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Lessons learned from women in leadership positions



Eileen Elias has decades of experience in leadership positions within government and nongovernmental organizations. As the first female Commissioner for Mental Health in the Commonwealth of Massachusetts and the US in the early 1990s, Elias gained experience on navigating gender-based challenges to attain recognized performance outcomes.


From lessons learned from women leaders, educate young women entering their careers on attaining leadership positions.


Comprehensive research of literature from 2012 through 2017 and interviews with women leaders representing non-Fortune 500 companies including academia, research, non-profit, for-profit, and primary and secondary education. Interviewees included:

  • 1. Gail Bassin, Co-Chief Executive Officer and Treasurer, JBS International Inc.

  • 2. Jeri Epstein, Executive Director, The Ambit Foundation

  • 3. Valerie Fletcher, Executive Director, Institute for Human Centered Design

  • 4. Christine James-Brown, President and CEO, Child Welfare League of America

  • 5. Daria Mochly-Rosen, PhD, Professor and Fellow, Chemical and Systems Biology, Stanford University School of Medicine

  • 6. Eileen O’Keefe, MD, MPH, Clinical Associate Professor and Director, Boston University Health Sciences

  • 7. Jeri Shaw, President and Co-Chief Executive Officer, JBS International Inc.


A comprehensive understanding of key women leaders’ lessons learned and recommendations targeting young women as they assess leadership opportunities in the public or private sectors.


Since the 2016 Presidential election, American women have experienced a wake-up call. The long, divisive campaign and the continuation of sex discrimination suits and announcements, has sent young women a clear message about the persistence of the glass ceiling and brought into sharp focus how far women in the working world have yet to go, understanding it is a man’s world, and a man’s workplace. Now, more than ever, women must understand this dissention and how to work with both men and women to achieve maximum personal and work-related performance outcomes.

1.1Women - know where you stand

Women bring an array of essential qualities to the workplace. Women are empathic listeners, who value collaboration and teamwork while also acting as experts at building relationships, encouraging others to achieve their maximum potential. These qualities work well with the skills men bring to the workplace, including assertiveness, risk-taking and self-confidence [1]. According to the January 20, 2014 Gallup study [1] when men and women effectively work together, their different viewpoints, ideas and market insights lead to an organization’s improved problem solving and performance.

This Gallup research study also showed that hiring a demographically diverse workforce boosts financial performance. The study of 800 business units from two companies representing the retail and hospitality industries showed that gender-diverse business units had better financial outcomes than those dominated by one gender.

An October 2016 Catalyst [2] study reported that Fortune 500 companies with the highest representation of women board directors had higher financial performance on average than those with the lowest representation of women. The study looked at return on equity, return on sales and return on invested capital. Yet of the S&P 500 companies, only 4.4 percent employed female CEOs, and full-time working women earned 83 percent of what their male counterparts do.

Much of the discussion on women and leadership has centered on large, for-profit businesses, especially Fortune 500 companies. However, the same leadership pattern exists in organizations of all sizes and within all sectors, including government, academia, research, medicine, primary and secondary education, small business and for-profit/nonprofit industry [3].

Women must understand how to navigate working in what is perceived as a man’s world. To be successful in this environment, women must understand the culture and values to offset the gender-based attitudes of male colleagues. They must ensure their supporting leadership teams consist of both men and women that represent necessary expertise within service, political and fiscal (SPF) topic areas. Finally, women must learn to assess the environment from the SPF perspective to help avoid gender-based pitfalls.

Advice: Integrate with and strategy into subject expertise, a popular approach among male colleagues: women should use humor when making a point, networking, serving on professional boards, presenting at conferences and publishing articles in top level professional journals.

1.2Create and nurture a network

According to the experiences women in leadership, one of the most important things women can do is network. Everyone networks, even if they do not realize they are doing so. Most people have natural networks of friends, relatives and colleagues they turn to when seeking advice or input. The importance of networking in the business world is primarily recognized when looking for a job, but experts say networking should be continuous. Building relationships based on trust is not optional, it is necessary, and requires both men and women be included in one’s network [4]. It is through working together and providing mutual support that trusting, work relationships are developed and sustained.

Research shows that women tend to spend significantly less time networking than men do. The same trend applies to seeking mentors. Jeri Epstein, Executive Director for The Ambit Foundation [5], noted a discouraging pattern: “Networking within a business, particularly with women of rank, can be challenging. Some women do not want others to climb the food chain with them.” Dr. Daria Mochly-Rosen, Professor at the Stanford University School of Medicine [6], agrees. She says, “Women had to work so hard to get to the top; many are reluctant to share that success with other women. [The] sentiment that comes across is ‘I did this on my own, so why shouldn’t you?” Anecdotally, women can be jealous and resentful of other women. American culture supports a kind of competition among women in both subtle and explicit ways. Women are more likely to be critical than supportive, thinking they are being helpful by being critical. In the workplace, women need to recognize this negative way of thinking and instead, learn how to support each other.

When Christine James-Brown, President and CEO of the Child Welfare League of America [7], had her eye on her first CEO position, it was a time when attention was being paid to the need for more women and people of color in senior positions. “I belonged to a professional group that formed with the goal of supporting one another in the process of identifying, and being hired into those openings. We had a specific focus: to pool our resources. We all made it. But once we met our goals, the group was not as high a priority any more. It’s unfortunate since I found it to be a fantastic source of knowledge and opportunity sharing.”

Women may network less because they resist asking for favors, even those as small as an introduction to another person. They may not see the potential benefits as much as the perceived barriers. A network can provide knowledge from the collective group, help with problem-solving, and provide guidance and support [8].

Among women who are willing to network, some opportunities may be missed because they do not see an immediate value in certain connections. “Be open-minded about who can and will be in your network. You do not need to be selective. There are often benefits you cannot predict,” says Dr. Eileen O’Keefe, Clinical Associate Professor and Director, Health Sciences Program, Boston University [9].

Advice: Besides joining and being active in the online networks such as LinkedIn, create and participate in in-person networks consisting of both men and women and invest time to nurture those relationships.

1.3Find a mentor

What better way to break ground than to learn from a more experienced version of yourself? Mentorship, especially for women working toward leadership positions, is essential but often underutilized. The August 2, 2015 Miami Herald article [10] written by Cindy Goodman reported that workplace mentorship boosts careers, skills and retention and is of benefit to all. However, too often mentoring relationships are limited, or nonexistent, in the professional world because supervisors are too busy or too close to the issues, there is a pervasive fear of appearing incompetent, or the potential mentors are not available to attend another meeting.

You may ask, “How do I find a mentor?” The answer is multifaceted and may require some research. Mentors can be inside your organization, but they should not be strangers. If hesitant to ask in a direct manner, the advice from the interviewed women who hold leadership positions is to seek out connections a couple of levels ahead of you and show that you are worth their time. Ask for advice on something specific and then follow through on it. Often the mentor relationship exists before either the mentor or mentee recognize it as mentoring.

Dr. O’Keefe says, “When I was a medical resident, I had a wonderful mentor. She helped me to see my strengths. She advised me on practical matters, like making sure maternity leave was covered in employment contracts [11].” This process only works, on a cultural level, if each generation chooses to support the next.

Valerie Fletcher, Executive Director of the Institute for Human Centered Design, emphasizes this responsibility. She says, “I have an active role as a mentor for the people who work for me, including interns, students and professionals. Mentoring is a pay-it-forward relationship; you do not get to give back to your mentors but you do get to share the things you have learned with the people you mentor. It’s such a valuable contribution; you get to prove to these people that they are not alone in their ideas and roles [11].”

Do not limit mentorship to women only. Men are successful because the workplace is their world and they know how to navigate it. Women can learn a lot from male mentors.

In a Miami Herald article, Eileen Elias speaks about mentorship saying, “Consider where you are now, where you want to be, who can help you get there, who is in your network and who has attained what you are seeking. Then, reach out to that person and say, ‘I am seeking a mentor. I have watched you. I think you are impactful. I want to learn from you [10].’ ”

Dr. O’Keefe says, “I see mentoring as a great thing. It helps us, it helps our department, so why would we stand in their way or not help them. It does not make sense. It is good for everyone [9].”

Advice: Find a mentor, be a mentor.

1.4Learn how to navigate unwritten rules

Women enter a workplace usually designed and managed by men. Even in industries created by women, the management structure and rules have generally been established decades prior by men. Women walk into that environment expecting to play by the rules that hard work will be rewarded. But women are often stymied by unwritten rules.

Dress the Part - For decades, men controlled the way women look. In the workplace, women need to conform to and be aware they are judged by both men and women. Women have long known they need to dress like a professional. In the 1980’s, women were told not to dress like a “secretary” with casual skirts and blouses and a cardigan sweater. “I recommend my female students and mentees learn what proper interview clothes are. I talk to them about proper covering and not playing with their hair so people are not distracted and can focus on what they are saying,” says Dr. Mochly-Rosen [6].

Speak Up - Experts also say women should ask for what they want. Be clear and be specific. Dr. O’Keefe says “women have to really fight for salary equality, which is problematic because women appear to be reluctant to even ask for a raise, let alone go to bat for it [12].” Women seem to really hold themselves back and in their experience, having a strong mentor has been the antidote, someone to remind you that you are worth it and to support you when you are battling to be recognized.

But speaking up in meetings has its downsides. In a New York Times article [13] on why women stay quiet at work, authors Sheryl Sandberg and Adam Grant said, “We’ve both seen it happen again and again. When a woman speaks in a professional setting, she walks a tightrope. Either she is barely heard or she is judged as too aggressive. When a man says virtually the same thing, heads nod in appreciation for his fine idea. As a result, women often decide that saying less is more.” The biggest challenge is finding the perfect balance to strike and being strategic in your approach.

Ms. Epstein discovered one rule: never use the word “I.” Instead, use “our team” and “we” because of the “natural” opposition to a woman, even when she did all the work. Ms. Epstein was further cautioned by a past boss not to “get cocky” when an announcement was made about her work [5]. It always had to be about the team. It was not the same for the men, who were never cautioned about appearing (or getting) cocky.

Be Strategic - Another recommendation from these women leaders is to make continuous eye contact when in a meeting facilitated by men. If the facilitator and other male participants look at others more than they look at you, call this to their attention. Ms. James-Brown said, “I had to pay a lot of attention to how people responded. For example, I would go to a meeting, the key staff member who would go with me was white and male and the male participants would make eye contact with him instead of me. I had to keep drawing the other party’s attention back to me. Sometimes I do it directly, sometimes I use humor [7].”

Having a family is often held against professional women. Subtle, perhaps unconscious, discrimination like, “She is not here, she is probably taking care of her kids,” says Dr. O’Keefe. “When I had to miss work because my children were sick, I never gave that as my reason. I let my team assume it was me that was ill. I did not want to be relegated to the ‘mommy track’ and its implications that I was not serious about my career. And in academics there is still much bias against motherhood. It is given lip service but not much is ever done about making progress toward that balance,” she said [9].

Jerri Shaw, President and Co-Chief Executive Officer at JBS International said, “I had to constantly prove I could do my job in prior work experiences. Often being the only woman in the room meant I was expected to take notes, despite being an active part of the discussion [14].”

Advice: Learn the unwritten rules in your office by paying attention to words and behavior in your workplace.

1.5Advice for women of color

As if being a woman seeking leadership roles is not hard enough, being a woman of color is even harder. A March 2016 report from the American Association of University Women (AAUW) [15] identified that from corporate boardrooms to the halls of Congress, from universities to the courts, from religious institutions to philanthropic organizations, men are simply much more likely than women to be leaders. The 2016 report, “Barriers and Bias: The Status of Women in Leadership [15],” identified that factors such as race, ethnicity, socioeconomic status, disability status, sexual orientation, gender identity and age make for unique experiences for any woman who tries to rise to leadership.

Black, Hispanic and Asian women hold just 3 percent of board director roles at Fortune 500 companies, according to the same study. That is in part because few women of color can even get a job at Fortune 500 company, where they make up 17 percent of the workforce. Once in, only 4 percent rise to managerial or executive posts [16].

Ms. James-Brown offers advice from her experience, “I am African American, so I always tried to figure out if what was happening was due to my ethnicity or my gender. I think it had much more to do with being a woman. I was the first woman and the first person of color to run that branch of the United Way. I went to two CEOs I was most comfortable with and they said, ‘The reason decisions are made on the golf course is because we are comfortable there with those colleagues. We would not be comfortable with you on the golf course, so pick someplace else where we will all be comfortable together [7].” This advice was James-Brown’s doorway into several leadership positions. She went on to serve on boards with those colleagues, so they would see her as their peer and see what she could bring to the table. She flourished in her career. She said, “This was a gift I was given very early on because I asked and asked directly. It helped that I was out doing things. It meant they saw me a lot. They got to know me and became comfortable with me. I think some of that is a responsibility for us, women and people of color, to make sure people are comfortable with us. I am not saying it is fair, but it is what works [7].”

Advice: Be a role model. The February 2016 AAUW study on the status of women in leadership reported that role models are especially powerful for women of color.

1.6Why women may avoid leadership positions

It is common for women to avoid putting themselves in a position to attain leadership roles within a company or organization. The assumption being they do not want or cannot handle the responsibility. That assumption is false, in fact, there are quite a few factors that contribute to why women are reluctant to take such as huge leap.

In her blog, Business Consultant Anne Loehr points out an interesting trend – that young women are leaving the workplace, thinking they will be better off freelancing, consulting or starting their own company [17]. Women and men may start at a company at the same time, but women receive lower pay, move up more slowly and rarely reach the top [18]. The March 2016 Harvard Business Review [19] reports that the number one reason young women leave the workforce is pay, and they are more likely to leave because of lower compensation than men for equal work.

Business leaders believe that the majority of women around the age of 30 leave because they are struggling to balance work and life or are planning to have children, whereas men leave because of compensation. However, according to young women themselves, in sharp contrast to the perceptions of their leaders, the primary factor influencing their decision to leave is their level of pay.

But some women do not seek leadership jobs because of work and family balance, according to Ms. Shaw. She has found that some women are not willing to relocate, or spend a significant amount of time on the road. Because of this, women do not apply for leadership positions. The 2015 Harvard Business Review [19] study addressed the work life balance culture, and showed that women with less than two years of work experience led men in ambition. However, for women with more experience, aspiration and confidence fell 60 percent and nearly 50 percent respectively. Declines were independent of marriage and motherhood, with much smaller changes for men, who reported a 10 percent dip in confidence. The study revealed that perceived success in business seems to be linked to the idea of giving your entire life to business (long hours, no vacations, etc.). The message women get is leadership means work has to be the focus of life.

Yet another issue is leadership style. With not enough role models, women do not always know how to retain their valued feminine qualities while leading an organization. “Women do not want to be labeled as aggressive or bitchy,” says Dr. Mochly-Rosen, and that may keep women from pursuing leadership roles [6]. When men take on leadership roles, the same qualities that are labeled for women, in men are confident, excited, dedicated. Ms. Epstein agrees that women have had to be extremely tough to make it to the top, which sometimes makes them difficult to work with, but often presents a classic case of sexist views. Females are “abrasive” for doing the same things that males do, who are instead labeled “forceful.” Gail Bassin, Co-Chief Executive Officer, JBS International, adds that “it can be a challenge to find that perfect level of assertiveness, not being aggressive but also not being too shy [20].”

Ms. Fletcher says that women often assume they always fall short. They need another credential, or more training, or more experience. She says, “It’s hardly ever the case. I cannot think of a time when I have seen men plagued by the same impossible standards [11].”

Ms. James-Brown thinks women need to find the right environment, whether that be an organization run by women or not. “Individuals take on the personalities of the workplaces [7].”

Ms. Bassin agrees. She says, “Women, in general, are more collaborative, much more cognizant of personal and other things, even if there is nothing you can do about it. There is a certain openness. This came naturally to us in our own company (JBS) [20].”

Advice: Seek out both women and men in leadership positions and learn from them.

1.7Pitfalls to avoid or how to flourish as a leader

This article highlights some of the inequities women face in the workplace. But the real treasure here is identifying the tools needed to persevere and achieve as much success as male counterparts. Decades of being talked down to and interrupted by men in their life and in their careers, have eroded women’s confidence [21]. Avoiding being labeled “shrill,” they speak softly, don’t speak up in meetings, and use tentative language. Speaking softly may make co-workers feel women are not confident. Dr. Mochly-Rosen says, “Some of the women I mentor speak more softly when they present in meetings than when they speak with me one-on-one. When I point it out to them, they are almost always shocked; they didn’t know they were doing it [6].”

Men speak loudly and with confidence, even when they might have less expertise than women [22]. In Dr. O’Keefe’s experience, in meetings of all sizes and types, women say, “I’m not an expert” or something else implying they do not know enough about the subject, despite knowing at least as much as everyone in the room [9].”

Ms. Bassin said she had trouble in an earlier position, because she was afraid to speak up in client meetings. It came out in her performance plan that she needed to speak up in each meeting, and she and her boss worked it out. Her colleague, Jerri Shaw, added, “Men tend to feel like they have to say something in meetings, where women tend to be more careful. Some men will even speak up when they really don’t know very much.”

Be a True Team Player - Learning how to be a team member helps people thrive in the workplace. Knowing how to work on a team is a skill men are adept at. Boys grow up playing team sports or working with others in groups, like the Boy Scouts. Little girls, although they are increasingly able to participate in sports, grow up often playing alone, with dolls or solitary games. Working in teams instills trust and support for both men and women and results in improved performance, particularly in a creative environment where everyone’s ideas and strategies are welcome.

Manage Your Emotions - Women are also advised to hold their emotions in check. That women are too emotional is a stereotype in the workplace that for decades has held women back as too “unstable” to hold a leadership position. Dr. Kimberly Elsbach, Professor at University of California/Davis, who has done academic studies on women and crying in the workplace, found that crying is perceived as unprofessional, weak and sometimes manipulative [23]. Eileen Elias stresses how important it is for women to understand the necessity of managing emotions in the working world.

Another issue for women is to know how to communicate forcefully, but not to attack. When people feel attacked, they do not hear what you are saying. They respond to the emotion and not the words. When women find a way to take a position on a difficult subject in a way that appeals to others it leads to collaboration and cooperation with the people you are addressing.

Be Confident “Act confident,” the seven interviewed women emphasized. In fact, Ms. Fletcher believes that confidence can make someone’s career [11]. She says that women tend to have a presumption that they cannot speak up without knowing every detail, that belittling of yourself can make you come across as cautious and doubtful, canceling out your strengths and expertise. It is critical to exude confidence when working with peers and clients. She says, “Apologetic behavior takes away one of the keys of brokering new relationships. If you are unable to portray confidence in your interactions, the client is not sure this is a person or organization I can trust [11].”

Dr. Mochly-Rosen says. “I think sometimes women do not succeed because they do not believe they can. Sometimes we put up our own walls [6].”

Advice: Believe in yourself, exude confidence, do not be emotional in the workplace.

1.8Taking action

With the realization that women are much further behind than they had thought, women need to use their voice. The election was an urgent signal for women, to network, mentor, be confident, ask for what they want, be role models for other women, be good team members, believe in themselves. And do not give up. Some women are already responding to the wake-up call with renewed purpose. A recent Boston Globe article, Women Stepping Up [24], reported that increasing numbers of women are becoming involved as political candidates. While previously they might have waited, they are acting now. Women can learn from leaders like the seven women interviewed in this article, women who have been successful and are willing to share the lessons they learned. By taking action, women can learn to reverse current trends. The ultimate prize is a public and private work world of equally powerful men and women who have respect, recognition and appreciation in a workplace where both are respected as valuable and effective.

* For this article, Elias received writing support from Aiyana Taylor, Research Associate at JBS International; Mariama Tejan, JBS International; Jean McMillen, Senior Vice President at a large public relations firm; and interview support from Carolee Noury, a blog writer. Elias interviewed seven of her peers who provided additional insight on how to improve the situation for current and future female leaders.



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