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Humor at Work: How to Navigate the Minefield

Career Column
My commanding officer in the army turned towards me and said, “You tell jokes when you’re anxious, and it drives me nuts.” He and I were managing a high-explosives training range, including anti-tank mines. It was my first time at this task. I was on edge, which was reasonable, even for a lieutenant. To my disappointment, my attempts to lighten the atmosphere fell flat. You might say I learned that humor at work can be a minefield.

Here is what I didn’t understand: Your goal as a leader in tense situations is to direct and persuade, not to entertain. However, there are times where humor can lighten the mood and boost morale. The key to workplace humor is to aim for warmth and friendliness. Learn what works for you by listening to the humor of others and by testing your approach in low-pressure situations before going prime time.

Humor and warmth are tools of business leaders

You’ve probably observed a connection between success and humor. Properly placed humor takes the edge off a difficult or boring discussion, strengthens relationships, and lets you steer conversations easily and pleasantly. In Executive Presence: The Missing Link Between Merit and Success, Sylvia Ann Hewlett reports survey findings that confirm that successful executives have a “sense of humor and ability to banter.” It is one of six components indicating that you engage listeners, keep their attention, and, thus, have mastered an important part of business communications.

Humor contributes to winning team dynamics. Jeffrey Johnson, anthropology professor at the University of Florida, has studied the rapport of Antarctic explorers to support Mars mission planning. His findings apply to any group striving together towards a distant goal. The most successful teams have a mix of roles, including a “clown” who maintains team spirit and lifts morale.

Rauld Amundsen, who won the race to the South Pole, said his cook “rendered greater and more valuable services to the Norwegian polar expedition than any other man” by breaking the tension with humor and helping teammates with their nerves.  

So how do you navigate the minefield?

Given my past military experience, I’m careful of using humor at work to avoid a misstep. Humor that doesn’t fit can dilute the seriousness of your message (e.g., a joke that is too goofy) or make you seem sarcastic, bitter, or anxious (e.g., a comment that jabs the person with whom you are talking). But there is a path to employing humor judiciously and effectively:

Go for warmth

Communication experts recommend aiming for a friendly tone. You can have fun and show your sense of humor conversing “around the watercooler” as you walk the hallways and chat before meetings. Such humor is low risk because it is not directly connected to the ideas you present during a meeting. Strive for a warm, friendly interaction that might crack a smile or elicit a chuckle.

If you want to hone this craft, two-time Emmy-winning journalist Bill McGowan stresses the value of humor in his book Pitch Perfect: How to Say It Right the First Time, Every Time. He advises using a humorous story connected to your central theme.

McGowan highlights a TED Talk from Geoffrey Canada to illustrate the point. He talks proactively about the slow pace of school reform and starts by recounting a humorous exchange with his wife that introduces how angry he is about the problem. Watch how Canada rings an alarm bell with a sly grin, supported by hearty applause from the audience.

Pay attention to what others do

Listening to others speak is the perfect learning opportunity. McGowan points out that you can use such experiences to observe what works and what doesn’t. The politician, talking head, conference or webinar presenter, and rock star CEO each must earn your attention, so systematically assess each part of a pitch with a mental thumbs up or down. As an upside, this gives you something to do when the speaker is boring. Take heed of effective uses of humor in each context.


Use opportunities outside of work to develop your own brand of humor. Ensure repeated success at networking events, with friends, and at-home rehearsals before you use something in a major presentation, client pitch, or the boardroom.

Avoid canned jokes

As Judith Humphrey pointed out in Speaking as a Leader: How to Lead Every Time You Speak, jokes that you’d find in a book or circulating on social media usually don’t work because they come off as forced, and thus not particularly funny or apt. What’s more, they’re sometimes insensitive or derogatory to a group (e.g., What do you call 100 lawyers at the bottom of the ocean? A school of sharks).  Political jokes are especially risky and should generally be avoided.  

Encourage humor in others

Humor does not have to come directly from you. You can nurture it in your team or in other parts of the company. For example, you can allow for compliance training to have an element of fun, such as a trivia game with a mix of lighthearted and informational questions.

Or, while being mindful of tone, your team could include memes when making announcements. It is extra work to develop and not undercut the efficacy of the messaging, but it can be worth it. Ensuring that the environment you control is replete with warm, humorous, or simply smile-inducing content creates a productive workforce whose members appreciate how the legal team takes their feelings into account.  


Gradually increase your use of humor to a level you are comfortable with, and a level your team expects. It is harder to get the delivery right if it is not habitual for you or your audience.

Practical examples

Adding color to punctuate your message

During a presentation about AT&T’s merger with Time Warner this past March at the Dallas Bar Association, AT&T General Counsel David A. McAtee gave a captivating speech that stuck with me. Below is an excerpt of the speech where he highlighted what the merger meant for the combined company by explaining its upcoming plans:

We’re going to build a plaza downtown where you’ll have some of the first 5G in the country, which you can use to access CNN. And we are erecting a big screen so you and your friends can gather for special events like the Game of Thrones finale — it will look like the dragons are zooming across the sky.

This vivid imagery was more memorable and effective than the clichéd, “You’ll love our new bundles!” or corny “Why do Game of Thrones dragons sleep during the day? So they can fight knights.” (Apologies to pun enthusiasts.)

Talking to the business about compliance

Some of in-house counsel’s most difficult conversations involve providing guidance to a colleague about potential non-compliance. Sometimes, an easy touch of humor as an on the spot reaction can diffuse what might otherwise be a tense situation.  

In more serious situations, humor is less appropriate, but there are still ways to include a personal touch. You can have a multifaceted conversation, including:

  • Inquiring about the situation to better learn the facts and your colleague’s mindset;
  • Explaining why the issue is important; and
  • Providing a story, statistic, or proof to validate your point.

By giving depth to the discussion, you can make room for empathy and warmth. This is not necessarily a humor-driven method. For me, this is easiest when hearing my colleague’s story. I strive to listen and add comments that lighten the tone while not moving the conversation off track.

So, try it out: Practice humor, warmth, and friendliness throughout your business conversations. You will be more persuasive. Colleagues will appreciate it, and you’ll be able to find your way, and lead your team, through a minefield.

About the Author

Noah WebsterNoah Webster is general counsel and secretary for Zix. Previously’s Litigation columnist, he has since become the Law Department Management columnist after moving to a more generalist role in his career.

The information in any resource collected in this virtual library should not be construed as legal advice or legal opinion on specific facts and should not be considered representative of the views of its authors, its sponsors, and/or ACC. These resources are not intended as a definitive statement on the subject addressed. Rather, they are intended to serve as a tool providing practical advice and references for the busy in-house practitioner and other readers.