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.

Related:

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.