Jon Carson | Crain's Connecticut

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Jon Carson


CollegeVine is a college prep company and education consultancy based in Cambridge, Mass.

The Mistake:

Back at another company that I had been a co-founder of ... I made three bad hiring decisions. I think the talent was mostly there but they were what I would call “bad apples.” One bad apple can set off the worst in others.

They were highly confrontational toward other team members if those people didn't fully agree with them. All three had a very difficult problem ever admitting a mistake. So they created an environment where the trust, which is sort of the currency of the realm for teams, began to corrode, and a walking-on-eggshells dynamic began to take hold in the organization.

The three of them actually didn't like each other, so they sort of set each other off. And they were building fiefdoms, like cults of personality, so their own teams were led to believe that they were embattled and that only their leader could protect them from the rest of the company.

The mistake was in hiring them and in not having the courage of my convictions. Like a lot of people, I don't particularly like firing people, and ultimately, I had to fire all three. I was not at the time particularly well-versed in how you manage these complicated people.

One bad apple can set off the worst in others.

The Lesson:

I learned first to recognize the symptoms of a bad apple. I learned that you have to move sooner rather than later, because this sort of toxicity starts to bleed out.

I'm pleased to say I've never made a bad hire since. I hired a professional organizational therapist, and he helps me sort through new hires, so I never interview somebody without gauging this individual first. I get more data. It's very clear all three of these would have been flagged if I had used this guy up front. I also dig much harder on back-channel references, and there's a much more extensive interviewing process and a whole bunch of different questions that I ask.

You can't afford not to—and it's not that much money. It's under $2,000, and I don't do it for every hire, it's only just the senior team. But the amount of risk reduction that's provided is basically like buying insurance.

One of the tests that the guy administers—I'll never forget it—is sort of a triangle that has different personality attributes, whether you're collaborative or aggressive or analytical. And it shows where you sit in steady state, and where you go when you're under stress. What you look for is people who don't move terribly far when they're under stress.

Follow CollegeVine on Twitter at @collegevine.

Photo courtesy of Jon Carson

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