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Written by Josh Lee Kok Thong

On 3 and 4 August 2023, the Singapore Academy of Law (“SAL”), in conjunction with the Singapore Management University (“SMU”), organized a conference titled “The Next Frontier in Lawyering: From ESG to GPT”. The conference provided participants with an overview of latest trends in the legal industry, and how these trends posed opportunities and challenges for lawyers and legal professionals. Held at the SMU Yong Pung How School of Law (“SMUYPHSOL”), the conference saw hundreds of attendees learn from global and local legal industry leaders about cutting-edge developments in the legal industry.

One of these global leaders and giants was Professor David B. Wilkins. As Lester Kissel Professor of Law, Vice Dean for Global Initiatives on the Legal Profession, and Faculty Director of the Center on the Legal Profession at Harvard Law School, Professor Wilkins is a prominent thought leader and speaker on the future of the legal profession, disruptive innovation, and legal industry leadership. He has written over 80 articles on the legal profession in leading scholarly journals and the popular press, and teaches several courses at Harvard Law School such as The Legal Profession, and Challenges of a General Counsel. 

At the conference, Professor Wilkins delivered a keynote address titled “From “Law’s Empire” to “Integrated Solutions”: How Globalization, Technology, and Organizational Change Are Opening “New Frontiers” for Lawyers, Clients and Society”. His address covered how law is becoming a more collaborative enterprise (with other knowledge domains) in a volatile, uncertain, complex and ambiguous world. While law would remain a domain driven by human capital, Professor Wilkins also urged lawyers to learn how to work with and understand technology. At the conference, Professor Wilkins also moderated a discussion on “Technology and the Legal Profession”, which explored how new technologies are transforming how lawyers work and interact with clients. 

Following his keynote address, LawTech.Asia (“LTA”) had the valuable opportunity of chatting with Professor Wilkins on his views on the opportunities and impact of technology on the legal industry, the training of future lawyers, how Singapore could strengthen its legal innovation ecosystem, and how legal technology could be better oriented to serve the underserved and under-represented in society. The interview, which is set out below, has only been edited for readability and brevity. 

LTA: In a recent article, LawTech.Asia highlighted how the dynamics and interaction between institutional and ground-up legal technology actors could be leveraged to better serve the legal and legal technology industries. In your opinion, what role(s) should each category of players play in the progression of legal innovation, and how can they dovetail together?

Professor Wilkins: Part of the big challenge here is the many regulatory restrictions on legal technology relating to the unauthorised practice of law. Developers are concerned about regulatory hurdles, especially how technologies that enable legal self-help impinges on the unauthorised practice of law. This impacts access to justice, and requires jurisdictions to work on regulatory policy. 

Yet, interestingly, while regulation is a hindrance, people think that it is going to determine the direction of legal innovation. This mindset needs to change. Innovation always comes from the bottom-up, as we have seen time and again how people have found ways to work within regulatory parameters. 

LTA: Regarding this age-old question about law schools: How can law schools adapt their curricula to better equip future legal professionals for the shifts – technological, regulatory or otherwise – we are seeing today? And how can educators better bridge the gap between traditional legal education with the new skills needed in this new era of legal practice?

Professor Wilkins: As you say, this is an age-old question, and a difficult one. We are in fact seeing a lot of bottom-up innovation. At Harvard Law School, students have been starting organisations on law, technology and innovation. These have put pressure on the law school as an institution. Now, we have something called an “innovation lab” where students can work on projects and business ideas. This is not limited to Harvard Law School, but is a university-wide resource. This means law students  can work with engineering students or business students. 

This is also true of faculty. If faculty are interested in teaching courses around these new areas, they have a lot of autonomy about what to teach. But as the Dean (Professor Lee Pey Woan, Dean, SMUYPHSOL) said in the opening panel, changing formal curricula means not just having to add, but to also subtract. The latter is much more difficult. Because you are taking away a professor’s ability to teach what they want, which – in a world in which professors have academic freedom and tenure – is extremely difficult to do.

For law schools to change, there has to be more pressure from the end users of law schools. These are the employers and people who need the skills of lawyers to solve complex problems. This pressure is building – just not as rapidly as I would have hoped. Because many legal organisations still think that if they hire in the old-fashioned way, from law schools that teach in the old-fashioned way, we can still train them once they enter the profession.

This is increasingly a problem. Many students do not want to do the traditional things lawyers used to do. Thus, they need to have skills that allow them to do new things. While academic institutions change slowly, I hope that conferences and discussions like these, and publications like yours, are going to put more pressure for law to join the rest of the digital transformation happening in other industries.

LTA: Today, legal technology and innovation is in a different place compared to where it was before the pandemic. There is a need for experimentation, but given the uncertainties in the world and the economy, experimentation should also perhaps not be as laissez-faire as it was previously. What do you say to that? How can we focus innovation to serve the stakeholders and interests that truly matter?

Professor Wilkins: This is a point I recently discussed with the SAL. When I last visited Singapore before the pandemic, I was very impressed with how SAL was trying to spur innovation, and how the government wanted to turn Singapore into a legal innovation hub. I hope that continues to be true, because just as it took resources, funding and strategic direction to turn Singapore into a banking and arbitration hub, the same needs to be done for legal innovation. 

This was what the liberalisation of the legal market here was designed to do – to turn Singapore into a vibrant legal hub. To remain as a vibrant legal hub, Singapore must be a hub for legal innovation. To do this, you need people who understand legal innovation. You need people who realise that technologies like AI and ChatGPT (as a subset of that) are getting exponentially more powerful, and they are reaching a tipping point about what they can do.

Let’s look a little closer at ChatGPT. If you asked ChatGPT a good legal question today, it would give you an answer that might be as good as a first-year lawyer from a good law school. While no one should publish or submit to court something that was handed in by a first-year lawyer, the difference in time and cost to get that document out between a first-yearer and ChatGPT is revolutionary. Then imagine the various tasks it might start to do more quickly, and as good as, if not better than, a mid-year associate. We need to realise that while ChatGPT is not going to replace everything, it is going to replace a huge number of things. 

If Singapore wants to be a hub for law and legal innovation, there must be systems in place to channel the investment and desire to the right places. I believe our young students and legal professionals still have the desire to innovate. They just need to be encouraged to do that kind of experimentation and know that there will be support and capital for them to do it.

LTA: Speaking of ChatGPT, a fun fact – a first draft of some of these questions were generated by ChatGPT, which I then had the benefit of tweaking. Since you spoke about young lawyers, my next question is this. How does this affect the training of legal professionals?

Professor Wilkins: This question behooves us to think of how we can utilise this technology to augment our young lawyers. To share an example, Dirk Hartung (Bucerius Law School) has been using ChatGPT to test his own knowledge about new things that he’s learning. In other words, he is using ChatGPT to test his own understanding. My point here is that there are many use cases (of ChatGPT) that we are just beginning to explore. 

This raises the question: If ChatGPT can generate the first draft, how will people ever learn not just to write that first draft, but to evaluate writing? We know that when you just read what others have written, it is not the same as writing it out yourself. How many of us have had the experience of having a good idea, but realise it needs more tweaking when we actually have to write it? It changes the way you think, and this is an important skill we cannot lose. 

Having said that, we make all kinds of assumptions about what we need to make young lawyers do to make them “good lawyers”, such as anecdotes on how one cannot be a good lawyer unless you spend all night at the printer or in the library. We do it because it is the way we have been trained. But has anyone ever tested or verified that these tasks are in fact necessary to produce good lawyers?

Let me give an example. In an interview in the HLS Center on the Legal Profession’s digital magazine on The Practice with Jason Boehmig (Ironclad), Jason shared how he had to improve the accuracy of contract analytical tools to 99%, because no lawyer will ever use a tool for understanding what is in a contract that is less than 99% accurate. But who has ever tested the accuracy of the bleary-eyed associate reading through boxes of documents in a windowless basement of warehouses in Phoenix, Arizona in August? We just assume that it is 99% because they are humans, and because they are smart and well-trained.

In other words, we need to be careful about the heuristics we use. There is no “perfect human” for doing this work, and you do not need to do these tasks repetitively for the first five years of your career. Instead, we need to ask: what are the important skills these associates need, and how we can train them up? 

LTA: This brings us to the final question. How can we ensure that legal technology is accessible and beneficial to the under-served and the under-represented, especially those who are economically disadvantaged? Is there more potential for this, now that we have technologies like ChatGPT?

Professor Wilkins: Some people have commented on how ChatGPT has democratised access to AI because it is free. Well, the most advanced versions are already not free, and it is unlikely they will be for future iterations of ChatGPT. This applies to information technology more generally – it tends to improve access most for people who know how to use the information. Our problem today is not a lack of information, but rather, how to make sense of the flood of information we are facing. 

This is why learning about legal technology and how it operates cannot be just the province of lawyers. It has to be that ordinary citizens are also able to use technology to get access to justice – much like how WebMD helps me, as a layperson, ask better questions of my doctor. Think of what happens if ordinary citizens can ask better questions not just of lawyers, but also of regulators, government officials, and policymakers.

Much of this, however, will need to be subsidised by the government, because doing it is not going to be profitable. If we leave it to legal tech start-ups, the profit incentive means they are going to develop solutions for the well-heeled. But to help those who are not of means, one either needs to subsidise it, or figure out other ways for the developers to make money. Part of the issue is having to educate the public that these services are not going to come out of thin air. If governments are to provide it, people need to pay more taxes. If it is the private industry, then it needs to be profitable or monetisable.

But what is the incentive to do this? Maybe it is that legal tech companies might need to license some of their software for free – like how law firms do pro bono, perhaps that should be a responsibility for software companies to do the same. This kind of ethos has not been there. Brad Smith (Microsoft) once said that technology today is where banking was in the 1930s. Banking then was a completely unregulated enterprise. It then basically crashed the global economy, and today, banking is one of the most heavily regulated industries. Technology is moving in that direction, because technology is as important today as banking was in the 1930s. But what are the obligations of tech companies? How much should it be enforced by governments? How much should be about disclosure and the expectations of consumers? How do we educate consumers to choose tech companies not just based on their speed and efficiency, but their responsibility? These are questions  we are just beginning to explore, and they are the kinds of discussions we need to have. 

LTA: As we are wrapping up here, to the young lawyers reading this, what is the most important thing you would want them to take away from this interview?

Professor Wilkins: I want them to know that this is going to be your world very quickly. We are seeing a generational change to millennials and Generation Z’s. You understand technology way better than the people who are now in control – both its costs and benefits. 

Since your world is going to be shaped by technology, you need to be an active participant in shaping it. You need to educate yourself, not just about how to use technology, but the fundamentals of what it’s doing. You do not need to know how to programme your iPhone, but you should know what your iPhone is collecting about you, what it is doing, and what it’s capable of doing. And that is true about every piece of technology. 

You should then ask of your educational institutions and employers you work for: what is your strategy for dealing with AI, or other emerging technologies? And if they do not have an answer for that, look for another job. You are human capital, and believe it or not, they need you more than you need them. You need to know that there is a war for talent out there, and talent always wins. Trust in yourself and demand (nicely) that people have a strategy for the future. Because if you enter an organisation that does not have a strategy for the future, it might not have a future – and you might not either.