Advice to Young Associates Who Want to Be Trial Lawyers

Vol. 37 No. 4

The author is a partner at Freeborn & Peters LLP, Chicago.

Five years into my practice, I realized that I had spent nearly all my time reviewing thousands and thousands of documents, drafting discovery, responding to discovery requests, presenting unopposed motions for extensions of time (most of which I won), writing compelling letters expressing discontent with the other side’s obviously deficient discovery responses, arguing discovery motions, participating in lengthy joint-defense meetings, crafting motions in limine, and watching the senior lawyers win summary judgment motions and argue in the courts of appeal. There had been no jury selection, no direct or cross-examinations, no opening statements, no closing arguments, no interminable waiting for a jury to return with a verdict, no victory lap, no despair from the loss of a hard-fought battle.

This was not why I had gone to law school. I amassed my best grades in Evidence and Trial Ad, not document review or mind-numbing database-box checking. Would it ever end? Was there any hope?

To curb my frustration, I began doing some things very early on, most of which I still do today. When I started on a new case, I practiced my opening statement. When I saw the other side’s list of people with knowledge, I imagined my cross-examination, an artful craft with the perfect first question and the perfect last question. When I found a document that my opponent would call a “smoking gun” and that I might objectively call a “case killer,” I dreamed up ways to show how that piece of evidence actually helped my theory of the case.

The collision of how my mind works (always thinking about trial) with the reality of how many cases actually go to trial compelled me to figure out how to prepare to be a trial lawyer even when there were no cases to be tried and how to put myself in the best position to be called upon if a case needed to be tried. From the moment I graduated from law school, I knew I wanted to try cases, but I nevertheless chose to start at a law firm where, given its size and complexity, fewer cases than even the norm get tried. I was at that firm for five years, and everyone I came into contact with knew that what I wanted most, professionally, was to try a case. My assistant knew, those in my associate class knew, the junior partners I worked with knew, the senior partners knew, the review committee knew. This is to say nothing of my friends and family. In those five years, I never tried a case. Yet, I became a trial lawyer.

I didn’t realize it until I had my first trial, well into the sixth year of my practice, but six habits—­or perhaps they should be called disciplines—helped me to get to where I wanted to be. These six disciplines helped me to develop trial skills, escape from drowning in documents and petty fights, and gain a “go-to” reputation among partners and colleagues. What are they, you beg?


• Forward the plot.

• Say yes to the strange stuff.

• Become indispensable.

• Know the rules of evidence.

• Do pro bono work.

• Get training.


Several of these disciplines are intertwined, and they all arise, in some ways, from the first. But here they are, and here is how they work.


Forward the Plot

A tip frequently given at writers’ conferences and in books about writing the next great American novel is this: Every single word you write should serve a purpose in forwarding the plot. No exceptions. Similarly, everything a trial lawyer does leading up to trial should have a purpose in the trial. You can bill more hours, be more organized, collect more cases, review more documents, and write more letters than anyone else, including your opponent, but if you don’t connect any of these things to the trial (whether it ever comes or not), you will not be ready for trial and you will not be a trial lawyer.

I almost titled this section “Think,” but that seemed too elementary. That is what I mean though: Think about the trial; think about what you’re doing; think about why you’re doing it. We all have drafted dozens of sets of interrogatories, document requests, and requests for admission. And I suspect that more than once, you, like me, have cut and pasted them from a set you served in another case. You run a Find and Replace on the plaintiff and defendant, and presto, you have a new set of interrogatories for this case. You can get them out the door and move on to your next task.

These requests are standardized. There are five subordinate clauses and four gerunds in each sentence, and every word is defined by another word instead of standing on its own—you would never want your family members to read these because the lawyer jokes would never end. Yet despite the wordiness, the requests are so generic that you don’t really even need to read the responses when they come in 30 days later; the only response you can expect (and you know this because it happened in your last case) is a long list of objections for ambiguity and vagueness. What follows, then, is an endless tennis match of letters to and from your opponent trying to clarify questions you could have made clear from the beginning. If, by some miracle, you do receive a good answer and want to use that answer at trial, you cannot just slap it up before the jury. You will have to put up the answer, then point to the “definitions” in the original requests so that the jury can understand what you meant by the three capitalized terms in the interrogatory. Then you will have to flip back to the answer and explain why the answer means that your client is not liable or that your opponent is.

Why do we keep sending such requests? Because the rules allow them? Because we do it in every case? Because it’s the next item in the scheduling order? Because the partner asks us to? If you were thinking about trial when you put together the original interrogatories, wouldn’t you draft them differently, so that you said just what you meant and cut out all that was unnecessary? Why not free yourself of all past interrogatories and draft brand-new ones? Why not draft only three, or whatever the number is, whose answers will forward the plot? And not three good ones followed by 15 others like “describe the complete Factual Basis (defined above) for Your (defined above) allegations in paragraph such-and-such of your Complaint (defined above), including (defined above), but not limited to, all the reasons You (defined above) believe You (defined above) have been wronged in this way.” I have not seen a good answer to an interrogatory like this. But I have served many and responded to more.

Believe it or not, adjusting your discovery requests in a way that is more particular to your case, not so canned and replicable, and more geared to trial may actually result in some push back from the partners you work with or your clients. Not too long ago, I reviewed some interrogatories that my client was supposed to serve and was really bothered by the lengthy definitions and instructions at the beginning of the document. So, I moved them all to the end. Of course, I included the obligatory sentence that the interrogatories are to be answered in accordance with the instructions and definitions.

Before serving the interrogatories, I sent them to the client for a final review. I received a surprising response (with a copy to the partner I was working with), chastising me for including the definitions and instructions at the end. The client was not accustomed to seeing discovery like this. Could I please revise them so they looked normal? I was tempted to do just that, shoulders slumped, my great idea rejected. Instead, though, I picked up the phone and explained first to my partner and then to the client why I thought this was a better approach.

I explained that at trial, our precise interrogatories would enable us to show the first page to the jury and a single question would appear. No lengthy definitions and instructions loaded with legalese and cross-definitions at the outset, just the question. Clean and neat. In contrast, because the question would require the other side to dance around a key issue in the case, I envisioned that the other side’s response would start with a paragraph or two of bogus objections, followed by a squirrelly answer. The jury would understand instantly what was going on: We were asking a very simple, straightforward question, and the other side was doing its best not to answer. Juries don’t like that. I served the interrogatories with the definitions and instructions at the end, and I do so in every case.

There also are ways to forward the plot in your seemingly endless document review. After all, the documents are the evidence. Live testimony is important, of course, but juries will believe the documents first. If you are identifying key documents and organizing them, you are forwarding the plot. Ever notice how the same email sent to six people will result in six copies, each with different formatting? Which one will look the best for the point you want to make with it in front of the jury? Mark that one as part of your key document collection, not the one you can barely read. Or is there an email you like, but you’re not fond of the response to it that comes from another witness? Mark both versions as key so that you can use the one you prefer with the jury. Also, create a chronology of key events as you go through the documents—nothing sophisticated requiring expensive software, just a list of the key documents and events. Time lines are one of the most frequently used demonstratives at trial. Your chronology is a nascent version of that time line.

If the interrogatories you serve do not get you any closer to understanding the evidence or gaining admissions to use at trial, they are not a worthy part of the story. If you are mindlessly reviewing thousands of documents without any goal in mind other than getting through them and getting the responsive ones produced, you are missing opportunities. As an associate in the trenches, you have huge opportunities to forward the plot.


Say Yes to the Strange Stuff

Obviously, you can’t say yes to every project offered to you. One of the most difficult conversations you may ever have is explaining to a senior partner that you need to back out of a matter you previously had accepted but can no longer commit to because you took on too much. Been there. (And it’s better to have that conversation than do work that is not excellent.)

Before I get to what I mean by “say yes,” let me start with what I don’t mean. As a general rule, when a partner asks if you have time to work on something to help out with a matter, she wants to hear one of two things: Yes or No. Not, “I should have some time in the next couple of weeks. I have a wedding coming up and will be somewhat busy with that, and I’ve got some other projects I’m working on for so-and-so, but I should be able to manage.” If you have tried that kind of response, it probably didn’t go over well.

What I mean by “say yes” is this: When someone comes to you and asks for your help on a project, and it sounds strange, a little out of your comfort zone, figure out a way to say yes. The one case on which you’ve spent more hours than any other is typically not the one you will try. More often, it will be the case that came to you in a strange way—someone goes on maternity leave, and the partner needs you to step in; an associate gets overwhelmed on another case, and you are needed to pick up the slack; a partner believes this case will never go to trial because it is so one-sided but needs you to shepherd it through to settlement; a client needs to bring a temporary restraining order (TRO) in the next day, and your help is requested. At first blush, none of these cases sounds appealing. You would have to get up to speed quickly; you don’t want to be someone’s second pick; you have too much real work to shepherd a case to settlement (you are a trial lawyer!); and you have a relaxing weekend planned, and a TRO is going to mess that up.

Recently, a partner asked me to take on a case he believed was so one-sided that it would never go to trial. But he committed to me that if the case were to go to trial, I could try it. I agreed, both because he needed help and because I thought I had nothing to lose—if by some chance the case didn’t settle or we didn’t win on summary judgment, I would first-chair the trial. Well, the case didn’t settle, and the summary judgment motion was heard the same day we were to start trial. So I prepared the case to try it, met with my witnesses, gathered my exhibits, and prepared my direct- and cross-examination outlines. All on my own. For the first time. We won summary judgment the day of trial. No trial, but a great necessary step to understanding how to be ready next time.

Another time, a partner at my firm was trying a case, and that trial conflicted with a hearing date in another case. He believed the hearing would be a one- or two-hour non-evidentiary hearing. He asked another partner to step in for him. He also asked me to help out. I had other cases in the middle of discovery and creeping toward trial, but I agreed. The one- to two-hour non-evidentiary hearing turned into two separate three-day evidentiary trials. I second-chaired the trials, put on two witnesses, and conducted my first cross-examination.

It is the strange stuff that turns into trials. Say yes to it.


Become Indispensable

Some cases are extremely complicated and only you, who have looked at every document, have a grasp of all the details. If you know all the documents, the types of documents your client or your opponent created as part of their business, whose handwriting is whose, and all the people who had a particular document or type of document in their files, you are indispensable to a team. In preparing for depositions and trial, we create witness kits, and in doing so, we collect all the documents on which a particular person’s name appears. We typically also include key documents in a case. But what can get missed are documents that may not mention a witness by name, but that deepen the lawyer’s understanding of the case and the witness’s role in the underlying facts. Database searches or a paralegal less familiar with the documents and the story may not gather them; someone who knows the documents is more likely to catch them.

As an associate, I worked on a toxic tort case that involved mining and milling. One of the issues at trial, if it got there, would be where the by-product of these processes went. To understand this, one had to understand how the processes worked at every step. In reviewing thousands of documents, I came across diagrams of the mill, the town, and the mines. So, as I reviewed documents for responsiveness, I also collected tens of key diagrams and maps and put them in a binder. Doing this allowed me to understand more than I otherwise could have about the milling and mining process. I knew where each of the mines was located, the name and location of every piece of equipment in the mill, every point where dust or gas or sludge could have been emitted and how, how the equipment changed over time and when, and who among our list of witnesses worked where and when. Both my binder and my knowledge grew. When it came time to interview witnesses, I was called upon not only to identify the key people but also to conduct the interviews. The interviews were much more productive than they otherwise would have been. Witnesses opened up more because I understood so much about the processes they described and the environment in which they worked. I knew what questions to ask, what areas we didn’t need to discuss, and why they explained certain topics in greater detail.

I had become indispensable. With that indispensability came responsibility and new skills. The interviews were critical to our decisions about how (and whether) we would present these witnesses at trial. In the end, the case didn’t go to trial; we won on summary judgment. Had it been tried, though, I had put myself in the best position to put witnesses on the stand. The witnesses trusted me and knew I had taken the time to understand their story and their role in the bigger narrative. More importantly, though, from a career perspective, the partners I worked with knew that the witnesses trusted me and that I knew the facts cold.


Know the Rules of Evidence

You could not possibly imagine how many lawyers do not have even a basic understanding of the rules of evidence. It’s shocking really. This is particularly true of young lawyers. If you know the rules of evidence, you are already in a better position than almost anyone else. There are many lawyers who expect that anything will get into evidence at trial (and perhaps this is true, for better or worse), but if you have thought about this in advance and are sure to do all you can during the discovery phase of a case to set things up so that a piece of evidence is admissible, you are making a valuable contribution to your case. Plus, doing this keeps things interesting and may just save you from losing yourself in the document database you have started to regard as your closest friend.

An example. I have come to view the client-created chronology as either my worst nightmare or most wonderful dream. You know these chronologies, the ones that, as things start to go downhill in a particular matter, get created by a mid-level manager on her computer. Sometimes she calls it a “chronology of events.” If you are among the unlucky, she will entitle it “How XYZ Company Screwed Us.” The problems with these chronologies are many. If there are things in the chronology that are harmful or worded differently than you would have advised, you want to know whether it was created at the request of counsel. They almost never are. The events on this chronology almost always occurred long before the person created the chronology. The drafter typically lost interest in the chronology at some point either because things got so bad that counsel became involved or because the creator was too busy putting out fires. So the chronology cuts off right around the time of some key events that any person keeping a record would have included if the events were truly important.

The point is that whatever side of this you are on, you either need to think about how to get the chronology into evidence or how to keep it out. It’s hearsay, remember? Hopefully, the partners you are working with have thought of this at least at some level. Most likely, though, if they have considered it, they have not worked it out completely; this makes it a perfect opportunity for you not only to demonstrate your rules-of-evidence prowess but also to draft some questions for the chronology-creator so that at her deposition, you are sure to nail down all you need to get the chronology in or keep it out.

This seems like a small thing, I know. But this strategy has never failed. And now that I manage my own cases and have junior lawyers working with me, I can tell you why: Partners are managing many different cases at once and want and need to rely on junior lawyers to be creative and energetic and to be thinking ahead. Few things stand out more than a young lawyer who has anticipated a problem (or benefit) of a particular piece of evidence long before trial—when you can still do something about it. And when trial comes, if it does, you are at the top of the list when a partner is considering who is going to try the case with her and what role each person will have.


Do Pro Bono Work

As an associate, and particularly a young associate, your primary job in most cases is to make sure that applicable rules are complied with; you have correctly considered the three days it would have taken the other side to mail their response brief (even though they emailed it to you) in calculating your reply brief due date; and the key case relied upon in that soon-to-be-filed brief has not been overturned. In pro bono cases, though, you get two significant growth opportunities.

First, you do most or all of what needs doing. You counsel the client. You write all the words in the briefs. You decide which discovery battles to fight and which ones to let go. You argue the motions. You take the depositions. You marshal the evidence. And, if the stars align, you try the case (and live with all the decisions you made).

In the first pro bono case I had as an associate, a partner had been appointed by the federal court to represent a man in a Section 1983 civil rights case. Our client was a former gang leader who, while being arrested for stealing baby formula from a grocery store, was beaten up in a parking lot and a back room by the arresting officers. Our client had sued the police officers and the municipality. We came in, filed an amended complaint, and I was on my way to developing key trial skills. In this case, I didn’t do every task needing work on my own. After all, I was a first-year associate, and we all realize pretty shortly after law school that we know virtually nothing about, well, almost anything except how to spot issues. Everything is brand new, and issue-spotting is often left to the more senior partners. In this case, though, I got to do more. The facts were straightforward enough that I could draft precise interrogatories, seek particular sets of documents (like personnel files or disciplinary actions), create a key document binder, draft deposition outlines for the depositions the partner would take, and take depositions myself. This experience, so early in my career, simply would not have come my way but for the fact that it was a pro bono case. Neither I, nor my fellow associates at my firm or elsewhere, had such responsibility on cases that were not pro bono.

The second advantage to working on pro bono cases is that you will learn, right out of the box, how to identify what matters most in your case. Although there may be a time and a place for a “scorched-earth” approach, knowing how to work efficiently and still uncover all the evidence you need will become an invaluable skill and one that matters to clients and partners alike. The tendency in large pieces of litigation is to ask for the names of every person with knowledge and then depose every person on that list. More and more, parties will also, at huge expense, videotape the depositions of each of those persons. Being involved in these kinds of cases leads one to believe that this is the only way to practice. But it is astonishing how much time and money are wasted on discovery and depositions that ultimately are not used at trial and on witnesses who have either no knowledge or no unique knowledge.

When you run your own case, even if it is a small pro bono case, you have the opportunity to choose whom you will depose and how (i.e., video or not). Making these decisions not only takes confidence, it also grows confidence. Indeed, deciding not to depose someone or not to take certain discovery means risk—calculated risk, but risk nonetheless. Many lawyers are not willing to take even calculated risks because they are lazy or because they lack confidence. It is much easier to depose everyone on a list than to go through the list and choose to depose some and not others. It is much easier to videotape every deposition instead of deciding to videotape certain witnesses and not others. When you are in charge of a pro bono case with a strict budget, and the other side identifies 20 witnesses “with knowledge,” you must take some calculated risks. Once you do, you become more comfortable doing it later.

One of the first things I do in cases I work on now is to get together with the team and, based on the documents in the case or the knowledge we have from our client, work through whom we will and will not depose. There is nothing I love to hear more than a young associate who says, “I don’t think we need to depose that person,” and then explains why. Even if I ultimately disagree, to be thinking that it is acceptable and even most appropriate not to depose certain witnesses shows confidence and big-picture thinking. This kind of thinking occurs consistently for the associate who has had to make this call in a case she manages.

I get that there are billable hour requirements, tasks to perform for clients who pay your firm lots of money, and only so many hours in a day. Pro bono work is one of those things, though, that you should make time for if you’re serious about getting experience and developing trial skills.


Get Training

At the first firm where I worked, one of the senior partners organized and managed an associate training program. The program was mandatory for every associate and the only acceptable excuses for nonattendance were giving birth or a real trial. The program included two modules: deposition training and trial training. The materials for the program came from the National Institute of Trial Advocacy (NITA). The training, particularly the trial training, was first-class. The firm hired professional actors to play witnesses, used firm staff to play jurors, and required the senior-most partners to play judges. Each trial team had two or three members, and every year for six years, we put on a full trial—voir dire, opening, witnesses, closing argument. The juries returned a verdict. The judges critiqued our skills. We learned how to get documents into evidence, how to cross-examine a witness, how to redirect a witness, when to object, when not to object. Trial training was the most burdensome and rewarding experience of my time at that firm. Nothing else prepared me more, from a technical standpoint, to be a trial lawyer. Perfect example: I learned (from a blunt juror during a critique) that every time I stepped up before the jury, a giant, red splotch appeared on my neck. Nervousness. But I also learned the next year that breathing deeply made this red splotch disappear or not ever appear at all.

Keep in mind that during these trainings, we were all up to our eyeballs with “real” work. We had briefs to draft, documents to review, letters to write. But the trial training was mandatory and took priority over all else for three or four days. The thing is, some lawyers didn’t take advantage of this amazing opportunity. They saw it as a distraction, something that took away from their billable hours. If you took it seriously, and for six years devoted yourself to learning, you would be light-years ahead, in terms of trial skills, of those in your same class year at your firm or others. While participating in the program, I knew I was learning helpful skills, but I didn’t know just how realistic the exercise was until my first trial.

I called my witness to the stand. The jury, which looked much like the juries I had seen in my training trials, waited with anticipation as the witness sat down and drank a cup of water. I breathed deeply, wanting to avoid the red splotch on my neck. This witness’s testimony was central to our case. She had written many of the emails that the other side loved to slap up for the jury to see. But she had an explanation, and it was my job to allow her to provide it. I remembered from my training that on direct, the jury should be focused entirely on the witness, not the lawyer. So I lobbed open-ended questions to this witness. She spent much more time talking than I did. The jury was rapt with attention. When it came time to review certain documents, I knew the questions to ask to get them into evidence. I could have recited them in my sleep:


Q: Ms. Witness, I’m handing you what’s been marked as defendants’ exhibit number 200 for identification purposes. Do you recognize that document?

Q: What do you recognize it as?

Q: Have you seen that document before?

Q: Is Exhibit 200 a document that Company X keeps in the normal course of business?

Q: Is that your signature at the bottom of Exhibit 200?

Q: Your Honor, may I publish Exhibit 200 to the jury?


On about the fifth or sixth document for which I did this, the judge interrupted me, bored, I suspect, with these endless technical questions: “Ms. Fabian, what are you doing?” This threw me a bit, of course. I thought my questioning had been flawless so far. “Your Honor, the other side has objected to these documents, and so I am laying a foundation for their admission through this witness.” My legs shook; my mind raced. I wondered what I had done wrong. The judge turned his attention to the opposing lawyers with raised eyebrows: “You objected to these documents? Aren’t these fundamental documents in this case?” The other side stood up sheepishly to provide an explanation, but the judge wanted none. “They are admitted,” he said. I exhaled quietly. “Thank you, Your Honor,” I said with relief in my voice. I knew by glancing briefly at the jury that although they were pleased the judge had stopped the technical questioning, they understood that I had followed the rules and that the only reason I had to drag them through those questions was because the other side had forced me to with their baseless objections. I knew how to manage this situation only because of the training I had received.

Obviously, not every firm (and not even most) can or will put on trial training like I’ve described. I have two suggestions. Either go to the trial training put on by NITA or challenge your firm to start a training program modeled after the one I’ve described, using NITA materials. I did this at my current firm. We don’t hire professional actors; instead, we use staff as witnesses. They enjoy participating and learning more about what a trial looks like and what we’re always working toward. Our program builds trial skills into our associates so that when the real thing comes along, they will be ready.

Reviewing endless collections of documents, many of which are nonresponsive, writing first drafts of briefs or letters, and drafting unusable discovery requests is not satisfying work, plain and simple. If you continue practicing law this way, you are headed for frustration, boredom, and probably a career change. But if you have trial as your central thought as you are performing your work, you will find meaning in what you are doing. If you forward the plot, say yes to the strange stuff, become indispensable, know the rules of evidence, do pro bono work, and get training, you will develop trial skills, and when a trial comes along, partners looking for help will find you first in line.



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