We have a fraught relationship with management. Think of your favorite managers from television. They fall into one of three categories: lunatic, monster, or narcissist.
None of these people are role models and our collective unconscious seems to like it that way. In video games, it’s a boss or mini-boss that stands in the way of progress. “You’re not the boss of me” is a put-down and its opposite, “You’re the boss,” is a sarcastic statement of indifference. The only boss anyone’s ever respected is Bruce Springsteen and even he hates that nickname.
But bosses aren’t all bad. You can even learn something from your managers. Here are a few lessons that have stuck with me.
Before achieving greatness, I dragged a two-wheeled cart full of newspapers around my neighborhood for $45 a month. My boss (let’s call him “George”) was a Persian man who emanated cigarette smoke even when he wasn’t smoking. He was legendarily uninterested in my performance. When I signed new subscribers he didn’t care. When I lost customers he didn’t care. When I quit he didn’t care. He taught me my first lesson about managers: they might not care.
In high school I sold knives door-to-door. Our sales manager was balding and stout like George Constanza. He was either 24 or 44 years old and our training felt like something out of Glengarry Glen Ross—except all the trainees were 17. Between specifics on carbon steel and serrated edges, George hurled motivational phrases and promises of succulent commissions. One afternoon, he got weirdly serious and paced the room. With his palms up, as though holding an invisible football, he tearfully told us about his wife’s miscarriage. When I had to quit a month later, I shook from nerves. George taught me the value of a powerful performance.
Since the knife gig didn’t cut it, my cousin found me a job at his construction company. The start time was 6am. In high school, 6am is not a real time. I briefly considered faking my own death, but took the job anyway.
My boss, the site foreman, resembled a slim George Lucas. He was exceedingly supportive. I redesigned an attendance sheet for the workers and George acted like I had invented new tech or something. Even though it was criminally early—and I had no internet all summer—George made the job something I looked forward to. He taught me the power of gratitude.
In my final year of university, I worked at a pizza place a block from campus. It should have been busy, but the restaurant twisted their menu into an upscale monstrosity. Students rejected our $4 gourmet slices, so I spent most of my time cleaning surfaces and listening to my boss, George, talk about The Stone Roses. They were his favorite band. (Let that sink in for a minute.) He was also a practicing Wiccan. I ate lots of free pizza and George talked a lot about Beltane and the Madchester sound. It was the best job I ever had.
My first job after graduating was at a small construction company. A starter gig that ended up hooking me for four years. My boss George was a maniac. Some anecdotes:
I later learned that when George was hiring for my position he collected all the resumes from men and threw them away. He only kept mine on the suspicion that I was a “hot Russian chick.” The person who interviewed before me was literally a cheerleader. I learned a lot from George, but most important was the value of chaos in the workplace. And that’s it’s worth it to hire a wildcard sometimes. I invited George to my wedding.
For a very short period, I was fully embedded in the corporate world. I worked in a skyscraper downtown, I wore a Hugo Boss suit, and I talked to investment bankers all day. My boss’s boss was George, a gregarious Aussie, and our most memorable interactions bookended my tenure.
First, was the job interview. George asked me far out questions like, “What’s your favorite color?” and “How many Tim Hortons are there in Canada?” Remarkably I got both of these right.
The second moment was when I gave my notice. It was only 8 months into the gig, but an actually life-changing opportunity was at hand. I thought George would be disappointed, but instead he was surprisingly real. He encouraged me to go for it. “Be loyal to yourself; no company will never be loyal to you.” Some managers do in fact care.
Upon entering tech, I got to experience five managers in five years. In a happy irony (considering the industry) four of those five managers were women. The short and overlapping experiences with these managers makes it hard to single anyone out, but here is what what I learned in aggregate.
In Silicon Valley, five years is a long time to spend at one place. I am genuinely glad I did.
I worked at a place with a faux-holocratic structure. Technically, no one was a manager and yet everyone was a manager. I learned a lot at this job, but one lesson is forever branded into my skull: People trump process. There’s no technology that can replace human interaction and no algorithm to represent leadership; sometimes there’s needs to be someone (a human) in charge.
These days I am my own manager. I must devise, undertake, and mark my own tests, which really isn’t fair for anyone involved. I am ruthless and impatient and I never, ever say thank you. It occurs to me as I write this that there is so much I can learn from my past managers.
Interestingly, the lessons I remember most aren’t the ones about increasing performance. They are the ones that remind me that the best managers served me as much I served them. I could stand to cut myself some slack once in a while. To every so often interrupt my day with a wooden toucan or a dose of Mancunian beats.