AI looms over every conversation these days, equal parts promise and threat. While there is much talk about how chatbots and generative AI will start writing briefs and crafting arguments, those discussions miss the point. The real value lawyers bring to the conversation goes well beyond raw intelligence and the ability to craft a cogent argument. Our value goes deeper than knowing what words to put on the page. Our value lies in understanding the subtleties inherent in every situation.

In his book, Truth in Our Times: Inside the Fight for Press Freedom in the Age of Alternative Facts, David McCraw, the vice president and deputy general counsel at The New York Times, details decades of struggle to battle libel lawsuits, respond to subpoenas seeking information on sources, to pursue FOIA requests and deal with threats to press freedom. The lessons he shares are not about how to respond to a cease-and-desist letter; they are about the judgment calls on whether to respond at all. His stories about working to gain the release of reporters and other staff taken hostage in areas of conflict focus on the nuances of human relationships, the pursuit of information, and the weighing of whether that information is reliable. Those judgment calls are at the root of effective lawyering. If you’re a Trust & Estates lawyer, the value you bring isn’t in knowing the ins and outs of GRATS, SLATS and other trusts. The value is in sensing when a client is clearly struggling to decide how to pass on an estate to children with different needs, different competencies, and different trustworthiness, and asking the deeper questions to help the client through their turmoil.

In, Crisis Lawyering: Effective Legal Strategies in Emergency Situations, edited by Ray Brescia, the associate dean for Research & Intellectual Life at Albany Law School, and Eric Stern, professor at the College of Emergency Preparedness, Homeland Security & Cybersecurity at the State University of New York at Albany, more than a dozen lawyers from government, private practice, public interest law and academia share their perspectives on how to help their clients or organizations through crises. (Full disclosure, I wrote the final chapter, regarding how to communicate in a crisis.)

Whether the lawyers were dealing with PR crises for their corporate clients, or global human rights challenges, their approaches and successes were based on making judgment calls that required weighing factors well beyond what can be gleaned from reading briefs and legal memos. Their responses were based not only on a thorough understanding of the law, but on the relationships between various parties, an intuitive understanding of human nature, and, in some cases, a last-minute shift in strategy in response to maneuvers by the other side of the struggle or just an evolving fact pattern. In other words, their responses required a human touch.

How can law firm leaders help their attorneys hone the critical thinking skills that allow them to make the right judgment calls? Here are three suggestions.

1. Coach on the subtleties. We tend to think people pick up ideas and guidance by osmosis. They don’t. We have all participated in debrief discussions after a call with a client or a particularly important meeting. Often, those discussions focus on the next steps needed. We share with the junior person what we just agreed to with the client or opposing side and who needs to do what. If that’s all we discuss, we’re missing a huge coaching opportunity. Start those debrief discussions with an assessment of why you said what you said on the call, and, importantly, what you left out. You likely made quite a few decisions during the call or meeting based on how the call progressed. Point out how your approach might have been different if other players were involved, or the discussion had happened at a different point in the overall process.

Your junior colleague isn’t inside your head and doesn’t know what you added or omitted, or why. Discuss what you think the other party to the discussion had in mind and why you think they approached the conversation the way they did. You don’t have to belabor the point or take a long time. Just hit on two or three takeaways.

It’s also helpful to ask the junior person what they noticed about the interaction. Their response will give you insight into how well they pay attention to the nuances of the discussion and what you need to highlight for them.

2. Discuss the players involved. Every situation we face as attorneys is unique and multifaceted. Many of the variables arise from the people involved rather than from the details of the deal or facts of the case. We adjust our approach to a conversation, a negotiation, or a battle in large part based on who else is involved and our knowledge about them. Having regular discussions with junior team members about the participants with whom you are interacting highlights for them the importance of considering the other person in the discussion.

Encourage your junior attorneys to consider not just the role of the other person, but their hopes, dreams, fears, and aspirations as those apply to your situation. Before you get on the phone with “Jack,” the client, ask the junior person, “What do you think ‘success’ looks like for Jack?” That forces your colleague to think about their language, that approach, and their positioning of their ideas. It helps them discern what information to share and what topics to highlight. It helps them become more deliberate in their communication.

3. Teach humility. In the stories in Truth in Our Times and Crisis Lawyering, what stands out is the humility that each author has in their approach to a given situation. Learning to make better judgment calls requires gaining perspective on our own position and the rationale behind our thinking. It’s important to second guess ourselves on occasion. Three good questions you can ask yourself about your decisions are:

How much is my ego playing into this decision? Do we like our own idea over someone else’s suggestion just because it’s our idea, or because it’s truly the best idea?
How much is my own self interest involved? This is separate from ego. I may decide to follow someone else’s plan because unbeknownst to them, I profit more from their idea, even if it’s not the best idea for the group or in this situation.
How much am I part of the problem? This is a tough one. It takes a lot of honest reflection to recognize that we’re the ones mucking up the works. Sometimes we realize we’re our own worst enemy.

Reflecting on these types of questions for ourselves and encouraging the junior people around us to do the same helps us become more self-aware, more discerning, and more engaged with the broader and deeper nuances in our interactions. That awareness and perspective allow us to make the tougher judgment calls.

AI might be able to think by itself, but I’m not sure it yet knows how to think about itself. The technology that recently drafted a brief citing fabricated cases was, I have to believe, unaware that it was writing fiction, not a legal brief. While much of the work we produce as attorneys might be replicated by sophisticated algorithms in the coming years, the core value we bring to our organizations and those we serve will continue to be the ability to weigh numerous factors well beyond word choice and syntax. Instilling those more subtle skills in our junior colleagues will ensure we continue to meet our primary obligation – to bring genuine wisdom.

Jay Sullivan is a former practicing attorney and the former managing partner at Exec/Comm, LLC, a communications consulting firm. He is the author of “The New Nimble: Leading in the Age of Change,” “Simply Said: Communicating Better at Work & Beyond,” and “Raising Gentle Men: Lives at the Orphanage Edge.” He can be reached at [email protected].