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Here’s what my worst boss taught me about success–and the undue respect we have for cruel leaders



I remember the longest conversation I ever had with my boss because it was the day I interviewed for the position. For the occasion, I’d swapped out a fresh glittery manicure for a more conservative neutral, but I needn’t have worried about the girlishness of my nail polish. My future boss favored feminine skirt suits with metallic accents herself. Sitting opposite from her at a small conference table on the day of my interview, I wanted to impress her. To me, she was a paragon of corporate success, and I hoped if I played my cards right, I could be like her one day. Of course, that was before I knew her.

There’s a theory of the world where the ends justify the means. The work got done, ergo, it was done right. The fact I remember so little of the actual work and so much about the interpersonal dynamics of our team perhaps speaks to my own weaknesses: a frivolous interest in human behavior over the technical demands of the task.

A leader who is feared may be obeyed, but the risk in their absolute authority lies outside the bounds of their knowledge, which for all people have finite ends. What they cannot anticipate themselves will catch them unaware. Russian President Vladimir Putin’s yes men agreed him into the quagmire of Ukraine. Of course, in the situation I am describing we weren’t at war. We were at work.

The spoils of brilliance often include a certain license to bad behavior. In exchange for great contributions, we as a society have historically been willing to tolerate some mischief–and more. Among the revelations of the Walter Isaacson biography on Elon Musk released over the summer were anecdotes of the lionized founder oscillating between charm and what his girlfriends described as “demon mode.”

Modern corporate structure has policies and tools in place to discourage such actors from expressing the worst of themselves, but not all behavior rises to a level that might be rooted out with lawsuits and anti-harassment training. What should we make of the mild bully, the unpleasant person who makes work difficult, but not impossible?

I imagine the qualities I discovered in my former boss are probably not the ones celebrated by management consultants and eagerly cultivated in the next generation of MBAs: rigidity, vindictiveness, and pointed cruelty toward working parents in particular.

For almost two years I worked for this woman. Here are some things she did: deny a colleague his two-week paternity leave for no apparent reason; lay off another colleague while she was on maternity leave, in what appeared to be retaliation for working from home during the last few weeks of a challenging pregnancy; prevent a third from going to the closing appointment for his new apartment because he had been five minutes late to a meeting once. And that excludes all the quotidian indignities, that she might snap at someone reflexively gazing at the caller ID on her Polycom when a call came through during a meeting to accuse them of spying on her or embarrass someone else in a large meeting with a snide response. She would not allow working parents to use sick leave for their children’s doctor appointments. Vacation time was granted or denied on an arbitrary basis (“No consecutive Fridays off.”)

Any deviation from her desired optics would be met with censure. All of this existed in a separate sphere from the work itself. The job had two primary components: actually handling the assigned tasks, and handling them in a way so as not to upset the emotions of the person supervising them.

And yet for all the disdain with which she regarded her people, nothing would rile her more than a departure. When a senior member of the team went into her office to share the news that he had accepted a new role, I watched through the glass walls enclosing the two of them as all color and excitement drained from his face and she told him she had never been more offended in her life because she was upset he had accepted the role without speaking to her first. She seemed to thrive on making life more, not less, difficult for the people who worked for her.

Every day, my boss wore her hair tied back. The ponytail was part of her impenetrable uniform. Until one day, after I’d been there for a few months. She stepped out of her office into our nearly empty floor, holding her hair in place with her hand, and announced the hair tie had broken. Her short-haired assistant had nothing to offer. This was my chance. I had a full pack in my desk drawer. What my junior status prevented me from demonstrating with work, I could show with my organized preparedness for life. I imagined I would give it to her, and it would somehow be the thing that convinced her I did care about the work and wanted to do a good job. She accepted the elastic tie without thanks and with a glare that suggested witnessing her capacity for human vulnerability was yet another crime I deserved to be punished for. Oh no, I realized. My boss hates me.  

It’s not the most dramatic story. Certainly, other people have dealt with worse. We respected her expertise and knowledge, and if you could learn to operate within the narrow confines of her preferences, the work itself was interesting and engaging for most people on the team.

My job was so simple I felt from the first day how easy it would be to build a program to perform my primary duties, a basic automated decision tree of logic that could take over 90% of my responsibilities. If I’d had any sense that this boss appreciated new ideas, I would’ve shown her my program. Instead, I was happy to let the colleague who offended her poach me to his new team. She responded by blocking my transfer for six months.  

“Have you ever been afraid of someone you work for?” I asked a friend at dinner once. The invisible threat behind my boss’s rules was that she would make life difficult for anyone who challenged her by blocking promotions or adding them to an industry blacklist.

As my employment limbo dragged into the sixth month, the invisible threat, once sharp, turned dull. “I wanted to let you know: the boss noticed you’ve been coming in late,” her sidekick told me one day, at 9:35, after I had just arrived.

“Oh, interesting,” I said, at this point relishing the chance to play chicken over my stalled transfer.

At the time I worked for this woman, I considered her behavior normal. I imagined that the tradeoff for proximity to talent and expertise meant remaining slightly off-balance and concerned. Today, rather than the passage of time neutralizing my understanding of her, experience has only reinforced how unnecessary her behavior was. What kind of person doesn’t let her report take a meager two weeks to spend time with his newborn baby when the rest of the team would be happy to cover for him?

What I learned from my boss is that if behaving like her is what it takes to succeed, then I’m fine without it. In the time since I left her team, I’ve watched my former colleagues, who were always kind and hardworking despite our manager’s cruelty and paranoia reach professional success with more emotionally balanced employers. I’ve met enough brilliant people to see cruelty is not one of its essential components.

At the end of the day, when she retires, she will be replaced, as all worker-drones are. When I think about her now, I don’t feel any respect for her at all.

Kara Panzer is a writer based in New York.

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