Jun 23, 2026 · 34 min · 14 segments
This week I’m joined by Jeff Arnold: five-time bestselling author, founder of RightSure (North America’s most awarded insurance firm), and a guy who somehow turned…
Kate DavisHost
When you were a business leader, were you serious? Did you find the humor to build the trust and all that? And how did you do that?
Oh, I think any great leader has to recognize the power of humor in the workplace, right? In the boardroom, in meetings, what have you.
I will submit this, that you want to be careful as a leader that some humor can be construed as bullying.
We can laugh at ourselves and avoid the kind of this failure mentality or fear of failure mentality.
So we used to meet, of course, have morning conference meetings every beginning of every morning for about 20 minutes.
At the beginning of each meeting, I want you guys to start using humor, find a joke.
One of the young folks raised her hand and said, well, we're going to tell a joke, but you're still here.

When you were a business leader, were you serious? Did you find the humor to build the trust and all that? And how did you do that?
Oh, I think any great leader has to recognize the power of humor in the workplace, right? In the boardroom, in meetings, what have you.
I will submit this, that you want to be careful as a leader that some humor can be construed as bullying.
We can laugh at ourselves and avoid the kind of this failure mentality or fear of failure mentality.
So we used to meet, of course, have morning conference meetings every beginning of every morning for about 20 minutes.
At the beginning of each meeting, I want you guys to start using humor, find a joke.
One of the young folks raised her hand and said, well, we're going to tell a joke, but you're still here.
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