Guest Chapter 13
Name: Alfred Levitt
Current Position: Chief Executive Officer for RPTC Inc. and President and General Counsel for Hugo Enterprises LLC. RPTC Inc. is the private trust company for the Ricketts Family and holds assets including the Chicago Cubs and an extensive portfolio of investments.
Hugo Enterprises is the holding company for the operating businesses and investments of TD Ameritrade Founder, Joe Ricketts.Former Post-Law School Positions: Clerk for the Honorable J. William Ditter, U.S. District Court, Eastern District of Pennsylvania (1994-1996); Litigation Associate at O'Melveny & Myers (1996–2000); Partner at Boies, Schiller & Flexner (2000–2007).
Legal Practice Area: General Counsel. Started as a commercial litigator.
Law School and Year: Temple University, 1994
Time between undergrad and law school: None
One or two books I recommend: I don't like reading books. For a long time, I thought this was a sign of being dumb. Then I discovered Audible and I found I love books, just not reading them. Favorites include Earnest Hemingway, For Whom the Bell Tolls, James B. Stewart, Den of Thieves, and Amor Towles, Rules of Civility.
Short background on why I went to law school
My friend Scott Gant once said to me, “Law school is the first resort of the generalist.” In my case, it was more like the first resort of the clueless. As college graduation approached, I didn't have a master plan. In fact, I didn't have any plan. My brother and uncle were lawyers, so I figured, why not. I was rejected at every school to which I applied except Temple University (and Villanova, which waitlisted me). So off to Temple I went. The school and experience changed my life. They taught me how to think. And once I figured that out, the pieces started to fall into place.
What frustrated me most about coming out of law school and/or what frustrates me with regards to people I work with or hire who are newly out of law school
The fact that Judge Ditter offered me a job out of law school felt like a miracle, so I had zero frustrations.
I was thrilled with the opportunity and experience. A federal clerkship is the greatest thing a litigator can do to sharpen his toolkit. I got to see and learn how decisions were made. My clerkship was like a postdoctoral degree in practical decision-making. Temple had been good at teaching me the law and how to think, but I needed the clerkship to learn how to apply those things. I remember one time during a case the judge came back to chambers and said, “That woman should get some money; figure it out.” The judge relied on us in many instances to build scaffolding around his innate sense of right and wrong, and through that process, I began to learn about the real drivers underlying decisions.As far as frustrations today, I work with a lot of younger lawyers. It's a different time than when I joined the profession. And while there are many extremely bright, talented, hard-working young lawyers, the pathological focus on client service feels diluted in many cases as compared to when I began my career.
I hear a lot about work-life balance. That wasn't a big thing when I began practicing law. As Don Flexner said to me when I interviewed with him, “This is a service business, and it's not for everyone.” He was right, although I didn't fully get it until about 5 years after he said it.
It sounds a little harsh, but as a consumer of legal services in a time when rates for those services have skyrocketed, I don't care a lot about the work-life balance of outside counsel. My expectation is that questions will be answered quickly, clearly, and accurately. It's how I approach my client relationships and it's what I expect from lawyers who work with me. It's a service business, and it's not for everyone.
On another note, escalating compensation and billing rates have fundamentally changed law. More than transforming it from a profession into a business where young associates at big firms need to bill huge hours to support their salaries, those rates have also made it harder for young lawyers to build their own client relationships.
It's difficult for an associate billing $500 per hour to originate new business or take on smaller matters. But as my friend and former client Rich Baer emphasized to me years ago, building those client relationships is incredibly important; just as important as being a great practitioner.How have you used (or not) the core concepts of lawyering as this book proposes: Empathy, Listening First, Asking Questions, and Giving Advice?
I think that those four concepts perfectly encapsulate what being a lawyer is, or what it should be. It's hard to do all four well, but if you do, that's the game. Even three out of four make you a solid lawyer.
It starts with empathy. Whether your client is being sued, or is suing, or is involved in an important transaction, she is under stress. Often intense stress. Empathizing with your client's predicament and experience is hugely important. It not only builds trust with your client—a critical element of a successful attorney–client relationship—it informs your approach to the matter.
Empathy can, however, be taken too far. It took me some time as a younger lawyer to strike the right balance between empathizing with my client's situation and maintaining some objective distance. I had to work to find where I “ended and they began.” If a client is going to trust you, you have to show genuine empathy but in a way that preserves your ability to provide clear and unemotional counsel.
Listening is also essential. A lawyer needs to give people the chance to talk through what they are experiencing. Through active listening, you better understand your client and the matter on which you're working. Listening builds human connection and sharpens your focus. (Fun fact: listening is pretty good for your marriage too.)
I think asking questions as a lawyer is a notoriously difficult thing to do. People are often concerned that asking questions will make them seem dumb and diminish their authority. I have learned to ask a lot of questions and not to care how it makes me look.
I've found that asking the “dumb questions” often is the single best thing you can do to provide good counsel and representation. Keep asking questions and listening carefully to the answers until you understand the issues.As far as giving advice, this is what lawyers get paid to do. When you do it, give practical advice. I still get too much talking at me from lawyers. On highly technical issues—issues where I don't have a good grounding in the underlying law—I want clear counsel on what the lawyer thinks I should do. Caveats are fine, but at the end of the day, you're being paid to offer informed, smart counsel. On issues that involve a business judgment, I want the tradeoffs framed in a way that permit me to make an informed decision. And when I'm the lawyer, that's what I try to do.
The wrapper around these four concepts are authenticity and integrity. By authenticity, I mean speaking and behaving in a way that is honest and never phony. That often takes courage as there's something of a fake it ‘till you make philosophy in the law. My view is that people can spot a phony a mile away. (It's what juries do, by the way.) Speak honestly to your colleagues, your clients, and yourself. People will trust you more for it.
And then there's integrity. None of the four concepts matter if you don't conduct yourself with professional and personal integrity. That means doing the right thing and not cutting corners, even when doing the right thing isn't easy. It can be a “small thing” like how you complete your time sheet or treat colleagues. It can also be a “big thing” like how you handle a conflict of interest. And often doing the right thing is most difficult when the stakes are high, but that's when it matters most. In the end, high-integrity people generally succeed.
Biggest mistake(s) you made while in law school
I didn't have confidence during my first year. I was too focused on what everyone else was doing. When I started to run my own race, I did better.
I didn't do study groups or share outlines, or anything. I just put my head down and did the work. It proved to be a successful recipe that has guided my career.What class(es) did I wish I had taken while in law school? In or outside the school?
If you might want to go into commercial litigation, take accounting for lawyers or finance for lawyers. I wish I had taken more (um, any) economics or finance courses. When I practiced law at a firm, my work was focused almost entirely on matters that involved complex financial issues—e.g., antitrust, securities fraud, business disputes. I had been a creative writing major and felt adrift in the deep end of the pool. I had to learn on the fly while litigating cases. It would have helped to come to the practice of law with a stronger foundation (um, any foundation) in these concepts. By the time I worked on the Cubs acquisition, I had gotten better.
Most useful classes in law school
Federal Courts. For commercial litigation it is super helpful. If you don't take it, you'll miss the issues. And it's still useful to me today despite not having set foot in a courtroom in 15 years.
How did you decide what to do post-law school? With hindsight, how good of a job did you do?
For some people, it can feel like there's a well-worn path: do well in law school, make law review, join a big firm or clerk. I tried to follow that path, which I thought was the only one. It worked out great for me. But the truth is, there are many ways to apply the disciplined approach to thinking law school teaches you. Keep an open mind about your career, particularly in the early years, and don't put blinders on.
Biggest mistake you made at your first job
The biggest mistake I made in my first job was citing to the wrong case in a draft opinion. It almost embarrassed my judge. And while the mistake got caught, it was horrifying: in a clerkship, the clerk is supposed to protect the brand of the judge. It didn't happen again.
Best advice you received or have given for those coming out of law school
There's not a lot of people who will stay up at night worrying about your problems.
Maybe your parents. Maybe your spouse. To be a great lawyer who connects deeply with his clients and colleagues, you need to care deeply about their issues. Get into work early. Stay late. Solve your client's problems.Worst advice you received or have given for those coming out of law school
I didn't get bad advice. I was lucky. I also didn't get a lot of good advice. Truthfully, most lawyers are terrible managers, unskilled at giving structured feedback or sustainably mentoring in a way that works. Don't worry about it. Figure things out for yourself.
How have you remained happy in your profession? Have there been times when you were not? If so, what did you do to improve your situation?
I have a personal failing: I'm wired to be a Golden Retriever; I like a pat on the head when I do a good job. It isn't a good thing; you surrender a lot of power in your relationships when you crave positive feedback. I've had hard times when I've gotten smacked upside the head rather than patted. It often didn't seem “fair” at the time.
Careers inevitably have ups and downs. There were times when I wasn't sure if the law was for me. Over the course of the past almost 30 years, however, I always come back to loving my job. I'm not much of an everyday lawyer anymore but the diversity of my work keeps me happy and interested. I love solving complex problems.
Then again, I also like solving small problems, including fixing my client's WIFI in his New York apartment.
If you could go back in time and tell your younger self something about making the transition from law school to the real world, what would it be?
Be authentic with people. Authenticity builds trust and this business is all about trust and deep relationships with clients, bosses, and colleagues. Lawyers are insecure and pretend too much. It's corrosive to building lasting relationships. And most importantly, be resilient. Life directs a lot of negative feedback at you. Don't let it get you down. And when it does, listen to Toots and the Maytals.