How Chatbots Make Room for Lawyer Soft Skills

Tom Martin

To date, the common #legaltech narrative has been a drumbeat of anxiety about robot overlords taking over the legal profession.



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On the one hand, we are told that artificial intelligence (AI) and automation will “free up time for lawyers to perform higher-level, more intellectually satisfying work that clients would be willing to pay for.” (This platitude is generally advocated by most legal tech companies to soften the blow that AI and automation will have on the legal profession.) On the other hand, news articles pronounce how robots are on the march to replace lawyers wholesale. (Fear helps to sell media advertising.)

Both Ideas Are Wrong

The first narrative is wrong because higher-level analytical work will not be safe from AI and automation. In AI circles, there’s a concept called Moravec’s Paradox:

Coined by Hans Moravec, Rodney Brooks, and Marvin Minsky in the 1980s, the paradox is the discovery that, contrary to traditional assumptions, high-level reasoning requires very little computation. Instead, it is low-level sensorimotor skills that require enormous computational resources. In other words, as Moravec wrote, “It is comparatively easy to make computers exhibit adult level performance on intelligence tests or playing checkers, and difficult or impossible to give them the skills of a one-year-old when it comes to perception and mobility.”

This is why computers have been so successful in beating humans in checkers, chess, Jeopardy!, and Go. Just at the time I was writing this article, a Google voicebot known as Google Duplex fooled real people into thinking it was a real person calling to book a table at a restaurant and calling to schedule an appointment at a salon. Higher-level work won’t be far behind.

The second narrative is wrong because not everything lawyers do lends itself to the application of AI and automation. Also, on a nitpicky side note, there are not yet any actual robots coming for professional jobs. C-3PO in a tie and a briefcase will have to wait.

An Often-Ignored Third Perspective

There is a third point of view that isn’t discussed as frequently (and is, in fact, almost always ignored): Bots can help us to be more fully expressive, empathetic, and human.

I know. It sounds counterintuitive, right? How can machines make me more human? Doesn’t artificial intelligence, by its very nature, make intelligence itself something that is no longer special and unique, but a replicable commodity?

Yes, but . . . what AI taketh away, it giveth as well.

By focusing on the logical, analytical, left-brain aspects of intelligence, AI gives us the space to focus more of our time and energy on creative, emotional, right-brain intelligence.

A great example of a law firm that uses the right-brain approach is Billie Tarascio’s Modern Law. By systematizing the intake process, Tarascio focuses her family law firm’s energies on connecting with potential new clients emotionally, listening to their stories, empathizing, and being there. This smartly accommodates the needs of the client who, when presented with divorce, a fight over child custody, or both, is in crisis and needs a helping hand and attentive ear. This approach also works from a business standpoint; as it turns out, more clients retain Modern Law because of how their emotional needs are met during the process. Clients feel validated and heard.

There is a reason lawyers are referred to as attorneys and counselors at law.

AI Helps Lawyers Embrace “Soft” Skills

The AI revolution will encourage us to embrace our right-brain identity as counselors and provide clients with the soft attention they need. It may take getting used to, but this is the value we can offer clients that automation can’t.

There is a notion that “fuzzy” disciplines such as humanities, philosophy, and law are less relevant and less bankable than “techie” degrees such as computer science, engineering, and physics, which may open the door to a coveted job with tech titans such as Apple, Facebook, Amazon, and others.

Whereas 20th-century lawyers were encouraged to develop a deep expertise in a narrow area of law, the 21st century calls for T-shaped lawyers. R. Amani Smathers describes a “T-shaped lawyer” as one who has deep legal expertise and also possesses the ability to collaborate across many disciplines, such as technology, business, analytics, and data security. Lawyers are encouraged to learn to code, participate in hackathons, study blockchain, and utilize design thinking.

Can Liberal Arts Give You an Advantage? Maybe.

None of these exhortations are bad advice per se; in fact, it’s a good thing to push professionals outside their comfort zone—so they learn and grow. However, it is not necessary to become a coder to succeed in the world of legal tech. In fact, the opposite may be true. Your liberal arts education may give you a distinct advantage.

Scott Hartley, a Stanford grad, venture capitalist, and author of The Fuzzy and the Techie, names a few examples of tech entrepreneurs who have succeeded despite their lack of technical skills.

Stewart Butterfield, founder of business messaging platform Slack, who studied philosophy at the University of Victoria and Cambridge, credits his ability to develop a successful product to following lines of inquiry to their logical conclusion. LinkedIn’s founder, Reid Hoffman, earned his master’s degree in philosophy at Oxford University. Peter Thiel, founder of PayPal, studied philosophy and law. Ben Silbermann, founder of Pinterest, studied political science at Yale University. Joe Gebbia and Brian Chesky, founders of Airbnb, earned bachelor of fine arts degrees from Rhode Island School of Design.

Now, of course, having a liberal arts background, such as an education in law, does not guarantee success. It does, however, provide valuable skills:

  • Creativity. Skills taught in the liberal arts include creativity, critical thinking, problem solving, decision making, and persuasive arguing. These fundamental thinking and communication skills are the foundation to, in the words of George Bernard Shaw, “dream things that never were” and ask “why not?”
  • Human nature. Humanities and social sciences are dedicated to the study of human nature. The theory of how government, for example, should work is less important than how it actually works, why dysfunction persists, and what can be done to create a system that accounts for real-world challenges.
  • Emotional intelligence. Empathy is key to understanding and can help us to communicate in ways that allow us to connect directly. Designing products and services using empathy can be a great differentiator. Think of Apple’s success with the iPhone by focusing on intuitive functionality and beautiful design.

Of course, that’s not a complete list of important skills that come from degrees that aren’t totally based on hard science or logic. Yet, when it comes to the practice of law (and legal tech), the three above are practical, useful, and can give you a competitive advantage. Let’s look at those three areas a little more in-depth to highlight how they benefit the legal and legal tech profession (as these are not skills provided by AI or automation).

Creativity: A Much-Needed “Soft” Skill in the Legal Industry

Let’s start with creativity. Of course, there are a lot of great AIs available that seem creative. They can solve problems. They can make decisions. They can even make us laugh. Think about Cleverbot. It can answer questions. It can make you laugh. It can make you feel like you’re having a conversation with a sentient being. It can also make you wonder why it replies with some weird or unfitting replies. It’s a program, after all. It can respond because it’s a chatbot, but that doesn’t make it perfect.

Most chatbots are designed to have responses to certain questions about specific topics. Think about all the times you’ve been on the phone with a voice-responsive automated system. Has it always understood you? Have you ever heard, “Sorry, I didn’t get that. Would you try again?” How many times have you pressed zero or kept asking for an operator multiple times because you know you’re getting nowhere? Chatbots are great. AI is great. Automation is great. It can be a creative endeavor and provide great information, but it has its limits. It certainly is not nearly the same as talking to or chatting online with an actual person. And, obviously, I love chatbots. I love what they can do. I love the possibility. I also understand the limitation from the human perspective.

While there are many practice areas that can evoke a wide range of feelings, let’s revisit family law. AI just wouldn’t be able to provide clients or potential clients with answers to more than basic questions (and completing intake forms and common documents). It couldn’t calm others and explain the process specific to their facts. It couldn’t truly communicate the various potential outcomes related to the person’s options for their legal problem.

Lawyers aren’t really expected to be warm and cuddly from the perspective of a client. They are expected to help make problems (and stress) go away. One of the best ways lawyers can do this is by communicating well with their clients. And communication can be a very creative process. Communication is more than just a lawyer talking and a client listening. Communication is a two-way process. For lawyers to effectively do their job, they must know when to listen and know when to speak. This takes critical thinking, decision making, and often persuading clients to consider certain potential outcomes.

AI and automation do not truly listen. They take data provided by the client or potential client and reply with either more data (such as the answer to a basic question) or complete a specific process (such as fill in an intake form or complete a commonly used legal document). They don’t listen. They don’t engage in a dialogue. They don’t (and can’t) ask follow-up questions based on what the person didn’t say. They don’t (and can’t) ask for more details based on an answer. Humans can (and should) engage in the active listening process. Not only does this make the client feel heard and more comfortable, it also provides lawyers with an amazing amount of information from which they can work. Active listening isn’t a hard or new process. It does take practice. It is something that we must use each and every time we talk with another person (regardless of whether we’re looking to win or keep their business).

Human Nature: Creating a Connection with Others

It may be argued by some that many lawyers (as well as AI) lack human nature. To some degree, it might be true. We spend years in law school learning to look past emotions and feelings to instead rely on fact patterns and laws. Obviously, there’s a lot of merit to what we do as a profession. We’re trained to be objective. Yet, it can also cause many lawyers to forget that their clients feel emotions on a regular basis. Human nature is something AI and automation cannot offer. . . and it’s something lawyers should provide. Many don’t provide it at a level that makes their clients think the lawyer actually understands and cares. As such, lawyers who can effectively provide a professional level of both empathy and sympathy, not carry a dismissive air about them, and talk to clients as humans (this includes providing appropriate updates on matters) using a vocabulary that is easily understood will ultimately have happier clients and likely even more referrals.

The legal profession is about solving problems. Lawyers must be able to combine their objective analysis along with a professional level (and range) of emotions. Most of us do not serve clients who went to law school. Even those of us who do defend other lawyers can attest to the fact that those who come for help are just as emotional and distraught as non-lawyers. The best way to get started with regaining your ability to act from a “more human” place is to think about how you would feel (pre–law school) if you were in this person’s exact place. Of course, you don’t and won’t base your decisions from this place, but this can help you act in a way that is more human. That connection can help put clients at ease. That connection is something AI and automation simply cannot provide.

Emotional Intelligence: Caring for Yourself and Your Clients

Emotional intelligence, at its most basic form, is our ability to perceive and react to emotions. (Have you noticed that creativity, human nature, and emotional intelligence have a lot in common? It’s because they’re interdependent.) Emotional intelligence is just as good for you as a lawyer as it is for your law practice. While it may seem as if we’re getting a little off-track (as the discussion is largely about AI, tech, and the importance of these so-called soft skills), I promise it ties in. When you can take better care of yourself as a lawyer, you can take better care of your clients. If you don’t understand your emotions and how to deal with them, they can quickly disrupt your entire practice. You won’t be objective when necessary. And you also may not be able to appropriately connect with clients. By the way, this isn’t just about feeling sad, depressed, stressed, or anxious. It’s also about identifying and addressing unhealthy habits such as too much rigidity. Burnout isn’t a nice place to be, friends. It can cloud your vision and diminish your capabilities. AI can’t save you from that. Neither can automation.

When it comes to others, emotional intelligence is having the ability to identify and properly interact with others. For lawyers, it can take some work to (temporarily) discard skepticism when it comes to emotions. To really connect with clients, you must be able to process what they’re feeling and why they’re feeling that way (even if you don’t agree with it; and you probably don’t need to tell them you disagree with how they feel). At a very basic level, the ability to identity and accept the feelings of others can help make you a better communicator. You learn how to frame what you need to say to make your point known. (Hey, look, critical thinking and creativity!)

Interdependent Skills Can Help You Understand the Why

“Fuzzy” skills are interdependent. And they’re not “soft” as many people believe. They take a lot of practice. They take consistent work. It’s a work of art to combine these abilities with a legal practice. These skills provide you with information and relationships that AI and automation do not provide. That’s not to say that AI and automation don’t have a place in a law office. They most certainly do. However, they are not meant to replace the human component of relationships.

It’s not always about how something gets done. Yes, clients want the outcome that’s in their best interest. Yes, techies (even those who don’t code) know how to create something like a chatbot or an automated sequence to complete basic documentation. And that’s great. We can’t forget the why.

Both techies and fuzzies have a lot to learn from each other, and the sum of their ideas could be greater than the parts. I encourage you to join a group where cross-pollination between fuzzies and techies is encouraged.

And, remember your “fuzzy” skills can help you succeed (and even gain a competitive edge) in an ever-evolving industry where tech continues to play a large role.


Tom Martin is a legal bot advocate, lawyer, author, and speaker. He is CEO and founder of LawDroid Ltd. (a legal AI company dedicated to helping lawyers automate their law practice). Tom is also co-founder of Vancouver Legal Hackers, advisor to the ATJ Tech Fellow Program, member of ARAG Technology Innovation Committee, board member of Group Legal Services Association, and mentor at the Yale Tsai Center for Innovative Thinking. Born and raised in Los Angeles, California, Tom now lives in Vancouver, British Columbia, Canada, with his wife and two daughters.