Tips from the Top: Sheila Wilson-Freelon

Sheila Wilson-Freelon is a Vice President and Assistant General Counsel at Discover Financial Services, a Fortune 500 company, headquartered in the Chicagoland area. Prior to her current role, Ms. Wilson-Freelon was Vice President and Assistant General Counsel with Morgan Stanley, a premier financial services firm headquartered in New York and the former parent company of Discover Financial Services. Ms. Wilson-Freelon received her Bachelor of Arts Degree (cum laude) from the University of Mississippi and her Juris Doctor degree from Northwestern University School of Law, where she was an Earl Warren Legal Scholar. She also earned her Master of Divinity at Northwestern University, Garrett Evangelical, where she was an Archibald Carey Fellow. Ms. Wilson-Freelon has received numerous awards and honors in recognition of her personal and professional accomplishments: “Attorney of the Year”, the “Supplier Diversity Success” Award, the “Who’s Who in Corporate America” Award and “Corporate Trailblazers” recognition by the NAACP “Crisis” magazine. She was honored for her youth, community and church work by the 100 Black Men of Chicago. She was also honored as one of “America’s Best and Brightest” business professionals by “Dollars and Sense” magazine. Her personal and career accomplishments are featured in the American Bar Association’s publication entitled, “Dear Sisters, Dear Daughters – Words of Wisdom from Multicultural Women Attorneys Who Have Been There and Done That.” Ms. Wilson-Freelon’s approach to the legal profession is to get wisdom, grow, serve and give back.

How did you begin your career?

When I began my legal career in law school, I was enlisted in the United States Army Reserve as a Legal Specialist. This position was similar to a paralegal role that was responsible for researching, writing and preparing for courts-martial.

Did you have a plan or career strategy?

My plan was to help someone. My strategy was to be prepared when the opportunity arose to secure positions that would allow me to truly help someone in need. This plan and strategy began when I was in high school. I told the Career Guidance Counselor that I wanted to pursue a profession in which I helped individuals in need. She immediately steered me to the field of social work. So during college, I began preparations to become a social worker until I read an article in Ebony Magazine that there was a need for more Black civil rights lawyers. At that time I declared a major in Political Science and set my sights on becoming a civil rights lawyer who would help right the wrongs done to individuals who were discriminated against. After earning my law degree from Northwestern University School of Law, I served as a Judicial Clerk in the Illinois Appellate Court. Thereafter, I worked as an employment attorney for the Chicago Transit Authority for five years and for the Quaker Oats Company for 10 years. After Quaker Oats, I worked for Morgan Stanley’s Legal Department as a Vice President in the Employment Law Unit until they spun off the Discover Card division of the business in 2007. I now serve as the Vice President and Assistant General Counsel, responsible for Global Employment Law at Discover Financial Services. For a long time, I felt that I had reneged on my goal to become a civil rights lawyer because my career had been spent largely in Corporate America. My view shifted after attending seminary at Northwestern University. There, I learned that the employment law field fits into the social justice stream of ministry. I said: “Whew, I really am a civil rights lawyer after all.” Today, I view myself as an in-house civil rights lawyer, ensuring that the corporation treats the employees consistent with all of the laws that govern how an employer treats its employees. This approach is beneficial to the employees and the corporation.

How do you know when it is time to move jobs?

It is time to move jobs when you have mastered and conquered the challenges of the current position. I am a life-long learner who is always seeking greater wisdom and greater responsibility for a greater impact whether in Corporate America, community service or in the church. If there are opportunities to learn, grow or provide greater services, then it is fine to remain in the current role. However, if you have outgrown the role or plateaued, it is time to take advantage of fresh new opportunities to grow and serve.

What is the best way to obtain a promotion?

There are a couple of occasions when the time is ripe for seeking a promotion: 1) after you have delivered on a major assignment that has demonstrated your skills, knowledge, leadership abilities and readiness for greater responsibility; and 2) when you have exceeded expectations, i.e., gone above and beyond and everyone is aware of it, including management, clients and business partners. The key to both scenarios is to document your accomplishments, seek feedback and input from colleagues, clients and business partners and work with a sponsor who will vouch for you at the decision-making table.

What advice do you have for less experienced women?

First, the key to advancement in most careers in the industry today is relationships. You must learn how to work with others in a positive, collaborative and collegial working environment. Second, you must demonstrate your legal prowess and expertise. Begin to make a name for yourself as the go-to person in the legal department. Become the one who will provide quick, thorough advice and counsel. Third, develop your leadership abilities by being proactive in identifying compliance gaps and establishing work teams to close those gaps for the benefit of the organization. Many organizations have leadership development departments that can facilitate honing one’s leadership abilities. Additionally, do not be apprehensive about asking management and Human Resources about opportunities to work with an executive or alignment coach who may be capable of accelerating your leadership skills and abilities. Finally, insure that your accomplishments, collaborative and leadership efforts are well documented through performance reviews and other memoranda so that when the time comes for a promotion, you have the documentation, documentation, documentation… to justify the request.

What kind of relationships do you need to build in terms of obtaining a promotion or keeping your current position?

First, and foremost, know and learn how to manage up. Managing up means working effectively and efficiently with your manager and beyond. Your relationship with upper management is integral to your success. Managers are responsible for oversight and results in particular units. Managers are responsible for the contents of your performance evaluations. The goal is to maintain a positive, open, transparent and trusting relationship. Seek feedback from managers when appropriate. Keep your manager aware of critical issues and concerns. Ask your manager to lunch. Inquire about the manager’s children. Additionally, having the proper alignment with others within your unit and outside your unit is also important. As mentioned above, collaboration is critical within a legal department because it affords individuals opportunities to know one another and prevent legal exposure as a unit.

Be intentional about developing relationships within the organization. For example, when I worked for one organization, I had to provide employment law advice to the Chief Legal Officer of the company, who was a 65-year-old white male. Others were apprehensive about working with him because of his reputation for harshness. I took the approach that I would treat him no differently than any of my HR clients. I planned to give him his legal options and make my recommendation even if the recommendation was “NO.” I also asked him questions about his farm and what he grew on the farm. He saw that I was knowledgeable, no-nonsense, respectful and approachable. He came to respect me for my legal knowledge, conversation and lack of apprehension. As a result, he became my corporate sponsor who vouched for me at the decision-making table. Before he retired, he wanted me to head up a major department within the organization, but I loved the law too much to leave the legal department. The moral of this story is to demonstrate your ability, humanity and professionalism; and people will respect you for that.

What have you personally observed which stalls career growth?

Sitting on the proverbial “island” stalls career growth. In a corporate law department, you cannot sit in your office and respond “only” to your clients. Collaboration is critical to your growth and success. Another thing that stalls is a lack of desire to grow personally. You must develop your leadership skills and set out to grow personally every day. If you are the same person, with the same skill set, same abilities, same approaches of the “You” of three years ago, then you have not grown and you are definitely not ready for the next level of career advancement whether within the organization or external to the organization. Lawyers have a tendency to focus only on their technical abilities. However, how you accomplish your responsibilities is just as important as what you accomplish. How you accomplish tasks, how you interact with managers, clients and business partners hinges on who you are as a person. For example, some individuals have very aggressive personalities, which may turn people off or interfere with the progress of the team. Other individuals may be so passive that they turn people off or interfere with the progress of the team. There are unique balanced approaches one can learn to influence the decision-making or to get everyone on the same page. Those who approach clients in an aggressive manner may inhibit their advancement within the organization. Be kind and respectful to everyone in your legal network and always think about your approach. If a person is emotional and you are too, you can lose your ground. Instead, maintain your professionalism, control your emotions and speak in a normal tone of voice.

What are the top five tips that you would leave with women lawyers?

1. Develop and hone your leadership abilities and don’t forget about personal growth.
2. Seek the expertise of an executive or alignment coach to accelerate your leadership skills, knowledge and abilities.
3. Become a 360 degree leader that is properly aligned with management, direct reports, clients and peers, etc.
4. Mentor and sponsor others in your legal network; the rewards are exponentially high!
5. Give back, particularly to the youth, because to whom much is given much is required...




Great interview! Love tip #5—“to whom much is given much is required…”


Thank you for taking the time and care to provide invaluable advice and a personal perspective. Your insight is helpful for just about any work place.


Outstanding interview with great questions and insightful information!  Very inspiring! 

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