Sonya: When did you first realize that you wanted to become an attorney? What first drew you to a career as an attorney? What do you enjoy most about your career now?
Reginald: I realized I wanted to become an attorney when I was a junior in college. I attended a law school fair where I learned great deal about law school and the career opportunities open to law grads. At about the same time, I started reading more about Thurgood Marshall and his path to the Supreme Court and that solidified my desire to attend law school and ultimately become a lawyer.
As a practicing attorney, I most enjoy using my legal skills to help my clients solve problems. Whether it be solving a complex contractual issue, structuring an employee retention plan in an M&A deal or helping the business manage its data collection practices to comply with privacy laws, the real satisfaction comes when we are able to solve the hard problems.
Sonya: Have there been specific people (real or fictional) or pivotal situations/events that have inspired you, helped shape your career?
Reginald: Yes, of course. First on the list is my mother who has supported me in all things, including my pursuit of higher education. One of my earliest memories is of my mother subscribing me to a book club – I was probably 7 or 8 years old – and me getting excited whenever that package of new books arrived in the mail. I can’t be certain, but I think that is what inspired my love of reading.
Sonya: Are there particular traits that you believe successful attorneys share? Traits that you believe you have yourself and which you look for in hiring outside and in-house counsel? How about common traits you’ve observed in other successful GCs?
Reginald: Successful lawyers – successful people for that matter – are genuinely curious and have an insatiable desire to learn. Successful lawyers tend to be voracious readers and have tremendous work ethic. One less obvious trait of successful lawyers is their willingness to take calculated risks. Lawyers are stereotyped as being risk averse, but in my experience, really successful lawyers are quite comfortable taking calculated risks, both in their careers and in delivering legal advice to clients.
Sonya: What professional accomplishment are you most proud of? What would you like your legacy to be in your company/law department?
Reginald: I am most proud of helping Rakuten build a strong and vibrant enterprise here in the Americas region. Rakuten entered the US market in 2005 through its acquisition of a digital advertising business. Since then, Rakuten has grown significantly in the Americas, diversifying its Americas portfolio to include e-commerce, consumer loyalty, data intelligence, e-books, streaming entertainment content and educational content. I have had the incredibly good fortune of having advised Rakuten on many of the initiatives that led to its growth in the Americas. I am extremely proud of the progress that we have made.
When I think about leaving a legacy at my company, two things come to mind. The first is knowing that processes that I put in place are adopted, relied upon and continue to be improved long after I have moved on. The second is seeing my team members achieve career success. Leaders empower their teams to succeed in their jobs and there is no better measure of my success in that regard than seeing members of my team advance professionally.
Sonya: Have you had mentors/sponsors? Have you acted as a mentor/sponsor to others? Is mentorship/sponsorship important? How? Why?
Reginald: I have never really had a formal mentee/mentor relationship – meaning one in which I made a request to be mentored – but I have had several people that I consider to be mentors, including my former supervisor who supported my path to General Counsel. I have also had the benefit of being mentored by other senior attorneys, including GCs and law firm partners. Additionally, I have mentored lawyers interested in becoming legal executives and college students interested in pursuing careers in law.
Mentor/mentee relationships are very important. The mentor/mentee relationship represents an important knowledge transfer, where the mentor shares critical, relevant and timely personal insights with the mentee and the mentee, in turn, can capitalize on those insights. The targeted and relevant nature of the information makes it all the more powerful for both the mentor, who likely has a vested interest in the mentee’s success and the mentee, who relies on information to make important life decisions.
Sonya: Think about the legal profession over the course of the next 10 years. What do you see as the big changes that are coming which you believe will most significantly impact the profession and the role of the GC/in-house legal department?
Reginald: I think technology will drastically change the legal industry. Rapid improvements in artificial intelligence and machine learning will fundamentally change how important decisions are made and lawyers will need to have a deeper understanding of these advancements in order to effectively advise clients. Robotics and automation, including autonomous driving vehicles will impact our workforce and lawyers will need to help businesses and individuals navigate the employment law implications. Cryptocurrency will change the way businesses think about payments systems, intellectual property and data and security, among other things, and lawyers will be at the forefront of ensuring these applications comply with industry rules and regulations. Lawyers will also be essential in helping to resolve the profound ethical issues presented by these new technologies.
Sonya: Describe a significant challenge you have faced in your life or career. How did you overcome it? What did you learn from it?
Reginald: I found making the leap from being a lawyer on the team to being a lawyer leading the team to be quite challenging. Leading a team of smart, skilled, experienced professionals requires a skill set wholly different from the skills required to just be a good lawyer. The first thing I did was dig into whatever written material I could get my hands on that offered advice on management, leadership and being a General Counsel. Even now, I regularly block off time to do outside reading that will help me be a more effective leader. I am currently reading Leaders: Myth and Reality by General Stanley McChrystal. I sought out advice from other leaders both within and outside my organization. I worked hard to allocate more time to meeting with other executives within the organization to build relationships, learn as much as I could about the business and to ensure that I had a firm understanding of the company’s objectives. I also made sure to spend more time with my individual team members to ensure that we were working toward company goals and to gauge whether they had the resources necessary to move projects forward. My biggest takeaway from this experience is that moving into a position of leadership takes time and commitment. An appropriate analogy might be when one gets a driver’s license. You learn just enough driving to get the license, but it is only after some real experience behind the wheel do you feel confident enough to call yourself a good driver. Constant feedback from supervisors, peers, reports and even the external world is essential to developing the skills necessary to manage a legal department. What I learned about myself is pretty simple – I really like the job.
Sonya: What does Diversity & Inclusion mean to you? How important is D&I to you personally? As a GC? To your company/legal department?
Reginald: Diversity and inclusion, at least within the business context, means taking full advantage of different perspectives and points of view to foster thoughtful and effective decision making. In my opinion, diversity and inclusion is critically important for businesses, as it increases the likelihood that different points of view are represented when important decisions are made, which ultimately results in better outcomes for business. I think the same holds true for the delivery of legal advice. It is essential that we seek out different points of view in order to provide well rounded legal advice.
Sonya: What advice do you have for GCs and others seeking to make a positive impact on the progress of D&I in their organizations and in the legal profession?
Reginald: I would advise GCs to be intentional in their efforts to foster diversity and inclusion within their departments and to develop detailed processes designed to institutionalize diversity and inclusion. One might consider the play Hamilton when thinking about the end game. We want to have diverse representation in “the room where it happens.”
Sonya: If you were not General Counsel of your company (or of any company or even a lawyer at all), what career do you think you would most like to pursue?
Reginald: Given my passion for sports and how much time I spend reading reviews for sports equipment, it is very likely that if I were not practicing law, I would own some kind of sporting goods, fitness or wellness business.
Sonya: Knowing what you know now about being a lawyer and a GC, if you could give one piece of advice to your younger self, what would it be? At what point in your past would you give yourself that advice?
Reginald: I would tell myself to take calculated risks in my career. Take on that new project or new position practicing in that cutting edge area of the law. Think of every new experience as an opportunity to become a deeply experienced and well-rounded attorney.
Sonya: Tell me something fun about yourself. A personal skill or hobby that, while not directly related to your day job, you feel makes you more well-rounded, helps you be better at your day job and/or helps relax and focus you to do your job as a GC better.
Reginald: Staying active helps keep me balanced and relieve stress. I am an avid cyclist and still compete in endurance events. I occasionally run, but basketball remains my number one sport. I play every once in a while, but mostly you will find me in the gym getting up shots with my sons who enjoy the game as well.
Sonya: Hashtag/Brand yourself in 5 words or less (For example, mine is #SelfiesWithSonya )