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 know it, but instead they can rationalize not being so. They actively and effectively stop you from getting things done and spend what little effort they do exert pleasing their boss or sucking up to the person with the most political power and otherwise being everybody’s friend, as opposed to getting the job done. They thwart you in what you want to do and believe is right and provide the most unsatisfying answers. It’s so demotivational. I hated this situation more than anything else, and I would say this is what most entrepreneurs hate.”

Lesson: “Being willing to stand up for your employees. If they believe strongly in something, especially the very good ones, be willing to ride with them. If you are not, sit down and explain your reasons clearly and make sure they know it is not because you are lazy. Be very careful when you tell your employees they can’t do something—you better have a damn good reason and then communicate it to them.”

Bob Metcalfe, general partner, Polaris Venture Partners: “My worst boss ever allowed personality politics to run rampant among his reports and, after giving me a raise, broke a written promise to [promote me].”

Lesson: “One of the pathologies of companies is when winning internal political battles becomes the focus of its people instead of competing to win and serve customers—when keeping your job becomes different from doing your job. The wrong people advance and the company declines. One special case of this pathology is when accountants or lawyers manage to take over technology companies. Another is when governments are taken over by demagogues. Rome fell from the inside.”

Dan Sullivan, Founder and President, Appswell: Sullivan says his worst boss ever seemed to regularly shift attention and resources to whatever new effort temporarily appealed to him, or to what Sullivan describes as, “his latest fleeting flights of fancy.” These could be anything from a new marketing plan to deciding to launch new products.

The Boss Is MadLesson: “Focus is definitely an aspect of the lesson,” says Sullivan. There is a real difference between pursuing a flight of fancy and a true passion, he says. “Unlike other forms of business, in my opinion, entrepreneurship is ill-suited towards observing a need and positioning a product towards it, unless that need is something that you care sincerely about. If you’re not running after something you’d be chasing anyways, then the effort is just exercise, and eventually you’ll get exhausted.”

Michael Greeley, Xconomist and general partner, Flybridge Capital Partners: Greeley says he’s had several bosses who could be “mean and nasty.” But his worst boss experience came from a different type of practice Greeley found demeaning. They had offices very near each other—so that if the boss just raised his voice slightly Greeley could hear him. Similarly, says Greeley, “If he turned his head, he could see me.” But when the boss wanted Greeley, he would typically page him.

“That just seemed so humiliating,” says Greeley. The paging, he believed, took far more effort than simply calling out or just waving him over. But, Greeley felt, “he thought so little of me that he couldn’t get up to try to find me, he’d just page me.”

Lesson: “For me it was actually kind of a profound lesson. In the office environment treat everybody—junior, senior—not necessarily as peers, but as human beings. That lesson’s always stayed with me.”

Jeff Janer, co-founder and CEO, Spring Partners (creators of Springpad): “My worst boss…demanded blind loyalty and played his direct reports off each other rather than promoting teamwork.”

Lesson: “I learned two important lessons from my worst boss. One is the importance of surrounding yourself with people who are smarter than you and listening to them—rather than…surround yourself with ‘yes’ (wo)men. The second lesson is that it’s key to define reality—both good and bad—and say thank you on a regular basis, as respect accrues to the leader who is a servant to his employees—as opposed to the other way around.”

Feel free to share your own Worst Boss Ever story below.

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

Trending on Xconomy