore a selling point. The sidebar offers a number of advisor-tested jokes that may be appropriate for professional settings. 

If you must tell a joke, just remember one big guideline. There’s only one legitimate butt of jokes and that’s you. Everyone else—and that includes mothers-in-law and lawyers—are out. The only person or profession you can make fun is you and your own.