RODNEY YAP: FROM LEGAL HACKATHONS TO WINNING A PROMPT ENGINEERING COMPETITION
How experimenting with GenAI tools and various prompting frameworks have helped Rodney master the art of prompt engineering
BY MATHANGI ELANGOVAN
Rodney Yap’s interest in legal tech was cemented in 2018 when he participated in the first Global Legal Hackathon, which was co-organised by the Singapore Academy of Law’s Future Law Innovation Programme (FLIP) and Thomson Reuters. This event brought together legal professionals, technologists, and innovators to solve complex legal challenges. His dual passion for law and tech was further fueled by the advent of tools like ChatGPT.
“When ChatGPT came out, I was immediately drawn to it,” Rodney recalls. “A friend told me, 'Hey, this is quite a cool tool.' I tried it out, and that was it—I started experimenting and using it more in my daily life.” This hands-on approach, fueled by curiosity and an eagerness to learn, led him to explore the world of generative AI more deeply, eventually leading him to prompt engineering.
The Art of Prompt Engineering
On 5th November, at the TechLaw.Fest Open House held in conjunction with the Singapore Fintech Festival (SFF), Rodney Yap was recognised as the winner of the inaugural prompt engineering competition, organised by SAL with support from Microsoft and Lupl.
Mr Rodney Yap receiving his award from Mr Jeth Lee, Regional Legal Director of Microsoft, APAC and Mr Paul Neo, Chief Operating Officer & Chief Financial Officer of SAL.
The Prompt Engineering Competition was designed for legal professionals and students. It focused on creating innovative AI prompts that assist in legal tasks such as legal research, drafting contract clauses, writing correspondence, and analysing contractual and business documents.
While Rodney had long been experimenting with prompt engineering—especially after realising that more thoughtful prompts lead to better results—he had never entered a formal competition. When he discovered a prompt engineering competition in the legal domain, he saw an opportunity to apply his skills in a focused, competitive environment.
“I had heard of a few prompt engineering competitions before, but I always missed the deadlines. When I saw one directly related to my domain of expertise, legal and tech, I thought, 'Why not?'”
His approach to the competition was meticulous and well-informed, drawing on both his experience and insights into how to optimise prompts for better results. “The first thing I did was look at the rubrics,” he explains. “Understanding the guidelines is key. But beyond that, having a framework helps—something like the COSTAR framework can be really useful. For me, with ChatGPT, establishing context is crucial. I try to set a clear role and structure for the output I want.”
Rodney’s technique also involves careful structuring of the prompts for reusability. “I like to create prompts that I can reuse. I focus on setting up a context, crafting the output structure and ensuring that the response can be easily reviewed and checked for accuracy,” he says. For idea generation, Rodney often uses “tree of thought prompting,” a technique that organises thoughts in a branching manner to help guide the prompting model towards more creative and expansive responses.
Leveraging Generative AI for Legal Work
At PwC, where Rodney currently works, strict confidentiality and cybersecurity policies mean that employees can’t access public Gen AI tools like ChatGPT on work computers. Instead, the firm has its own internal tools and domain specific tools like Harvey and Leah, which have been specifically built for legal use.
Rodney has leveraged these tools for a variety of legal tasks. “For daily work, I use AI tools like Harvey for drafting emails and summarizing notes, ” he says. He also uses Copilot for general tasks, noting its seamless integration with Microsoft tools.
Learning and Sharing Knowledge
For Rodney, the key to success in the prompt engineering competition was a commitment to experimentation and continuous learning. “I follow a lot of people on TikTok and Medium who experiment with different prompts and share their results. Some of these people are in sales and marketing, and they share their prompt tricks and techniques. But even with these resources, the most important thing is to try things out yourself,” Rodney emphasizes. “You need to experiment, generate the output, and compare results to understand what works best for your specific needs.”
This mindset of experimentation has not only shaped Rodney’s success in the competition but also underpins his broader approach to technology and law. “Tech and law are a constantly evolving space. You can’t just rely on what works today; you have to stay ahead by trying new things and learning from the results,” he notes.
Rodney Yap has been awarded several prestigious prizes for his outstanding performance in the competition, including a free flight and accommodation to join the Singapore Academy of Law’s (SAL) next TLF Business Mission trip to Shenzhen He also received $5,000 sponsored by Microsoft, recognising his innovative approach in the field. Additionally, Rodney is granted 1-year free access to the Academy Library, sponsored by Academy Publishing, providing him with valuable resources to further his professional growth and development in the legal and tech space.
Rodney Yap is a Manager at PwC NewLaw, connect with him here.
At TechLaw.Fest 2024, SAL unveiled its Prompt Engineering Resources in collaboration with Microsoft. These resources are now available here.
