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 chairman. You can email him at [email protected] Follow @bbuderi

Trending on Xconomy

By posting a comment, you agree to our terms and conditions.

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

  1. Jules PieriJules says:

    My worst boss had it all going on: untreated bi-polar disorder, racist and sexist attitudes (predator,really), insecure and untravelled, and unbridled ego. The ego was the hardest part. When I joined the company I found he had turned some very smart and motivated people into a team of “yes men/women.” They were smart enough to realize there was no reward or payoff for thinking, so they just stopped. They did what he told them to do, nothing more or less.

  2. Jane says:

    Why were no women interviewed for this story?

    My worst boss mixed OxyContin and Bombay Sapphire at the most important party of the year, barfed in front of clients, and mauled me physically — he wasn’t after my body, he just needed help standing up — before someone called his family to drive him home. No matter what kind of boss you are to your employees, when you drive away customers and drive the company into bankruptcy, they’re the ones who suffer most.

  3. Hi Jane,

    Thanks for your note. We always try to get a range of views into survey articles like this: younger, experienced, men, women, people from different fields, etc. And I did indeed query several women CEOs for this article. They either declined to participate or said they would come up with a story and failed to get back to me.

  4. StillWorkingThere says:

    Ahhhh… my worst boss. Asks for input then promptly argues against it. Assumes every request has an motive, because his do.
    Hires friends at the expense of the company.
    Has no respect for past success. Does not talk to his inherited staff. Actually the last one is a blessing!

  5. maj says:

    I’m currently experiencing the worst boss of my 15+ professional career. The best way to describe it, is as though I’m in an abusive relationship. Think it’s time for an intervention.

  6. I’ve had a number of bad bosses, but the worst was not my boss, but my bosses boss.

    My direct boss one day told me to choose between my job and my wife. It wasn’t a fair decision to put on me.

    But what I realized later, when I found myself working for him again, was that it wasn’t that he was such a bad boss, but HIS boss was horrible and that created terrible working conditions for all involved. The beatings extended down the line until everyone was abusive to everyone else.

    Lesson Learned: If the top of the org chart has lousy management skills, expect problems throughout.

  7. I am not sure there is a worst boss (barring harassment or abuse).

    I have learned the most from the bosses i had that were bad. What’s more, their bad behavior mostly comes from insecurities – if you can figure out what is bugging them, you can contribute positively and they will reward you.

    Its all about the learning, and sometimes it takes a bad boss to do that!

    Rick Smith

  8. Sometimes the worst bosses aren;t that obvious as they are not outwardly abusive but kill you career but not being hands on enough.

    I can appreciate every bad boss I have ever had as inspiration on what not to do and to help me appreciate a good boss.

  9. ska says:

    My first boss treated me like the village idiot. Constantly berating me if the fax machine ran out of paper or if the copy machine was jammed and left in disrepair. The best was when she handed me a huge tub of spare change and told me to go to the supermarket to buy candy for the office…and she wasn’t kidding. I found out later that she was laughing at me behind my back to other employees, just trying to get me to quit!

    This was a sales job and in order to thwart her and her constant jabs I did my best to prove to her I wasn’t an idiot by becoming the top sales person in the company therefore making myself very popular to the executives in the company.

    She was so bad I volunteered to work weekends until one Saturday she showed up trying to tell me how to arrange the front desk of the office among other micro managing garbage requests. I then sat her down and told her I had enough of the constant crap. She pretended that she didn’t know what I was talking about and quickly stopped her behavior and set sights on my other co-worker. That co-worker was SO upset with me, but didn’t have the gumption to stand up to the boss so ended up quitting.

  10. Charles Q. Tran says:

    I was fortunate to have a few great and worst bosses in my 20 years career.
    Lessons: Great bosses would not last long and he took you down with him. The worst bosses with his cronies ended up destroyed everything else later. Nobody care.

  11. My worst boss – in 1981 – had me working on his crap QBASIC AR system.

    Buggy, crufty, full of gotos and with no comments or docs at all, if you asked him what stuff did, you were an idiot and he would tell you you were an idiot, loudly, in front of the entire office.

  12. Todd Lian says:

    The worst boss I ever had was bi-polar, manic who was probably on some type of amphetimine turned into a president of a company by her dying brilliant but ill 80 year old father. She made sweeping generalizations and management decisions based on innunendo and hear say from her mentally retarded (truly) sister who stalked people at the company, a lady who claimed to have an escape route booked in case a gun man came to shoot her down. She runs one of the worst Websites of all times, and still uses PIC for her systems work (invented before Bill Gates was born), was once fired by her own father for having sex in the office with a married man, is known to get so drunk she passes out on bars, talks so fast in rapid succession but yet makes no logical sense whatsoever. She now is systematically destroying the lives of everyone in the company rearranging deck chairs while her father’s Titantic sinks. A glorious publishing company in it’s day turned to a political quagmire of political dinosaurs who claw and scratch each other to death while pretending to be your friend and Christian too, as this pathetic, sexist, racist company turns in it’s rat infested, mildewed grave in Nokomis, Florida.

  13. Jinx says:

    My worst boss became my boss on the literal day I was 9 months pregnant. Her first words were, “What a shame you have to take a leave right when I should be getting to know you.” The upshot of that conversation was that, rather than taking an already too short 8 weeks off, I took six. When I returned, I became the second victim in what her 10-odd direct reports realized was a pattern: She would pick the weakest person, and make that person’s life miserable for a couple of months. During that time, you could do nothing right. The first victim had been a competent, but weak and defenseless benefits manager. I was exhausted (infants don’t sleep for longer than 2 or 3 hours, so neither do you) to the point of being unable to think. When she started in on the third victim after destroying my self-confidence, several of us recognized a pattern and discussed it. We began to do everything we could to help the current victim. We began to work around our boss and directly with other executives in the company, because she was simply an obstacle in serving our internal clients. They knew it (one actually asked me why she felt she had to be so mean and difficult), so they were approaching us directly anyway. By the time our company was acquired by a much larger company in the same business, she was totally ineffective, and that was communicated (by one of my colleagues, another of her direct reports) to people in the new company. She was fired the day after the acquisition was completed.

    I now work with academics, which will make you lose faith in acadamic research, which is subject to the same silly fads as business practices.

  14. Unfortunately, I’ve had a series of bad bosses, but I think the worst one I had was early in my career. He was verbally abusive, a nitpicker, and had a severe drinking problem. I lasted a year, and it was a horrible year at that. I realize now that I am a little bit older than he was at the time that the man was very insecure because of his many issues, and probably felt threatened by me.

    I still made the right decision to quit, it wasn’t worth the man making his problems my problems. I think the best solution when you get a really bad boss is to go find another position, these type of people cannot be dealt with.