Winckworth Sherwood - True Picture

Winckworth Sherwood training contract review 2025

The Firm

Looking for something a little different? Well, you’ve come to the right place – Winckworth Sherwood is far from your typical London outfit. Sitting somewhere between a boutique and a City firm, Winckworth balances the thin line between being considered something of a full-service offering while also having a diverse set of niche practice areas. These areas include the firm’s parliamentary and public affairs practice which is recognised by Chambers UK as top-notch nationwide. Winckworth is also characterised by its infrastructure and property industry focus which form a large part of the firm’s client base; the firm is awarded top Chambers UK for its nationwide transport (rail: planning and authorisation) work, while the social housing and real estate practices receive a firm tip of the hat. There’s plenty more to Winckworth’s story, but you’ll have to head over to chambers.com for a complete picture of the firm’s awards.

“…it feels like you’re making an impact.”

This appeal of something slightly more unique chimed a chord with our interviewees, who noted: “With national infrastructure and social housing projects a lot of the work is socially positive – it feels like you’re making an impact.” There are also the leaner intake classes of just eight a year, giving newbies plenty of room to hit the ground running. All trainees join the firm’s London office, though it’s worth noting that Winckworth has a further two outposts in Oxford and Manchester.

The Seats

A training contract at Winckworth sees trainees take on four six-month seats, though it’s worth noting that, given the focus of the firm, it’s likely one of those seats will be in the property department. For the remaining three seats, trainees can submit preferences for where they’d like to end up, and as is the case at most firms, second-years are given priority.

The firm’s property focus is also evident in the client secondment opportunities on offer; past trainees have undergone stints at Telford Homes and Barratt Homes (construction), and Greenwich Hospital (property and governance), either for a full six months, or as part of one of their seats. Alongside the property-related opportunities is the secondment to Sainsbury's, which focuses on employment and governance.

Winckworth’s large real estate practice is split into smaller teams, primarily separated into either social housing or big developers. Seats in this department cover the corporate, construction and planning aspects of real estate, assisting clients like McDonald’s, Oxfam and the Gym Group. Though interviewees noted it’s likely “you’ll have to help wherever is needed,” if you have a particular interest in something and you let the firm know “they respond to that really well.” On the commercial side of things, trainees are able to work on drafting leases for places like “bars, restaurants, supermarkets… you’re licensing for them to sell things like tobacco and alcohol.” There’s also some telecommunications related work, where the team “negotiate leases with landowners where there’s a farm or someplace that is best situated for telecoms infrastructure.” This can occasionally stray into disputes-related work too, “when the landowner refuses or decides they don’t want the infrastructure on their land anymore!”

Day to day, trainees run negotiations on things like leases on substations, reporting on titles and helping companies refinance their property portfolios. For example, working on office leases includes getting drafts from the other side and “picking out bits that need negotiating. We add comments on what we think they should change and why and send it to the other side.”

With the volume of ecclesiastical clients lining the firm’s client lists, it comes as no surprise that the firm’s got a separate ecclesiastical and regulatory department. “The Church of England has a lot of land,” so the team here mainly works on property and conveyancing for vicars and “seeing how the church uses their land to generate revenue.” The practice does extend beyond real estate however, with matters also covering employment, charity work and navigating complains against clergy.

Those interested in the more contentious side of matters might want to cast an eye to Winckworth’s litigation practice. As is becoming somewhat of a theme, property-related matters make up a large chuck of the team’s work. Interviewees spoke of working on a number of High Court actions heading towards mediation, as well as some advisory work for the firm’s clients. In fact, the firm is the sole legal advisor for Greenwich Hospital on its landmark and heritage London estate in Greenwich town centre. In this seat, newbies can expect to be “assisting partners directly” on matters, including disclosures and plenty of drafting. There’s also a “slightly smaller”commercial litigation team who work on a range of cases. Examples include crypto-related insolvency matters, disputes between art dealers and artists, and one involving a professional poker player… so while “you get the bread-and-butter stuff,” there’s also “a whacky range!”

“You’re speaking with school heads and deputy heads who don’t often deal with lawyers…”

School support (which encompasses special educational needs work), HR and academy conversion work make up the three divisions of the firm’s education department. The HR and academy conversion work is all in the name; the team assists with HR matters and helps convert schools into academies. School support matters involve working with educational institutions on retainer agreements, either providing telephone advice or written advice for clients like the Church of England Education Office and a number of school trusts. “You’re juggling so many clients at once!” a source exclaimed, adding: “Oftentimes, you’re speaking with school heads and deputy heads who don’t often deal with lawyers – it’s nice to see a different category of clients and get given a lot of responsibility.” Trainees here are kept busy with things like queries on GDPR, safeguarding, parental complaints and defamation matters. “It’s quite good practice learning to deal with something on the spot,” we heard.

Winckworth’s banking and finance seat falls under the firm’s corporate practice, so much of the work comes from the same client base, including financings for charities like the National Trust, Cancer Research UK and Oxfam. The firm’s large ecclesiastical focus also sees this team working with the Archbishop of Canterbury on all legal matters relating to his office. Here, trainees assist with negotiating agreements, drafting loan agreements and ensuring CP checklists are up to date. Beyond charities, clients in this realm also extend to a number of property developers. “All of the bigger clients are more real estate-focused,” so the team also works for developers on revolving credit agreements.

One of the most sought-after seats at the firm is within the parliamentary department. “There can’t be more than six or seven firms with this practice,” said an insider. The group’s clients are – unsurprisingly – government entities, including local authorities like the West Midlands Combined Authority or the Port of London Authority. The firm’s expertise in infrastructure projects means it’s called upon to advise on a number of rail and transport schemes (“things that are so large it’s not enough to just get local planning!”), with completed projects including the Channel Tunnel and Crossrail. More recently, Winckworth was involved in advising the Department of Transport and HS2 on a bill to construct and operate the railway. Trainees spoke of opportunities to attend parliament as observers and “really learn so much about how legislation is made.” Outside of this, much of the work is research-focused, “because it’s very technical public and environmental law – it’s definitely for people who are particularly bookish!”

Trainee Life

On matters of work-life balance, one source made clear: “If you want to be up at all hours working on a deal, then this is not the firm for you!” Yep, you read that right. Insiders reported rarely working past 7pm, with the culture described as “more relaxed, less tense, less heavy…” Of course, bearing in mind the slightly lighter hours than at counterparts in the City, when it came to matters of compensation trainees made sure to note that “compared to other mid-market firms, it’s not the highest paying.”

Trainees are expected to be in office at least three days a week, but it ultimately depends on the practice: “Some partners are fine with three days, while others encourage more.” The general consensus was that five days was common too. The office itself has recently moved into a new space near Blackfriars where interviewees raved of enviable views of Westminster, the London Eye and the Tate Modern. We heard the space was also pretty good for socialising between meetings too: “we have a big social area with a ping pong table, so we’ll sit there for catch-ups.”

“…there’s always an event going on.”

The general sentiment around social culture at the firm was also pretty positive, with a budget on offer for trainee socials and a tight-knit cohort. “Over the last year or so we’ve been introducing events not just for trainees,” one interviewee outlined, “so we now do some junior socials for paralegals, trainees and people who recently qualified – not everyone joins as a trainee, so it’s a good way to get to know other junior people at the firm!” The social side of the firm is also supported by “so many internal networks and groups – whether it’s the disability or the equality network, there’s always an event going on.” Highlights include the world food event, as well as frequent guest speakers.

CSR is similarly interwoven in Winckworth’s culture. Alongside its charity practice, the firm gives everyone a CSR day to use once a year, and there’s at least one big annual event to support their charity of the year. This year Winckworth is raising money for the Brain Tumour Charity, which has been supported by “a walk up a mountain in Wales in May, where around 20 of us went up!” Insiders are also involved in more low-key (and local) CSR related activities such as “the gardening club around a local church, litter-picking along the banks of the Thames and employment and family clinics through our partnership with the Citizens Advice bureau in Southwark.”

Though “the partner’s role tends to be more hands-off,” everyone we spoke with beamed with enthusiasm at the training and supervision conducted by associates and senior associates at Winckworth. “It’s really lovely across the board,” one trainee smiled: “I genuinely feel like anyone will give you the time of day.” Alongside a platform of “a lot of training sessions,” trainee development is supported by the typical mid and end of seat reviews. “They also encourage casual catch-ups” and, importantly to one interviewee, “they would really involve me in understanding the commercial side. They are really interested in knowing your input.”

Turning to qualification, a jobs list is released around June and hopeful NQs are asked to apply to one or two positions with a cover letter and a CV. Groups typically ask trainees to interview with around two partners, usually including the head of department. Some teams also having a follow-up interview if more than one person applies. Overall, the process typically takes around two weeks, with offers sent out at the end of June. In 2024, Winckworth retained five of eight qualifiers.

How to get a Winckworth Sherwood training contract   

Assessment day and training contract deadline (2027): 28 February 2025

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.

Successful candidates are drawn from the firm's assessment days in July. Once applicants have completed one of these, there is a second interview with a panel of partners.  

WS screens applications on a rolling basis, but interviews are held after the deadline to ensure all applicants have the opportunity to apply. The firm encourages applicants to submit their application ahead of the deadline. 

Assessment days  

The firm typically receives around 350 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.