Thought Leader Spotlight: David Greenspan

What attracted you to your chosen field and profession?

I grew up in a family of attorneys. My father was a prosecutor who eventually worked for a law firm. Two of my uncles, three of my cousins, and my younger sister are also lawyers. But the biggest influence truly came from my dad. I looked up to him and wanted to be like him. I also remember going to court with him as a child. I'd watch him in court and thought being a lawyer was "cool" and exciting.

I'm sure there was a moment when I wanted to be an astronaut or baseball player, but I honestly can't remember a time when I didn't assume that I'd become a lawyer. My decision stems from this combination of the "the family business" and admiring and respecting my father.

I'm also hard-wired with a passion and what I believe is my strong ability to communicate, advocate, and problem-solve. Having these skills really gets to the core of what are a litigator's most important jobs.

In terms of my work in the sports industry, that's something that I stumbled upon thanks to some good luck. I was at the right place at the right time, and I was given a great opportunity that's guided my legal career in sports.

What person, opportunity, or game-changing moment had the biggest impact on your career?

My "person, opportunity, or game-changing moment" are one and the same. When I was a young lawyer at Dewey Ballantine, Jeff Kessler joined the firm after I had been working there. He brought his amazing sports practice with him, and needed young lawyers to support his work. A young partner that I was close to and had done a lot of my work for told me that Jeff was going to be a big player at the firm. So he marched me down to Jeff's office to introduce us the day that Jeff arrived - encouraging Jeff to work with me and saying I was one of the best associates at the firm.

I started working with Jeff, and particularly loved doing the sports cases. They were challenging and I only wanted to do more of them. Within a short period of time, I was doing all of my work with Jeff - including our work on behalf of athletes and their unions. Jeff constantly challenged me with new opportunities. It could be daunting, but I embraced the increased responsibility. I loved the work. Jeff is not only a great mentor who's impacted my career, but he's also a great friend.

Sports cases can be different than a lot of "big law" cases because they're often about individuals. When a person's reputation and career are on the line, it becomes very personal. Sports cases also tend to move quickly, and it's fun to see cases that have a beginning and end in a relatively short period of time as compared to other litigation matters that can go on for many years. The stakes, the provocative issues, and the short-life cycles are in part what makes sports cases both challenging and satisfying.

I have had the opportunity to work on some high-profile cases - from Tom Brady's "Deflategate" to Ray Rice's suspension from the NFL. It doesn't matter to me that these cases are in the newspaper, but it's fun when my kids, family, and friends are all fully engaged in what I am doing and want to discuss it.

What is the biggest challenge you faced professionally? How did you overcome it?

It was the bankruptcy of my first law firm - Dewey & LeBoeuf. I became a partner in 2010 at the beginning of the firm's financial issues. Professionally, personally, and for many of my friends and colleagues, it was a terribly stressful and sad event. It was difficult practicing law and serving clients when you literally didn't know if the lights would be on or your computer in your office the next day. Even the mail room and copy machines were gone. Lawyers were going to outside copy centers to make photocopies and down to the post office. It was intense and disruptive.

But what came out of it for me was an incredible group of friends and colleagues who chose to stick together and collectively move to Winston & Strawn. I'm not aware of any lateral lawyer group like ours. We're a rare and special group. Our situation is poster-worthy for when good comes out of bad. This includes Jeff's leadership, generosity, and selflessness in keeping our group together. A lot is revealed during times like that, and what he did to look out for as many people as possible was remarkable.

I also learned a key lesson about needing to keep your head up, looking around the corner, and not taking what's going on around you for granted. You can't be complacent or get too comfortable.

What tools or tactics do you rely on in being a more effective leader and team member?

I see lawyering as a team sport where everybody has an important role to play and has got to be hands-on. A competent litigator can only delegate so much. Just because I am a partner doesn't mean I don't have to focus on the details - everyone on the team has to roll up his or her sleeves. Today, I'm still "in the weeds" as I was as a junior lawyer, it just comes later in the process.

I think it's also important to make sure every team member understands they're critically important to the process and results so they feel valued and fully included. I try to keep junior lawyers informed and involved in discussions.

Share a story about an interesting or difficult negotiation and how you were able to gain more influence and leverage as a result.

I can't really go into detail about particular settlement negotiations. But, generally speaking, it is often clear where there is a deal to be had and where there is a case that simply can't be settled. What is particularly frustrating is when it's the former scenario and the other side's lawyers get in the way. There are some lawyers who think their principal job is to be disagreeable. Of course, there is no way "around" an intransigent lawyer. So the challenge becomes figuring out a way to make sure that your client's message gets through - as it was intended - to the ultimate decision-maker on the other side. Solving these kind of people problems - which are non-legal problems - is a challenge. But it's one you've got to be able to navigate if you are going to positively influence a deal.

What do you see as your unique value proposition and how has your personal background prepared you to excel?

My style is different than many attorneys. I'm transparent and pragmatic. I'm very honest - if someone has a good point against me, I will acknowledge it. Being transparent about weaknesses gives credibility to points about the strengths.

Clients like the fact that I listen and I am not tone deaf. I see the bigger picture and know that legal strategy needs to fit their broader objectives. I'm always amazed by how really smart lawyers nonetheless have a hard time with practicality, making good decisions, and knowing how to effectively communicate. I also try to be practical about formulating strategies that are the least disruptive and expensive for their businesses.

Ultimately, I try to be very user-friendly. This is a really good formula for being able to cut through a lot of BS and finding the common ground.

What is your proudest achievement?

I'm most proud of my family. I'm fortunate to love my job, but at the end of the day, I'm someone who looks forward to returning home above all else. Work-life balance is a struggle for lawyers, but if you don't take up golf and you compromise on sleep, there's enough time left in the day to be a good lawyer, husband, and dad.

I'm a full-time member of my household. For me, it's not a "chore" to drive carpool or help with homework -it's what I'd prefer to be doing. I am very proud of how I have made my family the priority, and I work hard to make everything fit into my life.

Opinions expressed by the author are not necessarily those of WITI.