11 Rule-Breaking Women In Business

Women, increasingly, are assuming top positions in their chosen field of work – whether that means a corner office, the director’s chair, or literally out in the field helping others achieve their potential. Yet women are still the minority at the top of the proverbial ladder – a ladder that I’d argue was built by and for men. There are a plethora of reasons for this, but one I’d like to bring to the forefront is our inherent comfort level with risk-taking and even rule-breaking. 

I’ve climbed the corporate ladder myself over the years but ultimately decided to toss it aside and build my own company. In my life as a woman in business, I’ve come to notice that one of the fundamental differences in how women approach work is in how they deal with rules. I’d venture to say that, more often than not, women take action according to the letter of the law while men are more inclined to flout rules to be true to the spirit of the law. Women are rule followers and perfectionists. They want to be right. They dot I’s and cross T’s. But that is not always the way to win the war—particularly a war that’s being fought in a world of masculine values. 

This first came to my attention in a pretty mundane way: coupons. Turns out male cashiers will accept expired coupons – female cashiers won’t. Not that I necessarily condone a complete disregard for the rules, but the underlying insight I’ve gleaned from this trend (other than which line to jump in at the supermarket) is that men are more willing to bend rules if it makes business sense (e.g., speeds up the line, keeps the customer happy and completes a product purchase), while women are more prone to focus on the sanctity of the rule itself. 

This may sound like a gross sexist generalization but I point it out because women who want to be leaders can start by recognising what it means: Sometimes it’s not only OK to bend or break the rules – it’s critical to professional success. 

Plenty of women are doing this as I type. And here are a few that have done a particularly fine job breaking – or at least bending – the rules.

Sheryl Sandberg, COO, Facebook

Christine Lagarde, Managing Director, International Monetary Fund

High-profile, frank-speaking Lagarde breaks rules in her role with the IMF by being public and honest
with her assessments of the economy. Lagarde took risks early in her career as well, foregoing
traditional French political experience to serve as William Cohen's congressional assistant at the United
States Capitol.

Indra Nooyi, CEO, PepsiCo

Arianna Huffington, President, Editor-in-Chief, AOL Huffington Post Media Group

Huffington broke traditional news media rules and launched online and blogging-focused The Huffington
Post after a failed run for Governor. In addition to original content, the website aggregated other sites'
content -- much to the chagrin of media traditionalists. She was onto something big: AOL purchased The
Huffington Post for $315 million in February, 2011.

Jacqueline Novogratz, CEO, Acumen Fund

Martha Stewart

Yes, she went to prison for conspiracy, obstruction of an agency proceeding, and making false
statements to federal investigators. While in prison for five months, Stewart befriended fellow inmates.
Since her release, she and Martha Stewart Living Omnimedia have made a comeback.

Lady Gaga, Singer/Songwriter, Performer, Activist

This celebrity uses her fame to speak out directly to her fans with an anti-bullying message. With a
Catholic School upbringing, Gaga breaks rules in the way she embraces (or doesn't) her fame: music and
fashion that fights against the media and expresses her personal opinions -- whether socially acceptable
or taboo.

Susan Lyne, Chairman, Gilt Groupe

Wendy Sue Kopp, Founder, Teach For America

As the founder of Teach For America, Kopp conceived of the concept as a Princeton undergrad based on
her belief that her generation was searching for a way to make a real difference in the world. She took a
risk in suggesting that top college students would choose teaching over more lucrative opportunities if
a prominent teacher corps existed, and her gamble paid off--Teach For America recently celebrated its
20th anniversary.

Shirley Marie Tilghman, President, Princeton University

A leader in the field of molecular biology and the first woman ever to hold the position of President at
Princeton University, Tilghman is the second woman to serve as president of an Ivy League university.
She has disquieted some Princeton alumni by promoting a more diverse university community, and
recently announced that Princeton will ban freshman affiliation with fraternities and sororities,
beginning in the fall of 2012.

Those high-powered ladies might break the rules, but these bosses take it too far

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