My Worst Boss Ever: Hard-Earned Lessons on Entrepreneurship and Leadership From Members of Boston’s Innovation Community

Bosses come and bosses go. Great bosses can inspire and mentor and lead through the toughest times. Really bad bosses can poison and divide an organization, and lead it to ruin even if things aren’t that bad.

In the course of my career I’ve come across many a successful person with a bad-boss tale to tell. Which means that bad bosses have mentored numerous entrepreneurs and future leaders—though maybe not in the way they intended. So what do these awful managers have to teach us? I asked a few leaders in the Boston innovation community for their best worst-boss stories, and the lessons they learned from the experience.

My own “worst-boss” is really an amalgamation of several bosses rather than a single person—and includes traits I sometimes observed in a boss’s boss, rather than someone I reported to directly. But I was watching.

These Worst Bosses Ever did several things I vowed never to do. First, they pointed fingers at others when problems arose rather than look at their own management or strategy. Second, and even more insidious, they would bully subordinates by pointing to the successes of other companies—sometimes competitors, sometimes not—as proof that their reports were not successful, without taking into account the fact that ours was a totally different organization, with far different (and usually much more modest) resources. They even would sometimes employ the dark art of “lying with statistics” to make it look like people—their own colleagues—weren’t performing. But when you examined the facts behind the stats, it was clear that oftentimes people deemed to have failed actually had succeeded stupendously given the resources at their disposal or the time they were given for a project. These kinds of practices created a huge atmosphere of distrust inside groups or companies—and many good people either left or did not feel at all motivated to do their best work.

One big lesson I learned from these various “un-mentors” was to take into account the whole picture of a group or organization as best as possible—its role in the company or world, its resources, and so on—and to set goals and expectations based on that, not what others are doing. Another was to play absolutely fair with metrics. Lastly, I vowed to take responsibility when bad things happen, and to try to find a constructive solution, rather than blaming colleagues.

What follows, then, are My Worst Boss Ever stories from five leading members of the innovation community—two CEOs, two venture capitalists, and a member of academia. They aren’t intended to embarrass anyone. We don’t name names, and we have tweaked descriptions to protect people’s identities. And I would stress that these are perceptions and opinions that are colored by specific circumstances, the employees’ own makeup, and other factors—and that bosses sometimes make decisions based on factors that employees can’t be privy to, or can’t fully appreciate because they aren’t the boss. Indeed, one person’s worst top dog might well be another’s best.

The point isn’t to condemn the bosses—it’s to provide some insights and lessons that might make us all better bosses, and maybe even better employees who can help our bosses! See if these experiences ring true with you.

Bill Aulet, Xconomist and Acting Managing Director, MIT Entrepreneurship Center: “It’s not obvious, because you’d think it is the most incompetent one—but the worst boss I ever had was smart and political, but lazy.”

“If they’re incompetent, then you don’t have to worry—you just go do your thing. When they’re smart, political, and lazy it just drives you crazy. They’re capable of being helpful and they … Next Page »

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Bob is Xconomy's founder and editor in chief. You can e-mail him at, call him at 617.500.5926. Follow @bbuderi

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