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In defense of leading with humor

(April 8, 2024 Newsletter)

When was the last time you and your colleagues had a good laugh together?

A few days ago, Facebook reminded me of this old picture and it put a huge smile on my face. In the photo, I’m pouring water on my boss while he’s blindfolded (we were either preparing for or debriefing from a trust walk during a staff retreat).

  • It might seem counterintuitive to risk damaging the trust I had with my boss by taking advantage of the fact that he’s blindfolded, but I assure you that after my bold choice, his only responses were shock and laughter.

What I love so much about this picture is that it is one of countless times in the years I worked with him when we had a really good laugh while taking our jobs extremely seriously.

It also left me with a mix of nostalgia and sadness, as I was reminded of how often I used to describe my work as “serious fun.” I don’t know if it’s because of how my work as evolved, my age, or the era we’re in, but it definitely seems like fun is less present at work for many people these days. I’m curious if this is – or isn’t – your experience… please reply and share.

Why it matters:

We spend many of our waking hours working – with all the seriousness we deal with, don’t we still want that time to be enjoyable?

How times have changed…

A quick google search of “humor at work” brought up an HBR article and TED Talk from 2014 both making the case for using humor as a leadership tool. The author and speaker describe the many benefits and encourage us all to try it out.

And yet, as I’ve cited several times over the last few weeks, a recent HBR article about “The New Rules of Executive Presence” relegate humor (specifically “joking and bantering”) out of the top 6 communication traits associated with “executive presence.”

  • This lines up with pushback I got in a webinar about 2 years ago from a group of young managers when I suggested that humor can be a fabulous tool to diffuse conflict. Many of them vocalized that this would be unwelcome, and even inappropriate, which I found shocking at the time.

Let’s make some distinctions:

I hear the fear among some of you – not wanting to offend, not wanting to seem out of place. Those are legit concerns, of course.

  • So let’s separate out a few terms: humor, joking, bantering, levity, and fun aren’t the same. Which do you want your organizational or team culture to include?

  • And we can also agree that humor at the expense of people is unwelcome – we should discourage the kind that belittles, marginalizes, or otherwise others. But so much of what puts smiles on people’s faces and brings them together is far away from that and not worth throwing out with the bathwater.

As always, start by setting the example

Your team is closely reading your energy, like all the time. Whether you’re physically present in the same office or communicate primarily over Slack, Teams, or email, they’re scanning your cues for what’s acceptable and how to win your favor.

  • So if you want to start making work a little lighter, add a meme to the end an email. React with a unicorn emoji instead of a thumbs up when someone makes a good suggestion in Zoom chat. Give silly names to projects.

  • During your next offsite, plan a funny activity whose only purpose is bringing people together – or better yet, ask someone who’s funnier or more creative than you to do it.

  • Add in an occasional ritual to meetings that will put a smile on people’s faces.

  • Once you do it enough, you’ll notice that some team members will feel permission to do the same.

Of course, I’d love to hear your examples – what have you seen work? What have you learned from attempts that didn’t?


The Coaching Corner

Keep your questions short


I love the phrase “God gave us two ears and one mouth for a reason.” If you want to have your team members do most of the talking in 1:1s, be conscious of the length of your questions. Here are some short and sweet examples:

  • In what way?

  • And what else?

  • Because…?

  • What do you think?

  • What’s next?

  • What are your options?



In addition to the TED Talk and HBR articles above, I found this article “5 Powerful ChatGPT Prompts To Supercharge Your Content Marketing” thought provoking. I believe that we’re just at the beginning of using generative AI tools to our benefit, so if you’re looking for some ideas of how to use it well, check out these suggestions.


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