How to Think Like a Lawyer

Freddie Roach, as history tells it, spent 20 years intensely training as a boxer from the tender age of six before retiring and easing into his career as a boxing trainer. After so many years of actively boxing as a competitor, Freddie’s fundamental skills were, of course, razor-sharp. But, what makes Freddie Roach arguably the greatest combat sports trainer of all time is his ability to see—and to train his fighters to see—the bigger, global picture of the fight. He trains his fighters to go beyond their sharp fundamentals, avoiding being overly focused on the blow-by-blow and minute-by-minute action, and instead seeing a much broader picture and game plan for each fighter’s opponent that Freddie would relentlessly drill into their heads leading up to the fight.

Understand the Bigger Picture

A smelly boxing gym may seem like an unlikely place to start a story about thinking like a lawyer, but I’m not one to follow the conventional storytelling crowd. Most contemporary fans know Freddie Roach as the man behind Manny Pacquiao’s legacy, but Freddie has made a long career of being a Kingmaker in boxing. Over the years, he has seen more than 20 of his athletes crowned champions, including Mike Tyson and Oscar De La Hoya. Freddie’s philosophy and track record illustrate an important point: Most professional boxers have the tools to play the game. But, becoming a champion isn’t simply about executing perfect fundamentals and formulas, trading each punch with a counterpunch. The key is to understand the bigger picture of what you are trying to accomplish. That is Freddie’s secret sauce. That is his sweet science.

I am no Freddie Roach. But I take a page from his book in the art of practicing law. “Thinking like a lawyer” may incorporate the sharpened fundamentals we learned in law school, but thinking like a good lawyer transcends that. The art of practicing law requires us to go beyond blindly executing techniques, focusing solely on what is immediately in front of us. Great lawyers always have their weather eye on the horizon.

You Already Know the Basics

If you managed to get through law school (or at least your first one to two years of it), you have the basic tools to think like a lawyer. Whether or not you agree with those who lament the shortcomings of law schools in preparing students for the actual practice of law, law school does, at minimum, drill the basic rules of how to play the game: case law comprehension, canons of construction, civil procedure, recognizing basic torts, understanding fundamental criminal law, applying facts to legal precedent, etc. This is akin to learning and perfecting your basic boxing combinations. Jab-jab-cross. Jab-cross-hook. Hook-cross-hook. Jab-jab-slip.

Now Transcend the Basics

And this is where many young lawyers get stuck. They stay in the gym, doing the same 20 to 30 combinations on the heavy bag, focusing on what is right in front of them, flawlessly displaying all their wonderful fundamental skills, increasingly sharpened and honed over time. Don’t get me wrong, we must deeply respect and fully understand the details, structure, and power in the practice of law. As world-renowned surfer and undisputedly cool human being Laird Hamilton once said: “If you don’t understand the wave, you can’t respect it. And if you don’t have respect, it’s only a matter of time before the ocean teaches you to get some.” The foundations of law are like the ocean. Understand and respect the waves, or they’ll teach you some respect.

So how do we get out of the gym and onto the wave? How do we move from simply thinking “like a lawyer” into the transcendent realm of thinking like a good lawyer?

Give Yourself Time to Think Even under the Gun

One of the most valuable things a lawyer can give themselves is time to think. We are paid to evaluate the client’s circumstances under prevailing law, assess the risks, and advise on their options. It seems simple, but can be a daunting task. In an age of constant and immediate communication—email, text, cell phones, instant messaging—the value of unadulterated and uninterrupted thinking time is lost in the shuffle. The pressure to have all the answers and all the angles at our fingertips can obscure a lawyer’s ability to retreat into thought, and the necessity of quality thinking time is rarely understood by clients. As the head of an in-house department, I don’t always have the luxury of time on my side. Our business can move very quickly, and my client relies on me to see all the angles, not just the immediate legal upshot. Endless considerations such as public-relations risks, possible impact on other aspects of our business, setting unfavorable precedents, and consequences to our relationships all float like land mines across my radar.

None of these land mines or time constraints, however, change my duty to give quality advice to my client in light of their business landscape. Everyone is under the gun at some point. So how does one think like a good lawyer when there’s simply no time to do it?

My Golden Rules

• Shut the office door (if you don’t have an office door, put on some headphones—it usually does the trick and stops people from starting useless conversations).
• Close your email for at least 15 uninterrupted minutes.
• Put your cell phone away from reach and silence it.
• Resist the urge to divert yourself toward all of the seemingly endless other items on your to-do list. Instead, focus on all the possible aspects of the problem at hand. Start with the strictly legal issues and then beset yourself on the bigger picture ramifications. Take notes. Draw pictures. Sketch diagrams. Get creative with the different narratives that could conceivably play out (more on that later).
• Most importantly: When you think you have contemplated every angle, sit back and ask yourself one last time, “What am I missing here?” Don’t take that question lightly. Approach it as if your arch-nemesis—we all have one—were scouring your conclusions. Then draw some more diagrams. I like diagrams.

Don't Go through Life with a Red Pen in Your Hand

If a law school course could ever be described as “fun,” first-year torts was just that. My torts professor had a particularly sadistic sense of humor and wicked imagination. Our final exam was a Harry Potter fact pattern; the more tort issues you could correctly identify and discuss amongst the sprawling grounds of Hogwart’s School of Wizardry and Witchcraft, the better your exam score.

The Art of Moderation

Despite the trauma of 1L year, most of us remember torts fondly. Why? Because we understood it. Torts is the street carnival of law for fledgling attorneys—noisy, frenetic, a bit greasy, a little sweet, usually digestible, fun, and usually warranting a good hand-washing afterward. Like a game of wack-a-mole, we were rewarded for our ability to identify and hit as many torts as we possibly could. And let’s face it: this proves useful. A lawyer cannot survive without knowing how to spot issues amongst the roughage and dissect them. But like the blue mystery Slurpee and funnel cakes at the street carnival, knowing when and how to implement this tool is about moderation; too much of a good thing can regrettably get you into trouble the next morning.

In “real-life” practice, you indeed need to spot all the issues. But thinking like a good lawyer requires a broader perspective on what your client actually cares about and who the party is on the other side of the table. As a very young lawyer, I confess, I went through life with a red pen in my hand. In reviewing contracts, my mantra was “Spot the issue and redline it!” Perhaps I expected a prize for identifying every single issue and asserting its importance. Regardless, I thankfully had some senior attorneys to filter my work at the time, walking through the truly significant issues with the client instead of allowing me to waste their time with my genius argument on why the canons of construction demand “and” instead of “or” in obscure Paragraph 25.2(a)(ix).

Your Edit Button

Over time, I began understanding the more global concerns at play and realized that I needed to use my “edit” button. Indeed, make sure you see all the issues, but beware of wasting your client’s time with minutiae. They will think you cannot edit yourself and therefore don’t have the requisite judgment to handle their most important business. Equally important, remember that negotiations often work best when they are collaborative. Don’t expect to gain cooperation from opposing counsel by pushing for inconsequential changes just to make a point or to prove that you are the superior scrivener; you will burn your capital and prove that you think more like a law student, not a good lawyer. Try putting down the red pen and using the “edit” button instead.

Take Stock of Your Resources

Approaching your practice as an endurance race is critical, and thinking like a good lawyer means always having a keen awareness of your resources at all times in that race. Young lawyers would do well to take a few lessons from CBS’s mega-hit The Amazing Race, featuring couples racing around the world in a beg-borrow-steal, free-for-all scavenger hunt:

• Think of your client as your partner in the race. You want to keep them close to you, don’t annoy them, and don’t throw them under the bus.
• You may have very limited time to fulfill your objectives, so keep an eye on the clock to ensure you don’t fritter your valuable time away on things that really don’t matter to you and your client.
• Always have a gambit—something you ask for, but if push comes to shove, don’t really need. You can barter gambits.
• Tread lightly on cultural barriers. Being an abrasive steamroller can either give you the upper hand or put people off and make your work unnecessarily adversarial. Consider respecting ingrained processes that you cannot change and simply go with the current.
• Never underestimate the value of common courtesy.
• Don’t burn all your favors upfront with a person you may need help from down the road.

Thinking like a good lawyer requires making shrewd resource decisions. When negotiating a venue deal for a live event, for example, I know most large event venues have a template contract they insist on using. I rarely waste time forcing them to use mine because often, the people I am negotiating with have no authority to deviate from their company’s template. And insisting they lean on their small in-house legal department to get permission will waste two important resources:

1. Time, as leanly staffed venue organizations can sometimes take months to get all the approvals necessary to issue any permissions, and especially with tribal venues, you must respect their internal processes; and
2. Capital, as my venue contacts may resent having to pressure their legal departments for quick turnaround and permissions at the outset—valuable resources put to better use when I need them to push their legal department for more even-handed indemnity and breach provisions later on.

My initial pass at their contract draft might yield more than 40 possible issues. But thinking like a good lawyer, I ask myself three important questions:

1. How much time do we have?
2. Who has the leverage?
3. What do we want our relationship to look like with the venue going forward?

If we are time-crunched with a mere four to five weeks before an event at a major venue we may return to in the future, chances are I won’t have the leverage to push for all of my revisions this time around. It would be exhausting to do so and poor use of the little time we have. Focusing instead on the six to seven big issues that matter to my client is a better play in these circumstances and uses my resources efficiently and more effectively. If I have more time to spare, however, and a handful of gambits (the revisions I want, but don’t absolutely, critically need), then I can go in for 15 to 20 big issues, knowing that I can cash in my gambits to get the deal done, if necessary, coasting into contract signature with my most important 10 to 15 revisions intact.

Don't Forget the Narrative

The art of great persuasion requires narrative. Each problem you face has one. Our job is to craft our client’s side of the story to cast them in the best light and give them an advantage. But once you have created a narrative, take a step back. Thinking like a good lawyer requires exercising self-awareness. Does the narrative simply sound persuasive to you because you slaved away on it for days or does it genuinely make sense? Does it stand up to the “scratch-and-sniff” test of common sense or is it too “cute”? In a dispute, realize that no matter how smart your arguments are or how clever the explanations, the people passing judgment—whether it be a judge, a jury, or the public at large—are likely looking at the story arc between the parties. If you ignore your adversary’s common-sense narrative and fail to craft one of your own, you may find yourself on the losing end of a dispute.

Transactions would do well with a dose of this same medicine. 

In crafting contracts, one of the single most important things a lawyer does is explore the alternate narratives of how the contract plays out between the parties. This isn’t simply about dreaming up the most extreme ways a certain provision can be abused by the other party; think about the real-life story after the parties sign on the dotted line. What if the contract yields huge revenue for both parties? What problems might arise then? What if the deal makes no money for either party? What if management at one of the parties changes and makes working together unbearable? And what happens if one of the parties starts bringing less to the table or their brand goes downhill?

I have had several fight managers, for example, who squeezed us for every penny in pursuit of the highest possible contract compensation for their fighters. Although their fighter clients were initially happy with their lucrative deal, the managers had ramrodded their contract demands through based on the assumption that their fighter would keep winning. They failed to ask themselves what happens when the fighter starts to lose. Without scaled-back pay after losses, a fighter who loses but continues to command top dollar provides little incentive for us to fight him or to even keep him on our roster. He’s expensive and is not moving the ratings needle as he did before. The managers, however, were so focused on the initial dollars that they didn’t structure the deal to account for the possible losing scenario. And at the end of the day, that fighter would probably have rather taken a pay cut than be in a position to be released from his contract coming off a string of losses, having to face a chilly free-agent market.

Sweat the Details. Then Don't Sweat the Details

A litigation partner I worked with early in my career had the same routine whenever I brought him a brief that we had slaved over for days. Just before filing it, I would anxiously hand it to him for a final look. He would take the copy, kick his feet up on his desk, check the front page, check the back page, hand it back to me and say, “Don’t stress about it, there is a mistake in there somewhere, but we got all the stuff that matters.”

As we know, stressing over the minutiae often falls to the youngest lawyers, and rightfully so; excruciating attention to detail is a necessary fundamental skill of lawyering. But forcing the parties to re-execute the agreement because you found three immaterial typos is not a good use of skill (or time). So do the best work you can. Scrutinize every sentence. Double-check the numbering. Triple-check the headings. Press “send.” And then forget about it. If you find immaterial typos later, so be it. Good lawyers know when to move on. Better to focus on the next couple of rounds of the fight.