Olswang publishing guru Tony Leifer on Captain Bob, Singapore prisons and preferring pineapples

Why did you become a lawyer?

I had a school holiday job in a solicitors' office just before going to Northampton College of Advanced Technology (now City University) to study optics so as to become an optician. The law seemed more fun and more stimulating, so I switched.

Who has been the biggest influence on your career?

By a mile, David Freeman, the founder of DJ Freeman, where I spent 26 years. He was, in my formative years and beyond: inspiration, mentor and friend.

What's your proudest professional moment?

Being presented with my admission certificate by Lord Denning.

…and worst day on the job?

In the days when I did litigation, it was when the client I was defending from extradition to Singapore following the collapse of Slater Walker was sent off to Changi Jail.

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

We were both young partners when I met David Cheyne, now senior partner of Linklaters. His approach was never to argue any point that didn't really matter. The chances are, with that approach, the other side will agree on most points and the deal will get done.

What's your strongest characteristic… and worst trait?

My best point is that I try to make a deal fun and my worst is that I can make it too much fun.

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

Focus on the economic drivers of the deal and what your client really wants.

What's the best part of your job?

As I grow into maturity, I really enjoy working with and having as colleagues clever people in their early thirties who still don't treat me as an old buffer.

What most annoys you about the legal profession?

Lawyers who can't see the wood for the trees.

What's the toughest ethical/moral dilemma your job has ever presented you with?

The great thing about having partners is that sharing your nightmare with them gives you a solution.

What's your strongest card – technical wizardry or smooth client skills (you can only pick one)?

Who said I had one?

Most memorable deal you ever have worked on and why?

I did a couple of deals for Captain Bob Maxwell. One was his attempt to buy the Today newspaper. He was the largest larger-than-life character – full of tricks, charm, aggression. He spoke German to Tiny Rowland (just because they both could) and interrupted the conversation to take a call from the Czech President.

What's your funniest Jonny Goldstein tale?

We don't tell tales about our esteemed clients.

Working at a media-oriented firm, is keeping up with celebrity gossip in your job description?

Yes, but I don't talk about my partners' personal affairs.

What is the daftest bit of corporate jargon you've heard (and did you smirk)?

Most of the jargon comes from the clients, who want to "reach out" to the other side and then "circle back" with you.

What will be the most significant market trend in terms of your practice area over the next 12 months?

Fewer deals.

Do you see yourself having a career outside law?

Probably, on a voluntary basis.

What's your favourite item of clothing?

My walking boots.

What's your favourite cheese?

I prefer the pineapple.