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Writer's pictureEdward Lee

Surviving Pupillage: 5 Key Advice

Updated: Aug 12

Surviving Pupillage

It's pupillage season again! Having recently completed my nine months, I thought to share some practical tips and insights that, in my experience, would help fresh graduates not only survive but thrive during their induction into the legal profession.


"Thriving" does not necessarily mean being retained in the firm (although that would be an indication). It simply means being able to make the most of your time by learning as much as possible and growing to be a better lawyer and person. This, in and of itself, is a significant achievement. (So, first tip before we even begin is: there is no need to compare and compete with your peers. This journey is uniquely yours!)


I'm gonna be very honest here. The following points consist of things that I did and didn't do well during my pupillage. If you're just embarking on your pupillage journey, I hope you can benefit from my experiences vicariously, and maybe avoid repeating the same mistakes I made.


1️⃣ Manage Expectations

to Avoid Burnout

Every firm has its own culture and expectations regarding work ethics. For example, some bosses are hardcore and more traditional in expecting employees to stay past office hours as long as they are still in the office. Conversely, other bosses will kick everyone out of the office at half past five, on the dot. Most firms fall somewhere in between both extremes, meaning that you may need to stay if there's work to be completed.


Before you begin your pupillage, it'll be helpful to find out early what your firm expects from you and what YOU expect from them. This is not only in terms of working hours, but more importantly on matters like:

  • Generally, what your superiors expect from you. Can you meet these expectations?

  • Your job scope — you may be expected to do administrative work in addition to legal work. Are you okay with that?

  • Workload and expected turnaround times for tasks. Can you handle it?

  • Opportunities for professional and legal skill development. Are there any?

  • Whether the type of cases the firm takes on aligns with your values and interest.

  • Whether the firm is paying for the costs of filing your papers.


Clarify these matters before you begin, and you will know if you are a good fit for the firm and vice versa. The last thing you want is to experience a burnout early in your legal career due to unmet expectations and misunderstandings.


Remember, there's a place for everyone in the legal profession — you just need to start off with the right foot by finding the right fit for you.


2️⃣ Communicate & Connect

to Gain the Trust of Your Colleagues

When you do begin your pupillage, you mustn't manage your own tasks only. More than the actual work that you are doing, the people in your workplace, from your pupil mates to the administrative staff to the partners, can make or break your pupillage experience.


In dealing with your superiors, you will want to "manage up." This means keeping them updated on tasks delegated to you. An effective way to do this is the 5-15 Method, where at the end of the week, you could spend 15 minutes to compile the status of your tasks into an update which takes 5 minutes for your boss to read.


You don't have to stick with the literal method, but the concept applies — keep others informed, don't leave your superiors scratching their head wondering when you will come back to them on a piece of research, for example.


The other benefit of keeping them updated is that your superiors will be well-aware of your contribution to the team, which will really help make a good impression.


But don't only talk about work, utilise every opportunity you can to maintain a positive relationship with everyone!


I quote Bill Nye, the Science Guy, in saying:

"Everyone you will ever meet knows something you don't."

Don't shy away from small talk with the staff and the lawyers in your firm. You never know when the conversations will reveal nuggets of wisdom.



I've had countless conversations with colleagues at my workplace, sharing opinions and stories on every topic under the sun. Through these exchanges, I've learned a great deal from them while building strong bonds.


Also, you can bet that your colleagues will be much more eager to assist you when you need help if you are a friend hehe.


3️⃣ Understand the "Why"

to Produce High Quality Work

Whether you are drafting a letter, a pleading, or a submission, there are probably templates or precedents that you could refer to. Precedents really do offer a sense of certainty, especially when you are drafting for the first time. However, try not to be tempted to follow the templates bulat-bulat.


There is no one-size-fits-all approach when it comes to drafting. The best practice is to figure out the purpose of the document, understand it, and then adapt the template to fit your needs.


For example, a written submission can be structured in various ways depending on the case. Sometimes you may want to weave the law into the facts, especially when the principles are trite. Other times, it might read better if you give the low-down of the complex legal principles before delving into the facts. In law as in life, by beginning with a clear understanding of the "why," you'll establish a strong direction and purpose. This will result in a coherent and effective work, as well as a coherent and effective life.


4️⃣ Think First Principles

to Research Effectively

The same goes for legal research. First things first, always understand the task that is being asked of you. Ask these questions before beginning:

  • What specific question are you trying to answer? Can you phrase it out?

  • Do you need more facts and context?


Figure these out and your work will be narrowed down. Now you have a focus. But hold your horses, don't go to Lexis, CLJ, or other online databases just yet! If you have the benefit of a library in your firm, always consult the textbooks first. A lot of times, the right textbook is all you need.

First principles thinking: 1. state your goal or objective; 2. Identify & challenge assumptions; 3. Break problem down to its smallest parts; 4. Come up with solutions to each part.
Think like this and complex legal issues will appear simple.

Why so? Because the books are where the first principles lie. First principles are the foundational blocks of an area of the law. If you understand these principles first, then you'll be able to start breaking down complex questions into coherent parts.


This approach will also build a solid foundation for your arguments and analyses, and help you comprehend case law more thoroughly and allow you to apply the law more effectively to the facts of your case.


If you start your research with a recent case from Lexis, it'll probably be very fact-specific, and you won't be able to appreciate why the case was decided in that manner.


While many judges do expound on the first principles in their judgments, it's rarely as convenient as consulting a textbook. After all, textbooks are always meticulously researched and written by seasoned scholars, with all the important cases cited on a silver platter for you! Why waste it?


5️⃣ Stay Humble & Curious

to Learn, Learn, and Learn

One thing many have noticed about great lawyers is this — they never stop learning. So, if my inductive reasoning is any good, if we want to be great lawyers, we have to be great learners first.


I believe every single one of us can do this because humans are naturally curious, born with a childlike enthusiasm to learn. It is often fear that stifles this curiosity. As the Bene Gesserit saying goes:

"Fear is the mind-killer."
Dune pain box meme
Just like the Pain Box from Dune, our mind creates fears that feel so real.

Often times, being in the lowest rung of the corporate food chain, pupils are too afraid to ask anything at all from their superiors. Y'know, the typical "what if they think my question is stupid?", "what if my request annoys them?" and so on and so forth it goes.


I am no stranger to this fear of judgment, which I realised stemmed from my ego. I (or my ego) didn't want me to ask something that would make me look bad.


But it helped me to put things into perspective this way: try to zoom out, it wouldn't make sense to be controlled by your ego when this fear viewed against the purpose of pupillage — to learn (it's literally in the name!). So, do be humble and learn.


After all the three most important virtues according to a 4th century philosopher, are:

"Humility, humility, and humility."

This is exactly what great lawyers have — the humility to learn from anyone without regard to status and seniority, and it opened up many doors for them.


Interested in being part of a case? Ask. Wanna join an upcoming hearing? Ask. Don't know how to do something? Ask. Wanna try your hand at drafting the submissions? Ask.


Another crucial thing a pupil should do is to contribute actively during meetings, especially with senior lawyers. Try your best to offer your input to the discussion. Don't be afraid! You'll find that the learning you gain when you articulate your ideas and engage in dialogue is far more valuable than staying silent (even when your ideas are rejected).


Not only does this exercise enhance your understanding (and ability to be humble), but it also demonstrates your proactive attitude and willingness to contribute. Remember, every question and contribution, no matter how stupid or small, is a step towards being a better lawyer and person.


If you are a pupil reading this...


...I know from many that pupillage can be very fulfilling, or it can be super dreadful. It all depends on you. A billion tips and insights will not benefit a person if they themselves are not clear with their purpose and driven by a genuine passion to do better


I hope my two (or five) cents can benefit you. May your journey be as rewarding as it is fulfilling!


Stay hungry, stay foolish.

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