My 5 biggest hiring mistakes

I recently had lunch with a B-school colleague who’s an investment banker. Her philosophy:  “If every investment you make pans out, you’re not taking enough risk.”

I thought about that, and it’s true. My current gig entails hiring a lot of people very quickly, and it’s not unlike investing: you apply logic to a limited set of data, add a dash of intuition, then cross your fingers and hope for the best.

I’m not the last word in hiring strategy, but I’ve hired 70 people over the past 15 years, and I like to think I’ve out-performed the market.

Some of the best hires I made were people I took a chance on–they didn’t meet all of the job qualifications, but they seemed smart, eager, and honest.

Some of the worst? Well, here are my top 5 (so far):

1. The Insane Person. She met all of the qualifications. Okay, she kind of had the Ally Sheedy Breakfast Club thing going, but I figured a little quirkiness might shake up the status quo. It did.

2. The Genius. He met all of the qualifications, in addition to acing his SATs and majoring in Astrophysics. Only problem: he didn’t like to do stuff that was beneath him–for example, work.

3. The Weird Guy Who Picked His Skin. He met all of the qualifications. We’d interviewed a lot of people. We were tired. We needed to hire someone.

4. The Guy Missing a Tooth. He met all of the qualifications. I didn’t want to judge based on appearance. Maybe he had a good reason for not replacing his missing tooth.

5. The Champion of Principles and Fighter Against The Man. She met all of the qualifications. Stubborn as a mule, and always an axe to grind. Drinking a Diet Coke meant you supported the labor practices of some evil Communist regime.

So my advice here is pretty simple:

• If you want to out-perform the market, you have to take risks.
• You’ll strike out a few times, but you’ll hit a few home runs.
• When in doubt, care less about whether  they’ve had x years experience in industry y using software z.
• Care more about whether they’re smart, eager, and honest.

 (Having teeth is also good.)