I recently went one-on-one with Jonathan New. Jonathan is a partner at BakerHostetler and previously served as a federal prosecutor in the U.S. Attorney’s Office for the Southern District of New York and as a Trial Attorney for the U.S. Department of Justice Civil Division.
Adam: What sparked your interest in the field of law?
Jonathan: It’s an interesting question, because I didn’t start out thinking I was going to be a lawyer. I was a science major in college and graduated with a degree in chemistry, but I’d always had an interest in history and politics. By the end of college, I realized I didn’t want to just be in a lab. I wanted to do something that involved people, where I felt I could make a difference, and use all my different skills and interests. Law school seemed like the way to go. I went to law school not knowing exactly what I wanted to do with a law degree, but I ended up loving it. I loved learning about the law and practicing it, and ultimately decided I wanted to be a litigator. Along the way, people asked whether I wanted to do something with science, become a patent lawyer, or work in science policy. My answer was always no, because I really liked the law and being a lawyer, and I wanted to pursue that as fully as I could. To the extent I could draw on my science background in certain cases or for certain clients, that was always a plus. I enjoyed that. But having a legal career has been really rewarding for me.
Adam: What were the keys to your early development as a legal professional?
Jonathan: Like a lot of students leaving law school, I did a clerkship. I worked for a judge in Washington, DC, and that’s an amazing experience. You get to see how judges decide cases and what’s important to them, and you’re there behind the scenes discussing legal issues with the judge. You also get to see some of the best lawyers out there practicing law. In my case, it was an appellate court, so I got to watch great lawyers come in, make arguments, and write briefs that were persuasive and influential. At that stage, a lot of it is just soaking it all in and seeing how the best lawyers practice. That’s really important. There’s also the mentorship that comes with it. The judge I clerked for has always been there for me when I’ve had questions or needed guidance about the next steps in my career. Mentorship is very important in law, like anywhere else.
After that, I went to work at a law firm in New York, where again I was exposed to great lawyers and really interesting, complex cases. Even if I had a small role on the team, you learn a lot from the people around you and how they approach their work and their cases. You also develop relationships with successful senior lawyers who mentor you as you move forward. That’s really been true at every step of my career. I’ve always wanted to challenge myself, do something different, develop my skills, and learn from the best. I think I’m still doing that today. Even though I’m now in a position where I’m mentoring younger lawyers, I’m still learning from the people around me and from people who have more experience than I do.
Adam: It’s a really important point. Learning may start in the classroom, but the real learning takes place outside the classroom. It happens through doing and through surrounding yourself with people who can teach you, coach you, and mentor you.
Jonathan: That’s absolutely true. Relationships are very important in any career because you learn from the people you have relationships with, and you also give back. No matter what stage you’re in, there’s always more to learn. I feel like every day I’m learning something new. Sometimes it’s in different subject matter areas. One of the nice things about the type of practice I have is that I see a lot of different industries and clients, and I get to learn about what they do. That keeps everything fresh. Whether it’s my clients or other lawyers, there are always people doing things that not only teach me something but also inspire me to do better. That’s always important to keep in mind as you move through your career.
Adam: You’ve hit on a really important theme, which is that the most successful people are lifelong learners. They’re continually focused on getting better and growing.
Jonathan: I agree. Learning is so important. One thing it does is keep you humble, which matters. No matter how successful you’ve been or how much you’ve done, there’s always more to do and more to learn. You can always get better, not only at your career but at life. There are different types of learning. There’s book learning, and there’s learning through practice, and both matter. As a lawyer, I’m constantly reading legal opinions, legal briefs, articles, books, and other academic work. You never know where something you read is going to feed into your practice. Keeping an open mind and maintaining a broad set of interests matters. Sometimes, if you get too focused on the narrow area you’re involved in, you miss opportunities for creativity and for thinking outside the box. Learning helps you avoid that.
There’s also learning in terms of dealing with people and navigating different situations. You’re constantly being put in different situations, whether as a lawyer or as a person, and there’s always something you can take away from those experiences. All of that feeds into what you do every day in your work.
Adam: Were there defining moments or cases early in your career that really shaped you as a professional?
Jonathan: Yes. The first thing that comes to mind is when I was at the Justice Department. I was in a unit that handled all sorts of litigation. Anytime the US government was sued, we defended it. They put me on a team that was about to go to a hearing in a massive arbitration against the US government under NAFTA. It was one of the first arbitrations under NAFTA. I got thrown into that team at the last minute. We were up against great lawyers, and the arbitration panel included a very well-known US judge, a very well-known Australian judge, and a well-known Canadian judge. I was thrust into that situation, had to learn the facts quickly, and had to find my role on a team of really good lawyers. I learned a lot from that.
The second example would be when I got to the US Attorney’s Office in New York. There, my job was criminal law, and you really learn by doing. They throw you in. During your first year, you’re constantly in court, constantly arguing in front of different judges, and handling your own cases from start to finish. You have guidance and supervision, but it’s still on you.
It’s terrifying at first, but it’s the best way to learn because there’s really no safety net. You’re out there, and sometimes you make mistakes. That’s okay. The important thing is to admit when you made an error, correct it, and learn from it so you don’t repeat it. That was instrumental in my career. There were also cases along the way that were more high-profile than others and helped me develop different skills.
A big part of being in the US Attorney’s Office is also learning to exercise good judgment. You’re representing the United States, and you have a lot of power as a prosecutor. Now that I’m on the other side as a defense attorney, I think prosecutors have too much power. But when you’re in that role, it’s incredibly important to keep things in perspective and exercise good judgment about what investigative steps to take, how to handle a case, and whether a case should even be prosecuted at all. As a line prosecutor, you do have supervisors looking over your shoulder, and you need approvals for certain things, but still, learning how to exercise that judgment, both in terms of the law and in terms of perspective, is critical.
Adam: How can you develop great judgement?
Jonathan: It’s a good question. People often think you either have judgment or you don’t, but that’s not true. A lot of it comes from being placed in different situations, experiencing different things, and seeing how things play out. A lot of exercising judgment is being able to analyze the particulars of a situation and figure out what the consequences will be if you go down different paths. Experience helps with that. Sometimes it starts with watching how other lawyers handle situations and asking yourself why they made the choices they made. They could have gone one way or another, so why did they choose that path?
I also think sometimes you have to trust your gut. Part of judgment is being able to explain it to a client. Some clients will trust your judgment right away. Others are very experienced, very intelligent, and very successful in their own careers, and they have their own views about how things should go. Sometimes what they expect is not what you believe to be the best course. So you have to be able to explain why, in your judgment, this is what they should do and convince them that you’re right. Law is a service profession, so ultimately the client makes the decisions. We’re there to advise. All you can do is give your best advice based on your judgment.
Judgment is part of it, but another part is being able to communicate with your client and advocate effectively for them and their interests. It gets complicated, but judgment is something you develop over time as you get more experience, are placed in more situations, and see the results that come from different choices.
Adam: Can you accelerate the process, and if so, how?
Jonathan: A lot of it goes back to what we were talking about earlier with mentors, relationships, and coaches. You need to be able to go to people you trust who are a little more senior and more experienced and say, this is what I think we should do. This is where my judgment is leading me. Can you give me a gut check? Am I seeing this the right way?
The answer may be yes or no. If it’s no, they explain why, and that’s how you learn. You need relationships not just with one person, but with multiple people, where you can have those frank discussions.
Sometimes it’s not just mentors. Sometimes it’s peers. One of the great things about the places where I’ve worked is that I’ve had great peers and great relationships. We constantly had each other’s backs. We had open doors, and people would walk in and say, here’s the problem I’m facing. Can we talk about it for a bit?
Those conversations with peers help you develop judgment and confidence in your own judgment. Early in your career, a lot of the issue is confidence. People think, what do I know? I’m just a first or second-year lawyer. Maybe I shouldn’t be doing it this way. But having those conversations helps you become more confident in your judgment and develop better judgment overall. Part of it is gaining experience and watching other people. But a lot of it is also having those conversations and gut checks with peers and mentors. That goes a long way.
Adam: It’s such an important point because it’s a team sport. You might be the person whose name is on the line and the one accountable to the client, but unless you’re a solo practitioner, you have people around you. Even if you are a solo practitioner, you still have the opportunity to build a network, join bar associations, and find other professionals whose advice and counsel you can seek. Trying to do it all alone is risky. If you want a shortcut to better judgment, a lot of it is turning to the people around you and marrying their experience with your own.
Jonathan: That’s exactly right. And even if you’re a solo practitioner, it’s much easier today to stay networked with people. There are so many ways to do it, and it’s an important part of anyone’s development as a lawyer and of their continued practice. I’m a member of various bar associations and very active in them. It’s great because you meet a lot of people, share ideas, share thoughts, and network all the time. Some organizations I’m part of have listservs or email groups, and people in those groups are constantly raising questions about things coming up in their practice and asking others for their experience or advice in a very collaborative way. A lot of those people are solo practitioners. There are so many ways to connect with other people in the same profession and practicing the same type of law. That’s a resource everybody should draw on, because it makes everyone better.
A lot of it is bar associations. There’s the ABA, which everyone knows about, and it hosts conferences and things like that. But there are also all sorts of local bar associations. In New York, for example, there’s the New York City Bar Association, which I’m a member of and very active in. It’s great. They have all sorts of activities, networking events, and programming. And it’s not just lawyers there. There are also judges and people who are law adjacent in some way. Another example is the Federal Bar Council in New York, where judges and lawyers in the federal courts get together on a regular basis. Some places also have Inns of Court, where judges and lawyers come together, learn together on various topics, and spend time together in a more structured setting.
So you have those formal bar association structures. Then, whatever law school or undergraduate school you went to will often have networking functions, events, listservs, or meetings where you can get together with people. As you move through your career, you keep building networks that create more ways to interact. For example, the alumni of the US Attorney’s Office get together regularly, and there are different ways for us to stay connected. As your career progresses, you keep building more ways to network, meet people, and stay in touch.
It’s also important to keep in contact with people you’ve worked with over time, not just professionally but personally. Some of your lasting friendships develop in situations where you’ve worked hard together. I was at an event recently where someone pointed out that when you’re in the US Attorney’s Office, and you’re on a very intense trial, you really bond with your trial partner. Usually, you end up very close. Sometimes people wind up hating each other, that happens too, but for the most part it creates an intense bond because you’ve been through a battle together. Those are the kinds of relationships you need to maintain as you move through your career and through life.
Adam: You’re touching on something really important, which is the intersection between professional relationships and personal relationships. Professional relationships can and often should evolve into friendships. On the flip side, relationships developed in a more personal setting can also benefit you professionally. You talked about spending time with judges outside the courtroom and then interacting with them professionally. Similarly, you might find yourself across the table from an attorney who, in one context, is your adversary and in another is your friend. Those relationships can change outcomes.
Jonathan: That’s absolutely right. It’s funny. When I have clients, and I’m in front of a judge I’ve appeared before before, or a judge I know outside the courtroom, the client often thinks, this is great. We’re going to do well because you know the judge. I always have to explain that it is a good thing that the judge and I are on good terms, because what that means is the judge knows that when I say something, I mean it. They’ll listen to what I have to say. They’ll take it seriously. They’ll show me respect. They’ll know I’m not just posturing for my client. That helps tremendously.
But they’re not going to cut you a break just because they know me. You have to set that expectation with the client. Still, it is a huge plus. The same is true with an adversary on the other side of the table. Credibility is so important in the law. If the person on the other side or the judge knows you and you have credibility with them, it cuts through so much. You can come to resolutions more quickly and hopefully get a better resolution for your client than you otherwise would. The main thing is that there’s a real dialogue. Good people on both sides listen to each other, and there’s credibility there. That matters more than anything else.
Another reason it’s important to have relationships outside the courtroom or outside the legal sphere is that it helps humanize your adversary and humanize the judge. It helps you communicate better with them. There are lawyers who are very aggressive and very successful being aggressive, but that doesn’t always work with the person on the other side of the table. If you know that person, know their style, and know what resonates with them and what doesn’t, you can be a more effective communicator and a more effective advocate. So those relationships outside the context of the case or the courtroom really do help.
Adam: How can anyone cultivate credibility?
Jonathan: It’s a very important question. Credibility is one of those things that takes a long time to develop, and you can lose it very quickly. The same is true of reputation. Those are probably the two most important things to maintain if you want to be a successful lawyer. And by reputation, I don’t just mean people saying you’re the best lawyer in the world. I mean, having a reputation for being honest, diligent, and a good advocate. It takes time to build that because you have to prove it. Credibility works the same way. You have to keep it in mind with every case you argue and every brief you write. You have to ask yourself how this is going to look down the line. I may be able to make this argument now, and I may have a good faith basis for making it, but what if the facts develop later in a way I can already see is possible? Am I going to have egg on my face because this argument won’t hold up in a week, a month, or a year?
You have to think carefully about that, because whether it’s within one case or across multiple cases in front of the same judge or against the same advocate, you want to maintain that level of credibility where if you make an argument or state what the facts are, people know they can take it to the bank. You build that over time. It’s not just over the years. It can be within a single case, too. So credibility needs to be part of your strategic thinking at every stage. As you develop your arguments and decide when to press certain points, you want to do it in a way that is not only persuasive and forceful but also credible. Hopefully, over time, you develop a reputation for being consistently rock solid in terms of credibility, advocacy, and all the other qualities that make for a good lawyer.
Adam: What are those other qualities?
Jonathan: We’ve talked a lot about credibility. That’s obviously important. Preparation is probably the number one thing, and that won’t surprise anyone. You have to be prepared and overly prepared. You really cannot prepare enough for an argument, a brief, or a legal situation. You always want to know the facts and the law better than anyone else. Part of that preparation is doing things like mock arguments and mock trials. We always want to face tougher questions in preparation than the questions we’re actually going to get in front of the judge, the adversary, or whoever it may be.
Another important factor is thinking for the long term. Lawyers who think beyond the immediate issue or the immediate battle are usually more successful. It helps to have a strategy thought all the way through to the end of the case. One thing that has made me and others with similar careers successful advocates is that we’ve tried a lot of cases. We’ve seen cases from start to finish, and we know how things play out in front of a judge or a jury. Litigation can go on for years, but it’s important at the beginning of a case to think about how you’re eventually going to present it to a jury or a judge, and then keep that in mind all the way through.
So preparation and long-term planning matter a lot. The last piece is being realistic and setting realistic goals for your clients. It can be hard when you have a client who is completely certain they’re going to win or completely certain they did nothing wrong. You may look at the facts and agree that they have a strong position, but that still doesn’t mean they’re necessarily going to prevail. You have to set realistic expectations as early as you can. That’s hard, because on the one hand you want the client to feel that you’re going to be the strongest advocate for them that you possibly can be, and you should be. But on the other hand, you need to be able to look them in the eye and tell them there are flaws in the case and they need to understand that.
Striking that balance can be difficult. Setting realistic expectations and communicating with the client as you go along is very important, because the last thing you want is for a client to feel surprised or feel that you didn’t tell them something or warn them about something. That’s a terrible situation for both the client and the lawyer, because you’re not doing your job if you haven’t prepared them for all the possible outcomes.
Adam: You’re really hitting an essential skill, which is communication.
Jonathan: I think that’s right, and you also have to be a good listener. When it comes to criminal defendants, a lot of your job is almost like being a therapist sometimes. I represent both companies and individuals, but with individual defendants, it can be very difficult, because this is an incredibly stressful situation for them and their families. They may be facing criminal charges, or they may already have been charged. There’s a lot of anxiety, fear, and pressure, and you have to respect that. You have to listen to them and be a sounding board for them when they come to you with those feelings and concerns.
That’s not something they teach you in law school. Unless you also got a degree in psychology, which I did not, it’s not an easy thing to learn. So yes, you have to be a good communicator in terms of explaining what you think and what you see, but you also have to be a really good listener. And that matters outside the criminal space, too. When I’m dealing with civil clients, and there’s litigation involved, it’s important to listen to what they want the outcome to be. It’s not always just about winning or losing. There are other factors involved. So it’s important to establish early on what a win would look like for them and what they’re really looking for. That requires a lot of communication. It’s not just what you’re telling them. It’s also about listening to what they have to say.
Adam: How can anyone become a better communicator and a better listener?
Jonathan: It’s a good question. When it comes to listening, a lot of it is discipline. It’s being willing to stop talking for a little bit and really listen. You have to be an active listener. You have to focus on what the other person is saying and respond to it. I also think it comes down to how you treat other people in your everyday life. This is another place where there’s overlap between work relationships and nonwork relationships. Whether it’s with your significant other, your friends, or your family, you have to be a good listener to make those relationships work. So part of it is realizing that the same skills you apply to your personal relationships should also be applied to your clients. That’s part of how you develop both as a person and as a lawyer.
Adam: What other skills are critical for legal professionals to possess and develop?
Jonathan: There are the obvious skills they teach you in law school, like legal writing. You have to be a good writer. In fact, let me take the word legal out of it. Being a good writer is just important, period. The most effective advocates are good writers. When you read a legal brief that’s really persuasive, it shouldn’t feel like a legal brief. It should feel like strong, persuasive writing, like a good essay or another form of compelling prose. So developing strong writing skills is obviously very important. The same goes for oral advocacy. You need to be a good advocate, and a lot of that comes back to communication. Being able to adapt in an argument is very important. You have to listen to what the judge is saying and respond to it, rather than just sticking to the argument you came in wanting to make. It should almost feel like a conversation.
Then, of course, the foundation of legal work is analysis and preparation. You need to take the time to sit down and deeply analyze the facts and the law, organize them in a way that makes sense, and then prepare. Just prepare, prepare, prepare. We’re all busy. We all have a million things going on, a lot of clients, and a lot of cases. You need to find a space for yourself where you can focus on one thing.
We live in a world full of distractions, and people multitask, which is fine. But when it comes to doing a great job for your clients, you need to put all of that aside. You need to be able to focus on one task at a time and really put in the time and effort. That may mean finding a quiet place or carving out a specific time for yourself. Thankfully, we have more options now. We can work remotely, so we don’t always have to be in the office. Personally, I like being in the office. I find that I concentrate and focus more there. Psychologically, it helps me compartmentalize the work I’m doing from everything else going on in my life.
So if I need to prepare for a big argument, a big case, or an important client meeting, I can come into the office, close the door, and focus. I think it’s important for everyone to figure out what environment works best for them and then make sure they have that space where they can zero in and be fully focused for as long as they need. And it may be a generational thing too. I’m getting a little older, and I see my kids. They feel more focused not being in an office or a library. They’d rather work in their room, at a coffee shop, or somewhere like that. You have to figure out what works best for you individually. That’s always the most important thing.
That’s actually something I didn’t mention earlier and probably should have. You asked me what’s important to being a really good lawyer, and one of the best pieces of advice I’ve ever gotten, and one that I believe completely, is that you have to be yourself. Whether you’re standing up in the courtroom, arguing across the table from another lawyer, or talking with your client, you have to be yourself. Some people are naturally bulldogs. They’re very aggressive, and that works for them because that’s who they are. If someone who isn’t like that tries to be that way, it’s just not going to work.
That’s particularly true in front of a jury or a judge. You want to communicate effectively and persuade people, and they’ll see right through you if you’re acting, if you’re not really being who you are. So the best advice I’ve gotten and always taken to heart is don’t try to be somebody else. Be yourself. Be the best version of yourself you can be, and then you’ll be successful. Authenticity is so important in everything in life. But in terms of being a good communicator and being effective as a lawyer, it’s right at the top.
Adam: You touched on how things have evolved, and it is no more evident than through the application of technology. When you were coming up, there were legal libraries. Are legal libraries still around?
Jonathan: I don’t think they really are, quite honestly. It’s funny, I was talking about this the other day. When I was in law school, they still taught us to do legal research by going through indexes and books. Now, of course, you don’t do that. Everything is on Lexis or Westlaw or other online databases. That old way of doing research was actually helpful to me, even today, because when you’re looking through an index or a book, you really have to formulate your question and your research in a certain way. You have to boil it down to what you’re actually looking for. I think that still helps now.
Of course, research is much faster today, and you have access to far more materials than you did then. Things have definitely changed. Even in terms of everyday work, I remember when I started out as an associate at a big law firm, and I’d be working late at night on a brief or editing something. Before I went home, I’d drop it off to a word processing pool, basically a room full of secretaries who worked overnight typing and editing everything. That doesn’t happen anymore. We also used to fax things to each other. I don’t think anybody even knows what a fax machine is anymore. Not to sound like an old timer or get nostalgic. I don’t necessarily think those were better times. Technology has made things much more efficient and much faster.
Court filings are another example. It used to be that someone actually had to go down to the courthouse and physically file something by a certain time so it could be stamped and entered. Then you’d send it by courier to opposing counsel. Now you can work until midnight and submit it electronically. So yes, things have changed a lot, and things move much faster than they did before.
We’re now moving into an era where a lot of AI is being incorporated into everyday life. Like a lot of lawyers, I’m still figuring out how best to use it. But it’s definitely a tool that’s going to make things more efficient, speed things up, and save time. Even before AI, legal research became much easier through technology. You have much greater access to materials. It also allows solo practitioners and smaller firms to do more. You don’t necessarily need as many lawyers working on things because you have access to technology that can help with research and other tasks in ways that just weren’t possible before.
One of the challenges technology has created is that we now have far more data than we used to. In litigation, you have emails, texts, messages, and all kinds of digital information that need to be reviewed and processed. But the flip side is that we now also have better tools to search through that material and get to the bottom of it. E-discovery is a perfect example. That really didn’t exist when I was first starting out, and now it’s basically its own field. There are so many tools for organizing, sharing, and reviewing documents that can make life a lot easier. I also think it helps to have vendors or other professionals who are experts in those areas, whether they’re lawyers or not, because they can help you figure out the most efficient and cost-effective way to handle those issues in a given case.
Adam: Was there ever a moment in your career that challenged your integrity?
Jonathan: That’s a good question. I’m trying to think of a situation where I felt there was a real choice to make. For me, I don’t think I’ve ever really struggled with making the right decision. That has always been important to me. One example that comes to mind is a case I had when I was in the US Attorney’s Office. I had been asked to investigate a drug case involving an informant who had purchased drugs from someone, and we were deciding whether to charge it. Then I had something else going on, maybe a trial, and I left the matter in someone else’s hands. They went ahead and charged the case.
When I came back to it, the defense attorney came in and presented pretty convincing evidence that we had actually charged the wrong person. We dismissed the case. There was never any question in my mind that dismissing it was the right thing to do, and my supervisors never had any question about that either. It was difficult in the sense that a colleague had gone ahead and charged it, and by dismissing it you were effectively saying they had made the wrong call. But it was still the right thing to do.
There were also similar situations where evidence came to light later that could be helpful to the defense, and we would turn that over. There was never any question about that either. So those kinds of situations came up, but I never felt like I had to wrestle with the right answer, because doing the right thing should always be easy. It goes back to what I said before. It takes a lifetime to build up a reputation, but you can lose it overnight. The same is true with integrity.
If you ever let yourself think about taking the easy way out or doing something that may benefit you in the moment but that you know is wrong, it can really ruin your career, and you’re going to regret it. It will weigh on you for the rest of your life. So for me, it hasn’t ever been a difficult decision, but integrity is absolutely critical. First, you need to make sure you can live with yourself after the decision you make. That’s the most important thing. Second, there are long term consequences to doing something that may seem convenient, but that isn’t right.
I firmly believe there’s karma out there. If you do something wrong, even if it looks like you’ve won in the moment, it’s going to come back and bite you in the end. So do the right thing. It really is the easy thing to do.
