Q+A: Civil Litigation Lawyer

Sterling Henderson on pursuing a law degree, getting through law school, and what it's really like being a lawyer.

~ 12 minute read

The CareerExplorer Discord Community had the opportunity to speak to Sterling Henderson, a civil litigation lawyer, in a live, fireside Q&A.

Sterling Henderson is an attorney licensed to practice in the States of Alaska, California and Washington and specializes in the prosecution and defense of civil litigation matters involving a variety of business and corporate disputes. He is a partner at the law firm of Gibbs Giden in Los Angeles, California, which specializes in business, commercial, construction, and real estate law.

Sterling is also experienced in matters of corporate governance, structuring, and operations, as well as the defense of civil and administrative malpractice actions and insurance matters.

Originally from Juneau, Alaska, Sterling has a B.A. in political science from St. John’s University in New York and a J.D. from Santa Clara University School of Law. After graduating from law school, he moved to Los Angeles where he has resided ever since.

The transcript below has been modified and abridged from the original conversation.

Pursuing a Career in Law

How did you decide that law school was right for you? Did you always want to become a lawyer?

I was always interested in law from as early as high school, and after studying political science in college, I knew that was the path for me.

My classmates at law school fell into mostly one of two camps — those who always knew they were interested in studying law, and those who found themselves having graduated from college and wondering what to do next.

How did you end up deciding to go into civil litigation?

While in law school, I wanted to be a criminal lawyer. In fact, I worked for everything from non-profit defense organizations to the Orange County District Attorney. But as I worked through those clerkships, I began to realize that a criminal practice wasn’t right for me.

More importantly, I graduated in 2010 when the legal profession (like most industries) was still feeling the effects of the 2008 recession. There were very few legal jobs and a LOT of young attorneys looking for work. So I took the first job I could, and the rest is history!

What does your practice specifically deal with?

My practice is focused on business and corporate disputes. Most of my clients are owners of commercial properties or in the construction field (general contractors, subcontractors, etc.) who end up in a dispute with another party.

I most frequently deal with breach of contract actions, where one of the parties to a written agreement claims that the other party failed to perform their obligations as promised.

Outside of practicing law, have you ever considered using your law degree to pursue another career?

I also studied music in college and I still haven’t lost interest in the arts. Even now, I’m constantly exploring opportunities to apply my legal experience in creative arenas, and have advised on music licensing and production matters.

I’m a junior in high school, and I’ve always wanted to become a lawyer. Do you have any recommendations?

It’s great that you’re thinking about the law already! Any exposure you can get to the law now and as you think about college is a great start.

For example, in my hometown, we had a Youth Court program where I worked as an advocate, which was created for at-risk youth to avoid the legal system. Begin looking into firms that interest you. If you can clerk for such a firm for a summer in high school or college, you’ll be ahead of most of your peers!

Would you recommend that students conduct informational interviews with local attorneys or law school students if they are interested in law?

Absolutely. I can’t encourage this enough, especially for those who aren’t quite sure if they want to go into law. Even if the feedback they receive from attorneys or current law students isn’t too encouraging, it’s a great opportunity for prospective law students to decide for themselves if they really want to go to law school.

I’d also stress that, with the exception of buying a home, going to law school will quite possibly be the biggest financial investment they make. Do your due diligence, explore the market for all the alternatives, and then decide if it’s the right life for you!

What personality type is best suited to becoming a lawyer?

I don’t believe there is any one personality type that is best suited for a successful law career.

I have colleagues who are incredible writers, capable of drafting persuasive legal briefs and complex transactional documents, but you will never catch them in a courtroom making an oral argument. On the other hand, I know some attorneys who are less academic but are extremely charismatic. Put them in front of a jury, and they will be successful.

That said, there are certain characteristics that will make success in the profession more likely. Especially now, when most of us are working from home, good attorneys need to be organized and self-motivated.

What are some recommended undergraduate programs for those who are looking to go to law school?

My advice to undergraduate students considering law school is to study what interests them. History, art, science, theater — whatever it is. I minored in music and it probably would have been my major had the program existed.

The great thing about preparing for law school is that your undergraduate curriculum is not determinative of your chances of success as a law student. Sure, law schools like to see students who excel in law-related studies and have a demonstrated interest in law, but equally if not more important is to see that students are capable of such qualities as being adaptable, inquisitive and curious, and even creative.

Of course, performance in college will obviously impact your law school options, so whatever the major, study hard and long! All that said, in my experience, the majority of students majored in political science, sociology, history, or pre-law.

How can students decide which field of law is right for them?

The great thing about deciding to go to law school is you don’t have to know what area of law you want to practice in. In fact, it’s far more likely that you won’t know.

I’d say the more important decision is to explore why you want to go to law school. What are your motivations? As I mentioned earlier, it’s a big commitment and a huge expense, so students should consider working for a summer at a law firm or clerking/interning for the courts if they have the opportunity.

A full-time law program is three years. Ideally, you’ll want to spend the summer after your second year with a firm (and in a field) that you enjoy. If all goes well, they’ll extend an offer for you to join after taking the bar exam in your third year summer.

How much can you make by getting into law?

Many of us were attracted by the thought of being in a career with high earning potential. This is true for many lawyers, especially in certain practice areas or at ‘biglaw’ firms.

The starting salary for lawyers varies greatly based on the market, what city you’re located in, the practice area, and the size of the firm, among other factors. For example, I have some colleagues who wanted to focus on public interest and nonprofit work, where a starting salary might be $50k/yr. On the other hand, I believe the starting salary for an associate at a biglaw firm is about $190k/yr.

Law School

Does where you go to law school dictate where and what you will practice? Do you recommend going to a law school where you wish to practice?

Great question! Students shouldn’t feel that going to law school in one city or state means they have to commit to living there indefinitely. But it is far easier to attend in or near a market where you would like to practice.

For context, I’m originally from Alaska, went to college in New York and law school in Northern California, and moved to Southern California after graduating. One challenge I was NOT prepared for was that I had no real social or professional network in Los Angeles. In hindsight, I failed to appreciate how important it was to start developing your network while still in law school.

How rigorous is law school, in terms of the work required and the amount of stress you will face?

Every student should expect a highly competitive and rigorous environment, and they need to be prepared to study, show up for tests, and deal with all the stress that comes with it. That said, we all manage and handle stress differently, and those that find stressful environments difficult may find law school more challenging.

Even more important, though, is to remember that law school isn’t only for the academic curriculum. Students will need to learn time management, prioritization, and organization. Those who have already begun to develop these skills will likely transition into law school more smoothly.

And lastly, it all depends on the law school. At Santa Clara, I was fortunate enough to be in a very collaborative and supportive environment. Sure, we all wanted to do the best, but there was a general sense that this was not a zero sum game. We could all succeed if we put in the work. There are horror stories about some institutions that are cutthroat — students hiding study guides, turning off each other’s alarm clocks, etc. I’m happy to say that wasn’t my experience or one that I’m aware of anyone personally having to endure.

Are you graded on a bell curve, and does where you land on that curve matter?

Yes, as far as I know all accredited schools follow the same model for grades. And yes, a student at the very bottom of the curve will need to do some soul searching to decide whether their performance is something they can work on and improve. Perhaps it’s an indication that they lack the interest or commitment to be in law school.

Some schools are great at supporting struggling students, such that withdrawing is the very last option.

Are there any strategies to get through law school without feeling overwhelmed?

This is a great time to recite the practices I mentioned previously, as all current and former law students can recall the importance of time management (including not leaving things to the last minute), organization, and prioritization.

Law school is not like college where you can study up before the big test. It’s a semester or quarter-long commitment, and you need to work consistently the whole way through. The most common stressor is getting behind and allowing things to build (also true in the practice). All of a sudden, the idea of the work that needs to be done is actually more stressful than the work itself.

If you just do the work, chances are you are going to be fine. Plus, you’ll have more time to do the things you actually enjoy and need to do for yourself.

Is it harder to pay off student loans in comparison to other degrees?

With the exception of possibly medical school, law school can be one of the most expensive graduate programs. For that reason, most of us will have to borrow more than if we were to study in another field, meaning it’s going to take longer to pay off those loans.

On the other hand, the hope for many of us is to end up at a firm with high-earning potential. This means that, although you may owe more than if you chose another path, you ideally have more opportunities to generate a higher income and pay the debt off more quickly.

Being a Lawyer

What types of legal disputes do lawyers negotiate and resolve?

In the broadest sense, the profession is divided into two practice groups: transactional and litigation.

Transactional can be any contract between parties, such as the purchase of real estate. Or perhaps somebody wants to form a corporate entity like an LLC, so a transactional attorney will draft the appropriate documents to form the company and establish the rules for governance. If everything goes well in a transaction, the parties are happy and there are no disputes. The owner of the real estate gets money for the property, the buyer has a new asset, and all is well.

On the opposite end of the spectrum are litigation (lawsuit) matters, in which it seems like everything is in dispute. So the amount of arguments and disputes really depends on the field.

There are a lot of attorneys out there, but the practice can still feel pretty small. Many of us have worked with each other on cases in the past, or at least with each other’s firms, so it helps to be professional and courteous as much as possible.

What are some misconceptions about the legal profession?

I think one of the biggest misconceptions is that successful lawyers need to be cutthroat. Yes, there is a time and a place to be assertive and even aggressive, but attorneys who conduct themselves that way all the time are typically well known and not well liked in the profession.

What do you wish you didn’t have to do on a day-to-day basis?

My least favorite thing to do is to keep track of billable hours. It’s important that the client knows the value of the work you’re putting in, but to be accountable for every time increment, in some cases as short as every six minutes, can be really discouraging.

What do you love about your job?

I think the single most important thing for success in your job is to be grounded in something that you truly value or enjoy. Whether it’s the subject matter, the work you’re doing, or even the people you work with. Look, it’s still a job and we’re all going to have days when we’d rather be somewhere else. But if you’re able to find something that drives you every day, you’re going to find success.

For me, I found that I love working with my clients to find creative solutions for their problems. Nobody wants to be in a lawsuit, but if I’m doing my job well, then my clients aren’t losing sleep thinking about their case. That part of problem solving for my clients is something I genuinely love.

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