Toby Ziegler: Teaching Us to be Better Lawyers

Unfortunately, I started watching The West Wing while studying abroad in London. The timing was unfortunate because I probably spent too much time catching up on previous seasons. But I enjoyed every episode (except the post-9/11 episode) and loved the show. My favorite character by far is Toby Ziegler, the White House Communications Director. He’s surly, opinionated, and sometimes crass. He has an appreciation for red meat, cigars, and liquor. But beyond those admirable traits, the character can teach us a lot about the practice of law. Aaron Sorkin’s creation can teach us about winning and losing, about teamwork, and about praise.

The Pitfalls of Wanting to Win

Josh Lyman: You like winning
Toby Ziegler: Keeps you from having to say the word please

Lawyers win and lose every day. Sometimes those wins and losses can make or break a career. Toby and I share a common trait: competitiveness. He wants to win. He believes that his side is (usually) right, and wants to beat the other side. But sometimes this desire goes too far. During President Bartlett’s re-election campaign, Toby becomes obsessed with beating the opponent. He doesn’t care about winning just to win. He wants to beat his opponent.

It’s easy for lawyers to fall into a similar trap. For example, I’m sure we all know attorneys that we don’t like. Maybe we think they’re unprofessional or unethical. Or maybe they just beat us once or twice and that soured the relationship. Either way, it’s easy to see the goal shift to beating the other attorney, instead of winning for the client. Of course, the latter should be any good lawyer’s focus. When we become too focused on beating another lawyer, it becomes easy to make snarky comments in briefs or sling ad hominem attacks during arguments.

Like Toby, we can all lose sight of the goal at times. But the important thing is to remember what winning is, and who we are winning for.

Being Prepared to Lose

Sam Seaborn: You wrote a concession?
Toby Ziegler: Of course I wrote a concession. You want to tempt the wrath of the whatever from high atop the thing?
Sam Seaborn: No.
Toby Ziegler: Then go outside, turn around three times and spit. What the hell’s the matter with you?

In Toby’s world, they lose elections and votes. On any given day we can lose something. We can lose a client. We can lose a case or a motion or a trial. But if we are prepared to lose, and prepare our clients accordingly, it is easier to handle. Toby, on numerous occasions, berates his staff for attempting to celebrate early. He doesn’t allow balloons on election night before the winner is decided. When waiting on a critical Senate vote, there is no congratulating or toasting until the fifty-first vote is cast.

Similarly, he always prepares to lose. He accepts it. As we learn in the second season, this is probably because he usually loses. He worked on six campaigns and lost all of them. This helps him go into most situations prepared to lose, and not accept a victory until it has really happened.

Before every hearing, I explain to my client the possibility that we will lose. I explain the ramifications of such a loss and attempt to prepare them for the worst. Mentally, I assume we are going to lose. Even when the law or facts are clearly on my side, I never assume a win. By preparing for a loss, it’s easy to make myself fight harder; to do more research and be better prepared than my opponent. That way, if I lose, I can tell my client we did everything we could.

Understanding the Value of Praise

Toby Ziegler: You’re a good deputy, Sam.
Sam Seaborn: What do you mean?
Toby Ziegler: That.
Sam Seaborn: You won money on football today, didn’t you?
Toby Ziegler: Yeah, but I mean it anyway.

Humans all value praise. It is simply our nature. A kind word here and there can go a long way. Specific positive feedback is even better. But solos and small firm lawyers can easily miss out on this. Unlike larger firms, most solo and small firms don’t have regular reviews. And depending on the kind of law you practice, it’s entirely possible that clients rarely give you any praise.

This is why it’s so important that we show praise when it’s appropriate. Toby is a bit of a curmudgeon. But every once in a while he still compliments his second in command, or tells his staff they’re amazing. We can all do the same. I even try to give opposing counsel positive feedback when possible. For example, I recently told opposing counsel she did a great job on a cross examination of my client, who was a particularly slippery witness. I must stress that the praise has to be appropriate and genuine. Otherwise it can be seen as demeaning or disrespectful.

Paper is for Wimps

Charlie: Aren’t you supposed to be writing [a speech]?
Toby: I am writing.
Charlie: I don’t see paper.
Toby: “We can sit back and admit with grave sensitivity that life isn’t fair and the less-advantaged are destined to their lot in life and the problems of those on the other side of the world should stay there, that our leaders are cynical and can never be an instrument to change, but that, my friends, is not worthy of you, it’s not worthy of the President, it’s not worthy of a great nation, it’s not worthy of
America.” Paper is for wimps.

This is not a quote about a paperless law office. It’s about working however you need to work. I do my best thinking in the shower and while walking around. If you need to bounce a ball off the wall to get your creative juices flowing, go for it. Don’t limit yourself to the way someone tells you that you’re supposed to do it.

The Importance of a Team

Toby: …We’re a group. We’re a team…We win together, we lose together, we celebrate and we mourn together. And defeats are softened and victories sweetened because we did them together…I’m simply gonna say this: you’re my guys. And I’m yours. And there’s nothing I wouldn’t do for you.

When someone on his staff leaks an embarrassing quote to the press, Toby is furious. But instead of chastising his staff, he gives the above speech. Toby understands that without everyone that works for him, he wouldn’t be able to do his job. We are no different. Without our partners, associates, paralegals, and support staff, we wouldn’t be as good at our jobs. It’s important that we remember that the next time we think a member of our team did something wrong.


1 Comment

  1. Avatar Dave says:

    What’s this? You didn’t like “Isaac and Ishmael”? For shame, sir. For shame.

    Yes, it’s rather preachy, and obviously not meant to be a part of the story arc. Just bear in mind when it was produced. At that time, it wasn’t a little risky to put together that particular story — I’m surprised it didn’t invoke the ire of Drudge and Fox News.

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