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The unexpected career moves that took one barrister from the CPS to Hill Dickinson

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By The Careers Team on

Partner Carl May-Smith on finding his niche, embracing change and seizing opportunities

Hill Dickinson partner Carl May-Smith

A matter of weeks into his new role at Hill Dickinson, Carl May-Smith sits down with Legal Cheek Careers to reflect on a career that has taken him from the Crown Prosecution Service (CPS) in London to private practice in Nottingham, and seen him develop a specialism in health, social care and special educational needs regulation.

“I can’t claim to be one of the people who always wanted to do law from seven years old,” May-Smith admits. Having studied mainly science and maths subjects at school, he was keen to try something new. “I fancied doing something a bit different and hadn’t done any law before,” he explains. While novelty was initially the main draw, he soon found himself enjoying his degree, “particularly the advocacy and the more human legal aspects.”

This interest led May-Smith to pursue criminal law, completing his pupillage at the CPS before spending four years there as a Senior Crown Prosecutor. “That involved a lot of advocacy and was a really interesting way to start my career,” he recalls.

Applications for Hill Dickinson’s training contract open evening close on 15 November

Looking back, May-Smith is in no doubt about the value of those early years. “The good thing about doing your pupillage and your first few years in the busy environment of the CPS office in London is that you get access to quality work and responsibility early in your career. I was in front of familiar courts with familiar opponents day in and day out doing four days a week of advocacy while managing a Crown Court caseload in the office.”

Those early experiences continue to prove valuable. “It taught me to work under time pressure, and going forward, it has helped me understand the perspective of regulators, the police, and the CPS when I am acting on the other side of things,” May-Smith shares.

His next move came when he was approached by Browne Jacobson to undertake contentious criminal and regulatory work in Nottingham. “I started doing the full range of regulatory and criminal work for big clients,” he says. Alongside this, May-Smith began building a specialism in health and social care regulation, initially acting for the Care Quality Commission (CQC) before increasingly advising health and care providers themselves.

Over time, his practice expanded to encompass non-contentious work, ranging from due diligence and restructuring advice for investors and providers to compliance advice and training. More recently, he has branched into related areas, including children’s social care and health tech, “which is a massively growing sector”. Reflecting on the breadth of his experience, he says: “It has been very varied and quite a journey, and I don’t think I’ve ever done the same thing for too long at any one point in time.”

Applications for Hill Dickinson’s direct training contract close on 10 January 2027

While the evolving regulatory landscape first sparked his interest, it is the people working in the sector who have kept him there. “What made me determined to make it my sole specialism is really the clients.” Almost all of them, he explains, put the needs of their patients, service users and pupils first. “It really is a great sector to work in from that perspective because you get to meet fantastic people who have done a huge amount to help vulnerable people and who possess an impressive ethos.” There is a personal connection, too. “I have a child with special educational needs and disabilities (SEND), so I have my own unique connection to the sector as well.”

As a barrister working in a law firm, May-Smith holds a litigation extension on his practising certificate, allowing him to carry out almost all the functions of a solicitor, with only a handful of minor exceptions. Until recently, he also undertook Crown Court advocacy, something he could return to if needed. Nevertheless, “my day-to-day job doesn’t look hugely different from my colleagues who are solicitors,” he shares.

The main distinction, he explains, is the different training and career starting point, with a greater emphasis on advocacy. The Bar’s focus on persuasive writing has also stayed with him and continues to inform his approach today. “Law firms increasingly value that diversity of perspective, background, and training.”

So what prompted his latest move to Hill Dickinson? “It’s their ambition, particularly in the health sector, both in terms of growth and what they can give back to clients.” With health forming one of the firm’s three main pillars, the commitment to the sector was a clear attraction. Equally appealing was “an exciting opportunity to help build our independent health and social care practice group by integrating my skills with existing expertise within the firm”.

Applications for Hill Dickinson’s training contract open evening close on 15 November

In his first six weeks, May-Smith has already met around a hundred colleagues, learning about their work and introducing them to his regulatory practice. The response, he says, has been overwhelmingly positive, with everyone “enthusiastic about coming up with ideas”. Looking ahead, his main priority is to grow the firm’s client base across the independent health, social care and SEND sectors.

As for what the role looks like day to day, May-Smith’s legal work is complemented by time spent on business development and management. This includes speaking with new and existing clients, delivering presentations and hosting webinars. The rest involves getting involved in client queries at an early stage, offering strategic advice and providing oversight and supervision to colleagues handling the day-to-day files.

Turning to advice for aspiring regulatory lawyers, May-Smith emphasises the importance of identifying key issues quickly and remaining focused on them, even under pressure. For trainees, the best way to develop this skill “is by working closely with senior lawyers to observe how they break down complex problems from an early stage”.

Attention to detail is equally important, as is the confidence to make clear decisions and offer definitive advice rather than sitting on the fence. After all, as May-Smith puts it, “Clients come to you for actionable direction.”

As our conversation draws to a close, May-Smith has one final piece of advice for prospective and junior lawyers: keep an open mind about where your career might take you. “Be open-minded about where your career path might lead. When I started in criminal law, I wouldn’t have anticipated doing corporate due diligence and regulatory advice for care providers, but I love what I do now,” he says. “Keeping your head up for new opportunities rather than just focusing solely on the day job is key.”

Applications for Hill Dickinson’s direct training contract close on 10 January 2027

Carl May-Smith will speaking at ‘Beyond the headlines: How regulation, risk & global events influence our work — with Hill Dickinson’, a virtual student event taking place NEXT TUESDAY on 10 November. Secure your place now.

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