Khurram’s Quorum – Ep 050: Shashi Kewalramani on compounding skills across a nonlinear career

Khurram’s Quorum – Ep 050: Shashi Kewalramani on compounding skills across a nonlinear career

Shashi Kewalramani has built a career most lawyers would not recognize as a career plan. He went from a Houston law firm to the U.S. Attorney's Office in the Northern District of California (a 75% pay cut), then to the federal bench as a magistrate judge in the Central District, then out to private practice as a mediator and arbitrator at JAMS, with a long stretch of CJA criminal defense work in between. His word for all of this is non-linear. Most people would just say unusual.

In this conversation, we dig into what actually compounds across those chapters: the trust-building craft he learned representing indigent defendants and now applies to C-suite clients in mediation, the process-as-substance framework he developed as a magistrate judge managing discovery in the most complex patent cases in the country, the "when you have the last word, don't say the last word" discipline that shaped how he wrote every opinion, and the top-three-priorities test he uses to filter every opportunity against what actually matters.

Keep reading below for the full episode and the complete transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Non-Linear Compounds: Shashi's career keeps looping back to the same skill: drawing truth out of people who have a reason not to tell it. He built that skill first as an AUSA, then refined it representing indigent defendants under the CJA, and now uses the exact same muscle on C-suite clients in mediation who are comfortable with silence and have practiced not answering questions.
• CJA Work Is a Training Ground: Big firms that avoid CJA panels are missing one of the best places to train junior lawyers on client counseling. Indigent clients are available to talk. They want to talk. They teach you how to ask questions, how to sit in silence, and how to handle clients who do not trust you by default.
• Process Is Substance on the Bench: The judge's job isn't just to rule; it's to anticipate the choke points in how a case will move and build guardrails in early. Setting a "substantial production" date, adopting Eastern District of Texas-style deposition objection rules, deciding between standardization and customization, those process calls shape the merits just as much as any ruling.
• Marry Credibility to Directness: From the bench, the advocates who stood out answered the question first and explained second. A lot of "well, it depends" is fine if you then walk the judge down the flowchart. Burying the answer or refusing to concede a harmful fact destroys credibility faster than anything else.
• Your Job Is Not Your Identity: Shashi deliberately had his clerks call him by his first name outside chambers, reminded himself the judgeship was a "temp position," and wrote opinions that were measured even when the other side lied. The discipline of suppressing ego on the bench is the same discipline that now helps him empower opposing counsel to close deals in mediation.

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Full Transcript

Khurram Naik: Shashi, I am glad to have you on the podcast. I saw you in action recently on a panel at a conference that a friend curated, and I enjoyed seeing you on the panel. Separately, I interviewed Neel Chatterjee recently and he mentioned, apropos of nothing, that you'd be great on the podcast. So this is a confluence that's bringing you here.

Shashi Kewalramani: Glad to be here. Thank you for thinking of me.

Khurram Naik: Something that's pretty clear from your career is that you've worn a number of hats. You've been in private practice in a range of areas, IP litigation, white collar, criminal defense work. You've been at a large-ish firm, you've had your own practice, you've been an assistant U.S. attorney, you've been a magistrate judge, and you've done these in different jurisdictions. The word you used for this was non-linear. At some point your career was linear, you clerked, you joined a firm, that's linear. Did you prospectively expect to have a non-linear career?

Shashi Kewalramani: Let me go back and correct something in my background. I was never the U.S. Attorney. I was always an assistant U.S. attorney. It's a big difference. One is senatorially approved. One is not. Have I always had a thought of a non-linear path? I would say my first non-linear move was after undergrad, to law school. I never expected to be a lawyer. In the South Asian community at the time, there weren't many lawyers who had matriculated through the U.S. system as lawyers. There may have been some folks who came from countries in Southeast Asia or South Asia who had been lawyers there and then became lawyers here. I had always thought I was going to go to engineering school, go work for a company, and potentially move up the ranks within that company, just as my father did, just as a lot of other folks in my family did. The closest thing to any entrepreneurial spirit I had in my family was folks who were physicians who had to open their own practice. So I don't think I had thoughts about what my future was going to be, whether linear or non-linear. It was just an openness to different paths that came along when I wasn't feeling particularly satisfied with the path I thought I had wanted.

Khurram Naik: You would use the word non-linear to characterize your career. Is that something different than openness?

Shashi Kewalramani: I think they go hand in hand. Linear is what people have in mind. My own linear thought was, get an engineering degree, go to a company, work through the system, move around within the industry, and then retire. Have a good and fulfilling life that way. I now understand, for me and my personality, that I had to be open to different opportunities that came along. When some people pushed back at it like, are you sure you want to do that, the safe path is to stay at the firm, make partner, and then bliss will follow, I didn't think that bliss would follow. When I say non-linear, it's probably more non-linear to other people. There are definitely risk aspects within my own life that are non-linear. For example, leaving a senior associate position at a law firm when you're not far away from partnership to join the U.S. Attorney's Office in another state and taking a 75% pay cut. A lot of people would consider that non-linear. I was leaving the safety of firm life. When I left the court to join JAMS after one term as a magistrate judge, I recognized I was leaving the cocoon, the safety of the federal judiciary, to go out and be an entrepreneur. I'm a little more comfortable with risk-taking. A lot of that is because of circumstances I've been fortunate to be in where I can take those risks. My wife works, so that helps me to allow to take some risks.

Khurram Naik: You mentioned as an associate you didn't see a path in bliss and partnership. Why is that?

Shashi Kewalramani: At least the path I was on, I was an associate, I'd been on trial teams. What I was looking at for people who made that jump to become the lead trial lawyer or lead person at the firm who gets clients, you had to distinguish yourself. The system started changing where there were fewer and fewer trials happening at any big law firm. So the experience wasn't going to be there. I wanted trial experience. I had also been intrigued by moving out of Houston and exploring opportunities outside Texas. That's why I joined and picked the U.S. Attorney's Office. Some folks could have said, I'll join the DA's office to get trial experience. I wanted to do it in a different manner. I was always comfortable in the federal system because of my clerkship and the practice area I was in. I wanted to do more white collar work, document-intensive work, rather than what would be violent crime or narcotics.

Khurram Naik: Did you feel the federal system is more meritocratic? Even in private practice, as a new entry trying to navigate a state court system or a federal court system, did you feel like one would give you a clearer path of success?

Shashi Kewalramani: The federal system is much more rules-based. There is always some level of vagueness in any system, but my feeling was, the judicial officers I had come in contact with as a clerk and practicing, because it is much more rules-based, I did feel I knew the rules of the game. There wasn't like, oh well, so-and-so goes to lunch with so-and-so, so they're going to get a good ruling in state court, not that it is like that. But I knew that was not, or at least perceived it was not, the case in the federal system.

Khurram Naik: You mentioned leaving Texas. What was the significance of leaving Texas for California?

Shashi Kewalramani: A couple of things. The offers I got at the U.S. Attorney's Office: I had interviewed in the Northern District of California, which is in the Bay Area, and the Central District of California. I was about to get an interview there when I accepted the offer in the Northern District. Applying for an assistant U.S. attorney's position is similar to a clerkship. You throw out a bunch of darts and see where you can get in. I had picked five or six jurisdictions that did a lot of white collar work and were places I also wanted to live. I had lived overseas as a child, but after high school I pretty much spent my whole career in Texas. I would come out to California with some frequency and I really liked it. I liked the feel of the place, I liked the opportunities out here, and I was lucky enough to get an offer.

Khurram Naik: Why were you interested in moving into white collar work?

Shashi Kewalramani: It was closer to the type of work I was doing, which was commercial litigation and IP litigation. So it's looking through a lot of documents. It also has, perception-wise, more transferability back to the private sector. I had never intended to be an assistant U.S. attorney for my career. It was a period of time. I was planning to go to a good U.S. Attorney's Office, get trial experience, do white collar work where you were also against attorneys usually at big firms, and then go back into private practice in big law.

Shashi's decision to leave a near-partnership track for a 75% pay cut at the U.S. Attorney's Office is the same class of decision Manisha Sheth walked through in her episode, leaving a partnership to serve in government and bet on herself. Listen to my conversation with Manisha Sheth.

Khurram Naik: Why is it that you had some early skepticism over institutions that attachment to them?

Shashi Kewalramani: I wouldn't say it's an issue with institutions. I would say it was something I didn't see myself at that time with the knowledge I had being a lifetime prosecutor. I thought it would be a four-to-seven-year term, which was very common in some of these U.S. Attorney's Offices, particularly in the Northern District of California, Central District, Eastern District of New York, Southern District of New York. It was very common to do five to seven years, get good experience, work really hard, and then go back into private practice. Versus some other offices around the country where people joined the office and stayed there until they retire.

Khurram Naik: Heading into that tenure, what did you in fact get that you thought you'd get, and what surprised you?

Shashi Kewalramani: The biggest surprise was the number and type of people I came in contact with at the U.S. Attorney's Office and interacting with Main Justice in the 2003–2004 time period. I really enjoyed the breadth of experiences people had. At the law firm, people had a pretty common route: undergrad, law school, clerkship, firm. It was very common. There weren't a lot of folks who had, let's say, gone undergrad, then taught for a period of time or done Teach for America, or joined the military and then gone back to law school and then clerked and then come to the firm. The firm I was working at was much more staid. At the U.S. Attorney's Office people had a lot of varied paths to the law. People taught, people worked overseas, people were in government at some point and decided to go back to law school and join the U.S. Attorney's Office. That was really refreshing, to see that there was not a single path to any career goal. I had been exposed to, there are steps and you follow those steps and it leads to an outcome. But sometimes what we perceive as linear steps don't necessarily lead to the goal. In fact they do, because they expose you to different ideas that tell you what you're going to enjoy and what you may be good at.

Khurram Naik: What's another instance in your career where you experienced an analogous insight?

Shashi Kewalramani: I saw that at the court too, where the people who had been selected for judicial positions hadn't necessarily just gone through what you would consider the steps of big law then getting on the bench. There were people who came from varied walks of life, legal defense funds, public interest entities, government entities, non-government entities, but still succeeded by getting nominated and appointed as a district judge or an appellate judge.

Khurram Naik: Can you point to any specific takeaways from people who walked down different paths?

Shashi Kewalramani: They learned a lot about the world, and I think it made them better people and also better professionals, because they weren't thinking in the way somebody who had just gone through school. They had experienced the world. They brought insight that sometimes I wouldn't think of, and they had unique experiences that gave them some flexibility and insight on how to deal with things. I remember somebody from the U.S. Attorney's Office who had been in the military before they joined, then went to law school. We were dealing with a case and he told me the defense attorney was taking positions that weren't probably beneficial to his client. I was having a hard time reconciling, why are you not doing things in the best interest of your client? I was naive. He explained to me certain things about the real world and how he grew up, the distrust that was probably there between the client and the counsel because of the counsel's relationship with the U.S. Attorney's Office, and that we had to recognize the client and counsel probably had internal friction we had to account for and give some grace to.

Khurram Naik: Did that impact how you took on criminal defense matters through the CJA after you left the bench? Did that impact how you approached your practice?

Shashi Kewalramani: 100%. Because I appreciated that not only being a court-appointed attorney may put me in a certain light with my client, but also I'd been a former assistant U.S. attorney. I would recognize that folks who have been through the criminal justice system, often rightfully so, had hesitancy of disclosing facts to me because they didn't fully trust me. I had to build up that trust over time. That taught me I had to give people space to trust me. I also had to take actions that would allow them to trust me. It couldn't just be words. I had to act in ways that showed I cared about their case and that I was going to fight for them.

Khurram Naik: What specifically didn't they trust?

Shashi Kewalramani: One of the things they don't trust: certain clients of mine couldn't afford an attorney. Under the CJA system, the court appoints you and the court pays for it. They are viewing it as, you're just part of, you and the judge are aligned, and judges in the past have done me wrong, therefore you will do me wrong. Oftentimes the first step in a criminal case is a bail hearing, and oftentimes people wouldn't fight for bail. I always believe the law requires bail except for extraordinary circumstances, and I would voice that position aggressively. The first time they meet me, I'm going to fight for you from day one.

Khurram Naik: What did you do to facilitate trust?

Shashi Kewalramani: Give the folks time. You have to fight for them right from the get-go and be fully transparent with your client and explain why you're doing what you're doing. Full transparency is a big thing in every aspect of garnering trust, both as an attorney and as a judge. In my opinions I wanted to put in everything I was thinking about as a basis for why I came to a decision. You'd see certain rulings that say "I find there's a fact issue, period." Okay, you've got to give me something more than that. Giving time, giving transparency. I would often meet with my clients for hours. I would go meet them in jail if they were in custody for hours, to talk and learn about them and give them the opportunity to speak freely. The fact that I was willing to come into the jail for eight hours in one day and be there as long as they wanted showed I mean what I say. I'm going to treat you just like the $700-an-hour client. Even though you technically aren't paying for me, you're going to get the service that all my clients get.

Khurram Naik: Someone trying to build a practice might say, I could use my time on the $700 client. What mistake are those lawyers making?

Shashi Kewalramani: I was warned about that by other attorneys: you need to stop doing CJA cases because it's taking away from your other cases and your other marketing. My sense is there's a public duty obligation. In the Northern District of California, big law firms would be on CJA panels not only as a way to get court contact with clients, but also to train younger associates on interacting with clients. Rather than them sitting at a deposition and watching, you could take younger attorneys to the jail cell or the meeting room and meet with clients. You have a lot more freedom and time speaking with a client in that setting who wants to talk to you, versus private clients who may not want to talk: give me a deliverable in two weeks, we'll talk then. CJA clients are amenable to strategizing, and it gives you great insight into thought processes. Big firms should do this not only as part of being at the bar but as a great training opportunity. As a former federal magistrate judge, I could say I appreciated when I saw somebody from a big or medium or small firm in my courtroom taking on a CJA case. My level of respect for them went up, and that transfers to other practices and other cases they may have.

Khurram Naik: What's the tangible benefit of that respect?

Shashi Kewalramani: Attorneys representing indigent defendants are in court more frequently. When I see an attorney more frequently, I feel they're less likely to play games with me, because they're going to be in front of me in another case. When they're making arguments, they know if I catch them in a lie, not a lie but a misrepresentation or a misleading thing, it's going to transfer to their other client. Human nature is not to say, I'll do this for the benefit of one and then lose my reputation for all my other cases. It's one more opportunity to build a good reputation with the judiciary.

Khurram Naik: How can skills from indigent-client work transfer to a big business client?

Shashi Kewalramani: One skill transfer is learning how to obtain information that's relevant to the case. Learning how to be patient. Learning to let people speak and tell you what they want to tell you. Practice makes you better. It makes you better at getting information out of whether it's the engineer who gave the specification for the patent or somebody who is not trying to tell you the whole truth about something else. Often the hardest thing to do representing a client is getting the truth out of your own client, letting them tell you where the bad issues are. Sometimes you have to sit back and listen. Some people are uncomfortable with silence. I have found the higher up the C-suite, people are very comfortable with silence. They're smart. They don't want to say more than they have to. Sometimes you have to know how to ask those questions and see the tactics that are taken to divert you from giving an answer. Folks who have, especially indigent, not "criminals," people who have done a bad thing, one of the best lines I've heard was, just because somebody did a bad thing doesn't mean they're a bad person. Sometimes these folks are very smart. They've had to get by in society with wits and intelligence, and you learn things through that process that are transferable to speaking with your own clients. Often your own clients at big companies are amateurs compared to what folks on the streets have had to do to get by.

Khurram Naik: Is there a moment that comes to mind, someone particularly sophisticated you represented in the CJA context, where you learned a technique that struck you?

Shashi Kewalramani: The biggest tell was when somebody wouldn't answer the question in a conference room when it's just you and them. That's the biggest tell. That's something I learned to deal with with my other clients. Sometimes people just need the space and grace to get to that point in their head to tell you the bad thing. Sometimes people need to be pushed. I can't tell you when one approach is appropriate versus the other. I've done it so many times you have a sense of, if I push here, is this going to rupture the relationship, or is this what this particular person needs?

Khurram Naik: Has there been a moment where you've taken something that was objectively a bad fact and inverted that into something beneficial or at least neutral?

Shashi Kewalramani: In certain white collar cases and civil matters, and particularly in mediation, one of the mechanisms to really understand whether a bad fact can be neutralized or at least diminished is, give me the context of this document. That allows folks to then discuss, no, this document isn't as bad as you think, and tell you why. Being able to just sit there sometimes for five minutes in silence while that person is talking, you do this for five minutes, it sounds like a long time, but just sitting there and letting folks speak, sometimes they give you the answer that actually does neutralize it. Or in their explanation they come to realize, yeah, this is a bad one. They internalize the aspect of the document that's going to be harmful, without me having to tell them.

Khurram Naik: You mentioned the CJA panels were much more active in the Northern District than the Central. You've been a prosecutor, magistrate judge, in private practice across two jurisdictions. What's your vantage point on how different districts actually are?

Shashi Kewalramani: The Northern District of California is a lot more tech-heavy, down Silicon Valley. San Francisco has historically been a financial center. There's a tradition of a lot of financial businesses as well as tech businesses in Northern California. It also had an SEC office, as does the Central District. San Francisco has an antitrust division office; the Central District does not. As a result of certain offices with priorities in particular jurisdictions, the practices have morphed to accommodate those enforcement areas. San Francisco has a lot more private antitrust cases than the Central District. Another district that has a lot of antitrust cases is the Eastern District of Pennsylvania. Those formed over years for multiple reasons.

Shashi Kewalramani: Central District of California is just massive, 19 million people. There are a fair number of historically narcotics and violent crime prosecutions at larger scale in the Central District than the Northern District. You had differences in practices of the prosecutors and investigators who would come to these jurisdictions. From the judiciary standpoint, you would see different types of cases, because ultimately we are the client, the attorneys are our clients. In the Northern District you would get a lot more IP, antitrust, and SEC, though there would be some guns and drugs and violent crime. It wasn't nearly as much as the judges in the Central District have to deal with. In the Central District there's a lot of contract cases. There's a lot of commerce, not only related to contracts but also in the entertainment industry, which is big in the LA courthouse. In the Orange County courthouse, a lot of real estate and IP. Riverside has a lot of contract commercial matters and civil rights investigations just because of the nature of the population. Even within the districts, the divisions have a different focus because of the types of cases generated within the counties that comprise the division.

Khurram Naik: What's the impact on the judiciary? What changes for judges as a product of these pockets of expertise?

Shashi Kewalramani: I can speak to myself. There's different ways you manage the case based on the nature of the case. If it's a PI case involving a trucking accident, different discovery, different timeline to get to trial, versus an IP case which may have international components, different motions, different discovery aspects. The more you see of a particular type of case, the more you can anticipate what problems are going to arise and how to put in safeguards in the management of the case. In a home construction contract case versus an IP case, you have to be mindful of what's the scope of discovery and how is that going to impact the deadlines you're setting. Should you put in an end-of-discovery date, or should you put in a date before that called a "substantial production of discovery" deadline, because there may be lingering things that happen. Working with a client in a different country that has different privacy laws. Whereas a two-party contract case has a pretty finite amount of material.

Khurram Naik: Do you think there's a benefit to codifying that in some way, so that sets the norm for peers on the bench?

Shashi Kewalramani: Certain courts have local rules for patent cases. Northern District does, Eastern District of Texas does. Central District of California, there's been talk about it for decades and they have not been adopted. What happens sometimes is the parties will agree, we'd like to use the Northern District of California rules for patent cases in this matter. Some people like that it codifies it. Some people believe it takes away the bespoke handling of every particular case. You have voices on either side. Fundamentally, you can't make judges do something they don't want to do.

Khurram Naik: This impact of procedure and process has been a running theme in this podcast. Judge Kennelly raised it in his episode, talking about the centrality of process for the administration of justice. Judge Chhabria picked up the same theme. It seems to me an underrated theme from the judiciary is the role of process in the administration of justice. The other thing I'm noticing is this tradeoff between standardization and customization for a particular matter. That's a canonical tradeoff judges consider. Are there other canonical tradeoffs?

Shashi's framing of process as substance, the set of discovery and pretrial calls that shape the merits just as much as any ruling, is exactly what Judge Vince Chhabria described in his episode as the core work of the bench. Listen to my conversation with Judge Vince Chhabria.

Shashi Kewalramani: Because I was a magistrate judge I had a lot of discovery matters. There are certain viewpoints that, look, the attorneys will deal with it, and when they have a problem they'll bring it to you. Versus putting in procedures to avoid those issues being brought to you. For example, depositions. If a party had consented to me, I could control a lot of the discovery issues at the beginning of the case. I would adopt the rules with respect to objections at depositions from the Eastern District of Texas, which were, you can only object to form, or you can only tell your client not to answer based on attorney-client privilege or work product doctrine, or you could submit the objection of non-responsive. That does away with speaking objections. In California state court they are supposed to do that. I had enough issues come up before me with speaking objections that were taking depositions beyond the seven-hour time limit that I thought it would be helpful to say, here are the rules, you're going to have these are the only objections you're going to have, and then I don't want to hear, I think you have less of a leg to stand on saying we didn't get all the information we needed in the seven hours allowed under the federal rules and we need more time. There is an involvement in the process that I thought would be beneficial to what I viewed as my clients, the attorneys. Other folks said, look, we're just refs, until we see a foul we just sit back.

Khurram Naik: My experience with magistrate judges is they're feeling so much of the discovery issues across jurisdictions. Article III judges are obviously the flashy role. What do you think people are missing from the opportunity of being on the bench as a magistrate judge, practicing before a magistrate judge, or clerking for one?

Shashi Kewalramani: The role is changing. A lot of districts now have consent programs. The Northern District of California has historically had one. When a case is assigned, in a civil case, if it got assigned to a magistrate judge, a lot of parties will consent. That's becoming more common in the Central District and is very common in the Northern District. So the role is changing. I thought it was a great opportunity. You're in the federal system, you're getting a lot of consent, you are dealing with a lot of the nitty-gritty stuff that happens in cases that actually can help move the process along efficiently. I thought it was a great opportunity for me to learn also how to think like a judge and what is really going on behind closed doors. Even beyond clerking. I clerked for a district judge, so when I became a magistrate judge I had a sense of what happened, but not really. You don't know it until you do it.

Shashi Kewalramani: In the Central District of California, the magistrate judges and district judges interact fairly regularly. In certain courthouses, for the vast majority, there was no distinction. You would not hear a district judge say, "This is Magistrate Judge So-and-So, I'm District Judge So-and-So." You just didn't hear that. You get a lot of insight into the whole process. As far as clerking for a magistrate judge, I just got off the phone with a former clerk yesterday who was arguing with his law firm because somebody wanted to go off and clerk for a magistrate judge. The biggest thing: they will become a better writer because of the product we have to get through. Especially in the busy districts, how many motions we have to decide. It really trains you to become a better, more efficient writer who gets to the point of what you're trying to convey. You get to see a lot of argument by attorneys. You can pop into a courtroom and say, oh, we hear so-and-so is giving a closing, go check it out.

Khurram Naik: What surprised you the most about how judges work, either in opinions or in the administration of cases?

Shashi Kewalramani: The volume of cases we have to deal with and the number of complex motions we have to address in a timely fashion in order to really deliver justice to the parties. You hear, oh, we have this many cases, but until you're there seeing the flood and the type of cases: social security appeals, bankruptcy matters. The most complex issues were often in pro se matters, particularly pro se 1983 cases, because a party would use some loosey-goosey language and we would have to ferret out, what's the constitutional basis for this? As a magistrate judge, we would have to screen these 1983 complaints from often prisoners and pro se folks, which have gotten better with AI. I remember handing a complaint to my law clerk: here's a new con law exam, what are Gideon and Gideon v. Wainwright, right? A pro se person raising these complex constitutional ideas in the most mundane and surprising ways.

Khurram Naik: From the bench, it's not about dollar value, it's about legal issues. That reminds me of a previous episode with Louis Tompros, in a very different context. He identified an opportunity to look at pro se patent application filings and look for ones that raised interesting legal issues, then argued one at the Federal Circuit. It's called In re Klein. It involved the doctrine of obviousness in the wake of the KSR Supreme Court decision and got a precedential opinion and changed the patent office's examination policies. These seemingly minor matters can have a big impact.

Khurram is right that Louis Tompros and I just talked about exactly that discipline: scanning for overlooked cases with big legal upside and stepping in pro bono. It's the same instinct Shashi describes from the bench, treating pro se matters as serious legal work. Listen to my conversation with Louis Tompros.

Khurram Naik: From the bench, you mentioned you're like a gym rat. In the gym there are different theories for what's effective. Sometimes you hear about certain advocates, such and such in the Supreme Court, they can get away with that because of their name. Maybe it's extremely personality-driven, or there are perfect approaches. What have you learned about advocacy techniques from the bench? Are there archetypes?

Shashi Kewalramani: Let's split it into two: advocacy to the bench in a legal matter, versus advocacy to a jury. With the bench, the common theme I saw across every advocate was, they answered the question first thing out of the box. They didn't preface it with a bunch of stuff. They answered the question, then gave the explanation. That was really appreciated and set somebody head and shoulders above the next person. The answer could be, "well, it depends," the most lawyerly of all answers, and then anticipate the next question. If we're going to go down this flowchart, let's create the flowchart. The best advocates would take you down that flowchart. The people who weren't that good would not. All of that is wrapped up with credibility. Within, say, four attorneys, two on either side, the attorney I could trust the most was the one who gave me that direct answer quickly with supporting basis, either legal or factual. It all comes down to credibility. Who am I going to trust when I don't have everything in front of me? Folks would first answer the question, be succinct, not necessarily succinct as in not giving requisite detail, but would sometimes give you the answer that's harmful to them, "well, no, we don't have that," and that again builds credibility, which is the cornerstone of everything. If you lose credibility, you're pretty much done arguing before a court.

Shashi Kewalramani: In front of a jury, what I found was there is no archetypal manner. People you would think were prototypically "smooth" are not necessarily winning. People who aren't prototypically smooth are winning day in, day out. That comes from genuineness and authenticity. Big thing is not being a jerk. Juries pick up on that, judges pick up on that. You can fight for your client hard without being a jerk. I don't know if there's a single type. With juries, if you get caught misleading or misrepresenting something, particularly a document, it's hard to come back from that.

Khurram Naik: What was it like when you first got on the bench? Was there an early moment when you went from doing the work of a judge to feeling like a judge?

Shashi Kewalramani: This was important to me. I never wanted to get wrapped up feeling like a judge. There's a story of Roman emperors who would have somebody whispering in their ear, and I'm not saying a judge is a Roman emperor, but there is such a thing as robe-itis. People start to believe, oh, I am funny, people laugh at my jokes, oh, I am smart. I would affirmatively take steps. My clerks outside the presence of other judges and not at bar events, I asked them to call me by my first name. I'd say it's a security issue. If we're going to lunch someplace, I don't want you to call me "judge," just call me Shashi. Those are little steps. I went through my whole career with some level of imposter syndrome of, thank you God, there are other people who could do this. You get comfortable with it, I can handle this job just as well as anybody else. But I always kept in mind that my job as a judge was a temp position I was holding. If I retired or if I passed, my chambers would go on to somebody else and I would be forgotten maybe a year later tops. That's just the ephemeral nature of the world. I was mindful I was a public servant. My job was to continue to serve my clients, which are the bar. I would remind all our clerks, we are not special, we are all replaceable, we have a job to do.

Khurram Naik: Is there something about your decision-making process from your time on the bench?

Shashi Kewalramani: As an advocate, you know what your position is and you're forwarding that position with a larger strategy in mind. As a judge, one thing you would try to separate is the effect of your ruling, oh, I don't like this person, or I like this person, and you had to separate that from the ruling. It was very much a chips-fall-where-they-may attitude. Michael Lewis did a podcast series about judges. He talked about how we have changed as a culture of attacking the ref. It permeates through society when a judge makes a ruling, oh, you're doing it for some nefarious reason, you suck, we don't have to follow it. I was mindful I'm not the player, I have a role: I make my ruling and the chips fall where they may. You're going to displease somebody.

Shashi Kewalramani: One thing in writing: I would write very, very dry, because you don't want to give any indication it was based on personal animus. There's this Parsi approach to life: "say kind words, think good thoughts, do good deeds." The hardest thing is think good thoughts. You start by acting and doing good things, and then hopefully it ingrains and you start thinking good thoughts. So the performative leads to the substantive. Saying things kindly, being polite, being measured, then you start thinking that way. You have clerks saying, "your honor, this guy just lied about the facts." I would rewrite that as "counsel does not provide proof for this statement. However, looking at the evidence…" You move on. You don't need to comment on what somebody did when you have the power to make the ruling. There was an NBA ref whose dad was a Chicago PD officer, and he said, "when you have the last word, don't say the last word." I don't need to be snarky. It is what it is.

Khurram Naik: Is there a decision you're most proud of?

Shashi Kewalramani: I don't think there's a decision. I'm most proud that in criminal matters, when folks were before me in detention and bail hearings, I heard comments from attorneys saying, even though you detained my client, he really appreciated you listening to him. The fact that I tried to give everybody the respect they were due, and actively suppress any ego, I think has helped me not only as a judicial officer but in private practice now, and has made me a better person at home. You have to internalize suppressing your ego. I didn't view myself as the most important person in the courtroom. It was the client's courtroom. We just happen to be there to facilitate resolution.

Khurram Naik: Were there experiences before a judge that helped you get reps in suppressing ego?

Shashi Kewalramani: Certain judges I would model myself after. In the Northern District in particular, Judge D. Lowell Jensen was a prince of a man. He would say my name correctly, which was nice. "Shashi Kewalramani." He took the time to learn how to pronounce it. He had been the former district attorney of Alameda County, then an assistant attorney general under Ed Meese and Ronald Reagan, even though I believe he was a registered Democrat, and then got back on the bench. I was at a mall with my one-year-old daughter and I hear "Shashi!" He was just that type of a guy. No ego. I was like, "oh, Judge," and he said, "no, no, it's Lowell." Everybody would clamor to get in his courtroom. Not that it was going to be easy, but it was going to be fair. There were certain judicial officers I would see who were just very kind, and it would let you know, yeah, they were credentialed, they had experience, but there was an aspect of serendipity to where they are, and that was a recognition I really tried to internalize.

Khurram Naik: Let's talk about your transition to mediation. Mediation is different from the bench. You mentioned this concept of taking a client-centric approach. What are the skills that transfer, and what is the biggest departure?

Shashi Kewalramani: What transfers: being trained to listen. Some people have it innately. I had to work on mine, and I got much better at it as a judge, and before that as a criminal defense attorney. Recognizing, in a criminal defense or a civil case setting on the bench, I would be very mindful of anything I said about counsel, especially in front of their client and in any written opinion. If a criminal defense attorney is making a bad argument, I can't use the word "ridiculous." I would be mindful of making any comment because it could harm the attorney-client relationship. Similarly in a civil case, if I said counsel misled me, that order might go to in-house counsel, who might read into it and say, this judge doesn't like this attorney, maybe I need to find new counsel. My words had ramifications beyond what was said in the courtroom. I trained on that. It really became internalized. If I was thinking something, just keep it to yourself. Often upon reflection, the attorney's argument wasn't ridiculous, I hear where they're coming from. It trained me to be a little more mindful of my own prejudices and biases and tamp those down. That has transferred well into private practice, both arbitrations, where I'm essentially in court, and mediations. In a mediation I have to empower counsel. When I'm in the other room, he or she is in the jury room with the client trying to say, what the judge said kind of makes sense. I need to empower somebody and give them the ammo to persuade their client.

Khurram Naik: What's been hard? What's been surprisingly easy?

Shashi Kewalramani: Hard: I'm still surprised at how certain attorneys don't respond to emails or texts in a timely fashion. I have a theory that has been borne out: the most successful attorneys, the biggest names, are actually the most responsive. There's a direct correlation between successful and responsive. When I sent an email from the bench, I'd get a response back fairly quickly. Now, people just don't respond. Easy: because of my involvement in a lot of bar activities before I was on the bench, reaching out to networks I had been part of has been relatively easy. I'm not as introverted as I thought I was. Reaching out to folks I did mediations for on the court and getting such a positive response. I tell them, I could have been the biggest jerk, you saw what I was in a mediation and I wasn't, so what do you think I'm going to be in private practice? I'm going to be forceful, but always polite. People sometimes like that in a settlement conference. They don't want a notecarrier. "Suzy thinks they're cute, well, Tom thinks they're cute too." There's no value add to that. I'll make a call. I think this argument's strong, I think this argument's weak. They may disagree with me, but you've got to make a call. That's a value-add and a deliverable attorneys can take back to their clients.

Khurram Naik: How are you thinking about positioning yourself given there are a number of other judges at JAMS? What's your core differentiation?

Shashi Kewalramani: There's showing versus saying. In every mediation, I prepare a lot. People see that when I know the details of the case. There's a huge bell curve in the mediation business. A big middle, smaller tails on either side. I want to be on the smaller tail on the good side. My background in IP, complex commercial cases, securities work, and a very good understanding of federal statutes positions me more as a commercial and federal person rather than, I'm not your best person for a car wreck case and evaluation of soft injuries. My rate is going to dictate that as well. My sweet spot is commercial, IP, securities, trade secrets.

Khurram Naik: Do you have a preliminary view on niching versus broader-based approach? Chasing whales versus mid-market matters?

Shashi Kewalramani: In the commercial world, contracts, securities, IP, trade secrets, there's a lot of those cases out there. The dollar amounts don't have to be that high to warrant retaining someone like me. Let's say damages above $2 million, there's a lot of cases like that in the commercial realm. The practice picks you. I have resolved cases for particular law firms and now they're coming to me with slightly adjacent subject matters to the ones I helped them on. The response is, we just want somebody who's well prepared and will dig into the details, and the dollar amount meets what we can tell our client he's worth for the day. Even though I'm hired for the day in mediations, it's on average about 20 hours per mediation in prep, the mediation, and post-prep to get the deal done.

Khurram Naik: How do you think about the trade-offs of a roster of clients? 80% from three firms versus diversified?

Shashi Kewalramani: I want as broad a roster as possible. I'm not just focusing on big firms. I have a lot of colleagues and cases at smaller firms on the plaintiff side. Where business comes from is just like any marketing: you don't know where it's going to come from, you just need to put as many seeds out there. I am mindful I'm not just catering to big firms. I would be hesitant to agree to, hey, we want you for X number of cases to the exclusion of others, for two reasons. One, I don't want to be beholden in that regard. Two, it creates an impression of not being impartial. Especially as a mediator or arbitrator, I don't want to be known as beholden to certain firms.

Khurram Naik: Is there a differentiating point of view you have about how mediation or arbitration is conducted?

Shashi Kewalramani: I can tell you what I've heard from attorneys who have hired me. What they appreciate is the prep and the deliverable in the sense of a mediator's proposal that isn't just a paragraph like, you should settle for X. Everybody needs to know the why. If you're settling a case for over $2 million and you've got to go to in-house counsel, they need to know why they should pay or accept this money. I always try to explain why I'm making a particular recommendation. That's an extension of my job as a judge, where I would write sometimes a little more extensively than I needed to, because I felt the parties needed to have insight into the thinking, into how I came to a conclusion. That allows the parties to have a meaningful discussion after the mediation is ended, while I'm still involved. I try to provide an extensive deliverable the parties can rely on if they don't resolve it then.

Khurram Naik: Two questions to wrap up, both recurring themes. One interesting frame: strategy versus opportunism. You've talked about strategy to decision-making in your career, but I'm also hearing opportunistic movement. Do you identify with one more than the other?

Shashi Kewalramani: Your strategy has to change as your life changes. There's a difference between a 27-year-old with no kids and no spouse who can take more risks, versus having other responsibilities. You also learn about yourself as you grow. As a lawyer, performance is table stakes. You have to win, you have to be responsive. Those are all baseline. How do you differentiate yourself? You have to take a look at your own strengths and weaknesses and find where you could maximize your abilities. Going back to the gym rat thing, I'm not six-three, I can't dunk, I'm not going to play forward. Where do you fit, intellectually, geographically, on your platform? Where do you see a successful career five years down the road? One of the hardest things to do is predict where you're going to be more than five years from now. Life changes. You should have a general plan and then it gets hazier. Then you have to be open-minded. One of the hardest things is to identify the three most important things to you in life. I'm borrowing this from Stephen Covey. You write down the three or four most important things, and then how does every decision go to those things? The hard part is identifying those three things and then how every opportunity fits within that decision. I've tried to do that from time to time. Sit down and write: what are the three most important things to me, and how does my decision professionally impact those three things personally and professionally?

Khurram Naik: That's an interesting observation. It's exactly how my wife, who's my business partner as well, approaches ourselves. We share the same three priorities around work, family, and business. That means to the exclusion of things like travel, friendship, creativity, which is not to say we don't experience any of those, but they have to align with those first three. What I'll add is, I think what's hard, I don't think we had a hard time identifying those, I think we found it really hard to apply those. That involves trade-offs.

Khurram Naik: My other question: you proposed this concept, non-linearity. You've been around the block. What do you see as prospectively the value of this experience for something else?

Shashi Kewalramani: Prospectively, based on my life stage with our kids and family, I'm 54. I continue to keep an open mind. You never know what opportunities are going to come down the road. If the right opportunity came along, for example, would I pivot from being a mediator and arbitrator at JAMS? Yeah, I would have to think about it. I'm not wedded to, this is who I am, I am a former judge who is a mediator. It is not part of my identity. Work is separate and apart from my identity of who I am. That takes time and confidence to be comfortable with, because in our society people ask you, what do you do, as if that is who you are. You have to be comfortable saying, what I do is X, but that's not who I am. I continue to remain open-minded. When I say non-linear, I compare it to a lot of my peers who haven't done plaintiff-side work, haven't done defense-side work, haven't worked at a big firm, haven't worked at the U.S. Attorney's Office, haven't been a judge, haven't gone out to the mediation world. It's non-linear in the sense that it's not common. Is there a through line? Probably. We can always draw a through line through everything, that's just statistics. I continue to remain open-minded to opportunities. This is not who I am. This is what I'm doing now to fulfill those top three goals in my life.

Khurram Naik: I'm looking forward to what you do with this chapter and what the next chapter brings.

Shashi Kewalramani: I appreciate that. Thank you so much for your time.