Using Humor Effectively in Conversations

Using humor effectively in conversations can enhance communication and build stronger relationships.

By Matt Miner
communication relationships humor

Humor

One of the most attractive qualities of a person is their sense of humor. Being drab and serious is the quickest way to avoidance. Humor is a superpower that unlocks trust.

Having confidence to be humorous can be difficult for some, but worry not! We have some tips that will help.

Self Deprecation

The most common target of your jokes should be yourself. It signals to others that you don’t see yourself as “perfect”. These aren’t knee-slappers, but it’s a great go-to technique used by comedians to connect their humanity with the audience.

This is related to the practice of accusation-auditing (signaling to your audience that you think they have the upper hand).

“I’m going to tell you about the meeting—knowing me, I’ll go on a wild tangent again, but that’s the spice of talking with Matt, but I’ll try to keep it on the rails.”

“I can’t stand peanut butter and chocolate. You may think I have bad taste, but what I’m about to demo is so good, it might make you re-think peanut butter cups.”

Punching Up

Light ribbing about folks with power in your organization can work well. Your people will appreciate that you’re willing to engage with a leader and remind them of humanity.

Who are valid punch up targets? Leaders,

Rules for punching up:

  1. Do so only when that person is present. Otherwise it’s back-stabby and poor taste.
  2. Do so in moderation, they’re people too, and if you make it too consistent you can build a reputation for singling out an individual.
  3. If you find yourself as a target of a light roasting, take it as a compliment! Roll with it with positivity and a smile.

Joke Sourcing

You don’t need to be a master of joke writing. There are myriad rules of jokes and humor, like “rule of three” and expectation subversion. But you’re not a professional joke-writer or comedian, use resources as a short cut, like joke books (one is built into ClarityBoss).

Good Jokes

  • Always, 100% “safe for work”. The cliche “dad joke” is the sweet spot. Puns won’t win you awards at a comedy festival, but they will absolutely keep you out of HR’s office. In today’s climate, jokes about religion or politics are out of the safe zone, unless it’s an agnositc joke about “all politicians”.
  • Use quick call and response type jokes. Knock knock is about as long of a joke as you can tell. Jokes with long setups are brutal, in a business context folks have distractions pulling their attention, and your 5 minute joke is not a priority.

Bad Jokes

  • Never ever ever make jokes about your direct’s income or their employment. They are working to provide for themselves and their family. Calling that into question for a joke is a massive loss of trust and safety.
  • Do not joke at the expense of a client or partner, even if you think you’re following the “punching up” rule. Doing so in private settings can be a pressure relief, but repeatedly it can cause a trend of jadedness that can cause long term harm.

Captive Audiences

Don’t assume you’re actually, truly funny because your directs are laughing. If you’re in a context in which you’re in charge, you have a “captive” audience. Your audience is compelled to laugh, because you’re the boss, and they don’t want to offend you. All the more reason to be humorous and move on.

Time for Seriousness

Being humorous has an additional benefit. It provides a stark contrast when it’s time to convey seriousness. If you’re delivering a serious conversation or announcement, the absence of humor will be noted and understood by the audience.

Reading list

  • Humor, Seriously
  • Culture Code
  • Pretty Good Joke Book: A Prairie Home Companion