I am writing this because I have the genuine hope that it shall help those who read it in their voyage for pupillage. I realise navigating those seas can be a long arduous journey for some, though not for others, but in either case some form of confirmation that you are doing the right thing (or steer if you are not) should be helpful.
When I started to apply for pupillage I enrolled myself onto a course with my Inn aimed at providing information and practising interview skills; I found it very helpful and I believe assisted me in getting pupillage. I have tried to boil those tips and set them out below for you.
Firstly, always think of any application as written advocacy. You are persuading the reader of your point of view; that you would make a good barrister at their chambers. That naturally means being concise, efficient, and keeping their attention.
To add some flesh onto the bones of that sentiment, think, for example when you are writing about work experience or mini-pupillages, that just saying that you have done something is not very helpful. What you should be doing is explaining how the experience developed you in a way beneficial for a role at the Bar.
Novelty in your arguments can sometimes be good if well executed. Those doing the first sift read a lot of applications and so something which stands out is helpful. I knew someone who argued that being a barista helped her as a barrister and this seemed to make her stand out, and thus get her a lot of first interviews. If you are doing this though, the argument has to be very well made.
The word limit, like a speed limit, is not a target but a maximum threshold. If you can be persuasive and get your point across under the word limit, great! That demonstrates your written advocacy skills.
Naturally there is a fine balance between doing yourself justice and not over writing, but remember sifting through information and highlighting that of importance is a skill which you use often as a barrister and so this is a good time to practice it.
Secondly, remember you are applying for a career at the Bar, and think carefully about where you want to go and why. I was once asked whether an applicant should just apply to criminal sets because they had heard it was easier to get into them. Putting aside whether that statement is true, if you get pupillage and then tenancy you want to be somewhere you can see yourself having a career. If you are not committed to a particular type of work, it will show.
Having that conversation with yourself will also help you be able to justify why you are applying to the chambers you are applying to and tailor your applications for each set. Please do not just copy and paste answers for one application to another, if you can do that your answer is most likely too generic and will not stand out.
Lastly, I was often told you needed a little luck to get pupillage. Naturally you have little control of that but I put it here to remind you that getting pupillage is hard and making multiple applications and getting rejections is not always a reflection of your ability.
Having said that if you do not have any first interviews after a round of applications then it is probably time to reflect on your written advocacy. Improving that is likely the key to getting through the sift and then unlocking those first round interviews!
Good luck and make sure that you set aside enough time to make your applications. Once you have pupillage it is a real joy and privilege to learn from others at the Bar (or it felt like that for me at least) and then represent your clients when you are on your feet. All the effort will be worth it!