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Lessons I Learned From My Old Boss, Who Hated Me

Written By Annie Goodman | Mar 22, 2019

Three days, nine hours, 12 people.

That’s how many people it took and how many hours I spent interviewing for my first official job as an Account Coordinator at a small, boutique ad agency in Los Angeles.

The agency was 21 people large, so I had, in essence, met with over half of the entire company over three separate days of interviewing. Although my most notable work experience had been several years as “Camp Counselor” at a day camp and “Hostess (With the Mostess)” at California Pizza Kitchen (three separate times, by the way), I had been deemed a “culture fit” due to my sociable nature and self-deprecating humor.

The job was mine and I would be the youngest person on an account team of two men with monosyllabic names and years of rapport under their leather belts.

Three weeks into the job, my Account Supervisor, who managed me directly, announced that he’d be moving to another state for a new job and a new relationship… which meant that I was going to be reporting directly to the most senior-level person on the team – aka the only other person on the team.

It was around this time that I learned that my boss-to-be was not looking forward to being stuck with the outgoing 21 year-old, who thought the world was waiting for her. Yes, that was me.

So, even though my boss got me a chef’s knife for Christmas, which is technically bad luck, I learned many things from him during the process of our intricately-complex dynamic over the 10 months that I worked for him. And don’t worry: I secretly placed pennies on his desk when he wasn’t looking to undo the knife’s curse!

Lesson 1: Sit Down And Shut Up
About three months into the job, my boss’s best friend (who also worked at the company) pulled me aside in the kitchen.

My misguided and hyperbolized effort to tell everyone who I was resulted in an inability to see the clearly-laid boundaries that had been set by my colleagues.

“You need to rein it in and show your boss some respect. You’re a little too comfortable.”

I was rocked. As a Millennial, I was used to positive feedback, cooperative learning, and personal encouragement. I had entered this job thinking that showing my whole self was a priority. I thought that the sooner everyone could see what I housed inside my figurative trench coat, they’d have no choice but to love me and see how special I was.

Whether or not I believed in the feedback I received, I realized, in that moment, that I needed to take a big step back.

My misguided and hyperbolized effort to tell everyone who I was resulted in an inability to see the clearly-laid boundaries that had been set by my colleagues. In boldly and immediately trying to connect through presumptuous comfort and intimacy, I falsely assumed that:

  1. Everyone wanted to socialize on my terms
  2. My way of engaging was the only way to connect
  3. Building a personal rapport was everyone else’s priority

Accepting that my personality wasn’t the work, but rather that my personality needed some work, forced me to sit down, shut up, listen, learn, absorb, and then acclimate to a new community where there were bottom lines and deadlines. In spite of my only-child upbringing, I wasn’t the most important person in the room and it turned out that no one was dying to hear what I thought at the meeting room table.

Lesson 2: Your Time Is Not More Valuable Than Anyone Else’s
“What is 100% of your day is actually 12% of mine.”

These are words my boss said to me after I had followed up with him several times about a project I had been asked to complete.

As an Account Coordinator, I had been given very specific (albeit tactical) tasks to complete on a daily, weekly, and monthly basis. Once I got the hang of my job, I constantly sought out approval, validation, and, most importantly, celebration from my boss for my finished work (did I mention I’m a Millennial?).

It’s encouraged me – in moments where I feel frantic about an unresponsive email – to remember that everyone has something else they’re dealing with and that I have to patiently wait for them to make my priority their own.

I always assumed (yes, there’s that word again) that a lot was riding on my work because I had been asked to do it. I often thought, “He can’t do his job without my job, right?”

So when he sat me down in a conference room on a cloudy Wednesday, I was yet again paralyzed into perspective, zooming out just a little bit to see the other person on the other side of the table.

As I gave it more thought, I understood that even though my work assisted my boss’s goals, he had his own tasks and priorities. And the completion of my daily tasks was not at the top of his list.

Throughout every job I’ve had since, valuing other people’s time has been… well… invaluable. I still see incoming, entry-level employees jump on senior staff with urgency, almost begging for their work to take precedence over everyone else’s. It’s encouraged me – in moments where I feel frantic about an unresponsive email – to remember that everyone has something else they’re dealing with and that I have to patiently wait for them to make my priority their own.

Lesson 3: Not Everyone Is Going To Like You
Growing up, children are taught to be affable and well-liked. Popularity is sought after and valedictorians get the keys to the kingdom. As a child, the idea that someone doesn’t like you creates an unresolvable anxiety that leaves most scrambling for any solution to move the needle in the other direction.

I felt this way until I worked with my boss.

Aside from the humbling lessons I had to learn from just being a young and entitled post-grad, my boss and I, very plainly, had no chemistry.

For 10 months, to no end, I worked really hard to continue to iterate my behavior in the hopes that reversing each identified flaw would somehow reverse his distaste for my presence.

We even reached a point where he had asked that I not approach his desk and simply email him a “List of Reminders” at the end of each day instead. He placed as many barriers between us as he possibly could and refrained from any constructive commentary, fearful that I might get too complacent.

I went through my personality with a fine-tooth comb, searching for the next thing to fix, so that we could finally be copasetic. But in looking for outliers, I found myself bloated with fear and worry instead (which, by the way, led to psychosomatic and digestive repercussions).

At this point, I realized that the only thing that mattered was the work itself and that I needed to compartmentalize all of this self-doubt and personal strife – not only for the sake of my health, but also because my personal relationship with my boss didn’t take priority over the work. Sure, it would have been an incredible add-on, but in order to have clarity, I had to separate the upset that there was someone out there who didn’t like me from the fact that I was actually really good at my job.

The almost-year that I worked with my boss was a mentally-intense one that included tension one could cut with my gifted knife. He still hasn’t accepted my request on LinkedIn, but he did make me a stronger, more humble person and a sharper employee. And yes, that was meant to be another knife pun.

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