
Kesha Tanabe has spent more than two decades in bankruptcy law, moving seamlessly between the public and private sectors. In the public sector, she has worked as an Assistant Attorney General, a Subchapter V Small Business Bankruptcy Trustee appointed by the U.S. Trustee Program within the Department of Justice, and she served as a U.S. Bankruptcy Judge for the District of Minnesota. Currently, Tanabe works at Vogel Law Firm, where she is a co-chair of the Firm's Technology Committee.
In this conversation, Tanabe assesses the current state of technology in the legal field and how advancements in artificial intelligence are shaping the way attorneys work.
Every law firm has some early adopters who can’t wait to try something shiny and new, and its fair share of lawyers who don’t even want a password or a free trial. But at our firm, we share a common commitment to providing great service to our clients. We try a lot of products, but it doesn’t matter how innovative a recent technology is if it does not directly translate to a better experience for our clients.
To that end, I think we’re finding that AI is great for expediting certain tasks. It's great for automation. For example, I have been investing in and utilizing custom software applications that are tailored to my subject matter and practice area for over a decade. It’s great for analyzing data sets or executing form-driven tasks on a repeat basis. We also use AI in discovery when we have a large volume of information to process. This reduces “grunt work” and makes our work faster and more cost-effective. We can pass those benefits along to our clients.
But AI can only do so much. In a legal context, it cannot “drive.” There is a big delta between what has been promised in pitches versus what these products can do in the context of real cases. I demo various products all the time, and I have yet to encounter a product that can replace the human element of lawyering.
In our business, distressed companies are often referred to as a “melting ice cube.” If you cannot work quickly and efficiently, there will not be anything left to fight over. We need to help a company make payroll or manage a property on the verge of foreclosure. If we fail to develop a strategy and implement it quickly, value will be lost to both the debtor and its creditors. Bankruptcy lawyers must manage the very real risk that everyone will lose if we cannot work skillfully, quickly, and pragmatically. So, anything that might help us to be faster, more agile, or more cost-effective is an exciting possibility to a bankruptcy lawyer.
In my first year of law school, I had to physically go to the library and pull paper books off the shelf to complete my assignments. If someone did not put a specific volume of a treatise back on the shelf, you and your classmates might have to travel to a different law library and make a photocopy for the rest of the class. (Yes, that is a true story, but I digress.)
By the time I got a Westlaw account, I thought it was going to change the world. And it did speed-up the process of legal research. But it did not render lawyers obsolete. Again, it eliminates some of the tedium of lawyering. Gone are the days of hourly contract attorneys sifting through document review for weeks or months at a time. But the human part of lawyering has not really changed much in my experience.
When you practice bankruptcy law, you are in constant conversation with other practitioners about the law and how it applies to real cases. A bankruptcy court is not a vending machine that spits out an order if you push a button. AI does not replace any of the negotiation, compromise, mediation, problem solving, or decision making in real cases– all of which are very human processes.
One of the most basic obligations of a lawyer is to make sure that clients are giving informed consent. Clients need to know what is happening in their case and make informed decisions about how they want to proceed. This is a fundamental human dance between business owners or investors and their lawyers. A lawyer can have great technical skills and professional experience. But if a lawyer does not get to know his or her clients: their style, their approach to risk, what upside they're chasing, and what downside they're dreading, the lawyer really cannot effectively counsel a client when decisions need to be made. Large language models might be able to cobble together a memo, but they can’t replace the judgment of an experienced restructuring professional, and they can’t counsel each unique client who is trying to understand and evaluate their options in real time.
Bankruptcy law seems to require a wide variety of skills. How are you able to adapt to the nuances of each case?
I once read, "the world is a harmony of opposites." I've never forgotten it because it perfectly sums up the daily experience of being a bankruptcy lawyer. Sometimes a lawyer must be solitary for many hours at a time, doing focused work that is analytical, competitive, and task oriented. But this technical ability is not enough by itself. You can’t solve real problems without good listening, empathy, and interpersonal communication too. I admire lawyers who find a way to embody these seemingly opposite characteristics.
I'm excited about making the practice of law faster and more cost-effective. But I am skeptical about whether AI will ever truly exercise judgment or counsel unique clients who are faced with challenges. So far, I just don't see AI changing this aspect of our practice yet.
At the end of the day, the practice of law is a fundamentally human exercise. It's about communication, understanding people, and navigating complex situations. AI can help us do some of the grunt work more efficiently. But the advocacy, strategizing, and the ability to sit with someone in a vulnerable moment or a high stakes situation and help them to see a path forward—I doubt that can or will be automated anytime soon.





