When to Hire the Wildcard

If you want advice on who and when to hire, it’s not hard to find. In fact, I’ve written more than my fair share of “advice about hiring” articles too. It’s good, dare I say, vital information. Not to be taken lightly. It’s also often incomplete. Here’s why. At some point, you will be confronted with the chance to hire a “crazy person.”


Now, I’m not talking about a literally insane person. I’m talking about the sort of person some people on your staff may describe as “crazy.” They might even say it about themselves. Not in a pejorative way, mind you, but the description may just be apt. I’m talking about the non-conformist, the wildcard, that hyper-creative and “crazy” talented person you encounter from time to time. He or she doesn’t necessarily fit in your scheme as designed, but they are too good to pass up. They may not even have a designated role or purpose on your team, but you know you are better with them than without them.

In professional sports, this is the “super athlete” that can play any position, he’s so good a team will draft him even if they don’t need anyone at that position. They know he will make their team better.

The same thing can happen in business. You come across an individual that doesn’t quite fit, but they are so good, you are willing to find a way to make them fit. Here’s the kicker, if you get the genuine article, you will not need to do much “fitting” … these folks can find a way to gel without your help. In fact, they might just be better at finding their spot than you are in making one for them.

Now, don’t be fooled. There are a fair number of imposter wildcards out there. These are people who think they can “play any position,” or they just aren’t happy where they are, and they’re willing to “do anything” for advancement. Problem is, they CAN’T do anything. They are good at some things and work best where they are…even if they argue otherwise.

The genuine article wildcard may not be in “business” at all. They may be a struggling filmmaker, a serial entrepreneur or a member of a community theater group who “always thought they were too creative” to succeed in a business context. But, if you have the courage and fortitude to bring them in and allow them to be brilliant, you might just find a tremendous addition to your team.

Jonah Engler is a finance expert and a business owner who hails from New York City.