My Female Bosses

A belated celebration of International Women’s Day

My dream boss. (Don’t tell Xavier.)

In 1989, I was a kid from Kansas who sold all his possessions but for two suitcases, and moved to New York City in search of adventure and career. “Kansas? That’s where Dorothy’s from,” I got used to hearing. I wasn’t yet self-confident enough to tell them to go to hell, that Superman was also from Kansas.

It wasn’t long before the planets aligned and I had a job working for one of the world’s most famous advertising agencies with an office on Madison Avenue. I soon learned that in the American labor market salaries are inversely related to glamour, and advertising, like publishing, attracted many who didn’t need the money.

But, some months later, I had figured out the advantages of coming from the land of Dorothy: I was harder working than most, and people who travel 2,500 kilometers for a job do not fail.

Do you want the foreplay?

Because I was a 20-something MBA who had all the answers, it didn’t take long before I approached my (male) boss to ask for a raise.

“Do you want the foreplay about how valuable you are?” he asked. “Or shall we cut to the chase?” There was to be no raise, but in recognition of my tangible contributions, which I’d typed up in great detail, I was invited to abuse an expense account within reasonable bounds.

Little did I realize that I was part of a play where all the principal actors were male. Sure, there were women in the office, but they were rarely assigned to sexy accounts. While I was arrogant enough to approach the boss for a raise, women were more reluctant to do so. My girlfriend at the time also worked in advertising, and I was too insensitive to recognize the differences in our circumstances. As a young white male I had it made. She didn’t.

I don’t want to say female employees weren’t taken seriously, because any smart opinion was valued. But women had to fight for everything they got.

Women bosses

Once I had my first female boss I started to see things differently. While I enjoyed the access to the boys’ club that my gender afforded me, I found it easier to work for women.

They were more direct and played fewer games. They were quicker to go to bat for you. And they were far less likely to put a knife in your back.

I was too self-absorbed to learn the stories of most of the women I worked with, but I still remember those who had significant impact on me. Some were my superiors, others just senior to me, but all of them were clearly the boss of me.


She was “Glo” to her friends and closer colleagues, and I was once proud to be known as “Glo’s white son.” She was the CEO’s gatekeeper extraordinaire and I suspect as loyal to him as he was to her. Even though she ran the entire office, Glo still referred to herself as a secretary. And she brought real dignity and professionalism to the job.


Growing up in a house of boys I never had a sister, but I would have wanted her to be like Cynthia. In addition to having a wicked wit, she once bought me a beautiful scarf at Saks Fifth Avenue when I earned so little money that I would work until 8 p.m. just so I could expense dinner and transportation home. The scarf was a small gesture, perhaps, but the attention of an older, stylish woman, who was also my superior, made my day, if not my month.


I can’t recall if I ever reported directly to Cathy or not, but in addition to my senior she was my therapist. She was quick with both career- and personal advice. Cathy was a straight shooter who always had your back, and she would eventually go on to be international new business director for one of the world’s largest agencies.


Pat ran the research department at the agency. It was a small department that had the ears of everyone, because Pat’s team was as articulate and intelligent as anyone else around. Even the allstar creative teams, who would occasionally throw tantrums, showed deference. Pat always kept her cool in a room full of men competing to be the Alpha. While the male executives swore like the cast of The Wire (one ad exec in the room would, ironically, go on to star in that show), Pat was always above it. I never saw her join in the melee even once. She did her thing and did it well, always the professional.

The pay gap

I’ve had a few female bosses in Europe and my preference to report to women has not changed. What has changed is information. In the ’80s and ’90s in New York we probably all knew women were earning less, but I doubt we knew how much. In 2017’s Europe, all you have to do is open the internet.

I regret to report that the country where I live, Estonia, boldly leads the way in the pay gap. I have no clue why Estonia so resoundingly beats Italy, especially in light of how qualified the women in the Estonian workforce are (I like Vello Vikerkaar’s thoughts on this). I suppose it’s explained by a joke I heard when I arrived: “The bad news is that women’s liberation is coming to Estonia. The good news is that it won’t be here for 100 years.”

While reasons for the disparity are surely complex, the main reason cited is that women did not ask for higher salaries. To speed Estonia along and close the pay gap faster I have publicly advocated for the funding of a team of foreign salary negotiators to fly in and do a one-day session on how to ask for more money. No kidding. I’ve actually tried to organize NGOs and find funding. But I’m not having much luck.

I have this vision of thousands of Estonian women going to their bosses and asking for raises, all in the span of a week. The men won’t know what hit them. And my guess is a few of them will actually grant the raises.

Scott Diel calls himself the Alan Alda of Estonia. But nobody here knows who that is.