The CIO Questionnaire: David Jack, CIO at Thetrainline.com

Q. Which business (or other) books have been influential in your career? A. I have to admit I am not a huge fan of business books, they tend to make me feel inadequate rather than encouraged or uplifted. There is a fabulous book by Lauren Slater that has influenced how I think about people and the way that they think called Opening Skinner’s Box. It is a fascinating tour through the biggest psychological experiments of the last century and every time I read it, it makes me re-evaluate some of my preconceptions, especially about why people do what they do.

Q. Who have been the most influential people in your career? A. I have been fortunate to work with lots of amazing people over the last 20 years and have learnt something from every single one. Additionally, I suspect that I have actually been influenced more by the not-so-good people as I can see what doesn’t work and have been forced to find ways to influence or bypass them!

Q. What is your approach to training and mentoring? A. I have a brilliant professional coach. She is highly irreverent, energetic and challenging and has really helped me to work out what I want at this stage of my career, and she prods and pokes me to get done the stuff that I tend to avoid. I can’t think of any senior executive who wouldn’t benefit from having this type of professional coach. As for mentoring, I have a couple of former colleagues that I have deep respect for and who I turn to when things are hard or if I’m stumped on how to proceed. I mentor and coach a number of people across some very different businesses myself, and in addition to the fun of taking a look at other people’s challenges, new ideas are created and I often find myself thinking that perhaps I should follow some of my own advice.

Q. Which tools or tactics have given you most success in communicating up/down/across? A. It is obvious but if you find yourself avoiding saying something because it is too hard/complicated/sensitive, then make it a priority and make sure you say it – it doesn’t matter which direction the communication is going. My favourite adage is “simplicity and clarity”; I have even set objectives to my team to show that they give attention to simple and clear communication of highly complex problems and systems. Q. What has been your biggest mistake? A. Other than the obvious ones of buying and selling equity at the wrong time, I have made so many other business mistakes it’s hard to find one that stands out… probably not learning from my mistakes enough in the early part of my career and repeating them later on.

Q. And your greatest success? A. I have had great fun over the last 20 years and I have been fortunate to work with cool people on fabulous stuff that I’m really proud of. I have even been at the right place at the right time a number of times to share some of the spoils so I’m pretty happy.

Q. What is your greatest strength? A. Persistence – I really don’t ever give up if I know there is a solution to a problem (either human or technical).

Q. And your greatest weakness? A. It is probably persistence: I always want to get things right, whereas sometimes, I guess, I should just give up and move to the next thing.

Q. How do you keep up to date with the march of technology? A. I sponge off others. I surround myself with smart people who I learn from and get to ask the dumb questions. Of course I attend conferences, read the press, the magazines and the newsfeeds but overall I learn from other people that are doing something exceptional or I’m in a business where we are driving some of the new technology advances ourselves. It’s so much easier to keep up to date when you are building the future.

Q. How do you deal with stress? A. Well, firstly, I think I encourage stress; I think I’m addicted to the stress that comes with the sort of roles I have played over the years, whether it is another board member jumping up or down, a vendor not delivering, or trying to manage the human consequences of technology and business transformation. I think that stress is unavoidable, and in fact desirable.

Q. What profession would you most/least like to attempt? A. My sister is a doctor, and I have always been jealous of her vocation, her success in the field and her ability to instantly explain what she does at dinner parties. But I suspect that I don’t have either the patience to study anymore, or the sensitivity to other people’s problems to make for being a great physician. I do rather fancy being an astronaut, but that hasn’t changed since I was five.

Q. Which word or phrase do you most use/overuse? A. “I know it sounds like a stupid question but…”

Q. Which technology companies and people do you most admire? A. The ones that I have worked for, of course. As a blue-chip, Citrix was a fabulous place to be, both in terms of what we were doing and how we were doing it. I look at the way that Mark Templeton, the company’s CEO, has steered the ship over the years and I can’t help but be massively impressed. Generally, the companies and the people who really wow me are the ones who are working on the fringes – trying to get ahead of the pack, even if they are seen as lunatics. The energy that people can generate in these types of startup is extraordinary.

Q. And which do you find most frustrating? A. For me it’s all about pace: any supplier that doesn’t understand that when a 24/7 internet business has a problem, action is needed now, not tomorrow or next week. It is speed (or lack of) that drives me nuts. Betfair was a great place to learn how to drive vendors hard and it was brilliant to see that even the slowest could be cajoled, forced and driven hard to fall in step with the speed of change that we required to keep the business running optimally.

Q. Do you have a sport you practise or sportsperson/team that you follow? A. I’m not a great sportsman but love running, swimming, cycling, skiing – anything in fact to get outdoors. I have managed to take time out and do the Cresta Run a few times. Simply put, skeleton luge is so utterly frightening and intoxicating, it puts everything else in the shade!