Preparing lawyers for the no-win scenario

Failure is an unavoidable reality for lawyers — but we run from it all the same, afraid to face our imperfections, unable to forgive our errors. We need to teach new lawyers how to fail and survive.

Most people, unfortunately for them, have never seen the 1982 movie Star Trek II: The Wrath of Khan. Their lives are poorer for having missed the only science-fiction film that could plausibly be turned into a Wagnerian opera, as well as the apogee of William Shatner’s overacting. But many people will be familiar with one element of the movie that has long outlived its theatrical run: the concept of the Kobayashi Maru.

Briefly (because believe me, I could go into detail): The Kobayashi Maru is the name of a spacecraft used in a training simulation for aspiring Starfleet officers. Early in the movie, a trainee cadet is acting as captain of a starship on patrol that receives a distress call from the Kobayashi Maru — a supply ship fatally damaged and adrift in a demilitarized zone of space that Starfleet ships are forbidden to enter. The Kobayashi crew needs immediate rescue before the ship explodes. What should the captain do?

What the cadet learns is that this is a no-win scenario: If she enters the demilitarized zone to rescue the crew, the distress call will turn out to have been a decoy, and her ship will be attacked and destroyed by enemy forces. If she refuses to help, the distress call will turn out to be genuine, the Kobayashi will be lost, and the cadet will likely receive a reprimand for her failures of nerve and humanity.

The test is not whether you make the right choice, because in this simulation, there is no right choice. The test is about how you deal with failure.

While The Wrath of Khan is set late in the 23rd century, much of our modern lawyer formation system is still stuck in the mid-20th. You’ve read my extensive diatribes about that, as well as my favourable review of several recent innovations and advances. We’re getting better at exposing aspiring lawyers to client contact, inculcating business skills, and developing their professional identity. I’d estimate we’ve made more progress in the last 10 years than in the previous 40.

But there’s one aspect of being a lawyer that we have almost entirely failed to train and develop: how to deal with failure itself. When we design new systems for forming lawyers, we have to make certain we include teaching lawyers the reality of failure — to show them how to fail, and still survive.

Failure, of course, is just about the worst experience for a lawyer to go through. You feel embarrassment for your inadequate performance, guilt at letting down your client, shame at losing face in front of your colleagues, and even humiliation if there are opposing counsel who proved themselves superior. For most lawyers — smart people who breezed through school, were praised for their intellect, and sailed from success to success — their first real failure can shake them to their core.

That’s probably why nobody in the law wants to talk about failure. A particularly insightful observation from Professors Alice Armitage and Heidi K. Brown on a podcast last summer was this: Law school pathologizes failure. Being wrong about something is an excruciating experience. Any student who failed a “Socratic” interrogation by a professor can still remember the mortification. Law students are afraid of poor marks that could wreck their career ambitions, but they’re terrified of losing social standing with their peers by looking stupid. By the time they enter the profession, most new lawyers have shut failure away in their bad place.

But failure is an integral part of being a lawyer. Every lawyer fails. It’s part of the job. If you’re a litigator, you’re going to lose cases — on average, half of them. Whenever I read a litigator’s biography, boasting of some great victory and handsome award for the client, I spare a thought for the lawyer on the other side: How did they feel? How did they face their partners when they returned from court? What did they say to their client when they reported the loss? What did they say to themselves, alone in their office after everyone else had gone home?

And do you suppose the winning lawyer in that case is undefeated? That they’ve never had to make the long walk back from the courthouse, mentally preparing how to explain the outcome, kicking themselves for what they did or didn’t do?

It’s not just litigators; it’s every lawyer. We’re human, and humans mess up, and there’s nothing any of us can do about that. Most of our errors will be trivial, while others will be substantial irritants, but a few are going to be serious — real opportunities missed, real damage done. And they are unavoidable, like bullets with our name on them. That’s just life as a grownup in an imperfect world.

But lawyers, burdened with perfectionist tendencies and often deeply insecure about their competence, aren’t ready for failure when it comes, and they pay the price. They weren’t told any of this during their formative years, so they have to find out the hard way, the traumatic way. And they suffer the consequences, which can and frequently do include emotional turmoil, mental anguish, and even descent into addiction.

We can’t keep lawyers from failing. But we can keep them from being ambushed and broken by it.

As early in their formative period as possible, we should introduce aspiring lawyers to failure, and tell them to get comfortable with it. They’re not going to win every case. They’re not going to get every piece of advice correct. They’re going to make a bad judgment call, probably several. They’re going to miss a deadline or misunderstand an instruction. It’s not good that these things will happen. But they are going to happen, and pretending otherwise is foolish and self-destructive.

Describe for new lawyers the steps they’ll have to follow when they realize they’ve made a mistake. Explain the concept of “errors and omissions,” and point out to them that the fact there’s an entire professional insurance category named for this phenomenon means it’s remarkably commonplace. Making an error or an omission won’t end your legal career; but deeply internalizing the mistake until it metastasizes and manifests as a drinking problem very well might.

Maybe subject licensure candidates to some exposure therapy, too. Have practicing lawyers come into the classroom and talk about their worst screwup — or more usefully, just their most recent small mistake, to drive home the point that this happens to everyone, often. Produce and show them videos in which a lawyer fails in ways large and small, and show the range of possible results, from complete forgiveness to client outrage.

Above all, be clear with aspiring lawyers that the perfectionism with which they entered law school will hurt them in the long run, impairing their ability to become successful lawyers. Give them permission to forgive themselves for their mistakes and failures, and explain to them (since hardly anyone seems to know) exactly how you forgive yourself, or anyone else. Assure them that being kind to themselves is not a violation of their professional obligations. There’s a middle ground between taking your work and your duties seriously while also accepting your own flaws and failures. It’s called adulthood.

Maybe a future lawyer formation program, powered by incredibly realistic AI simulations, will even include a legal version of the Kobayashi Maru test: an agonizing choice that goes badly no matter what the lawyer decides. Starfleet refused to promote an officer to captain until they’d been forced to experience and accept the consequences of failure. We should make sure nobody becomes a lawyer until they’ve done the same.