Legal leadership today extends far beyond interpreting laws; it demands sound judgment, ethical clarity, and the ability to navigate complexity with confidence in an increasingly dynamic business environment.
For experienced legal leader, Frederick Tay, Director, Joyce A Tan & Partners LLC, the key to being an effective legal leader requires one to rely on fundamental legal principles while approaching stakeholders with empathy.
With over a decade of experience in corporate law, Frederick specializes in mergers and acquisitions, corporate transactions, and legal strategy across the healthcare and consumer healthcare sectors.
In an exclusive interaction with CEO Insights Asia, Frederick shares his perspectives on building a principled decision-making philosophy, navigating ambiguity and balancing legal risks with commercial priorities. He also talks about integrating AI into legal practice, and influencing stakeholders through empathy and reasoned judgment.
Drawing from years of experience across high-stakes transactions and leadership roles, he highlights the importance of discipline, adaptability, and ethical responsibility in shaping effective legal leadership.
Read the following interview for deeper insights on leader leadership in today’s complex business environment.
Q1. From the beginning of your legal leadership journey, what early experiences first shaped how you approach judgment, complexity, and responsibility as a legal strategist?
A. I started off in the private practice as a Mergers and Acquisition lawyer before going into in-house in GSK as a legal manager. The main leadership opportunities in my career really began when I rose to senior associate in my first law firm where I have to lead the team of associates in multiple transactions in particular a highly complex due diligence that involved multiple entities as well as my first transaction as the lead associate working directly with the head of M&A who eventually became the managing partner of the firm.
Both experiences gave me the first taste of what it feels like to have to navigate complexities by exercising judgement through the earned experiences. However, it was only as a legal manager sitting on the senior leadership team of the local consumer healthcare business then in GSK that really dawned on me that there are people relying on my decisions and advice to navigate the legal complexities and one principle in doing so is always look at fundamental legal principles instead of jumping straight into the complexities and never fail to do a balancing approach towards the risks shown.
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Q2. Building on that philosophy, how did you consciously evolve the principles that now guide your judgment across highly ambiguous and high-stakes situations over time?
A. I still very much look to fundamental legal principles whenever there are new laws or changes to laws or even in the face of increasingly risky transactions. However, I have also began to start shifting perspectives and appreciate the regulators’ concerns and mindset that could help shape the laws in such situations. This is something that you can only acquire over time having worked in any industry for at least a decade.
Q3. When translating those principles into practice, what internal cognitive discipline or mental models help you stay consistent when information is incomplete or conflicting?
A. Empathy is key which requires empathy for your clients, the counterparties as well as the regulators. Without empathy as a key mental model, you will sometimes lapse into what you believe is viable and proceed on a basis of a blind faith.
Also, it is important to be disciplined enough to take an alternative path and accept that not all your decisions are always accurate and it is important to take on different functional perspectives. Finally, always have the comfort of proceeding even if they don’t have all the facts to a situation but cater for the risks that may arise. I will say almost like having a cognitive mental discipline of a chess player!
Q4. In moments of extreme ambiguity, how do you personally decide what not to consider, ensuring clarity emerges without overwhelming analytical noise affecting judgment?
A. Exercising empathy to truly know what the client wants and not what the client thought they want. In most cases, there are ambiguity as the clients themselves are pre-occupied with all the red herring that they fail to appreciate their ultimate objective. It is this failure that creates anxiety and ambiguity that will cloud judgements with unnecessary mental noises. To cut through all this, having empathy to fully and truly understand the client’s actual needs and having the discipline to pursue it by cutting through the noise.
Q5. How have you developed the ability to influence senior stakeholders through reasoning alone, without relying on formal authority or positional leverage in decisions?
A. Reasoning is only part of the equation. When working with stakeholders, you must accept that there are different personalities and stakeholders with different receptiveness towards accepting an alternative argument. Some stakeholders accept reasoning but there are some who find security in aligned agreements amongst the majority. There are some stakeholders who believe in aligning with the higher decision makers who are higher in the hierarchical chain of command.
Knowing your different stakeholders and ensuring that you are able to address their considerations in accepting alternative views are very important.
Q6. As technology and artificial intelligence increasingly shape decision landscapes, how do you integrate machine insights while preserving distinctly human judgment and accountability?
It is imperative in receiving insights and outputs generated by AI to not be reliant and always exercise intellectual curiosity in questioning the outputs. Avoid relying them completely but consider the outputs as starting positions that can help better frame your thoughts prior to exercising judgement. Eventually, it is the acknowledgement that AI is just a tool and cannot make decisions on behalf of humans.
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Q7. How do you internally define and protect ethical boundaries when strategic recommendations might be technically possible but personally uncomfortable or morally complex?
A. Different people have different ethical boundaries as they are not universal. Most ethical boundaries are very much influenced by a person’s environment, upbringing, religious considerations and education. Accordingly, to impose one’s ethical considerations on a decision to be undertaken at the corporate level may not be ideal.
Nonetheless, there can be situations where the decisions of the company may straddle between what is legally permissible and what is not. In such cases, depending on the extent of such complexity, it may be a situation where you need to find peace without yourself and accept that what you believe strongly is morally relevant has a spectrum that you have to learn to calibrate based on the facts presented at the point in time bearing in mind that there are occasions where the facts can warrant a crossing of your moral line in which case, you will need to exercise your legal guardian role to step in and prevent it from happening.
Q8. What methods have you used to translate your personal judgment into repeatable frameworks or systems that others can reliably apply under pressure?
A. Always learn the technique of influencing individuals which can be done either by having multiple check-ins with your stakeholders so that your stakeholder trust your judgement and understand the basis of your judgement or building a relationship with your clients beyond the professional interactions. This is especially for in-house legal counsels where their clients are usually their internal stakeholders who counsel should not see them as pure colleagues but take the opportunity to know these individuals.
LAST WORD: Advice for emerging leaders seeking to develop a durable decision-making philosophy rather than short-term tactical expertise:
It will be important for emerging leaders to truly identify the principle that they are able to adhere to and sustain them through their legal career in navigating legal complexities and conflicts of principles. It does not necessarily need to remain stagnant as in can viewed from my own responses above where the approach can change but being able to identify a principle to work with is key. Once such principle is identified, it will then be critical to start identifying the mental models and steps to be disciplined in adhering to it. Sometimes that may appear in the form of external help to remind you of such principles.