Conversations with Josh Lee

By Gracia Chua and Lin Min Htoo

Josh Lee is a Legal Policy Manager for AI Governance in the Infocomm Media Development Authority of Singapore. He co-founded LawTech.Asia, Singapore’s foremost publication on legal technology and serves as the chairperson of the Asia-Pacific Legal Innovation and Technology Association (ALITA). In this article, he shares more about legal policymaking, the opportunities that accompany a rise in AI, and how to embrace technology in law.

I would describe myself as somebody who is deeply passionate in issues at the intersection of law, policy and technology. To these ends, I am the Chairperson of the Asia-Pacific Legal Innovation and Technology Association (, a pan-regional industry platform consolidating legal innovation and technology initiatives in the region. I’ve also co-founded LawTech.Asia (, a virtual publication that drives thought leadership on law and technology in Asia.

In my day job, I am a Manager in the Artificial Intelligence (AI) Governance team in the Infocomm Media Development Authority of Singapore, where I support the development of AI governance initiatives to build trust in AI. Currently, however, I am on a sabbatical, pursuing my LL.M (with a Law and Technology Specialisation) in UC Berkeley Law. Prior to these, I served as the Assistant Director for Legal Policy in Singapore’s Ministry of Law, where I worked on criminal and civil legislative reform, and practiced as an international arbitration lawyer in Lee & Lee.

In the last couple of years, the phrase “new normal” has been quite heavily used. But in the field of law and technology, we are always working on ascertaining what the new normal is, because things just move so fast. This means having to strike a balance between the former state of the world, industry and economy, against upcoming changes. While there are many new and exciting updates every day, it is important to be able to identify the signal amidst the noise.

For AI specifically – an exciting and fast-paced industry driven by both internal and external changes – the fluidity of this space means that global norms are still being discussed, debated, and developed. That’s what makes it such an exciting time, as a lawyer, to be able to shape these developments which will affect generations beyond me. In other words, I see myself as an architect — someone who reshapes societal relationships that have been disrupted by technology, so that humans can work with, not against, technology.

External changes cover both technological and regulatory developments. For instance, last year saw an explosion in applications for AI in the healthcare sector. Developments in new models, such as GPT-3 have also come up. Such technological developments could spur policy discussions and changes in companies and countries, which we have to grapple with at the national and international levels. New directions, recommendations or guidelines are also put forth by bodies like UNESCO, OECD and G20. These changes are constant, which leads to a continuous chase in order to be at the forefront of innovation.

I have always been very interested in technology. For instance, when I was younger, I used to spend time troubleshooting printers and exploring ways to piece the computer together using the different components that my parents bought me.

With that context in mind, while working on legal policy and legislative matters in MinLaw, I was given the opportunity to work on the technology-related aspects of legislation. For example, I was involved in shaping new computer offenses in the Penal Code, creating a new offence of doxxing (the release of personal information to harass somebody) in the Protection from Harassment Act, and amendments to the Electronic Transactions Act. This made me realise that I could tie my childhood interest in technology with my values and legal training to improve the lives of people in the digital realm.

Around that time, I came across a book called The Sentient Machine, written by former Google computer scientist Amir Hussain. The book’s core argument strongly resonated with me: the author argued that our true purpose as humans is to pursue knowledge. In that light, AI need not be seen as a replacer, but an enabler to bring humans closer to our true purpose.

Inspired, I began to engage in dialogues and discussions in this area. After attending a conference on AI and legal liability hosted by the Deputy Commissioner of Personal Data Protection Commission (PDPC), he shared an opportunity to be a part of the AI Governance team in IMDA – and that’s how I got to my role. In summary, it was quite a natural transition, because AI was truly a frontier space in which I could use my legal knowledge to shape rules and norms for society.

It was definitely a challenge, but one that I welcomed. As the senior management in IMDA stresses to us, technology policymakers and regulators must have an epistemic understanding of technology in order to be effective. While doing AI policymaking was a natural evolution of my interest in law, policy and technology, it remains a challenging journey to be well-versed in the technology.

This is where an ability to adapt and take initiative comes to play. Personally, I took the initiative to dive deep into books, attend conferences, research and even take up courses from AI Singapore to expose myself to the industry. These were critical in helping me with my work, be it drafting the second version of Singapore’s Model AI Governance Framework, or participating in international expert platforms and dialogues. Internally, IMDA also conducts courses to help me grow my domain knowledge. While passion and interest contribute in some way, it is just as crucial to take initiative and to treat all challenges as a learning journey.

The objective is always to put Singapore and Singaporeans first. As I studied law, my perspective might be different from somebody else with a different background. Pragmatically, we start with an overall policy intent, and then take into account a few considerations. First, how does the policy benefit or impact Singapore and Singaporeans? Second, what does the public think about the policy? Third, what is the international picture like, and what we can learn from the experiences of other countries? Fourth, do the benefits outweigh the costs and risks, and how can we maximise the benefits while managing the risks? We also must look at implementing and operationalising the policy well. After, what separates a good proposal from a good policy is implementation. These are things that all policymakers must consider regardless of the domain.

From my experience, there are four points that I will make about the public sector and how it is different from the private sector.

First, the public sector has to be accountable to a much wider range of stakeholders. In the private sector, the primary stakeholders are the clients and the court. Conversely, in the public sector, the primary stakeholders are the public and the political leadership. Often, the expectations between these stakeholders are different.

Second, in the public sector, a legally-trained person is no longer the primary subject matter expert. In a law firm, a practicing lawyer is the primary legal adviser to the court, or to the client. One would be expected to know most if not all of the legal knowledge and framework relevant to the case. In fact, in the Legal Profession Act, there are professional regulations to ensure that practicing lawyers are able to fully understand the law and carry out duties for the client. However, in the public sector, our work covers multiple domains, from understanding what citizens think of policies, to finding out what is happening internationally and what industry perspectives are. Due to the complexities, we often have to consult a wide range of stakeholders – both in and out of the public sector – for our work.

Third, the variety of work involved differs. This is not to say that a job in the legal practice is not varied or interesting — it certainly is — but I would say that the bulk of it happens in a fixed context, either a boardroom deal or a courtroom trial. In the public sector, a lot of our work involves identifying new challenges and innovating solutions for them. We need to find out what has been done, come up with a feasible and acceptable solution, and continue to chip away at a problem, one step at a time. This process is also interesting as there is rarely a fixed template to solving these big problems.

Fourth, people working in the public sector often function as a team. This includes not just within our own teams, but as one entire government. While teamwork is definitely crucial in the private sector as well, those working in the public and civil service often work as one “Team Singapore” – which means being comfortable working across teams and agencies, to solve problems.

There is definitely a plethora of opportunities available. For instance, being in the private legal profession allowed me to help my clients with legal issues while practicing courtroom advocacy as a litigator, which is very meaningful. It is also beneficial to understand what happens in the legal profession because that forms a huge bulk of Singapore’s legal industry.

However, managing the expectations and demands of clients (especially when it comes to the time to render your bill!) can be challenging. It can also be pressurising to deal with opposing counsel in a dispute, especially when it is on a tight timeline set by the court or arbitrator, or when tensions between the client and the opposing party are high.

On the other hand, the public sector has allowed me to take an industry-wide (or nationwide) perspective to large issues. It is also an opportunity to be involved in the highest levels of strategic thinking and national priorities, and even interact directly with political office holders. This, at least for me, is truly exciting. More importantly, as I remember from my orientation in the Civil Service – the public sector is really the only place where you can say, hand-on-heart, that “my job is to make Singapore a better place”!

Nevertheless, there are definitely challenges on this side of the house too. A common one is learning how to work with other ministries and agencies that may have their own priorities and working styles, especially when part of a larger system, like the criminal justice system or the digital economy. Another challenge is that measuring the quality of work in the public sector can often be more amorphous. In legal practices, it is simpler to learn what a good submission in court or a good trial is. However, when it comes to national policies, how do we know whether something is right for Singapore in the long run? This means we need to trust our policymaking processes, as well as constantly seek public feedback to know if a policy is robust, well-rounded and balanced.

Generally, I think having experience in both the private and public legal sector allowed me to gain a more holistic understanding of how society works, and develop a deeper appreciation of the roles and good work done by both lawyers and policymakers.

If we take the common assumption that legal education prepares one for a career as a lawyer, I would say that my career has turned out to be not so conventional! Nevertheless, my legal education did give me some essential skills and traits that have been valuable in my journey. First, it trained me in academic and analytical rigor, which are valued characteristics required in all my roles. Second, it ingrained in me a discipline to complete tasks to the highest standard possible. This has served me well both as a lawyer and a policymaker.

Third, my legal education has also shaped my perspective on things. It taught me the Singapore way of governance, and the institutions and systems that are in place for government, industry and society to function effectively. This also made me more interested in national-level issues and policies, which led me to my career in policy making.

Having worked for half a decade, I am now getting ready to step into school again – I have chosen to do a Master of Laws (LLM) in UC Berkeley. This is primarily to secure my fundamentals in technology and better understand its legal and societal implications. Entering UC Berkeley is a dream – its proximity to Silicon Valley, rich campus life, spirit of entrepreneurship and innovation offer truly exciting learning opportunities that I cannot wait to uncover and discover.

Generally, I would urge students to try out more internships – especially beyond those traditionally related to one’s field. For example, as law students, try out internships beyond law firms. This could include roles in the government, in in-house legal departments, NGOs, or even in start-ups. These are valuable, “risk-free” ways to broaden your horizons – you really never know where you might eventually decide to go!

Let me use my experience as an example. I realised after entering the workforce that having a feel of other types of work would have saved me much worry when I decided to move from legal practice to policy-making. Thinking back, an internship at the Attorney-General’s Chambers, MinLaw, or even in an in-house legal department would have given me a better idea of the different possibilities out there.

Regardless of your preferred field, my advice would be to choose a career that helps you become the person whom you want to be. Beyond being known as a lawyer or a policymaker, it is more important to be known for your values – such as somebody who is respectful, humble, and disciplined. A saying I constantly remind myself is to “not be a lawyer who happens to be a good person, but a good person who happens to be a lawyer”.

On a practical note, I would advise youths to be willing to ask for opportunities, respectfully and humbly. Nothing has ever been gained by keeping quiet about what you want or need.

In terms of preparing oneself for one’s career in school, I take a slightly different tack from some others. Some see university as the last chance for them to have fun before work kicks in. To me, however, university is the best time for one to get exposed to the world without having to worry about long-term implications. Hence, I would advise students to step out of their comfort zones as much as possible. Remember that whatever you do in university can have a multiplier effect on your future development.

Nonetheless, every person’s path and motivations are different. I will be more than happy for anyone who needs advice to reach out and connect with me personally – please always feel free to reach out to me on Facebook, Instagram or LinkedIn!

I believe AI powered by data will be able to transform our economies, improve our lives, and bring us new discoveries and hope. Personally, I was inspired by this idea after reading The Sentient Machine. More importantly, I believe humans will learn to work with AI to produce results that are greater than what could be expected from humans or machines alone.

Nevertheless, a lot of work must be done to get there. When we talk about concerns about AI today, many of us instinctively think of autonomous human-looking robots and how they could out-think humans. This is understandable, as this is often the common portrayal in our media. However, I think the real questions that we should be looking at are on the fairness of AI systems, and their propensity for perpetrating human biases. Are we able to explain the decisions of AI systems and ensure that they are unbiased? How can we put a human in control of an overall task, while still obtaining the gains from automation? These are some of the issues that Singapore has raised in its Model AI Governance Framework and other initiatives, along with recommendations on how organisations can address that.

Beyond that, a broader concern is the increasing reliance that we have on technology. For generations, humans have relied on our own personal stores of experience and knowledge. However, in today’s world, we see numerous cases where humans – even trained humans – rely too much on tools, and lose their own abilities to think when that tool is taken away from them. In the context of AI, could this lead to a loss of our natural understanding or instincts? Personally, I think being able to strike this balance between human expertise and reliance on tools that enhance our abilities is – along with the questions of governance and ethics – longer-term conversations that need to be canvassed today.

There has been so much change since I first started on AI governance policy making in 2019. Back then, the world was still grappling with the ethical principles that AI should be governed by. There were a lot of general discussions on the possible risks that AI systems pose. Today, the world has gained a clearer idea of the risks of AI and broadly come to a consensus on the key principles that are needed for trustworthy AI. There have also been efforts by overseas jurisdictions to regulate AI through laws and regulations. One example is the European Union’s draft Artificial Intelligence Act released in April this year.

In IMDA, our policy work has also grown with these developments, right after issuing the second edition of the Model Framework in January 2020. We have developed industry implementation guides for AI governance, and even a guide on how to redesign jobs in an age of AI. We have also participated in international discussions related to AI regulation to stay up to date with developments and key industry players while learning about the importance of using AI responsibly. More broadly, Singapore has also seen the roll-out of its National AI Strategy in November 2019.

More recently, IMDA organised Asia Tech x AI (ATxAI) Conference that brought together industry leaders, policy makers and experts from the East and West to discuss leading tech trends and the implications for business and policymaking. I am excited to have worked on IMDA’s AI governance testing framework, which was shared by Minister Josephine Teo during the ATxAI Conference.

My lifelong goal is to be able to make a beneficial and lasting impact on our collective future. At present, this means being an architect, shaping policies and disrupting societal relationships along the lines of my own personal values: respect, humility and discipline.

One memorable example that I have on this is my role in the Ministry of Law, where I helped introduce amendments to the Protection from Harassment Act, including introducing new laws on doxxing. The entire experience taught me the relevance of such values as respect and humility, because what we say or do, online or off, can have a lasting impact on someone else. It remains deeply meaningful and humbling to me to have been part of a law-making exercise that really helps shape a values-driven society, and is something that I hope to continue contributing towards.

I will start with the more abstract, before going into the specifics. The three things I value the most are respect, humility and discipline, which I learned from my own personal hobby – street dance. What I hope to do is to understand what these values mean to me, as I get older and get exposed to different situations. For example, I hope to find out what it truly means to respect everyone I meet, to be humble in all my endeavours, and to have discipline in all that I do. These values are my moral compass towards becoming a better person.

Specifically, I want to create a meaningful and lasting impact in both the areas of technology law and law of technology. To achieve this, I would say resilience and doggedness are key. I believe in pushing oneself as much as possible (but not to the extent of burning out), because like our muscles, our brains and mental resilience need to be constantly stretched to grow.

To help me balance all these commitments, one of the things I do is to utilise time management techniques. For example, the Pomodoro Technique, where I focus on a task for 45 minutes and take a break for 5 minutes. Another to give myself very little time to complete a particular task, to force myself to focus on it.

Another key method I use is to find “flow” in all that I do. This means entering a state where you are in effortless control (read this). This allows me to shut out distractions and personal worries, and focus on the task at hand. Moreover, when I come out of a flow state, I often feel a tremendous sense of satisfaction, even if the task itself was not something one would not normally consider as “fun”.

While I am definitely far from what I would consider being successful in my career, one thing that has helped me push on thus far is resilience. Resilience can be honed by being more mindful of ourselves, while being willing to push ourselves even when the going gets tough. Sometimes, resilience and discipline may also mean doing things that seem strange to others – like going out of your way to pursue your passion – but may be necessary to achieve our goals. What matters is that doing it makes sense to you.

Moreover, I think it is important to pursue a values-driven career, instead of merely focusing on what others define as success. While material wealth and status are nice-to-haves, they bring pleasure but not fulfilment. Rather than being caught up with superficial comparisons and angst in “getting there”, my conception of the good life is one in which an individual finds meaning in living and embodying one’s values to the fullest, seeking inspiration and being an inspiration to others, and being on a quest for constant learning and improvement. In this regard, I believe in inspiring others not by the example of my achievements, but by the achievement of my example. This is a powerful mindset that puts into perspective why I do what I do.

The last way is to give back to the community, by returning the favor of what we have gained from our society, and to those who need our help in the community. I think this act can give us a tremendous sense of satisfaction while teaching us many things.

These are not skills or mindsets that one can pick up overnight. They do require, however, discipline, constant reflection and mindfulness, and recalibration. It also requires a sense of humility and community. Even with these, I do not believe we can ever truly master these skills – every day will bring a new challenge and opportunity to be better than we were the day before.

In the recent IPS SR Nathan Lecture Series, MAS chief Ravi Menon identified technology as one of the Four Horsemen facing Singapore. While technology isn’t apocalyptic, it brings benefits, risks and disruption – to all industries. The legal sector is no exception. While we may not see drastic changes in the next few years, I am often reminded of a particular quote by Bill Gates, who said that humans often overestimate the changes to come in the next two years, but underestimate the changes in the next 10.

Relative to other industries, the legal industry is more conservative and risk-averse. No surprise, coming from a time-honoured profession! Nevertheless, the disruptiveness of technology has seen it make huge headways in both the private and public legal sector. For example, in China, there are AI systems in court that verify the veracity of statements made in court based on a witness’ affidavit – in real time! Another example would be automated document generations coupled with chatbots, which can help to push out entire agreements with minimal human intervention. In the public legal sector, there is an app made by a young British-American developer, Joshua Browder, called DoNotPay. The app helps to draft appeals for parking tickets, and has gained tremendous popularity. Such developments challenge the notion that lawyering is a profession that can only be performed with a human touch.

Nevertheless, I do not think that technology will entirely replace lawyers. Instead, technology will change the notion of what lawyering means. To me, the ultimate tag-team is that between humans and machines, where legal professionals are augmented by technology to enable greater efficiency, productivity, quality and access to justice.

The most challenging factor in digitalising the industry remains the mindset. One example can be seen from the COVID-19 pandemic. With the onset of the pandemic, law firms and courts were forced to digitalise, such as by having Zoom hearings and remote desktop connections in a matter of weeks. Fears about the legal system crumbling if technology was too abruptly adopted turned out to be misplaced. What this shows, I think, is that our current state of technology is already sufficiently capable of transforming the way lawyers work. All we needed was a change in mindset – from good-to-have to essential to survival – for technology to be embraced.

There are other factors that give rise to resistance. There will inevitably be costs in overhauling systems and training people to adopt technology. Sometimes, it may be borne from a mismatch in expectations – people expecting technology to be a panacea, but later realising that it is not so straightforward.

Going forward, we need to continue with the mission of clarifying technology’s value to lawyers, as well as to allay fears (like whether technology will replace their jobs). While I may not be practicing as an advocate, this is still a form of advocacy, and gives me great fulfilment in being part of this industry.

That is a great question. There are two kinds of technologies in the legal industry, or what we call “legal tech”. There are the emerging, sophisticated AI technologies like natural language processing, but there are also simpler, more long-running technologies that people are more familiar with. For the latter, I think the trust and reliability are largely there. Regulations are also in place to regulate the use of these technologies.

On the other hand, the more complex technologies are where attention is being focused on. One example is COMPAS. This is an AI system that recommends to judges sentencing outcomes based on the statistical likelihood of an offender re-offending. There is massive debate about whether its use is ethical, given that people may not fully understand the data that is used to train the system, how the system processes the data to make decisions, and how much weight should judges place on this system’s recommendations. In cases like this, there needs to be a lot more work to ensure that such technologies are trusted by the lawyers, the courts, and the man or woman on the street. This is why there are big conversations around the world today about how to regulate these “high-risk” systems, and to put in place standards regarding their use.

The first step is to realise that technology is not here to replace lawyers, but to improve the way we do lawyering. So, we shouldn’t see it as a threat that we need to defend against at all costs.

The second is to not see legal technology as a domain just for geeks. While some may view the use of technology in law as simply a side hobby for lawyers with an interest in computers, I urge them to think otherwise. I believe that if as long as a lawyer carries the desire to improve the legal system, the laws and how these laws apply, then technology must be seen as a tool to better enable this improvement going forward.

As for how to embrace technology, I think that there is no other better way than to simply dive in and get your hands dirty. It is exactly what I did when I started writing my virtual publication. I used to think about the intricacies of technology, but as lawyers we have the ability to absorb huge amounts of information, so this is definitely possible.

There is tremendous opportunity for Singapore. In many ways, Singapore is already seen as a thoughtful and practical leader in the adoption of technology in legal practice,. This has earned us a tremendous amount of trust. One example of this is how Singapore has been recently ranked the number one arbitration seat in the world, together with London. A significant part of this was due to our willingness to adopt technology to ensure that processes are cheaper, more efficient, and more trustworthy.

I definitely see an opportunity for Singapore to serve as a legal technology hub. In 2019, the UK Law Society published a study that lists places like Singapore as key competitors in this industry. With our status as a competitive legal tech hub, we can not only provide better quality legal services, but also bring more talent and ideas into Singapore to further improve our legal services. We can also tap on Singapore’s intrinsic strength as convenors to converge perspectives from the East and West, and to strike a sensible and pragmatic balance between them.