Alumni Spotlight: Tom Boss ’24L Tom Boss is an associate at Williams and Connolly in Washington, D.C.

Tom Boss ’24L

Tom Boss ‘24L grew up in Orono, Maine. In 2015, Tom joined The Young Americans as a dancer and performed on tour in Europe, Japan, and the U.S. over the next three years. He graduated from Leiden University in The Hague, where he majored in international studies and minored in intelligence studies, focusing primarily on East Asia. During law school, Tom interned for former Chief Justice S. Bernard Goodwyn of the Supreme Court of Virginia. He was also heavily involved in W&L’s Moot Court program, both as a participant and member of the Moot Court Board. Tom also taught hip hop and performed with the Rockbridge Ballet while at W&L Law. Tom is now an associate at Williams & Connolly LLP in Washington, D.C., joining the firm shortly after graduation. Outside of work, Tom continues to enjoy dance as well as his other passions of hockey, scuba diving, and board games.

Discuss your career path and how it led you to Williams & Connolly?

My path to law school, through stints as a professional dancer and studying abroad, was not traditional. Those experiences taught me how to handle new or difficult situations creatively and with perseverance, situations that I encountered often in law school and even more so as a practitioner. Applying to Williams & Connolly was similarly difficult. I knew it was at the top of my list based both on my desire to be in Washington, D.C., and its free-for-all model that prioritizes training its attorneys as generalists rather than placing them in specific practice groups. However, Williams & Connolly does not do on-campus recruiting at W&L, so my only option was to send a cold application directly to the hiring committee. I searched for any information I could find about the firm and its inner workings, and even read a book written about the firm to understand its culture and ethos. Whether it was a strong application, luck, or a little of both, I was granted a screener interview and ultimately received an offer to join the firm as a summer associate. Following graduation, I returned to the firm and have been working there since. I hope my experience encourages others to take similarly unlikely chances, because it may just work out!

What sort of legal issues do you handle on a day-to-day basis?

Williams & Connolly, in contrast with many other litigation firms, does not have set practice groups. I have had the opportunity to handle all kinds of different cases, involving topics such as commercial contracts, immigration, government investigations, criminal prosecutions, civil rights, appeals, and even trusts and estates. I joined the firm specifically because I wanted the opportunity to try so many different cases, and while I’ve found some areas I prefer over others, I still try to keep a diverse docket if I can. Currently, my day-to-day mostly involves issues related to arbitrating contract disputes and state and federal appeals. But by the time you read this, I’m likely already working on something else!

What do you like about your current job?

As I mentioned, I really love the ability to work on a variety of different cases and issues because nothing ever feels stale and I’m constantly in a state of learning. Aside from that, the firm maintains a really tight-knit culture and employees often interact outside of work. One highlight from this past year was the firm’s intramural soccer team, which is comprised of staff, associates, and partners. Every year, D.C. Scores (an organization dedicated to empowering D.C. youth through health and wellness) hosts a charity tournament, with one bracket composed of firms from all over the city. While our staff and attorneys are generally a competitive group in litigation, we kicked it up a notch for this tournament and not only took home the trophy but went undefeated the entire day. Sharing moments like that with my colleagues makes the long hours and late nights worth it just a little more, and the trust built on the field really does permeate throughout the building.

What are some practices you have in your daily life as an attorney to maintain wellness?

I cannot emphasize enough that, even more so than law school, the practice of being an attorney can take up all of your time if you let it. It’s so important to maintain your hobbies and be intentional about making time for them. Personally, I try to prioritize fitness as much as I can. I’ve returned to playing ice hockey three times a week and try to get in the gym any day I’m not on the ice. I also commute to work via the metro, and if I’m not responding to emails, I’ll be enjoying a book on the way to and from the office. Finally, my fiancée (also ‘24L) and I often organize game nights to stay in touch with our friends.

Looking back, what do you think is the most formative experience you had in law school?

It would have to be either the Davis Moot Court Competition or writing a Student Note, both for the same reasons. Both the Moot Court Competition and writing a Student Note take an immense amount of time and preparation to complete. They also involve honing arguments constantly, picking out any potential faults or flaws, to make an airtight argument. Finally, the culmination of both experiences was a body of work I knew was the product of my efforts that I felt truly proud of. Those experiences have been informative in my practice, where long hours of preparation ultimately result in trial or arbitration, and spending the time to be prepared makes a huge difference. While in the moment the work can be grueling, these experiences showed me that the payoff is worth it and hard work is always rewarded.

Which W&L classes and/or experiences do you think were most helpful in preparing you for this job? 

It may sound like a boring answer, but classes such as Civil Litigation, Administrative Law, and Federal Jurisdiction show up constantly in my work. Understanding the procedure by which cases make their way through the legal system is critical to being prepared and anticipating what the next steps in a case are, and you do not want to be the party whose case is dismissed due to procedural errors. Otherwise, the practicums (such as the Civil Litigation or Appellate Advocacy) helped me develop skills in connection with actual issues or topics I now see in my practice. Getting to write and argue these kinds of issues in a supervised environment is an opportunity that you simply cannot get in content-heavy classes, and making mistakes in such an environment is an invaluable learning experience.

What advice do you have for prospective law students?

Try anything. School is the best place to make mistakes, ask “dumb” questions, and explore anything you might have an interest in before going out into practice. There is no “right” way to do law school or “best” career path for anyone. Learn from your peers, and work together, but find what study habits work for you and what types of law might pique your own interests. As a close friend recently told me: “You’re all on this journey together, but your growth is your own.”

If you know any W&L alumni who would be great profile subjects, tell us about them! Nominate them for a web profile.