What lessons did your first boss teach you?

By Caitlin Kelly

One of my first national magazine stories...I entered an animal testing lab. Grim and gruesome. But it was part of my job as a reporter
One of my first national magazine stories…I entered an animal testing lab. Grim and gruesome. But it was part of my job as a reporter

As a follow-up to my Devil Wears Prada post, I’ve been thinking about my first editor(s) when I started out in journalism and my first full-time-job boss and the lessons they taught me — some of which might resonate for you.

I began freelancing as a writer for national publications when I was 19, having grown up in Toronto, the center of Canadian publishing.

Eager to join the world of journalism, I immediately signed up as a reporter for the weekly campus newspaper at the University of Toronto, and started writing as much as they would let me. Within a year, I had a good pile of articles, (aka clips), to show to professional magazine and newspaper editors I hoped would pay me for them.

I first started writing for a national Canadian magazine, then called Miss Chatelaine, now called Flare.

My editor was ferocious!

Her own mother was a legendary writer and so is her younger sister. I had never formally studied journalism or writing, beyond a BA in English literature from the equally-ferocious University of Toronto.

No one in my new worlds, either college or journalism, suffered fools gladly!

My editor would circle every misplaced or misused or lazy word with a red pen — this was in the day of typewriters and paper copies.

My first few stories were an embarrassing sea of red circles.

The New York Times newsroom...since 1990, I've written more than 100 stories for them
The New York Times newsroom…since 1990, I’ve written more than 100 stories for them

She taught me a lesson I never forgot: to use specific verbs in the active tense.

When we spoke on the telephone, (no Internet!), and she told me what was wrong with my work, I would occasionally end up in tears.

Was it always fun? Clearly not.

Was I learning (and getting paid to do so?) Clearly so.

I could give up and walk away — or continue to learn my craft.

She and I are Facebook friends today.

My first book, published in 2004...all the skills I learned in my 20s are still in play today
My first book, published in 2004…all the skills I learned in my 20s are still in play today

My first newspaper boss was a man so shy most people thought he was cold and unfriendly but he was really someone who valued guts and intelligence.

He took the crazy risk of hiring me — although I had zero prior staff newspaper experience — to work for The Globe and Mail, Canada’s daily national newspaper.

My first day, staring up at the large overhead clock that still rules every newsroom, I thought: “Wow, they want this story….tonight.

He kept throwing me into huge, terrifying, front-page stories, from covering an election campaign in French in Quebec, (I had never covered politics, anywhere, for anyone, let alone en francais), to a two-week national tour trailing Queen Elizabeth and Prince Philip from New Brunswick all the way to Manitoba.

The lizard part of my brain sent me to cry in the bathtub, scared to death I would fail every time and get fired. That was his agenda!

The rational part of my brain told me to shut up and get on with it. I was being offered tremendous opportunities to shine. The rest was up to me.

I did fine.

Reporting in Bilwi, Nicaragua for WaterAid
Reporting in Bilwi, Nicaragua for WaterAid in March 2014

I remain forever grateful to both editors for giving me amazing (scary!) chances, knowing I was still young and fairly green, knowing I might have proven a terrible disappointment. They had more confidence and faith in me than I often did.

That’s my definition of a great boss.

What did your first boss or job teach you that was most helpful?

16 thoughts on “What lessons did your first boss teach you?

  1. My first boss taught me constructive criticism. She focused on the task I did wrong rather than mixing up the person and the task. I worked for her at the beginning of my working life at 16, in a restaurant, and it helped me deal with bosses without that kind of division in making their employees better.

    I learned a lot from bad bosses as well like how not to lead. 😉

    1. That’s such a powerful lesson…no one knows everything and punishing someone for screwing up isn’t helpful.

      Leadership takes a lot of sensitivity and self-awareness, if done well. Good for you! 🙂

  2. Pingback: [BLOG] Some Monday links | A Bit More Detail

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  4. My first “real” job was a research assistant doing data entry for a grant. My boss taught me to believe in myself. She pushed me to learn things beyond what I thought I was capable of learning. After that summer job, she kept me on and I learned how to manipulate the data I so meticulously entered and, together, we analyzed it and wrote research papers. I got my first publication with her. She believed in me and, because of her, I began to believe in me.

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