Evolving with Intention: One Attorney’s Path from the Courtroom to Conflict Resolution

Discover her evolution from high-stakes litigation to transformative ADR work, the insights that shape her conflict resolution philosophy and her passion for helping individuals and organizations move forward with clarity and confidence.

Please provide a snapshot of your legal career prior to joining JAMS.

I spent the first part of my legal career as a litigation attorney, first at Seward & Kissel and then DLA Piper. While my practice included a variety of commercial and employment matters, I focused my practice primarily on complex commercial matters in the financial services, securities, structured finance and insurance industries. In the fall of 2010, I joined Ambac Assurance Corporation, a financial guaranty insurance company, as first vice president and assistant general counsel. When I joined Ambac, the company was in turmoil after the financial crisis. The parent company filed for bankruptcy on my one-week anniversary, and the insurance subsidiary was in insurance rehabilitation, which is the insurance equivalent of bankruptcy. The company faced billions in future insurance claims, and the focus of the business was to remediate losses. These circumstances created a myriad of legal issues across the company, and the experience was extremely rewarding, professionally and personally. I remained counsel to Ambac until the spring of 2019 and then served as chief compliance officer and senior counsel to an investment management firm before pivoting to ADR full time and launching my own practice, Gupta Dispute Resolutions, LLC, in January 2020. I am excited to continue my ADR practice at JAMS.

How did you get interested in ADR?

When I was in-house counsel, my responsibilities went beyond managing litigation. I often found myself responsible for leading meetings attended by individuals with differing interests, and it was my role to get everyone to agree to a shared goal and objective. Over time, I found that I loved this aspect of my job more than litigation management and strategy. I realized that I preferred strategizing and finding solutions to a problem over the daily conflict of litigation. Then, in 2017, during a mediation that I attended in connection with one of my litigations, I had a lightbulb moment and decided to explore becoming a mediator.

What are some of the highlights of your career to date, whether in alternative dispute resolution (ADR), in litigation or on the bench?

It is tough to pick because I have been fortunate to have had interesting and substantive opportunities throughout my legal career. The best years of my time as an attorney were probably my early years as in-house counsel. My colleagues and I were tasked with helping to develop and implement a remediation strategy for the company’s distressed insurance portfolio in a novel and undeveloped legal area. Those years were the most intellectually stimulating years of my career, and the people I worked with were some of the smartest legal minds I’ve encountered. In ADR, a highlight has been having opportunities to co-mediate with and shadow mediators who are among the best of the best in the commercial space. Those opportunities are few and far between and are incredibly valuable.

What practice areas are you passionate about and why?

I think having variety in my practice helps me continually refine and tap into different skills. That said, I really enjoy digging into complex commercial issues. If the issue involves a financial product, complicated transaction or securities, even better. I love an intellectual challenge and the opportunity to dive into a new subject matter. For different reasons, I also enjoy working in employment. These cases are often personally gratifying because, if I’m able to help the parties, at the end of the case, individuals can move forward and leave often very emotional experiences in the past.

How would you describe your mediation and arbitration style?

As a mediator, my approach is a combination of facilitative and evaluative philosophies, depending on what I think may be necessary to break impasse and what the parties’ expectations are. I’m a straight shooter and am thorough. I also do not give up easily, so until it is clear whether or not a deal is obtainable, I’m going to push the parties to stay engaged. My experience as in-house counsel informs my approach to each case. I’m realistic about what may or may not be feasible depending on the circumstances and corporate objectives at play.

As an arbitrator, my goal is to keep the parties focused on a cost-efficient and timely process. Because arbitration is a product of the parties’ contract, I encourage the parties to collaborate and make joint decisions as to the schedule and process. My role is to evaluate that agreement and confirm they have thought through all of the relevant procedural issues and consequences of their decisions, but assuming their agreement is reasonable, I am not going to dictate a different path. Where the parties are unable to agree, I will be guided by efficiency, due process and fairness in my decisions and orders. Case management is critical. I will regularly check in with the parties to keep the process on track and will make myself available promptly whenever an issue arises.

How do you handle particularly challenging or complex cases?

These cases require more preparation, commitment, patience and creativity. In all mediations, it is critical for me to spend time on the front end before the first mediation session, studying the case, speaking with counsel and the parties, and building rapport with the participants. In complex or challenging cases, I commit a greater amount of time before the first session. It is important to move the ball forward before the mediation so valuable time is not spent educating me on the issues. It is also helpful to work with the parties in developing a case-specific process that will best achieve a resolution in the most efficient manner. For example, in some cases, limited discovery exchange may benefit the parties, or spending time working with the party representatives in advance of the session may help not just with rapport, but in advancing the negotiations at the first session.

In arbitration, thorough preparation and case management are critical in all cases, but more so in challenging or complex matters. Taking the time to understand what the matter is about, the issues that need to be addressed and the parties’ expectations will lead to an arbitration schedule and process that give the parties what they intended when they chose arbitration. 

What are the key traits and skills needed to have a successful ADR practice?

I always tell lawyers who are interested in building an ADR practice that they need to stay patient, remain humble and hustle. You may have decades as a successful attorney, but the opportunities in ADR won’t come overnight. While the decades of legal experience are invaluable, in many ways, you’re starting over, and you need to have patience while those in your “Rolodex” learn to think about you as a neutral and not a litigator or advocate. And for the same reason, you have to hustle—taking whatever opportunities are available to network, speak, write and work. To maintain a successful ADR practice, you need to continually refine your skills to keep up with trends and maintain an unquestionable reputation of impartiality and integrity. It is critical to be a strong communicator, to always be prepared and thoughtful in every matter, and to stay calm under pressure, committed to the end game and optimistic. The clients look to the neutral to set the tone in every matter—whether it is in mediation or arbitration—and successful neutrals are mindful of that responsibility.

What professional accomplishments are you most proud of?

There have been a few pivotal moments in my career where I’ve had to take a leap of faith and trust both my skills and instincts. Each time I have switched jobs, there were respected colleagues who questioned whether I was making the right decision because the move was not always the obvious next step in a traditional legal journey. I trusted my gut and never looked back, despite how hard those leaps may have been in the moment. Currently, I am most proud of the ADR practice that I’ve built the last five years. Quitting my in-house job to pivot full time to ADR and start my own practice was scary and fraught with risk. It is not the path often taken at this stage of someone’s career, and I am not typically someone who goes against the grain. But the risk has paid off, and I joined JAMS last year. Throughout my career, I have always considered JAMS the gold standard of ADR providers, and I’m excited for this next chapter.

Did you have a mentor? If so, what was the most memorable advice given to you?

I have been fortunate to have had multiple mentors, without whom I would not be where or who I am today. The most memorable advice given to me was independently given by two mentors and was essentially: “Trust your gut. Take the leap. You’ve worked hard to build meaningful relationships, and you are not burning any bridges by leaving. If it turns out this move isn’t the right one, you can always come back.” These mentors, whom I immensely respected, trusted my decision-making and encouraged me to take the next step in my journey, even though my leaving wasn’t in their best interests. If they trusted me, I needed to trust myself.

What is your favorite pastime?

I am a beach bum and for me, there’s no better place to recharge the physical and mental batteries than on the beach listening to the sound of the ocean.