Old Square Chambers

Old Square by name but certainly not old and square by nature, this chambers’ work puts its barristers front and centre of some of the most dynamic areas of law.

Old Square Chambers pupillage review 2026

About the Set

Of course, it’s often the type of work they do that makes each chambers unique, but it’s not all that’s important: “I think the best way to describe our set is that it is an incredibly collaborative and supportive set of chambers,” chambers directorSarah Earl tells us. “Our practice areas are all about people and so is our management structure and style,” she says; “we very much focus on the development and training of pupils, making sure that their well-being is supported, making sure that we answer any questions they have – regular, silly or otherwise.”

“As you can imagine, there's quite a lot of alignment within those practice areas, and it means that they tend to have the potential almost to feed off of each other.”

Still, the set puts plenty of its identity into its work. In financial terms, about 40% of the work coming into Old Square is employment, 35% is personal injury and the remaining 25% clinical negligence, regulatory, professional discipline, investigations and a handful of others, Earl informs us. “As you can imagine, there's quite a lot of alignment within those practice areas,” she adds, “and there can therefore be a degree of cross over between them.”

The set is acknowledged in the Chambers UK Bar guide across all its primary practice areas (employment, personal injury, clinical negligence and professional discipline), with employment in London reaching the top-tier.

But what do these kinds of practices mean for the kinds of cases arriving on the clerks’ desks at Old Square? “There has been a surge in employment work, particularly post-COVID. As you can imagine, that contributed to an increase in employment claims,” Earl tells us. Going forward, “we’re expecting to see employment continue to increase over the coming months and years with the various introductions of sections of the new employment bill as they start to come into effect.”

The set is also seeing an increase in the amount of investigations work, “that's really closely aligned with the work that we do in employment discrimination and even regulatory and professional discipline,” Earl explains. Education is another growing area.

Work Highlights

Continuing Old Square’s long tradition of working with unions, Oliver Segal KC recently represented Aslef and ten other independent unions against the Secretary of State for Business, Energy and Industrial Strategy over whether it was legal for an employment business to supply agency workers to carry out the duties of workers taking industrial action. On the personal injury front, Ben Collins KC represented the claimant in a case considering when a defendant can require a claimant to undergo genetic testing when they do not want to do so.

Pupillage Experience

Pupils have four three-month seats, each with a different supervisor. The non-practising first six “will consist largely in assisting or following the supervisor's own practice,” James Chegwidden of the pupillage committee tells us; “we guarantee that our pupils will get exposure to our signature areas of experience,” meaning employment, personal, and clinical negligence. “Experience in one or two of our other areas is also to be expected,” for example, public law, professional disciplinary work or regulatory work.

“I thought it was really good that in the first six we had one supervisor in employment and one in PI, because those are chambers’ predominant areas of practice,” said one former pupil. Old Square tries to repeat this balance again during second six: “The reality is that lots of people in chambers do a mixture of both,” another recent pupil informed us, “so it wasn’t like it was completely siloed” during each seat.

In their first six, pupils will spend time on research and drafting skeleton arguments for live work, attending conferences to take notes and attending hearings. They also hone their skills by doing their supervisor’s recent dead work, such as pleadings and advice, then comparing their drafts to their supervisor’s. They may also get a taste of tasks like drafting chronologies for other members of chambers. All of the pupil’s work goes through their supervisor to avoid the pupil being overwhelmed by requests to help out other members.

The second six at Old Square is practicing and there is a reasonable balance between employment and personal injury matters. Personal injury, we heard, can be quite pupil-friendly, for example small claims and road traffic accidents. A second six pupil may do merits advice and quantum advice in their own name.

More broadly, “the vast majority of our pupils in their first year or two of practice are quite focused on maintaining a diverse practice between employment and PI. We do encourage that partly because of the work that's available, but also from a future-proofing perspective around individuals’ practices,” Earl explains.

“They're doing their own practice, but nonetheless they are guaranteed the constant mentoring and support on a daily basis of a supervisor…”

Pupils have three cases in court per week, but, as Chegwidden is quick to highlight: “They're doing their own practice, but nonetheless they are guaranteed the constant mentoring and support on a daily basis of a supervisor who will be with them in chambers and can also advise and assist them on their work.”

Chegwidden explains that there are three “streams” that contribute to the tenancy decision. Firstly, there are three formal assessments (consisting of both drafting and advocacy) which are assessed by the tenancy committee. The second factor is the supervisors’ reports (more on these in a bit). The third and final element is the summary of feedback from other members of chambers for whom the pupil has done individual pieces of work.

The tenancy committee considers these three “streams” and puts together a report for members of chambers who then vote. Of those three factors, “none of them are a deal breaker or a deal maker. They're all part of the overall pie,” says Chegwidden. “If there were problems, we were made aware of them well in advance and given an opportunity to improve on them,” a recent pupil informed us.

Chegwidden highlights Old Square’s high pupil to tenant conversion ratio: “We have taken on all ten pupils who have applied to become tenants” since he became joint head of the pupillage committee in 2021. “If we take a pupil on, it is in the expectation and hope that we can make them a tenant,” he adds; “they are not in a Hunger Games-style pupillage in which they need to essentially beat the other candidate to become a tenant.”

The three assessments take place at the end of each of the first three seats in December, March and June. Afterwards, the pupil has an hour with someone from the panel who takes them through the feedback and gives them pointers to help them do better next time. Pupils are given a few clear days in their diary before each to prepare. “The cases would always be just in that grey area that requires you to work really hard in your advocacy,” a former pupil shared, “they were fine, but a bit nerve-racking.”

Each supervisor writes a final report which they talk through with the pupil. In this report, pupils are graded on whether they met the standard needed for tenancy. When working for other members of chambers, feedback can come in the form of an email or a chat, “people would be really helpful and it was always useful feedback, both kind and constructive.”

What’s the approach to making mistakes? “I was told at the beginning that Old Square's ethos is very much that we want to see a pattern of improvement, like an upwards trend on a graph,” explained a former pupil: “I definitely felt that the message was ‘of course you can make a mistake; if you don't, you're learning. But try not to make the exact same mistake again, because that shows you haven't listened and that's much worse than making a mistake.’”

Standard hours are 9am to 6pm. “Sometimes I'd work outside of that, but I was never asked to. In fact, my supervisor would get cross with me!” shared one recent pupil. “But if you're asked to do some work for a KC, you're like ‘maybe I'll put in a couple of extra hours on a Saturday!’”

The Application Process

Initial applications are made through Pupillage Gateway: “The form is a chance for you to demonstrate your written advocacy and your persuasive skills,” advised a former pupil, “every part of that form is an opportunity for you to demonstrate why you're going to be a great barrister, so you want to keep things pithy, concise, relevant.”

There are two rounds of interviews, both involve a panel interview and an on-the-spot problem question for which candidates have a short amount of time to prepare. “There is no cap on the number of people we interview at round one and at round two,” says Chegwidden.

“We're looking for intellectual prowess, and so we need people that are in command of their law,” explains Chegwidden, who adds: “We are looking for their ability to communicate, not just in terms of legal pleadings, but the way that they would communicate with a client, for example.” Old Square likes to see evidence of candidates engaging with their community and “showing their ability to excel in areas other than law.” Chegwidden also suggests completing a mini pupillage at Old Square “which is not compulsory to become a pupil, but it is recommended.”

What was it like to go through the pupillage application process? “I was sure by the end of it that Old Square was sort of the place I wanted to go, because I found it one of the most transparent, well-run pupillage application processes,” revealed one recent pupil. “It was clear what was being asked of you in each of the rounds. There were no nasty surprises.”

“There's definitely not an identikit Old Square barrister. It attracts a wide range of people.”

“There is a pretty packed social calendar!” one former pupil shared. Social events include the Christmas party and more informal gatherings: “Sometimes our head of chambers will message and say does anyone want to go have a social lunch?” one former pupil told us, adding that the junior cohort also often get together for lunch. “There's definitely not an identikit Old Square barrister,” a former pupil told us, “It attracts a wide range of people.”

A Helping Hand…

“You feel part of a family,” enthused one recent pupil, “I go and ask KCs for advice on my work and they're always willing to give me time. I think that's really special and a really lovely part of chambers.”