One of the City's leading acquisition finance lawyers, Stephen Gillespie last year joined the London arm of Kirkland & Ellis

Why did you become a lawyer?

I had naive and fanciful notions of being a brilliant advocate at the Bar, and thought that this would be best advanced by studying law. Halfway through my degree, I realised that I was no barrister-in-the-making and, through a combination of lack of imagination, laziness and inertia, opted to become a solicitor instead.

Who has been the biggest influence on your career?

My parents, Hugh and Valerie Gillespie, and my wife Helen. They taught me the value of hard work and dedication, have been unfailingly encouraging throughout my career, and have given me the confidence and self-belief to persevere and forge ahead.

What's your proudest professional moment?

Seeing people I care about and rate fulfil their potential by making partner and going on to rank among the stars of their generation: Jonathan Bevan, David Lines, Chris Andrew, Charles Lindsay, Davide Mencacci, Gareth Price and Ian Borman at A&O and Neel Sachdev at Kirkland.

… and worst day on the job?

It's a toss-up between being sent, while an articled clerk, to Trumpers in Jermyn Street to buy a bottle of hair oil for the partner I was then sitting with and, as a first-year associate, while acting for the receivers of a failing manufacturer in Lancashire, having to tell a workforce of 150 that they were being made redundant with immediate effect and no pay-off.

Aside from your own firm, which lawyer do you most admire and why?

I have been privileged to work with and learn from some very clever and talented people – Geoff Wolff, Ruth Markland, Philip Wood, Jonathan Horsfall Turner, Gordon Stewart, Brian Harrison and, of course, Tony Keal.

How do you think assistants in your team view you?

I hope that they feel I am honest, open, approachable and responsive, that I would not ask them to do anything I would not be willing to do myself, and that what you see is what you get. I fear in reality they see a grumpy old git who works too hard.

What advice would you give to young deal lawyers starting out?

Pursue a varied range of work, do not become over-specialised or pigeon-holed too early, seek out the best coaches and mentors you can and stick to them like glue; never settle for second best.

What most annoys you about the legal profession?

Pompous and opinionated lawyers who love the sound of their own voices and believe that their clients should be willing to pay for, and to tolerate, their absurd grandstanding and posturing over points that do not matter.

You were part of a group of lawyers who were regarded to have established leveraged finance from a legal perspective in the 1990s – do you all stay in touch?

Not as much as we would like – when you are no longer in shouting/spitting distance of each other it requires an effort to maintain contact. Tony and I get together about once a quarter to collude with regard to market terms (joke) and to drink some good wine.

Moving from a finance giant to a relative UK start-up must be a dramatic change – has it been what you expected?

It has exceeded my expectations. There is a tremendous sense of energy, focus and intensity here, and the flat structure, and lack of departmental boundaries, means there is much less treacle to wade through to get the job done.

Kirkland has a reputation as a hard-nosed firm – justified or out of date?

Until you work inside a US firm, it is impossible to get an accurate perspective on all the myths that circulate about what it is like to work here. I have found Kirkland's dynamic no-nonsense approach incredibly refreshing, and I would not regard it as hard-nosed so much as good for business and good for the lawyers who work here.

What's your biggest extravagance?

Apart from my wife and four daughters, my collection of classic Nikon, Leica and Canon cameras.

What would you do if you weren't a lawyer?

I'd be a writer of some sort, though probably not a very successful one.

Where do you see yourself in 10 years' time?

Tanned, fit and two stone lighter, running my practice remotely from somewhere in the Swiss Alps.

What is your favourite lawyer joke?

What do you call a smiling, sober, courteous person at a magic circle departmental offsite? The caterer.

What's your favourite cheese?

While doing a deal in Spain, I was introduced to manchego, and have been hooked ever since.

Dealmaker returns in two weeks.