It’s my last week at TokBox after working here for two years. TokBox was the first company I worked for after graduating and it changed my attitude toward having a boss.

Cultural influences made me believe that having a boss is inherently unpleasant. Entrepreneurship is celebrated because it means having to directly answer to no one. My preconceptions were that nobody wants to have a boss, it’s just a fact of life that if you work for a company, you have a boss and hopefully they aren’t a jerk—that a boss is necessary to keep you in line, determine your tasks, and entice you to stay motivated.

Those things didn’t occur between my boss and I. My boss didn’t manage me. She was just there.

I was a midwestern kid starting a career in Silicon Valley, fresh out of school, riddled with some kind of inferiority complex. I wanted to make an impact and go beyond being a cog in a wheel, and to me that meant making my own decisions and being proactive in searching for problems. No extrinsic motivation was going to push me beyond the drive I already had. The tasks I needed to do and the things I needed to accomplish became obvious when I let curiosity and ambition drive me forward. I didn’t need to be managed, and my boss recognized and adjusted to that fact before I did.

I was motivated and proactive, but I lacked finesse. I was making rookie mistakes: unnerving coworkers, exhibiting arrogance, stirring up unproductive arguments, reacting slowly on my feet.

At the same time I was noticing the grace in which my boss seemed to perform her job. The things I struggled with, she made look effortless. When talking to customers, she knew what to say and how to say it. When dealing with coworkers, she communicated her point with just the right amount of force. She appeared rational and humble. She had a rhythm that I lacked.

Opportunities to observe her were so valuable. She was an example I wanted to emulate. Instead of pushing incentives and tasks to me, she was a source of motivation and information from which to pull.

When I saw her work hard, it made me want to work harder. I replicated the language she used and the attitude she expressed when speaking about our product. She gave me context and information as I became ready for it, and I swamped her with questions. Why do we give away our product free? How would you navigate this conflict? Why did we choose that feature? What customers are we targeting? What’s the rationale behind our strategy?

I was demanding with her for information and it made her tired, she often told me so, but she assured me my curiosity was encouraged and worth the effort. She was opinionated but she tried hard to not let that affect her answers.

But she had biases and flaws. She was, at times, cynical towards customers, unfair to coworkers, and temperamental with me. But she was usually the first person to point that fact out. Had she not done this so regularly, I wouldn’t have stopped to scrutinize her actions. She seemed so talented, and by comparison, I was so raw and inexperienced—it’s easy when you’re young to look up to your role model free of scrutiny. And when you’re inexperienced, it’s not always easy to discriminate good behavior from bad.

Looking for my next opportunity, I’ve met with a number of people that could be my next boss—several really smart, successful people. I try to imagine working for someone new, but so often I’m not enthused. I didn’t know what it was I thought they lacked until I consciously considered what I specifically appreciated about my boss.

My boss was shrewdly self-aware. She was aware of how she was perceived. Aware of her biases, flaws, and mistakes. It’s a trait I’ve sensed missing in other managers I’ve considered. To be fair, it’s a shallow judgement to say someone isn’t self-aware, but I get the impression seeing someone heedlessly frame an opinion, or humble-brag an accomplishment, that he’s not in the habit of stepping outside his own perspective to reflect on his opinions and self-image objectively.

My boss had that habit, and it made a difference in how I was able to absorb and learn from her. I emulated her in a lot of of ways. Inevitably, whomever I work for next I will emulate too. I’ll trust that person for context and information to make decisions and form opinions. But that person is going to, at times, be misguided, temperamental, and biased—as was my boss.

But when I can trust that person to know when that’s happening and say, I’m being unfair, or I’m being irrational, or you were right—it makes it easy to extract the good ideas and recognize the behaviors that I should emulate, and look past everything else.

And that ability she had that enabled me to trust and learn so much from her, constant self-awareness, is the same ability I hope to have gained from her most.

Thanks Janine~

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  • Alex B

    Jonathan, it is amazing for you to highlight a woman as your boss when there’s so much backslash going on about discrimination et al. Janine has my thumbs up!

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  • Jore

    Thanks for the article! I’m also totally happy with my boss, so what you’ve written is very familiar. I think for a young person it’s important to have role models and be able to see them every day at work. You learn both do’s and dont’s from them, and they are equally useful.

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