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 — 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 — when I am interviewing someone for an open position on my team — 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 (😆😆😆). 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 — ceremonially, at least — 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 — and it's gonna be a good meeting!!
There are other roll-based mechanics I’ve 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 — and perhaps that’s kind of the point.
Either way, I’ve 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. 😎😎😎

