Humor is a leadership superpower

“A cultivated wit, one that badgers less, can persuade all the more. Artful ridicule can address contentious issues more competently and vigorously than can severity alone.” - Horace

The case for being funny

Humor is a leadership superpower 🦸 It removes tension, creates a bond of camaraderie with those you lead, and binds your team with a sense of optimism as they face challenges. I’m not talking about knock-knock jokes or a well placed GIF (though both are great), I’m talking about using humor to build bonds and remove tension when it inevitably arises throughout the context of your life as a leader.

Tactically speaking, humor is one of the best ways to keep your team focused and engaged when the deck is stacked against them.

3 ways you can cultivate humor as a leader

Being funny is hard, but injecting a bit of humor into your leadership isn’t. Here are 3 common ways I like to do so.

1. Self deprecate

2. Use props

3. Make a pattern, break a pattern

Self deprecate

Of the ways to add humor to your leadership this one is the easiest, but also the easiest to overuse.

2 ways to self deprecate in a healthy way:

1. Make fun of your brand

2. Folksy family wisdom

Make fun of your brand

Note, an underhanded compliment to yourself is not the right way to self deprecate. For example, if you are the best Cold Caller on your team you don’t want to say something like, “25 meetings scheduled this week, what a dud!” This will come off as arrogant (duh). On the other hand making fun of your brand, essentially becoming a caricature of yourself, works.

Let’s take the same example, instead of giving yourself a phony compliment (which your team will see through) you could say something like, “You know me, never met a phone I didn’t want to blab into.” The difference is subtle, but important.

You can always self-deprecate by leaning into and poking fun at your brand (we all have them) but don’t do it as an underhanded compliment to yourself.

Folksy family wisdom

Another effective way to self-deprecate is to tell a humorous anecdote about your family. I call this the “folksy family wisdom” trick. It works because it’s a subtle way of poking fun at yourself which also connects your team / audience with members of their own family and brings a smile to their face.

The best way to do this is to take a theme, connect it to a specific family member, and tell the tale. I find the further back you go generationally the better the joke lands.

For example, “I learned everything I needed to know about closing deals with confidence by watching my Grandpa steal a 30 pound chair from a 5 star restaurant.” (true story)

David Sedaris is the master of the “folksy family wisdom” technique. I recommend reading his essays, or other humorous essayists, to get a feeling for ways you can weave their humor into your leadership.

The 2.0 version of the “folksy family wisdom” technique is to start a presentation with your story and then continuously weave the story back throughout the course of your presentation. This is a technique in comedy known as callback humor which is easy to emulate and very effective.

Use props

Tactically, prop humor is an excellent way to break up your routine and get a couple laughs. I was catching up with a friend the other day, he is very funny, asking him about simple tactics he uses to interject humor into his work and this was the first technique he mentioned.

Prop humor is great because it can be easy to use even if you don’t necessarily think of yourself as funny. It also works well in both a virtual and in-person environment. Think about iconic movie props like the coconut halves vs. the horse in Monty Python and the Holy Grail. Simple, silly, and easy to execute.

I once gave a wedding toast at a wedding in Wisconsin (I’m from Minnesota) where I proclaimed I would be a Green Bay Packers fan 🧀 for the evening by pulling a Packers hat (the full cheese head didn’t fit) out of my tuxedo pants and wearing it on my head. I can almost guarantee no one at that wedding remembers the content of my toast, but that most people remember the Packers hat which became a prop for the rest of the night.

Something as simple as a Zoom background mixed with a bit of misdirection can be a useful way to use props to lighten up the mood on your team. For example, you might be known as a more straight laced Marine (like me) so if you join a meeting in front of a large group with an animated Zoom background of a flying unicorn and start the meeting by saying something like, “I know what you all are thinking, did he get a haircut?” you’ll set the tone for the meeting and have a simple bit which you can continue to reference.

Make a pattern, break a pattern

The old bait and switch is a simple tactic you can use to be a bit more humorous as a leader regardless of your natural comedic tendencies. This is one of my favorite ways to script out a specific line, joke, or bit prior to a meeting.

Commonly referred to in comedy as the “rule of three” this is a technique where you list three items with the first two clearly aligned with the pattern and the third a deviation. The key with the make a pattern, break a pattern tactic is to bring your team / audience along with you and then introduce a contradiction.

The idea here is to keep things simple, something like, “I love Cold Calls, commission checks, and lists of 3”.

Try scripting out a few different make a pattern, break a pattern lines as introductions before your next team meeting or large group presentation. It’s a good way to loosen up your team and get them laughing before you bring them through what is, I’m sure, an otherwise thrilling presentation (who doesn’t appreciate a well designed slide).

Humor and storytelling

I believe that humor is a leadership superpower (and important for any leader to cultivate whether they think of themselves as funny or not) for 2 main reasons:

1. Levity injects a sense of optimism while projecting confidence

2. Stories help connect your team to your message so that it sticks

Telling better stories is a leadership imperative and leveraging story telling in order to close deals will be a blog post unto itself. For now, try one of the 3 techniques discussed in this post in one of your next team meetings and let me know how it goes.

The good news for you is that the barrier for comedic entry as a Sales Leader is very low. If you pay $100 for tickets to see Eddie Murphy’s stand up he has to be very funny. If your team is dialing in for your Monday morning meeting their expectations are low. Even a small amount of humor can help draw your team in with the messages you have for them.

Anyone can be funny, I promise. See ya’ll next week.

P.S.

🚪 Bonus points if you respond to this email with your favorite knock knock joke