Learning To Love My Boss Jennifer

When I was 24 years old, I was an assistant media planner at Young & Rubicam on Madison Avenue.  I worked on the media plan to support the launch of Kraft fat-free mayonnaise.  At that time, I wasn’t a big fan of mayonnaise  — and I liked my boss, Jennifer, even less.

She treated me like her personal assistant.  I had to check in with her as soon as I got to work, I had to ask her permission to leave for lunch, and I couldn’t go home at night until she said so.  Jennifer checked everything I did and corrected everything I said. I hated the way she smiled on Friday afternoons as she informed me we had to come to the office over the weekend, something we did for months while we planned this product launch.

Jennifer knew I didn’t like her, and we fought often and openly.  One morning, our group director, Ed, walked by my cube and said sternly, “Come to my office.” 

I grabbed a yellow pad of paper so that my walk down to his office looked to others as if I were being given a special assignment that required diligent note-taking.  I walked into Ed’s office and he asked me to close the door.   He then ripped me a new one.  The net-net of this one-way conversation was that Jennifer was my boss — and if I didn’t find a way to make her happy, she would no longer be my boss, because I would no longer be working at Y&R.



That Sunday morning, I showed up to the office and surprised Jennifer, our supervisor Sue, and Ed with a dozen bagels, some vegetable cream cheese — and a brand-new attitude.

Over the next few months, I went from an immature, self-entitled employee to a celebrated member of a team.  It was a personal transformation I will always remember, and I want to share this lesson with the Millennial work force out there in the online publishing and advertising world.

For starters, your boss doesn’t suck.  A bad relationship with your boss, however, can suck the life out of you and your career.  Secondly, you can’t fake liking your boss – that’s an act that won’t last. But the good news is that you don’t have to fake it in order to make this relationship great.

To have a great relationship with your boss, you have to fall in love with the feeling you get from pleasing them. You have to embrace the little things your boss wants from you, and commit to doing these things exactly as they have asked you.

For example, back to Jennifer, she set up a spreadsheet a certain way — but I wanted to improve the structure of the Excel sheet, often adjusting her columns and rows.  That was an error because I was forcing her to adapt to my vision instead of respecting hers.  When I learned to embrace working within her cells, her rows and her columns, she became easier to work for.  Same went for the structure of our decks, down to the font (she loved Helvetica).  Most importantly, I committed to being in the office before she arrived every day, and never leaving before she did.  This led to the biggest difference in how she treated me, because I earned her trust.

Having a great relationship with your boss isn’t about getting them to like you over drinks.  Real respect is earned when you commit to respecting your boss’s specific and daily expectations, owning these tasks versus fighting them, and then meeting these expectations every day you work together.  

In the end, by falling in love with the feeling I got by pleasing Jennifer instead of fighting her, I really did fall in love with her professionally — and in turn, she fell for me.  When you don’t have to fake that feeling for your boss, coming to work feels like less of a burden and more like a game you have a chance at winning.

5 comments about "Learning To Love My Boss Jennifer".
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  1. Bob Batchelor from Cultural Historian and Writer, August 20, 2015 at 2:13 p.m.

    Thanks Ari for sharing this experience publicly. I particularly enjoyed the insight: "I went from an immature, self-entitled employee to a celebrated member of a team." The transition from "I" to "we" is a difficult one for young professionals to make. Hopefully, this essay will help.

    I wonder if Ed might or could have also had a talk with Jennifer about being less of a micro-manager and allowing you some room to grow. I would rather see managers finding ways to build young people's critical and strategic thinking skills than just employing them as "personal assistants." It seems that you've admitted to needing to grow up on the job, but there might have also been some better coaching on Jennifer's part that would have prevented the chewing out from Ed.

  2. Barbara Morris from Put Old on Hold Journal, August 20, 2015 at 2:46 p.m.

    Yes, Jennifer could have been a more helpful boss, but let's be real. Managers don't like to be challenged about their micro management techniques because they are being micro managed by someone(s) higher up. 

  3. Andrew Boer from MovableMedia, August 20, 2015 at 2:48 p.m.

    Lets say you are the boss. Then to paraphrase:
    "To have a great relationship with me, you have to fall in love with the feeling you get from pleasing me. You have to embrace the little things I want of you, and commit to doing these things exactly as I have asked them."
    Wait, wasn't that a line from Fifty Shades of Gray? (i kid)

  4. Ari Rosenberg from Performance Pricing Holdings, LLC, August 20, 2015 at 3:28 p.m.

    Bob & Barbara and Andrew -- thanks for the comments.  Funny, when I submitted this column to my editor, she thought Jennifer would be upset because I painted her as a 'micro-manager' -- what I was trying to show is how immature I was -- I mean really, what was Jennifer doing wrong -- expecting me to follow her directions, asking me to work as hard as she had to -- this were all MY issues not hers -- my point is that at 24 years old I didn't know shit about being a professional and I almost lost my chance fighting the direction of my boss instead of just respecting it -- there is plent of room to be your own person, but everyone has a boss and if you meet their expectations instead of challenging them, you win more than they do.  That was my point.

  5. Chris Elwell from Third Door Media, August 20, 2015 at 3:56 p.m.

    My "Jennifer" was named Jeff. He was a smart, kind and patient guy. He took a risk hiring me.

    I was writing a piece and spelled Nielsen three ways in three paragraphs. He chewed me out; Jeff was incapable of ripping anyone a new one.

    That event changed everything for me professionally. And I was overjoyed when he noticed I'd changed.

    Thanks for sharing, Ari. It brought back fond memories and reminded me that I owe Jeff a long-overdue "thank you."

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