Winckworth Sherwood - True Picture

Winckworth Sherwood training contract review 2026 

The Firm 

Looking for a training contract in London isn’t something anyone would call easy, especially if you don’t necessarily want to be part of a massive firm or working insane hours. Before you make any assumptions, however, let us introduce you to Winckworth Sherwood, a firm that prides itself on its work-life balance and unique collection of practices. As training principal Eleanor Kilminster describes, “we’re a midsized, full-service firm offering quite a lot, but we’re focused on three core areas that distinguish us from other firms.”

Those areas are, she continues, “centred on the built environment, our private client and employment practice, and our social enterprise and charities practice.” The firm picks up a number of practice area rankings from the Chambers UK guide within its main areas and is listed as one of the best of the best in parliamentary & public affairs and rail transport-focused planning. Its work in employment, real estate and social housing is also recognised the guide, and Chambers High Net Worth also tips its hat to Winckworth’s private wealth law practice. 

“… the training is so tailored and personalised.” 

With some unique seats on offer – including parliamentary, ecclesiastical and education work – trainees shared that they were drawn to the firm thanks to its “cool teams which do some really niche stuff! It goes to show how the firm wants to stand out as a group of specialists.” Interviewees also boasted about the quality of training available, noting that the firm’s small cohorts of around eight trainees a year meant that “it seemed daunting initially but, once I started here, I realised that the training is so tailored and personalised.” It’s also worth mentioning that all trainees join the firm’s London HQ, though the firm has additional offices in Oxford and Manchester. 

The Seats 

Winckworth Sherwood rookies are actively encouraged to do a property seat during their training contract, such as commercial property, construction, planning, commercial real estate and licensing, real estate development or social housing development. When it comes to seat allocation, the first is assigned automatically, while subsequent seats take trainee preferences into account.

Trainees have two mid-seat reviews with their supervisor and training principal to discuss their interests: “You can tell them any potential areas you’d like to go into, and they’re very good at asking questions to understand your motives and make suggestions.” Sources felt involved in the process, sharing that, “even if there currently isn’t a trainee in the department but you want to do it, they’ll try to make an opportunity available.” 

“I’ll often walk through the city and see a building I’ve done a lease on!” 

As the firm’s largest department, it should come as no surprise that most trainees do a real estate seat at some point. Trainees who had sat with the team were impressed with the variety of the work, and proud to see their efforts having a tangible impact: “I’ll often walk through the city and see a building I’ve done a lease on! It’s nice to see that what you’re doing is actually happening in the real world.” Clients here include Oxfam, Fairview and McDonald’s, and one of the firm’s recent matters involved advising Sainsbury’s in relation to the relocation of its headquarters.

In terms of responsibility, trainees were happy to get stuck into drafting and correspondence with clients, companies and other firms. Sources acknowledged that it comes with some “more classic trainee work,” but felt confident that it’s “balanced with more intricate and detailed work, too.” The department is known for being one of the busier seats according to trainee sources, who saw it as a positive given that “there’s never a shortage of work, and you get good responsibility.”

Interviewees appreciated being given the opportunity to “do things a bit more independently” as well, with one sharing that they especially valued “hands-on work, like doing first drafts. They’re always reviewed, but it’s a great opportunity to learn very quickly.” 

One of the firm’s specialist seats, education, was described as one offering trainees a whole range of experience, just within a specific sector. The department is split between academy conversion, school support, property and schools HR, and even though trainees are technically based in one of these subgroups, they can try out work from the others, too. Academy conversion work often involves drafting funding agreements and attending client meetings, while schools HR is essentially education sector-focused employment work.

School support work, meanwhile, has trainees working with the firm’s school retainer service, overseeing the team inbox and responding to client queries. The firm is currently assisting the Association of Muslim Schools and its members schools in the process of converting from independent organisations to state funded voluntary aided schools. 

The education seat also involves some litigation work in relation to disability discrimination claims and matters going to the Special Educational Needs tribunal. “I had a huge amount of responsibility,” a trainee recalled, “I was drafting witness statements, speaking to clients, going to court and doing events with schools, too. It was a really good experience.” Interviewees were also pleased to tell us that they genuinely “felt like a part of the team. I didn’t really feel like a trainee because I did all the work everyone else was doing and got to research niche points of education law to understand how it interacts with regulations.” 

“There aren’t many places where you can do church law.” 

In Winckworth’s ecclesiastical department, trainees explained that “you learn some really niche things and get the chance to do a bit of regulatory, commercial contracts and procurement work. After all, there aren’t many places where you can do church law.” It certainly doesn’t hurt that the Archbishop of Canterbury is a client – can it get more high profile than that!?

Trainees here also had the chance to try a range of property work as “the Church owns a lot of land, and that means lots of leases, licences and site development work.” Employment also featured here, and trainees are typically in charge of the research side of it. “Even things like charity and governance work come under the ecclesiastical umbrella,” a source explained, so trainee tasks vary accordingly, and might involve things like drafting articles for the ascension of charities and reviewing trustee provisions. 

Trainee Life 

“… a trainee sat next to the CFO last week!” 

Now approaching the second anniversary of its office move, Winckworth is firmly settled in its new Blackfriars home. Trainees told us that the office is “a lot nicer than the old space. It’s very, very modern and open. You can sit next to the head of a department on any given day, and a trainee sat next to the CFO last week!” The open-plan office layout was something trainees thought really contributed to the collaborative vibes at the firm, alongside a social space complete with a pool table and a ping pong table. “There are leagues for both,” a trainee added, “so that’s a great way to meet people from all around the firm who you otherwise wouldn’t get to talk to.”

Coffee is always an important consideration for any lawyer needing a hit of caffeine, and trainees couldn’t have more positive things to say about the hot drinks facilities at Winckworth. “My coffee is made for me by an iPad!”one trainee joked but, if you’re not a caffeine fan, worry not as “it does hot chocolate, too.” 

All lawyers are required in the office at least three days each week, though sources shared that, “when you’re a trainee, you’re encouraged to be in as much as possible, but the details vary between seats.” More client-facing seats like real estate, for example, are likely to require five days of office attendance. Trainees felt their working hours were reasonable, however, noting that “I’m typically able to leave between 6 and 6.30pm on a standard day. In real estate, a 7pm finish would be the latest and even then, that’s not the norm.”

As such, trainees generally agreed that they felt well compensated. “The hours are pretty good for law, we’re getting good training, and we’re well looked after,” a source summarised, “It’s not the highest salary for trainees in London, but you’re not staying up until 11pm like you would elsewhere, so it feels fair.” 

“People really make sure that you get to have a life outside of work.” 

Trainees had high praise for the firm’s culture, explaining how there’s “a strong emphasis on mentorship and respect. Whoever you speak to, whether partner or trainee, is really approachable.” According to interviewees, “it feels like senior members of the team are genuinely interested in your growth as a trainee. They want to see you go through your training contract, qualify, stay at the firm and thrive.” The work-life balance certainly doesn’t hurt, as trainees were grateful that “people really make sure that you get to have a life outside of work.” 

Most agreed that the firm is a social place, with interviewees sharing that “there’s always a chance to meet people by the coffee machine or go to the pub!” Standout events according to trainees include arts and crafts for Pride, a world food day, and an end of financial year party. There’s also an annual trainee social which all current trainees, recently qualified NQs and the next two cohorts of future trainees are invited to. So, it’s safe to say that “they give lots to trainees, and that’s really lovely. I started going to those socials two years before I even joined the firm, so I felt like I already knew people by the time I got here.” 

Trainees felt encouraged by the fact that their supervisors got them involved in as much work as possible, even if that’s “just coming to meetings or sitting in on calls. They want you to feel part of the process and see how things work.” This was a sentiment shared by many of our interviewees, who added, “I think a lot of supervisors are keen to get to know their trainees and work closely with them.” The extent to which trainees work directly with their supervisors varies between seats. For example, “in real estate, I didn’t work with my supervisor much day to day, but they were always around to check in and catch up.” 

There’s a variety of training available at the firm, with most technical training happening at the beginning of a seat. External trainers often visit the firm to deliver practical sessions, but trainees were clear that, outside of this, “if you have no idea how something works, someone will always be there to show you or jump on a call to walk you through it.” Department-specific training happens regularly, interviewees noted, explaining, “there’s always a knowhow session on something, and you can attend other departments’ sessions if you’re interested.” 

DEI was another topic on the minds of our interviewees, who especially rated the firm’s many affinity groups. Many mentioned the new women’s network which “put on a great week around International Women’s Day.” Sources also noted the firm’s wellbeing efforts, including an annual wellbeing week, catch-up coffee mornings, and yoga and meditation sessions. The firm’s recent social mobility month also featured an event called ‘Slices of Opportunity,’ with pizza and legal career advice on offer. 

The qualification process is reportedly transparent, with trainees sharing that the firm has made an active effort to improve it. First, the firm announces a jobs list which includes the application process for each position. Some departments might ask candidates to complete a written exercise but, otherwise, the process involves a cover letter and an interview. “HR made the process really clear,” a source recalled, “They offered CV guidance and interview prep, and you can do a practice interview with them if you’d like.”

Trainees felt well supported throughout the process, and shared that the firm “makes it clear that they’d like to keep us all as we work so hard. We get opportunities to participate in the firm beyond our legal careers, too, and it’s important that we get to have a part in the culture as well.” In 2025, Winckworth Sherwood kept on 7 out of 8 trainees.

How to get a Winckworth Sherwood training contract 

Assessment day and training contract deadline (2028): 28 February 2026 

Entry routes 

Winckworth Sherwood expects its future lawyers to be: 

• Curious 
• Original 
• Creative and relish the challenge of solving intricate legal puzzles 
• Commercial in understanding our client’s needs 
• Passionate about continuous development 
• Entrepreneurial 
• Inclusive 
• Collaborative

Assessment process   

The firm typically receives around 450 applications for its eight training contracts. To apply for a place, candidates must submit an online application which includes a short essay on why they want to work at the firm and what they will contribute. Make sure to tell your story throughout your application, as to why you want to be a trainee at Winckworth Sherwood.  

Candidates who impress are invited to interview with the firm's recruitment manager via Teams. A shortlist of 40-50 candidates (from this first interview stage) are discussed during an ‘assessment day shortlisting meeting’ between the recruitment manager and the training partner. 

Successful candidates are then invited to an assessment day held in early July in the London office. The day includes individual exercises and group exercises which are assessed by a panel of partners and designed to reflect some of the day-to-day challenges you will face as a lawyer.  It is also a great chance to learn more about the firm and to speak to lawyers/trainee supervisors from a range of practice areas over lunch. There are also drinks with current trainees and newly qualified lawyers at the end of the day. Candidates who score in the top 16-20 spaces are invited to a final interview with a panel of partners, the following week.

Interview with Trainee Partner Eleanor Kilminster and L&D Manager Robert Knight

The Firm 

Chambers Student: How would you describe the firm and its position in the market? 

Eleanor Kilminster: I think that historically we’ve always said we’re a full-service, multidisciplinary firm that is very client focused. Over the last couple of years we’ve had a real drive to work out effectively what our direction is going forward, and what distinguishes us from the rest of the market. The key thing we’ve recognised, from discussing with clients and ourselves, is that we are very specialist. We’re a mid-sized full-service firm offering quite a lot, but we’re focused on three core areas which distinguish us from other firms. We’re centred on the built environment, our private client and employment practice, and our social enterprises and charities practice. All our departments fall either into one of those, or multiple, but that’s really where we see our drive to increase, whether it’s revenue, personnel, experience, or scope of clients, it’s those core areas we’re really focused on. 

CS: Are there any highlights from the last year you think it would be helpful for our readers to know about?  

Kilminster: We moved into our new office space in October 2023 in London, and we’ve spent the last couple of years really adjusting to the move that’s created. We’re also currently undergoing an office refurbishment in our Oxford office to bring it up to the same standards as the London office. That’s really given us a platform to secure the staff we have, who I think are much happier individuals in the new environment, as well as to attract all sorts of people that may not previously have looked at us as a potential employer, or provider of legal services. We feel we’ve taken a step up in the market because our people are a lot happier, and it’s a good platform for the next ten years in those two offices, and in our Manchester office as well. 

The Training Contract  

CS: How would you describe the training environment that you have aimed to create at the firm?  

Kilminster: All our trainees report having a very nice working environment and really collegiate colleagues. We’ve got a fairly flat structure; there’s no hierarchy of individuals you are or are not permitted to talk to. The open-plan office also means there’s an incredibly relaxed attitude to discussions with trainees, and the firm is quite a social environment. 

CS: What’s the current set up with remote working for trainees?

Kilminster: Our policy as a firm is no less than three days a week in the office unless specifically approved. We find that the majority of trainees enjoy working in the office more often than that, so most are in four, if not five, days a week. We also very actively encourage other members of the team, the people supervising or providing support to be in the office alongside them. We’re keen to ensure that trainees are getting the full work experience, not just legal knowledge, but social skills and enjoyment of life. That’s quite a focus for us, so it’s three to four days a week probably for most. 

Applications & Recruitment  

CS: What sort of person thrives at the firm, and how can a candidate really impress at interview? 

Robert Knight: I think this is a very accessible place, and colleagues are very open to, and willing to, engage with trainees, but there’s still a requirement for trainees to step into that space and own it. People who are proactive and show drive, energy and enthusiasm naturally respond better in the space, and people are more willing to support them. Those who thrive are the ones who drive it themselves, as they’ll get more from their career. Curiosity is important too, intelligent curiosity behind the law but also around clients and culture, how things are done, and understanding that, having that adaptive mindset and being open to that – that’s really positive. Having a sense of can-do attitude and willingness to get involved and to show initiative and enthusiasm. I’ve worked in a number of law firms, and it really does stand out here that this is a friendly place. There’s no hierarchy in terms of how you engage with business services, secretaries, paralegals, and recognising we’re all one, and we’re unified in our attempt to be successful and achieve our goals, and working within that is key. 

The other thing is being open and having an open, growth mindset. There’s been a lot of focus since I’ve been here around recognising and encouraging both supervisors and fee-earners generally to be engaging in a culture of appreciative and developmental feedback. For the trainees, it’s willingly embracing that as well, seeking it out, understanding it, and seeing how they could be even better, but also where there are challenges, seeing that as an opportunity to learn, reflect and grow. The more they’re in that headspace, they’ll be able to think about being better next time. When people demonstrate that in action on the next matter they’re on, people are really appreciative of that in the building, so it helps them to engage with that. 

CS: Does the firm have any set recruitment targets around diversity? 

Kilminster: The short answer to that is no. We are operating in an environment where we always want the best candidates, but those in recruitment are also very aware that the best candidate is not always necessarily the person with fantastic grades out of an amazing university we all wish we’d gone to. We’re also looking for candidates who have perhaps had a different path to law than some of the others. In seeking out the best candidates, we are always open-minded as to where they’ve come from and perhaps reasons why. Our client base is very, very diverse, and clients come from all walks of life, and are all types of organisations and individuals, and we need to be able to speak to all of them. We only achieve that by representing them in ourselves. As well as it being a good moral thing to be doing to ensure diversity, it’s actually a key business driver to ensure that we mirror our clients and as they evolve, we do too. There’s always more to be done I think, but there’s no set checklist of this, that or the other. 

CS: And finally, do you have any advice for those thinking about pursuing a career in law, either at your firm or more generally? 

Knight: One of the things I think is really important is to really make sure that wherever you’re applying, you’re able to demonstrate that you’ve understood what that organisation is, who they are, who they represent, and who their client base is. You need to be able to understand that, and to show you’ve taken the time to tailor your understanding in your applications to that organisation, rather than being a cookie cutter. Getting under the skin of an organisation will mean you can provide a better version of yourself, and it comes through if people haven’t done that.  

Kilminster: I agree entirely but would also go one step beyond that. Personally, at the time I was applying for training contracts, I felt a lot of pressure to secure one. It’s an important decision to make as to whether to go into law or not, and the type of firm you want to learn and grow with. In my case I’ve been here a very long time, and it can be a very long-term decision, so you’ve got to make sure you’re happy and enjoying the work. Find the place with the best fit for you and then you’ll make the best of it and hopefully enjoy it. 

Knight: Lots of candidates probably don’t see their interviews as a two-way thing, but it’s about them interviewing the organisation as much as the organisation is interviewing them.