Back to overview

Meet the lawyer

Naomi Winston

Naomi Winston

University: University of Leicester
Degree: Law (LLB)
Year of call: 2006
Position: Barrister
Pronouns: She/her

What attracted you to a career in law?

I took maths, art, classical civilisation and general studies A levels at my state school because I enjoyed the varied forms of thinking. I then went to art school but soon realised that I missed the more academic side of things. While doing a law degree seemed like a big pivot, I suspected that it’d allow me to carry on using my brain in lots of different ways. It was a good guess. As a chancery barrister, you get to think about the intricacies of the law, to problem solve, and explore both the commercial and human needs of your clients and the other side.  

How did you decide which chambers to apply to?

To start off with, I completed a range of mini-pupillages in sets with different specialisms and in different parts of the country. Once I’d worked out that I wanted to be a chancery barrister (which I based on the subjects I liked at university – land and trusts), I sought out a couple of chancery mini-pupillages. As it happens, I (happily) ended up at one of those sets. However, I made applications more widely, across a range of chancery chambers, using the paper resources that were available in 2006 and the limited information on chambers’ websites. There are now many more and much better options for researching chambers (including websites like LawCareers.Net), more comprehensive chambers’ websites, pupillage policies and chambers open days and webinars.

What was the most difficult part of the recruitment process/application for you?

The most difficult part of the recruitment process was the interviews. I never thought I lacked confidence, but it turns out that facing a room full of barristers for the first time can be absolutely terrifying. My first few interviews felt appalling and it took me a while to find my stride. However, practise really helps – whether it’s mock interviews beforehand or just gritting your teeth and doing the real thing until you feel less intimidated. It’s also useful to realise that the interviews aren’t the be-all and end-all of your life; this realisation will make you much more relaxed and allow you to think more clearly.

What sort of work did you get involved with during pupillage?

During pupillage, I saw the range of work on offer at Ten Old Square from trusts, tax and probate disputes to arguments among partners in limited liability partnerships, as well as fights between landlords and tenants. I was involved in whatever my pupil supervisors were doing, whether that was writing an opinion, negotiating a settlement at a mediation or cross-examining someone in court. I also got to see work at the junior end (eg, going to the ‘winders’ court and attending a fast-track trial), and was able to do some of my own work as well on smaller matters in my practising period.

What’s the biggest lesson you learnt as a pupil?

Don’t be afraid to ask questions, even if you feel like it might make you look silly. You can waste so much time as a pupil trying to hide your ignorance, when a quick and well-timed question could clear up your confusion and allow you to get on with the job of actually learning how to be a barrister. This advice still applies when you’re in practice. Don’t shy away from finding out what your solicitor actually wants from you, from asking your client that awkward question that might shine new light on the factual background to the case or from asking your colleagues to share their knowledge. Be brave and curious.

What do you most/least enjoy about your career as a barrister and why?

The aspect I like most about being a barrister is that it never gets boring. There’s always something new to learn, someone new to meet or a new idea to contemplate.

The element I like least about being a barrister is that sometimes it feels like clients won't stop arguing. On occasion, I do wish they would hush. I deal with this by having a varied practice, including some non-contentious partnership drafting work and Court of Protection work. The Court of Protection takes a more conciliatory approach and the focus is always on the best interests of the person lacking mental capacity, rather than on the demands of the other parties.

What skills/strengths do you need to be a successful barrister?

You must be bright and able to think through problems in a logical way. It’s important to be a good communicator and have the ability to express yourself with accuracy (both in writing and orally). You also need resilience – can you have an awful day in court where the judge has told you your client’s case is rubbish and pick yourself up and do it again the next day? Finally, if you’re able to build relationships with others (your instructing solicitors, lay clients and other members of the Bar), you’ll find this job to be both easier and more joyful.

What advice do you have for budding barristers who are contemplating a career in law?

While most (hopefully all) sets have put aside cronyism in favour of fair recruitment, that doesn’t mean that you won’t benefit from building up a rapport with the people you meet as you start to explore this world. Whether it’s your careers adviser, the barrister you chat to at the pupillage fair or the clerk who emails you about a mini-pupillage, take the time to be friendly, polite, interested and efficient in your responses. You’ll learn more that way and get to show off your people and admin skills.

What’s the work/life balance like at your chambers? How often do you have late nights/work at weekends?

While there are obviously times when you’re busier than others, you have a reasonable amount of control over how much work you do. For the first 12 years of my practice, I chose to keep a fairly steady workload so that I’d generally only have to work in the evenings if I was in trial and weekend working was occasional, rather than regular. For the past three years, I’ve had long covid, and am often severely fatigued. This means that I’m much less able to work long hours or undertake urgent work. Between us, my clerks and I are tailoring a practice to suit my current physical capacity. This means I’m not working as much as I used to and always have my evenings and weekends to myself (unless I choose not to).

What’s the wider culture like at chambers?

We’re a small set. This means that we get to know each other pretty well and we’re all there to look after each other. We genuinely have an ‘open door’ (or phone line or WhatsApp group) policy, so that people can ask each other advice on work or practice management issues, give each other support or just chat. When I first came down with long covid, both the members and the clerks jumped in to help me manage my case load and make sure my health was put first.

What diversity and inclusion initiatives is your chambers involved with?

  • We run an access mini-pupillage scheme where one-third of our mini-pupillage spaces go to candidates from underrepresented groups and those people get an automatic first round pupillage interview.
  • We take part in several social mobility programmes, such as Bridging the Bar and Inner Temple’s Pegasus Access and Support Scheme.
  • We run a programme with inner city London schools to teach their students some of the skills needed to be a barrister.
  • We just took part in a reverse mentoring scheme where diverse students from BPP University Law School mentored barristers and staff from key chambers’ committees about equality, diversity and inclusion matters.

Where’s your dream holiday destination?

I’d love to go back to Iceland. Whichever direction you travel in from Reykjavik, the landscape is astonishing (often otherworldly), the people are friendly without being too much, the air is refreshingly clear and there are hot springs to jump in whenever you fancy a break.