An interview with Oliver Fenn-Smith – The Property Chronicle
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An interview with Oliver Fenn-Smith

The Headhunter

Oliver Fenn-Smith has almost 30 years’ experience in the commercial and residential property sectors in the West End of London and is chief executive of The Portman Estate. The 110-acre estate has been privately owned by the Portman family since 1532 and is today a vibrant, mixed-use portfolio centred around Portman Square in Marylebone.

Having studied natural sciences at Cambridge, Fenn-Smith started his career in the city before qualifying as a chartered surveyor at Grosvenor in the early 1990s. He moved to The Portman Estate as property director in 2005 after a brief spell as a garden designer. Over the last 20 years 

The Portman Estate has pursued a strategy of taking back control of its assets and undertaking development, both directly and in partnership, to progress the transformation of the portfolio. Fenn-Smith became chief executive in 2018. 

What was your first job, and what is the worst job you’ve ever done?

My first job was as a graduate trainee at Deloitte Haskins & Sells back in 1986. I am not sure I was destined for a career as an accountant, and I left a year later to join Barclays de Zoete Wedd (BZW) on their graduate programme. 

I think the worst job that I have done was as a paper boy when I was 12 – it was seven days a week for the princely sum of £1.20.

Was finance your first career choice, and what were you doing before?

While finance was my first career choice, within three years of joining BZW I had decided to become a chartered surveyor and left the City to take a one-year master’s degree in land management at Reading University. This followed on from my three-year undergraduate degree in natural sciences at Cambridge, where I specialised for my last year in the history and philosophy of science. A rather circuitous route to what I do now!

Why did you choose a career in the commercial real estate sector?

I joined Grosvenor in 1991 and was involved in the management of their 100-acre Mayfair estate, covering all sectors. I have always enjoyed that mix and almost 30 years later continue to manage a contiguous property portfolio, albeit just the other side of Oxford Street.

Why do you enjoy the sector?

Managing a mixed-use portfolio in one area is a real privilege, as it is not just about property but also about placemaking and being part of the local community. The contribution we can make towards the success of the West End, and indeed London as the UK’s capital city, is very important to us.

What’s a typical day like?

No two days are ever the same, but typically it can range from shaping and evolving the future strategy for the estate to considering our wellbeing programme in the office and engaging with the trustees and family beneficiaries.

Who or what has had the biggest impact on your career?

Without doubt my father, who always supported me in all my career choices without pushing me towards any one in particular. I think I must have tried his patience a little, having had three changes of direction by the time I was 25. 

What advice would you give to people at different levels on developing their careers?

For me it has always been about cultural fit as well as the intellectual stimulation of what I do, so I would encourage everyone to recognise the importance of both and not to underestimate what they find comes easily to them.

Who inspires you and why?

I have always been inspired by people who live with adversity or illness but somehow keep going, enjoy life and continue to give something back. There are so many people falling into this category that I would feel unable to name one above others.

What are your strengths and weaknesses?

I think I am quite intuitive about people and recognise what motivates different individuals. I can perhaps be too much of a perfectionist and therefore have to resist the temptation to get involved in the detail at times.

What do you think are the common qualities that the best leaders have?

It has to be about inspiring others to perform to the best of their abilities: charisma, empathy, intellect and a touch of humility are all definitely in the mix. 

What are you most proud of?

The Headhunter

About Tim Green

Tim Green

Tim has been helping real estate businesses with their senior recruitment needs for over twenty years. He has worked with a wide variety of businesses both in the UK and overseas. Curious by nature, Tim has developed an exceptional network, and numerous people have benefitted from his positive contribution to their careers. Businesses have benefitted from his ability to source exceptional talent. He also runs a quarterly Real Estate CFO Breakfast Forum with BDO Real Estate.

Articles by Tim Green

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