Women Entrepreneurs and Leadership

How are we supposed to grow into successful women entrepreneurs without great examples of leadership? Obviously, women are figuring it out and finding their own way. But wouldn’t we have more success if there was some kind of playbook? Advice? Great examples?

Do we lead differently than Men?

Yes and No. By nature, women lead very differently than men, I know I do. For the past century, hierarchical leadership was recognized as exemplary and rewarded. This leadership style is more closely aligned with men but women have had to adjust in order to succeed. Some women have adapted to this male style brilliantly. One example is Margaret Thatcher, The Iron Maiden, she led like many British Prime Ministers before her, with a man’s brand of leadership.

Only recently, has business begun to embrace and value different dimensions of leadership. Skills that are more aligned with the natural abilities of women, adaptability, empathy, emotional intelligence, and collaboration. 

What are the leadership differences between men and women?

Besides style and skills, there is one (probably more) really important leadership trait that is very different among genders. This trait and its advantage has been identified in a study by Ready-Now Leaders: Cultivating Women in Leadership to Meet Tomorrow’s Business Challenges by DDI

Women are more humble when it comes to accomplishments

Women rate themselves less highly effective leaders compared to men. Men highly self-rate their own leadership skills and their ability to tackle management and business challenges. This is important because in this world – having a loud voice is effective and increases your chances at being not only heard but your chances of succeeding.

You have to toot your own horn, which can be uncomfortable.


Rate themselves as highly effective leaders


 Rate themselves as highly effective leaders

Because women are not openly touting their accomplishments, women are given fewer opportunities that would help to secure advancement in business. For example, women are less likely to have completed international assignments, or to have led across countries or geographically dispersed teams, all of which make up important development opportunities.

Where are the examples of women leaders?

When it comes to developing a leadership style as a female entrepreneur – there is no playbook for women, and few women entrepreneurs are household names. We haven’t produced a Steve Jobs, Tesla, Elon Musk or Henry Ford equivalent for women… yet

You can’t aspire to be something you don’t know

Women leaders are all around us in our communities and families, but highly visible ones – not so much.

While women have made some inroads in global politics, in the USA we still haven’t had any success at electing a woman to the highest office in the land. But in the rest of the world, 56 of the 146 nations (38%) studied by the World Economic Forum in 2016 have had a female head of government or state in the past half-century. Having a woman President would be a game changer for women entrepreneurs in the US.

The news out of Corporate America isn’t so great either. Based on the January 2017 S&P 500 list.* Women currently hold 29 (5.8%) of CEO positions at those S&P 500 companies. To find out how many women are at other levels of S&P 500 companies, take a look at the Women in S&P 500 Companies pyramid.- Catalyst

The overall representation of women in the media continues to lag, with some notable exception – the roles are limited. At the Oscars this year, only two of the nine films nominated for Best Picture featured women in leading roles – Arrival and Hidden Figures. Although I really love the fact that the protagonists are mathematicians and scientists – none of the films were Directed by women.

As a society, we have not been doing a very good job at teaching women how to lead differently through example. This has got to change!

Do entrepreneurial women, raise entrepreneurial women?

Personally, I have been lucky, from a very young age I attended single-sex schools all the way through College. This kind of education although uncommon has great value in that it allows young women the opportunity to learn leadership in a very sound way. I have also been influenced in my personal life by great women, unsung heroes who have taught me how to solve problems, be self-reliant, persist and lead as a woman. But not everyone is as fortunate, so we must do better and more at raising the visibility of women leaders, especially women entrepreneurs.

It’s interesting, all of the women entrepreneurs I have worked with cite their mothers or other female relatives as their example in business and leadership – almost everyone one of them had mothers who were themselves entrepreneurs in one way or another. I am not sure if this is statistically significant because it is a very small sample size – but I wonder just how important this is and how many more of these stories are out there.

Top books on leadership                                                   Written by men about men

ALL of the celebrated books that teach strategy and leadership are about men, not women. While there are some out there, it is tough to find a book on Female Leadership, or Female Entrepreneurial Leadership specifically. Please don’t cite “Lean In” because that book is just full of fluff and unicorns.


Examples of what are considered to be the top books that all leaders should read.

1. The Art of War by Sun Tzu

2. The Prince by Niccolo Machiavelli

3. Meditations by Marcus Aurelius

4. Endurance by Alfred Lansing

5. On Becoming a Leader by Warren Bennis

6. First, Break all the Rules by Marcus Buckingham and Curt Coffman

7. Emotional Intelligence by Daniel Goleman

8. Drive by Daniel H. Pink

9. ‘Crush It!’ by Gary Vaynerchuk

10. ‘Awaken the Giant Within’ by Tony Robbins

11. Never Give In! The Best of Winston Churchill’s Speeches by Winston S. Churchill


I could cite about 100 more – but none of them are written by women or about women.

Leadership and women – is it changing?

Throughout history, there have been exceptional women who have succeeded as leaders, despite living in a patriarchal society.

In the past, women were granted access to power either through birthright or marriage – this is still somewhat true. Some of the most powerful leaders in the world who also happened to be women came about their power this way – Eleanor of Aquitaine, Catherine the Great and Queen Elizabeth are in the history books, others have faded into anonymity.

In more recent times, entrepreneurial women have broken through and succeeded through talent, merit, and determination. There are a handful of household names, Coco Chanel, Martha Stewart, Estee Lauder and Oprah Winfrey, and more to come.

Why are so few entrepreneurial women household names?

In the past, women entrepreneurs have typically started smaller businesses in the service industries. Although they are the backbone of society, these are not sexy businesses and despite being hugely successful they receive little attention. This has changed dramatically, during the last decade, after the Recession women have moved into other industry sectors, including sexy ones like tech. This means a broader exposure to women entrepreneurs in leadership positions, let’s say that the next Elon Musk will be a woman.


Women entrepreneurs are growing in numbers. Now is the time to begin exploring what are the leadership skills and styles that will help them succeed!


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