South Square - True Picture

South Square pupillage review 2025 

The Chambers 

With two decades of recognition from Chambers UK Bar  for their insolvency work, it was no shock that it was a big part of the draw for pupils at South Square: “The set’s reputation precedes it,” one former pupil told us, “and since working here, they have continued to cement their legacy in this work.” According to senior clerk Dylan Playfoot, “restructuring and insolvency makes up a significant portion of our work. We have had a huge number of restructuring plans and schemes of arrange go to court in recent times, and we generally have teams of South Square barristers working across all parties on these matters. We act in the vast majority of high-profile administration and liquidation proceedings, and fraud and regulatory investigations. We also have a very strong presence in commercial litigation, and are often involved in long and complex trials before the Commercial Court judges and in arbitration proceedings.” In one recent example, barrister Charlotte Cooke acted for HMRC in its first successful opposition to a restructuring plan, a case which set the scope for compromising debts owed to HMRC without its consent. Elsewhere, barrister Edoardo Lupi worked on the first steps to implement a major Chapter 11 restructuring of Cineworld in the UK. 

“The set’s reputation precedes it…” 

Despite its sizeable insolvency offering, this Square meal balances its meaty restructuring practice with its offshore work. In fact, South Square’s offshore practice has touched on matters in Guernsey, Jersey and Bermuda, alongside work sourced from Dubai, Hong Kong, Singapore and Gibraltar. Playfoot was eager to tell us more: “We have one of the biggest footprints of all the London chambers concerning offshore work, particularly in the Cayman Islands, British Virgin Islands and Hong Kong.” This growth, Playfoot tells us, has been borne out of utility and property companies still feeling the effects of the pandemic. It has come too with a growth in numbers at South Square, including six recent lateral hires. Yet, as Playfoot adds: “We are not planning any further lateral hires as we are conscious to not grow too big too soon, so we are now focusing on our current strengths and establishing new pupils!” 

The Pupillage Experience 

Relatively unique to South Square is a supervision structure where a pupil’s supervisor rotates every six to eight weeks over the 12-month pupillage. The high frequency is intentional, as head of the pupillage committee Richard Fisher KC explains: “More rotations means that the pupils get more exposure to the different areas of work available.” This supervisor-heavy approach got the seal of approval from current pupils too, who highlighted that “we get more continuous feedback than many of my peers, so I know how to improve as I approach tenancy.” 

When asked about the kind of work on offer, one pupil noted: “I have had a mix of heavy court application work and slower but bigger cases. I have done a lot of work on skeleton arguments, which is complex and time pressured which I love!” We heard that as time passes, “you begin to see the finished product and what parts of your work are being used. It is so satisfying to be a part of!” Those at the junior end highlighted that the work is around 80% live, with dead work only cropping up around assessments: “I know people complain about doing dead work, but it is reassuring to have no urgency of deadlines, so you really get a chance to think about it” stated a pupil. Pupillage at South Square is non-practising, something worth noting if you were hoping for a chance to get on your feet in your second six: “The aim of our pupillage is to help our pupils develop through constant feedback from supervisors,” Fisher adds, “whilst also getting to see as much work as possible.”  

“We are aware of the feedback that goes into the central file, but it is good to know the relationships you form play a big part in the decision.” 

Advocacy experience is instead gained via assessments – between eight and ten formal written tasks or oral advocacies spread throughout pupillage. The assessments are spread across the year with the intention of not “overwhelming” pupils. “We receive the schedule over a three- or four-day period and have 48 hours to do the written tasks,” one pupil explained, “then the advocacy falls onto the final day.” The advocacy task is a mock trial with two members of chambers acting as judges. While assessments do hold weight in the tenancy decision, a heavier weight falls onto the supervisor feedback forms completed at the end of every seat: “We are aware of the feedback that goes into the central file, but it is good to know the relationships you form play a big part in the decision” praised one pupil. With this combination of assessments and reports, the final decision is made by the pupillage committee: “We don’t hold a vote with all members of chambers, as we don’t think that it is fair or sensible,” explains Fisher, “the decision to recommend for tenancy is made by the pupillage committee, having reviewed feedback from all supervisors, assessed work, advocacy exercises and any additional feedback from other members. As a consequence, negative comments from one member of chambers would not prevent the pupil from obtaining the support of the committee.” 

“This job isn’t a standard 9-5 but I love the flexibility I get!” boasted one junior when asked about  hours.  We were told that pupils work on average between 9am and 6pm, with later hours only occurring when live cases take longer than expected. The general consensus was that the power is in the pupils' hands: “It is very much the case that you are expected to manage your time and workload as a pupil. This is important because you need to adjust to managing your work life balance as you would in practice.” 

Almost from the off, those at the junior end felt the benefits of the active social life of the set: “There is always welcome drinks and lunches for new pupils, so everyone is welcomed in.” It doesn’t stop at a warm welcome either, with trips to the pub after work and lunches with colleagues often in the mix. “The head of chambers had people round his for a BBQ, which shows the relationships we all have!” a previous pupil told us. This close bond was said to be a result of shared characteristics between the set’s members: “We are all ambitious and hardworking people, but ultimately, everyone is expected to be their own person, and everyone is welcoming to that!”  

The Application Process 

“When we make offers for pupillage, we will only do it if we believe they have a realistic prospect for tenancy,” Fisher tells us. On average, South Square takes on two pupils. This number is whittled down through a three-stage process which begins when applicants apply through the Pupillage Gateway. There is an initial sift of paper applications followed by the first interview, but applicants who have secured a funded mini pupillage and complete an assessed problem proceed straight to this stage. The interview is conducted by a mix of two or three senior and junior tenants, scored with a social mobility weighting as part of efforts to attract diverse talent. “This is not an interview in which we are testing legal knowledge,” Fisher explains, “the questions posed may have a legal context, or concern general knowledge and political awareness. Our aim is to test a candidate's ability to argue both sides of an issue, and see how they approach problem solving.”  There is no fixed number of candidates that are put through to the next stage, “if there is sufficient merit, they will go through.” 

“We want to see that spark of enthusiasm, with strong analysis, so we know they will have the ability to thrive in the South Square practice.” 

For the lucky cohort that do go through, the second stage interview is described as more “rigorous” as they will be interviewed by two KC’s and three pupil supervisors. Interviewees are asked to attend early to answer a written ethical question, before discussing their response and application at interview: “We want to see that spark of enthusiasm for our practice areas, along with strong analytical skills, advocacy potential and willingness to engage in thoughtful problem-solving,” says Fisher.  

So, what is it that the folks at South Square are looking for beyond that enthusiasm for the set? “There is a minimum level of academic achievement we will anticipate candidates will have,” Fisher clarifies, “but we’re looking further. We want good technical and analytical skills.” Of course, legal expertise isn’t something you’re expected to have from the get-go, but there is an expectation that prospective pupils will “understand the nature of the work.” The interview process is about demonstrating “a degree of imagination in how they approach new situations or problems.”