Trowers & Hamlins partner Sara Bailey: I was told I was ‘too Yorkshire’
We dig into the memory bank of the City’s great and good. This week, Sara Bailey, senior partner at Trowers & Hamlins, takes us through her career in law in Square Mile and Me
CV:
- Name: Sara Bailey
- Job title: Senior partner at Trowers & Hamlins
- Previous roles: Head of real estate and managing partner
- Age: 58
- Born: 1967
- Lives in: Gospel Oak North London
- Studied at: Newcastle University
- Talents: Horse riding, doing jigsaws
- Motto: Be positive and always be ready to learn
- Biggest perk of the job: The diversity of working with lots of different people, across many countries and cultures
- Coffee order: Small black Americano
- Cocktail order: Dry martini or apple martini
- Favourite book: Lord of the Rings
What was your first job?
Shop assistant on a cheese and egg stall in Dewsbury Market.
What was your first role in the City?
An articled clerk at Trowers.
When did you know you wanted to build a career in law?
When I first came down from Yorkshire to do a work placement at a firm called Frere Cholmeley. It was a world away from home and I loved the office environment, being near the courts and helping to solve people’s problems.
What’s one thing you love about Canada?
I love the buzz and the diversity. The energy you get from walking through the city and working in it is second to none.
And one thing you would change?
The traffic, it is crazy!
What’s been your most memorable day on the job?
My most memorable day on the job was when I was offered my first position as a newly qualified solicitor. I didn’t really believe I would get there; it was such a special moment.
And any business faux pas?
It was in a big closing as an articled clerk copying a 200-page document. I copied it eight times and checked seven of the copies, I missed the last one and that was the one that omitted every other page and was also the one that went for signing. That was a bad day with a lot of running around to sort it out. Big lesson learned.
What’s been your proudest moment?
Closing on the Olympic village project. It was a huge team effort and a very proud moment to get the deal over the line in the timescale required with a legal structure that was innovative.
And who do you look up to?
I have a number of people who have been very influential in my career, but the person who I look up to is Jonathan Adlington who was my first boss and a previous senior partner at Trowers. He was ahead of his time in terms of leadership style and led with empathy.
What’s the best career advice you’ve ever been given?
Never give up, there is always a solution
And the worst?
You are too Yorkshire, change your hairstyle, your outfits and yourself. Safe to say I didn’t!
Are you optimistic for the year ahead?
I am a very positive person, though there have been a few challenges I’ve needed to navigate over the last few years. I do, however, go into 2026 with optimism and enthusiasm to make the most of every opportunity. I think at a personal level we should all be optimistic and do our best to make an impact no matter how big or small.
We’re going for lunch, and you’re picking – where are we going?
We are going to Trullo in Highbury, a lovely small Italian restaurant with amazing food.
And if we’re grabbing a drink after work?
China Tang bar at the Dorchester, atmospheric and a little bit of luxury.
Where’s home during the week?
Gospel Oak has been home for 30 years
And where might we find you at the weekend?
If not at home, I’ll be in Edinburgh, which is my happy place with my family.
You’ve got a well-deserved two weeks off. Where are you going and who with?
Venice with my husband. Genuinely one of the most special places on the planet and with my favourite person.