Top Lawyers: Kevin J O’Brien of Ford O’Brien On The 5 Things You Need To Become A Top Lawyer In Your Specific Field of Law

An Interview With Chere Estrin

First, you need the right experience. There are “naturals” in litigation, as in any skill, but raw ability won’t get you that far in such a complex field governed by such artificial rules. Edward Bennett Williams, a legendary trial lawyer, cut his teeth by working virtually out of law school for the Washington DC trolley company, defending personal injury cases on a weekly basis.

The legal field is known to be extremely competitive. Lawyers are often smart, ambitious, and highly educated. That being said, what does it take to stand out and become a “Top Lawyer” in your specific field of law? In this interview series called “5 Things You Need To Become A Top Lawyer In Your Specific Field of Law”, we are talking to top lawyers who share what it takes to excel and stand out in your industry.

As a part of this interview series, I had the pleasure of interviewing Kevin J. O’Brien.

Kevin J. O’Brien is a seasoned trial lawyer and partner at Ford O’Brien, LLP, based in New York City. He is a former Assistant US Attorney for the Department of Justice and specializes in white-collar criminal defense, commercial and securities litigation on behalf of plaintiffs and defendants, regulatory enforcement cases, and arbitrations. He has tried over 25 court cases and numerous arbitrations to verdict.

Thank you so much for joining us in this interview series. Before we dig in, our readers would love to get to know you a bit more. What is the “backstory” that brought you to this particular career path in Law? Did you want to be an attorney “when you grew up”?

Thanks for inviting me. From an early age, I’ve gotten an electric thrill standing in front of a crowd and having their attention — singing, public speaking, debating, even giving keraoke performances. That’s the root of my interest in becoming a lawyer, to tell the truth. It’s a kind of power.

Can you tell us a bit about the nature of your practice and what you focus on?

I’m a litigator, and I try to cast my net as broadly as possible because trials and courtroom work are increasingly scarce. But my specialty is white-collar criminal representation, with a focus on securities cases, because here in New York City securities is our local industry.

You are a successful attorney. Which three character traits do you think were most instrumental to your success? What unique qualities do you have that others may not? Can you please share a story or example for each?

Three traits that are conducive to litigation success: relentlessness (what a senior partner once explained to me as “going after the loose ball”); self-confidence (never let a disappointment affect you, especially in front of a jury); and persuasiveness (finding the narrative that makes sense of the data; what Charlie Parker called “connecting the notes”). I like to think I can call on these qualities, especially the last.

Do you think you have had luck in your success? Can you explain what you mean?

We tend to be more aware of bad luck, of opportunities missed, than good luck, which is everywhere. None of us “deserves” the parents or friends we have or the influential people we meet, all of whom contribute to our successes. So, in that sense: yes, I’ve been very lucky.

Do you think where you went to school has any bearing on your success? How important is it for a lawyer to go to a top-tier school?

I don’t think going to a top-tier law school in and of itself means much in our field. Talented people tend to go to better schools, but going to those schools doesn’t make them more talented. Besides, litigation isn’t closely correlated to test scores or academic performance, unlike, say, tax law. It draws on a lot of other talents, including confidence, personal appeal, and common sense.

Based on the lessons you have learned from your experience, if you could go back in time and speak to your twenty-year-old self, what would you say? Would you do anything differently?

I might have spent more time in theater productions and the performing arts, rather than worrying about my grades.

This is not easy work. What is your primary motivation and drive behind the work that you do?

It’s something I do well, pure and simple. After a while, the things we do become self-reinforcing.

What are some of the most interesting or exciting projects you are working on now?

I have one extremely challenging case representing a company that faces a range of business as well as legal problems, jeopardizing its survival and the welfare of its employees. Our firm has been called upon to deal not only with prosecutors and regulators but also with investors, creditors, board members, and past and present employees. We are functioning as much more than outside litigation counsel, drawing on management and negotiation skills we didn’t know we even had.

Where do you go from here? Where do you aim to be in the next chapter of your career?

I hope to continue doing what I’m doing for as long as I’m able. Each decade of my career has been better than the one before, and I hope the trend continues.

Without sharing anything confidential, can you please share your most successful “war story”? Can you share the funniest?

My funniest and best “war story” was the time, in a large criminal securities case in New York, I forgot to bring my cross-examination binder (which was meticulously cross referenced with exhibit numbers and various tabs) to court on the first day of cross examination. I proceeded to give the best cross examination of my career, and it was finished well before the day was out. There’s a moral there — in fact, several.

Ok, fantastic. Let’s now shift to discussing some advice for aspiring lawyers. Do you work remotely? Onsite? Or Hybrid? What do you think will be the future of how law offices operate? What do you prefer? Can you please explain what you mean?

Our new offices are still being built out, so I’m working from home even now. I think a hybrid model, with a core number of regular days in the office, makes the most sense for law firms in the future.

How has the legal world changed since COVID? How do you think it might change in the near future? Can you explain what you mean?

It will be many years before we can assess how the pandemic has affected us all in the legal world. Already I sense impatience at many of the old ways of doing things — commuting every day, flying to attend routine meetings, trouping to court on the slightest pretext. The pressure of this impatience will lead to real changes in how we conduct litigation and try cases. Litigation may finally enter the 21st century.

We often hear about the importance of networking and getting referrals. Is this still true today? Has the nature of networking changed or has its importance changed? Can you explain what you mean?

Networking hasn’t changed really but its importance as grown as more and more lawyers compete for a relatively fixed amount of work. This is especially true in New York City.

Based on your experience, how can attorneys effectively leverage social media to build their practice?

I may be the wrong person to answer that question. In my very limited experience social media is nice but not that useful in building a practice.

Excellent. Here is the main question of our interview. What are your “5 Things You Need To Become A Top Lawyer In Your Specific Field of Law?” Please share a story or an example for each.

Here’s a good list for an aspiring litigator.

First, you need the right experience. There are “naturals” in litigation, as in any skill, but raw ability won’t get you that far in such a complex field governed by such artificial rules. Edward Bennett Williams, a legendary trial lawyer, cut his teeth by working virtually out of law school for the Washington DC trolley company, defending personal injury cases on a weekly basis.

Second, you need dogged determination and relentlessness, what that senior partner termed “going after the loose ball.” No rock can be too small to turn over, since you never know what you’ll find. This is especially true in white-collar cases that are document-intensive and may involve thousands and thousands of emails.

Third, you need innate self-confidence to carry you through the inevitable setbacks, surprises, and disappointments. Juries can sense this quality; perhaps more important, so can clients. In litigation, in the long run, you have to act like a winner to be a winner.

Fourth, you need an instinct for narrative, the connections that make facts memorable and capable of persuasion. It’s been proven that juries don’t remember “evidence;” they remember the stories in which evidence is embodied. One of the best ways to hone this instinct is to read and write, well and often.

Finally, you need the ability to improvise on your feet. This isn’t the same as eloquence (which isn’t necessary at all, contrary to what happens in the movies). It’s the ability to object in the knick of time, to answer a judge’s challenge without fumbling, or to find the right question to ask a recalcitrant witness. Cases are won or lost in such moments.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might see this. :-)

Wayne Shorter and Charles Lloyd — two great jazz musicians who’ve transcended age. I’d like to know their secret.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!