Terry Whittaker

1) First boss: Duncan McMillan, claims manager at the Michael Payne & Others, Syndicate 386. Duncan personified integrity. God forbid you went in to ask him a question underprepared.

2) First job: Potato porter at Stratford vegetable market. It took me seven years to earn more in insurance than I did as a potato porter.

3) First moment of responsibility: I was sent to investigate an employers’ liability claim at a launderette in Walthamstow. The lady concerned had slipped on a wet floor. At the time it seemed like a great moment!

4) Most memorable claim: Syndicate 386 was the lead insurer for the owners and operators of a gold mine in South Africa, and I went with the adjuster to investigate the Merriespruit dam disaster, where, on the night of 22 February 1994, the huge tailings dam of the mine collapsed. More than 2.5 million tonnes of liquefied tailings ripped through the neighbouring village, ruining 280 houses and killing 17 people. Arriving there three days later, I will never forget the mind-numbing panorama of loss of life and destruction of property that I saw.

5) First pay packet: I started on 19 October 1979, and my first monthly pay packet contained the princely sum of £124.

6) Moment I most regretted after I’d done it: For a number of years, Syndicate 386 engaged in paintballing as a staff teambuilding event. Being relatively young and keen to impress, I spotted my then boss in my sights and realised that he had no ammunition. I confronted him and, in a rush of blood to the head, I shot him in a particularly painful part of his anatomy, which I thought was funny, but he didn’t.

7) Biggest influence on my career: David Constable; he demonstrates through all that he does the balance between humanity and ability that is needed to achieve excellence.

8) What insurance should be about: I settled a large and difficult stockbroker claim where virtually every client was aggrieved by the inept and fraudulent trading of one of their employed traders. We settled the case through mediation in a way that did not overpay and engendered loyalty from the clients of the insured due to the integrity and equity of the process.

9) Key changes in the market: When I joined, the London insurance market rested on some huge personalities. Every syndicate and company had its own style, driven largely by its managing director or active underwriter. These days, the market is so finance focused that there is almost no room for those personalities, and I think the world is a little more grey in consequence.

10) First memory of insurance: Visiting Lloyd’s for the first time and seeing a significant number of men wearing bowler hats and almost no women.

11) Best party: Michael Payne used to give Christmas parties in the Syndicate office in Gracechurch Street every year, which were renowned for getting just slightly out of hand. They were incredibly well attended but would never be allowed today.

12) Funniest moment at a meeting: David Harries (now head of professional indemnity at QBE) and I undertook a three-week business trip to Australia together. Visiting a broker, we sat outside on his balcony where he had a bird table filled with mouldy nuts and seeds for the local parakeets. David was so hungover and in need of something to pick him up that he reached over and started snacking on the nuts, much to the shock and amusement of the assembled group.

13) Most satisfying application of justice: I investigated a claim at a chemical handling firm where the proprietor instructed a young employee to clean the slurry from the bottom of a chemical storage tank, without any protective equipment. The young man collapsed in less than a minute. The owner then sent in a second staff member (also without protection) to get him out and carry on the job. He also collapsed. The subsequent health and safety prosecution and cancellation of his policy felt like real justice, albeit less so for the two youngsters sustaining the chemical burns.

14) Worst career moment: When I thought the Syndicate was being bought by Wellington. Not that Wellington was inherently bad, but its plan was to merge the syndicates into one, and effectively for 386 to lose its identity, which seemed like the opposite of everything I had worked to achieve. Conversely, one of my best career moments was when I heard that QBE, with its promise to honour our structure, had counter-offered and successfully concluded the deal.

15) Worst personal moment: Having to deal with a lady employee who was very sweet but had a monumental body odour problem.

16) Biggest changes in myself: Thirty years have added five stone and five children to my life!

17) High point at Lloyd’s: The signing of the Lloyd’s reconstruction and renewal deal at terms that I still believe reflected fairly the balance between the value and risk associated with the transfer of liabilities.

18) Most memorable management moment: Michael Payne saw me at my desk at the age of 22, fretting over a credit card bill that I couldn’t afford to pay. He came over, listened to my problem, laughed and then wrote me a cheque to cover the bill with the words “pay me back when you can”.

19) Biggest change in the market’s culture: It is certainly less common to drink port and brandy after a working lunch these days! In my early years, there was an unofficial competition for the fastest consumption of braised onions at Simpsons restaurant. I took the challenge, and the record, and afterwards the head waiter said “That’s the way, sir!”

20) Daftest moment: At 85 Gracechurch Street, our then deputy claims manager was interviewing a most attractive blonde lady. To indicate our team’s approval of the candidate, I climbed outside onto the ledge on the 7th floor, and walked along the parapet to his office window, where I waved a card showing the number 10. We didn’t employ her, sadly.

21) Standout regional insurance memory: I recall my first flight to Ireland. I sat next to a priest who was scared of flying and fortified himself with at least five miniatures of whisky before we had taken off and then grasped my cuff in terror for much of the flight.

22) Changes to the way we do business: The prevalence of the “big is beautiful” culture. Nothing wrong in principle but very few appear to get it right.

23) Biggest career surprise: Being given my current role.

24) Biggest achievement in current post: I find it very satisfying that we are now perceived as a threat by other insurers in this arena, including some whom I very much respect.

25) Regional low point: Staff retention is key for us all and people moving stirs up some passion. I was threatened at a Manchester CII dinner by someone from whom we had secured staff. It was late in the evening though.

26) Key date in career so far: When David Constable assumed the role of active underwriter for Syndicate 386 on 1 November 2002, and gave me the chance to become syndicate manager.

27) Key sporting moment: The promotion of Gillingham FC from Division 2 to Division 1, after beating Wigan with two extra-time goals in the 2000 play-off final at Wembley.

28) Biggest technology changes: The arrival of the calculator, the computer, and e-mail.

29) Biggest pain in the backside: The BlackBerry: 24-hour access and a culture that takes work everywhere with you, if you let it.

30) Key question I’ve learned to ask: How does what I do add value? IT