A serious case for inviting whimsy
Sometimes you need to combat the beige, joyless vacuum of a cubicle farm.
Last year I wrote about my deep and abiding love of Dungeons & Dragons β it was my second entry, only four days after I was removed from my job at Catholic Charities of St. Louis.

What I didn't realize at the time? In my next role, there would be a number of fellow fans and players on the team that I was hired to lead.
And future hires would be compelled to learn and love the game, too.
It's become somewhat of a running joke that β when I am interviewing someone for an open position on my team β I have to ask them whether or not they love Dungeons & Dragons to determine their fitness for the job!
Eventually during a weekly team meeting, as D&D super fans, we're going to build character sheets to help us better understand one another and make very important business decisions (πππ). But we've started small.
For now, we roll Meetings checks.
Our entire department meets bi-weekly in a big, fancy board room. With fancy, leather-look ergonomic chairs, a fancy (though usually malfunctioning) A/V system, fancy room lighting and climate controls, and fancy stadium seating. Fancy. Professional. Polished.
(Boring.)
Until someone on my team walks in with a 20-sided die (a D20) and proceeds to perform a Meetings check. We roll before the meeting begins, and whatever number comes up will indicate β ceremonially, at least β how good, long, or interesting the meeting will be.
Roll a one? Buckle up. It's going to be a long, boring, stupid meeting.
Roll a 20? That's an automatic critical hit, for the uninitiated β and it's gonna be a good meeting!!
There are other roll-based mechanics Iβve dreamt up. I have considered implementing a Leave Early check. If anyone on the team rolls a Natural 20 when prompted, they get to go home early.
(I haven't made good on that one yet, but I am also not opposed to it.)
Do we look like a group of infantile dorks with a silly shared ritual like rolling Meetings checks? Will Leave Early checks get extreme side-eye from other key decision makers if I allow them?
Yes, to both β and perhaps thatβs kind of the point.
Either way, Iβve learned over the years that whimsy is a powerful (largely underutilized) leadership tool.
If this kind of content resonates with you, I write all about Oddball Leadership every week!
No spam, no corporate jargon. Just real leadership, observed in slightly (or very!) strange ways. πππ

