In an exclusive interview, Sara Bailey, the senior partner at leading law firm Trowers & Hamlins, opens up about her remarkable career in the City of London, reflecting on challenges, triumphs, and a memorable piece of misguided advice.
From Dewsbury Market to the Square Mile
Sara Bailey's professional journey began far from the corridors of power in the Square Mile. Her first job was as a shop assistant on a cheese and egg stall in Dewsbury Market, a humble start that contrasts sharply with her current role. Born in 1967 and now aged 58, Bailey studied at Newcastle University before moving to London, where she has lived in Gospel Oak, North London, for three decades.
Her entry into the legal world came as an articled clerk at Trowers & Hamlins, a firm she has remained loyal to throughout her career. She recalls knowing she wanted to build a career in law during a work placement at Frere Cholmeley, describing it as a world away from her Yorkshire roots. "I loved the office environment, being near the courts and helping to solve people's problems," she says.
Career Highlights and Hurdles
Bailey's rise through the ranks includes roles as head of real estate and managing partner before becoming senior partner. Among her proudest moments is closing the Olympic village project, which she describes as a huge team effort with an innovative legal structure. "It was a very proud moment to get the deal over the line in the required timescale," she notes.
However, her path wasn't without its stumbles. She shares a business faux pas from her early days as an articled clerk, involving a mishap with copying a 200-page document that led to a frantic scramble. "That was a bad day with a lot of running around to sort it out," she admits, adding that it taught her a valuable lesson.
Overcoming Adversity and Bad Advice
Perhaps the most striking revelation from the interview is the worst career advice Bailey ever received. She was told she was "too Yorkshire" and advised to change her hairstyle, outfits, and herself. "Safe to say I didn't!" she asserts, highlighting her resilience and commitment to authenticity. This remark underscores the challenges she faced as a northerner breaking into the City's legal elite.
In contrast, the best advice she's been given is to never give up, as there's always a solution. She looks up to Jonathan Adlington, her first boss and a previous senior partner at Trowers, praising his empathetic leadership style as ahead of its time.
Life Beyond the Office
Outside of work, Bailey enjoys horse riding and doing jigsaws, with a motto to "be positive and always be ready to learn." Her favourite book is Lord of the Rings, and she opts for a small black Americano for coffee or a dry martini or apple martini for cocktails.
When it comes to dining, she recommends Trullo in Highbury for lunch, a lovely small Italian restaurant with amazing food. For after-work drinks, she favours the China Tang bar at the Dorchester, describing it as atmospheric and a little bit of luxury.
Personal Reflections and Future Outlook
Bailey expresses deep affection for the City of London, citing its buzz and diversity as unparalleled. "The energy you get from walking through the city and working in it is second to none," she says, though she laments the traffic as one thing she'd change.
At weekends, she can often be found in Edinburgh, which she calls her happy place with family. For a well-deserved break, she plans to visit Venice with her husband, describing it as one of the most special places on the planet.
Looking ahead to 2026, Bailey remains optimistic despite recent challenges. "I do, however, go into 2026 with optimism and enthusiasm to make the most of every opportunity," she states, encouraging others to be positive and make an impact, no matter how big or small.
