The path to success is an individual one. No two people take the same route as they make their way through their education and career. But one thing is certain: Much of our achievement—be it personal or professional—is thanks to guidance from important coaches, friends, leaders and bosses we’ve encountered along the way. This is especially true for women in the legal profession, who continue to face obstacles when it comes to career advancement.

In this story, InsideCounsel profiles several women of influence in law who have made a difference by working to advance women in the legal industry. Many of the women are true pioneers and trailblazers, having made a name for themselves in a highly competitive, male-dominated field. These women also were honored at the 2011 Transformative Leadership Awards for their perpetual efforts to promote and champion women lawyers. Read on to learn more about their career paths and the personal mentors who helped them accomplish their goals.

Kelly-Ann Gibbs Cartwright

Kelly-Ann Gibbs Cartwright: Partner, Holland & Knight

Age: 44

Law School: University of Florida College of Law

First job after law school: Holland & Knight

Favorite woman in history: Maya Angelou

As a young girl growing up in Georgetown, Guyana, Kelly-Ann Gibbs Cartwright had a talent for challenging others inconversation. “My parents always told me that I should be a lawyer because of my constant debating technique as a child,” she explains. Her family moved to the U.S. in 1978, and just a few years later when she was a junior in college, Gibbs Cartwright became seriously interested in following the career path her parents had envisaged.

Gibbs Cartwright attended the University of Florida College of Law in Gainesville, Fla., and during the summer of 1990, she clerked at Holland & Knight’s Miami office. One year later, she accepted a position as a first-year associate at the firm. She has remained with Holland & Knight ever since and currently is executive partner of the Miami office and on the firm’s directors committee.

“I’m celebrating my 20th year with Holland & Knight,” says Gibbs Cartwright, who admits she is somewhat of a novelty for remaining with the same firm for her whole career. She credits her long-term commitment to the mentors and guidance she has had while at the firm.

“When I was a young associate, I primarily worked for two female partners, who definitely mentored me, groomed me and taught me how to be a lawyer,” Gibbs Cartwright says. One of the mentors was the first female to head the Dade County Bar Association, and the other mentor was the first black woman to ever work at Holland & Knight. “Both of them were inspirations and people who I looked up to,” she says.

Gibbs Cartwright’s early mentors motivated her to continue helping other women and minorities advance and succeed at the firm. “Right now, I have a female associate that I work with. It’s my job to get her from associate to partner, and I take that seriously,” she says. One mentorship program Gibbs Cartwright is particularly involved in and enthusiastic about is the Rising Star program, a Holland & Knight initiative in which five women who are either junior partners or senior associates at the firm are selected each year to participate in an intensive leadership training program.

Another mentor who helped Gibbs Cartwright climb the ladder at Holland & Knight was Teri Plummer McClure, who is GC, corporate secretary and SVP of legal, compliance and public affairs at United Parcel Service (UPS). Plummer McClure championed Gibbs Cartwright when she was a young associate assisting UPS with labor and employment matters. With Plummer McClure’s praise, Gibbs Cartwright was promoted and soon became the relationship partner for UPS, handling all of the company’s legal matters. “Teri played a key role in that,” Gibbs Cartwright notes, “and I hope that the quality service and support that we have provided UPS has had a positive effect on her and her career as well.”

Both women were recognized for their mutual support of each other this past spring at the Transformative Leadership Awards, where they received the Sharing the Power Award. Gibbs Cartwright says the honor not only celebrates her ongoing relationship with Plummer McClure, but it also reminds her to remain focused on educating women about the importance of forming partnerships with other women. “In law firms, the ability to generate business is key to your advancement. To that end, my goal is to work with women on creating networking opportunities both internally and externally,” she says.

Teri Plummer McClure

Teri Plummer McClure: SVP Legal, Compliance & Public Affairs, General Counsel and Corporate Secretary, UPS

Age: 46

Law School: Emory University School of Law

First job after law school: Ford & Harrison

Favorite women in history: Shirley Chisholm and Maya Angelou

Teri Plummer McClure has been mentored by various women in her life, but she credits her legal mind and professional drive to a man: her grandfather. Although he had a law degree and a passion for the legal field, he couldn’t make a living practicing law due to the racial challenges he experienced as an African-American living in Kansas at the turn of the century.

“Instead, he went to work for the U.S. Postal Service and worked for them for many years before finally retiring. But he hung out a shingle after he retired and practiced law for about 10 years after that,” says Plummer McClure, who is the general counsel, corporate secretary and senior vice president of legal, compliance and public affairs at United Parcel Service (UPS).

Plummer McClure attended Emory University School of Law in the ’80s and was then hired as a labor and employment attorney at Ford & Harrison, a small law firm in Atlanta. She later worked at Smith, Currie & Hancock and Troutman Sanders.

She admits the law firm environment was challenging. “Even though I went to school in Atlanta, I didn’t know many other African-American female lawyers in the city,” she explains. A partner Plummer McClure worked with introduced her to another local African-American woman lawyer, and the relationship strengthened her confidence.

She went in-house in 1995 when she joined UPS as the company’s only employment attorney. Plummer McClure thrived at UPS, growing the labor and employment group and eventually heading it. She later worked on the business side but eventually returned to the law department, where she was ultimately promoted to general counsel.

“People were willing to take risks to provide me with opportunities that may have been outside of my immediate focus area,” she says. “I’ve always wanted to make a difference, fix problems and bring about resolutions when I see opportunities.”

Women in Plummer McClure’s life—both at work and at home—encouraged her to take risks and step outside of her comfort zone. She sought to do the same for other women by helping to launch UPS’s Women’s Leadership Development Program. “In order to ensure that there were a number of women in the pipeline developing within the organization to provide the company with effective options for leadership going forward, we had to do a better job of retaining that talent,” she explains.

Plummer McClure’s empowerment efforts extended beyond UPS. She helped to advance the career of Kelly-Ann Gibbs Cartwright, a lawyer at the law firm Holland & Knight who was promoted from a labor and employment associate to the relationship partner for UPS.

“We ultimately determined that it made sense for Kelly-Ann to be the relationship partner for UPS, given the fact that she was taking on more and more responsibility and doing a great job in representing the company,” Plummer McClure says. “She and I developed a relationship through the work she did for the company. It was mutual encouragement and support.”

The women’s shared efforts were recognized at the Transformative Leadership Awards in May when they received the Sharing the Power Award. Plummer McClure says the recognition is testament to the fact that women need one another to reach their full personal and professional development.

“You just can’t do it alone,” she says. “I want to encourage more women to learn and adapt ways to work through the different stages of their lives so they can work successfully in the practice of law.”

Deirdre StanleyDeirdre Stanley: Executive Vice President and General Counsel, Thomson Reuters

Age: 46

Law School: Harvard University Law School

First job after law school: Cravath, Swaine & Moore

Deirdre Stanley says she became a lawyer by default. While attending Duke University as an undergraduate, she decided to go to law school after graduation as a way to keep her options open.

“The idea was I could do something else if I figured out what that would be,” she says. “But I haven’t figured it out yet.”

What the Mary Ann Hynes Pioneer Award winner obviously has figured out is how to succeed in corporate America. After starting her legal career at Cravath, Swaine & Moore, Stanley went to telecom company GTE Corp. as associate general counsel for mergers and acquisitions. From there, she moved to USA Networks Inc., where in three years she served not only as deputy general counsel but also as GC of a division and head of business development for a business unit for the media and e-commerce company. In 2002 she joined Thomson Corp. as general counsel. When Thomson acquired Reuters in 2008, she became GC of the combined media company, heading a legal department of more than 100 lawyers in 11 countries.

But learning the ropes of the legal and corporate worlds wasn’t easy for Stanley. She says the greatest obstacle in her climb to the top was coming from a town that isn’t a corporate center (Huntsville, Ala.) and a family that wasn’t engaged in big business or law (her mother was a college English professor, and her father owned a construction company).

“How to navigate law firm and corporate structures wasn’t always obvious to me,” she says. “Some people came from backgrounds where they learned more about the politics of big law firms and big corporations and about how to advance their careers.”

Stanley says she never had a mentor to guide her career, though she feels she would have benefitted from having one. Instead, she learned to navigate the corporate landscape by observing several different colleagues over the years and emulating them.

And while she acknowledges that various women have credited her own mentoring skills with helping them advance their careers, she says she is just doing what comes naturally.

“If mentoring is sitting down and helping someone think through and strategize opportunities, to me that’s just having lunch with somebody,” she says. “That’s the way I interact in life generally, and I’m really delighted if people have found that helpful.”

She says she enjoys sharing the perspective she has gained as she has moved into senior leadership roles on what influences corporate decision making. One piece of advice she often passes along to younger lawyers: You will not get that promotion you want just by doing a good job in your present role. Instead, you must show your superiors that you have the skills required for the job you want to have. Otherwise, management may not see you as a person who can handle the responsibilities of the higher position.

Nadia Dombrowski

Nadia Dombrowski: Senior Vice President, Group Head, and Lead Region Counsel, U.S. Markets, MasterCard Worldwide

Age: 49

Law School: Columbia University School of Law

First job after law school: Rogers & Wells

Favorite woman in history: Eleanor Roosevelt

As a senior associate at her first law firm, Nadia Dombrowski faced the closing of the biggest deal of her career and, at the time, of her firm. Its client, Dreyfus Funds, was being purchased by Mellon Bank, and closing the multibillion-dollar transaction represented the culmination of 12 months of work encompassing complex banking issues by a sizeable, cross-functional team. It was also the culmination of something else—Dombrowski stood at the closing seven months pregnant.

“The moment represented an incredible confluence of professional achievement and personal satisfaction all at the same time,” Dombrowski says. She recalls similar moments—for instance, last-minute coordination with her working husband and their babysitter to accommodate her flying across the country on hours’ notice to meet with a client for three days of negotiations.

“Times like that were just crazy,” says Dombrowski, whose two daughters are now teenagers. “That’s what it was like to have children, and juggle.”

Dombrowski credits superiors and colleagues throughout the years with providing incredible support. It’s the kind of encouraging, driving spirit that has followed her throughout her career—from her formative law firm days at Rogers & Wells (since acquired by Clifford Chance), to her first in-house gig at GE Capital, a two-year stint as general counsel at Global Realty Outsourcing and now, at MasterCard Worldwide, where she is senior vice president, group head, lead region counsel, U.S. markets.

She approaches her career while maintaining good humor and perspective—a trait she learned from her Welsh mother. From her driven, ambitious father she took away the importance of self-reliance, creativity and viewing others’ differences as strengths. Combined with her Welsh and Polish grandparents’ emphasis on the importance of hard work, Dombrowski’s defining traits have served her well throughout her rise as a lawyer. They’re the kind of strengths that made her the 2011 recipient of the Pamela L. Carter Award, which recognizes a woman whose vision, values and philosophy of using her achievements are critical to her success.

“There were tests,” Dombrowski says of her career path. “Let’s see what she’s made of, let’s see if she can swim to the top with 100-lb. weights tied to her feet.” She faced skepticism from colleagues over how serious she was, conference rooms early in her career where she was the only woman present. Compared to men who are often recruited to work on deals, women have to make their case more frequently and directly, she notes. “Sometimes you just have to go in and be more forceful to convey that you’re serious and committed or that you want the opportunity, training or exposure.”

But she doesn’t see the challenges as obstacles.

Tenacity and maintaining high standards are lessons Dombrowski conveys to her daughters, to the lawyers she has mentored throughout the years, and to the all-female team she now leads at MasterCard. She encourages them to take charge of their career paths, never to settle for mediocrity and to go after their goals with force and determination.

“Believe in yourself and be bold,” she says. “Speak up and be willing to take chances. And never, ever give up. Even on those days when you think, ‘I’m just hanging on by a thread here.’”

Kim Koopersmith

Kim Koopersmith: Managing Partner, Akin Gump Strauss Hauer & Feld

Age: 52

Law School: Fordham University School of Law

First job after law school: Anderson Kill

Favorite women in history: Rosa Parks and Hillary Clinton

Much like her role model Rosa Parks, who lifted an entire group of people on her back through a simple act of civil disobedience, Kim Koopersmith has done her best to blaze a trail for women lawyers.

An attorney’s daughter, Koopersmith knew from an early age that not only did she want to follow her father’s career path, she wanted to crusade for betterment of humanity by doing public interest work. While the exact nature of her work didn’t come to fruition as she had originally planned, having spent most of her career as a commercial litigator, the interest in helping others endured.

One of the ways in which this interest manifested itself is in the work Koopersmith has done to develop business policies that ensure women have equal opportunity to grow and succeed at her firm. Koopersmith was handpicked for the task of drafting and managing Akin Gump’s reduced workload policy intended to ease some of the burdens on women with small children who want to have more time to spend with their families yet still desire to remain productive and on the partnership track. When she returned to full-time status after years of working on a reduced schedule, she was recognized by the firm’s chairman for distinguishing herself while working on a high-profile case. Impressed with her perseverance and ability, Koopersmith was lauded as a perfect example of the system working, and was given responsibility over the firm’s reduced workload scheduling.

“The key is to come up with definitions so that there’s some consistency in how people are treated, that they’re being treated fairly and that their contributions are being recognized,” she says, adding that 65 women have successfully taken advantage of the policy.

Koopersmith also has striven to ensure equality for women by completely overhauling the firm’s professional development plan. Specifically, she looked at revising the assignment system in an attempt to promote parity and rid it of any antiquated, gender-biased practices. “You need to take a heavier hand in making sure opportunities get distributed evenly,” she says, “and leaving it to chance is not a good step for diversity or gender issues.”

Koopersmith takes great pains in the recruiting process to ensure strong women candidates are given a good deal of attention. She also is on the firm’s compensation and partner admissions committees working to promoting diversity.

“In all of those initiatives,” she says, “I make sure there is someone who is always thinking, ‘How does this all play out and are people being evaluated fairly?’ ‘Is compensation being handled fairly?’ ‘Are the different ways in which people contribute being recognized?’ In both of those processes, I definitely have my eye on gender issues.”

Ultimately, Koopersmith truly believes it is incumbent upon her as a woman managing partner of a large law firm to set an example for those around her.

“I will continue to make sure that people see the value in having women in law firm leadership positions,” she says. “That will benefit everybody.”

Ellen Bastier

Ellen Bastier, Partner, Reed Smith

Age: 52

Law School: Golden Gate University School of Law

First job after law school: Research attorney for the presiding judge of the San Francisco Superior Court

Favorite woman in history: Eleanor of Aquitaine

Eleanor of Aquitaine, the 12th century politically savvy powerhouse, was queen of both France and England and ruled the English throne while her son Richard fought in the Crusades. She is credited with smoothing relations between England and France, and she showed business smarts too, helping to develop the French wine industry—all at a time when women were expected to be passive. It’s somewhat fitting that such a powerful, mold-breaking individual is Ellen Bastier’s favorite woman in history.

“She was very influential behind the scenes, strategically for her family and the country, and she was bold enough to go off to the Crusades personally,” says Bastier, who was recognized for being a powerhouse in her own right in an industry in which, even as women flourish and have found great success, so much of the economic power is still held by men.

Bastier, an energy partner at Reed Smith, was the winner of the 2011 Transformative Leadership Rainmaker Award, which recognizes a woman law firm partner for outstanding business-generation efforts and exemplary client service. She generates a book of business exceeding $10 million annually, making her one of Reed Smith’s top rainmakers.

Bastier has made her name in renewable energy, but she describes falling into it as mostly luck. It wasn’t exactly the dream of her 1960s childhood—renewable energy wasn’t even a sector then. It was in its infancy in 1987 when, as a second-year associate at Lillick & Charles, a partner-mentor at the firm assigned Bastier to a wind development deal. She excelled at it and enjoyed the work. Then came another project in the sector, then another.

“One thing led to another and it started fueling itself,” Bastier says. “It wasn’t an area I sought out, but I was open-minded to taking projects across the board, and I took to it like a duck to water.”

Bastier’s success in the field positions her as a lawyer helping to level the economic playing field for women, who are still outnumbered at the partner and executive ranks. Although she says law firms have made great strides toward hiring women in the partner ranks and putting women in positions of management with responsibility for important client relationships and significant business, she recognizes it’s an area that still needs improvement.

“Women have made tremendous advancements, and quite a few firms, including Reed Smith, have really done a lot in that regard,” she says. “But the fact that we stand out probably means there’s room for other firms to do more.”

Energized by attending the Transformative Leadership Awards, Bastier says she plans on carrying forward the spirit of the evening. That includes continuing to mentor younger attorneys, both women and men.

“It was very exciting to see so many powerful women in the room together and to see what was going on across the country, the contributions people were making,” she says. “I was very impressed with what people had been doing in their careers and how accomplished and committed they all were. My plan is to try to continue on with that momentum and energy.”

Carol Ann Petren

Carol Ann Petren: Executive Vice President and General Counsel, MacAndrews & Forbes Holdings Inc.

Age: 59

Law School: University of Missouri School of Law

First job after law school: Assistant prosecutor in Jackson County, Mo.

Favorite woman in history: Susan B. Anthony

As a teenager, Carol Ann Petren’s role model was the crime-bustingTV attorney Perry Mason.

“I was absolutely mesmerized by his ability to solve mysteries and cross-examine witnesses,” she says.

She made up her mind to be a trial lawyer and followed that dream through high school, college and law school to what she describes as the “first chapter” of her career—serving as a state and federal prosecutor.

“Those years were phenomenal, but I knew eventually I would be in private practice,” she says. Chapter 2 saw her representing clients as a trial lawyer defending professional malpractice cases. She spent 20 years in private practice, and was happily situated at Wilson Elser when Anastasia (Stasia) Kelly sought her out to join Kelly’s team in the Sears, Roebuck & Co. legal department.

“I was very, very happy where I was,” Petren recalls. “I had just been asked to be the first woman on (Wilson Elser’s) executive committee. I was completely content when Stasia came calling.”

While Petren had her doubts about working in corporate America, she was intrigued by the idea of doing something she had never done before.

“Stasia is very persuasive,” Petren says. “The chance to work for her and to try something new was quite irresistible.”

It turned out that working in corporate America suited Petren just fine, and Chapter 3 of her career has brought a series of successes as an in-house attorney, including being named this year’s winner of the Anastasia D. Kelly Award. After working as Kelly’s deputy general counsel at Sears, she followed her mentor to MCI—making the move even before she received an offer with a job title and salary.

“Stasia is the type of leader in whom you are willing to have blind trust, because Stasia rarely disappoints,” she says. “And it was one of those exciting opportunities that I was always yearning towards. At heart I’m a crisis junkie.”

She describes her experience at MCI as “three outstanding years of nonstop crisis,” that culminated with the acquisition of MCI by Verizon.

“Needless to say, I learned so much from Stasia,” she says. “The one lesson that stands out as particularly valuable is the importance of being surrounded by talented, committed people, providing guidance and trusting the team to deliver. What she taught me is that you are only as good as the team around you, and it’s OK not to have all the answers.”

Petren went on to become general counsel of CIGNA Corp. in 2006, a post she left earlier this year to join MacAndrews & Forbes Holdings Inc. She had the opportunity to turn her job at CIGNA over to Nicole Jones, a woman she had mentored much as Kelly had mentored her. She first met Jones at MCI, and recruited her to be deputy general counsel at CIGNA.

“I expanded her responsibilities in areas previously unknown to her, as Stasia had done for me,” she says. Jones eventually left CIGNA to become GC of Lincoln Financial Group, but agreed to return as GC when Petren offered her the post.

“I believe it is my responsibility to look at the people on my team, ID women who have special potential and impart to them what I benefitted from in my career,” Petren says. “Too many women don’t understand how much potential they have. Sometimes they have to be pushed, but once they are outside their comfort zone, they realize their potential.”

Transforming the web

Given the importance of promoting diversity in what largely has been a staid, male-dominated legal world, InsideCounsel has launched a special microsite devoted exclusively to our Transformative Leadership program. The new website is intended build upon our print coverage and be a central location for readers to learn about issues and news pertaining to women in law.

The Transformative Leadership microsite will be continually updated with fresh content, and keep readers apprised of InsideCounsel’s annual TLA program as well as feature expanded coverage of each year’s award winners.

Some of the features currently available at www.insidecounsel/transformativeleadership include:

• Extended write-ups on all 2011 TLA recipients, including a detailed question and answer section with each winner

• Video interviews with all seven award winners

• Regularly updated news and opinion from InsideCounsel staff and outside counsel on all Transformative Leadership-related topics

• Ongoing coverage of all Transformative Leadership events as well as nomination information for future years

Stocking the pipeline

Reed Smith lives up to its reputation as being a law firm devoted to cultural diversity and empowerment of women attorneys. With more than 550 female lawyers, Reed Smith recognizes the importance of having the proper programs in place to help promote the long-term growth of its women workers.

As part of this, the firm established the Women’s Initiative Network at Reed Smith (WINRS), which is a group of about 55 women firmwide in leadership positions led by Chicago-based partner Kit Chaskin. The purpose of the network, she says, is to serve as a communication network between the firm and its women, and then provide feedback to Reed Smith management.

One facet integral to WINRS is its PipelineRS program.

“PipelineRS is a concerted effort to capture women going into their fourth year of practice, which is a watershed time in any attorney’s career when they’re no longer just acquiring skills but starting to think strategically about their careers, starting to specialize and determining what practice group they want to join,” Chaskin explains.

The intent of the PipelineRS program is to reach out to women for whom partnership is a goal and provide them with the information they need to succeed at that critical juncture. Chaskin’s team guides women on how to raise their profile within the firm, develop business, write articles, join professional organizations and get themselves on teams doing sophisticated work for large clients.

Must read

Michele Coleman Mayes’ and Kara Baysinger’s newly released book, “Courageous Counsel,” is a compilation of experiences from current and former women general counsel in the Fortune 500. The book celebrates the achievements of current leading women while also guiding others to follow in their success.

Fifty women were interviewed about their careers in relation to three designated categories: mentoring, risk taking and key attributes. Mayes, GC of Allstate, and Baysinger, a partner at SNR Denton, said the interviews revealed varying histories among thewomen, but also a trend of courage that fueled their success. Mayes said her interviewees allowed her to “appreciate how [her] personal example had been lived in some form by each of [the women].”

Mayes and Baysinger hope these experiences will function as tools of empowerment for their readers, with each woman’s story paving the path for another to learn from her experience. Readers, however, will not find a to-do list that will lead them to the general counsel’s office, Baysinger noted. Instead, they will learn from women who created new paths in every direction they took in life.The most prominent lesson Baysinger recommends that readers take away is the need for an “honest awareness of one’s own assets and liabilities.” This, in combination with the examples shown through the book, will provide readers with tools to best take advantage of opportunities that come along.

Not taking risks, Mayes and Baysinger note, poses the greatest risk to career advancement. Whether it was her mother, sister, friend or teacher, each general counsel profiled in “Courageous Counsel” credited others who enabled her to tread outside her comfort zone. Mayes and Baysinger hope that by reading these women’s stories, women general counsel will find common experiences and tools to guide them to success.

Purposeful project

Anastasia Kelly says something unique happened at InsideCounsel’s Transformative Leadership Awards dinner in May: Attendees eagerly chatted with one another about the empowerment and advancement of women in law, and they weren’t done talking when the celebratory dinner was over.

“The conversations that began at some of those tables have continued,” says Kelly, a partner in the White Collar, Corporate Crime and Investigations Practice at DLA Piper and former general counsel of American International Group Inc., Fannie Mae, MCI/WorldCom and Sears, Roebuck & Co.

Other attendees also took note. Lloyd Johnson, CEO of Chief Legal Executive LLC , says the TLA’s were a reminder to the industry that while the legal field is filled with talented women, only a fraction of the top lawyers in the country are women. Specifically, there are only 101 women general counsel in the Fortune 500.

In August, Kelly, Johnson and InsideCounsel set a goal to increase that number so that women would account for 30 percent of the GCs in the Fortune 500. “Why not create some focus, some energy and personalities who can help accelerate to getting from 101 to 165?” asks Johnson.

The result of the brainstorming sessions was Project 5-165, a collection of events, publications and digital projects designed to boost the number of women GCs in the Fortune 500 from 101 (at press time) to 165 in the next five years. Johnson describes the project as “organic” in that its related objectives and activities largely will be shaped by its members. Project 5-165 is designed not only to increase the number of women GCs, but also to provide opportunities for networking and exchanging ideas. Additionally, women who currently are GCs in the Fortune 500 will mentor women who are new in-house lawyers.

“What I hope the focus will be over the course of the first year is on-boarding newly minted women general counsel,” Johnson explains.

Kelly says Project 5-165 will publicize women in-house attorneys’ talents, as well as their collective goal to break the glass ceiling. “While women have made a lot of progress in becoming general counsel, it’s not as significant an amount of progress as we should have made, in my view,” she explains. “There’s lots of energy and enthusiasm right now, and it needs to be harnessed and focused.That’s when we’ll see results.”