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A Cautionary Tale: When Your Boss Wants to Become Your Friend

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Today recently had a segment called "Should You Be Friends with Your Boss" addressed the question us lowly employees have pondered since the beginning of time. How much should our bosses really know about us? How much should we tell them? After all, the boss has the all the power.

HuffPost Small Business executive editor Rod Kurtz and Dr. Gail Salz say your boss should be a mentor, yes. Friend, no.

But as someone who has very clear lines between my professional and personal life, what is public and what is private, I wondered what point of the segment would address the inverse. Having sat on both sides of the interview table, I know that bosses often hire people they like first; qualified, second. So what do employees do if we find that it's our boss who wants to be our friend? Is that part of our job?

I once had a boss who claimed that his management style was to be a friend, not a boss. However oxymoronic, it made him sound pleasant and unassuming. But he had no life -- a lethal and too common combination since nowadays people can pretend to work practically 24 hours a day. Not that he made me work 24 hours a day -- quite the contrary -- he hardly made me work at all, which actually coincided with the nature of my freelance assignment. But it was his life -- his value -- that he determined through work. Professional value, social value (am I the cool guy?) and sexual value (do girls want me?), all took place in a tiny cubicle he called an office. He'd often compliment my clothing, strike up senseless conversation right as I was leaving for the day, ask me about my evening plans to the point where I made up a fictitious life that I now sort of miss. Uncomfortable, yes. Unbearable, no.

Respect is not earned by a title -- there are plenty of blatantly awful bosses -- it's earned by action, as I've learned via Dr. Phil and negative work experiences. But sometimes you still can't help but feel trapped in bad boss situations. Trapped.

Why?

Employees, according to Dr. Salz, transfer feelings of self-worth and parental guidance onto our bosses. And while this may be true for some, her conclusion is undeniably true for all. We think our boss has our best interest at heart but he doesn't. He's the boss.

A tough lesson -- one that belongs in your twenties -- because now in my thirties, when my boss wants me to just roam around his office/cubicle and talk about whatever until he's ready to leave and maybe go out for drinks with him, my defenses are up. I immediately have a boyfriend, a date, a lobotomy every night of the week.

But I do my work well. And I enjoy doing it too.

Months passed of my good job and lobotomies, and when a permanent position opened, I stepped up to the plate. I can navigate this, I said to myself. Why shouldn't I go for a job I like and that I'm good at?

But, like any relationship, and work is no different, it unravels the moment someone wants something.

"Well I'm just not sure," he stated. And once again he began flirting with the lines of appropriate and now decided to regale me with stories of past freelancers; past female freelancers who have thrown themselves at him and have gotten just the kind of work I was looking for. All the while grazing my knee with his hand, claiming that I have poor reflexes.

My reflex was to get the hell out of dodge. Must I wait for a line to be crossed in order to know there is one?

But I did everything right, I thought. I was fictitiously busy. What more could I have done?

"I think you need to just quit," said a friend who wasn't listening to me at all the times I told her that for the first time I actually enjoy my work, and the other people I work with, save my creepy crater-faced Napoleonic-complex boss.

So I thought about looking elsewhere within the company.

"No one will hire you if your boss doesn't want you," my mother said. "Maybe you should join a support group?" But I couldn't do that either. Rather, I wouldn't. It's hard to find a place where you actually fit in. I'm a creative writer. That never happens.

When my boss encouraged me to ask around within the company in the meantime, I was relieved. And then I learned he told a few people not to hire me. I was his, I realized. What was I on Dynasty? The object of a mastermind manipulation solely based on power and control? The problem, though, was that I had no idea how to get out of it. I was about five when Dynasty was on the air.

Up until then I hadn't told anyone at work of my situation -- as much as I love to gossip, gossiping about myself has always ended in my feeling paranoid and judged. But I wound up breaking my own rules -- following the rules didn't seem to be getting me anywhere as of yet, I reasoned.
I told another female colleague, an older woman just as experienced if not more than my boss. "Why don't you come work for me?" she offered.

And I did. And I felt great -- even though I continued to see my less-than-thrilled old boss everyday. Because while an employee may not have the power, she can take away the power that someone has over her. And I found there to be nothing more powerful than that.