The Accidental CIO

Introduction

If there is no struggle, there is no progress.

—Frederick Douglass

Be yourself. Everyone else is taken.

—Oscar Wilde

How do you get to Carnegie Hall? - Practice, practice, practice

—Anonymous

We think too much and feel too little. More than machinery, we need humanity; more than cleverness, we need kindness and gentleness. Without these qualities, life will be violent and all will be lost.

—Charlie Chaplin

It was my first day on my new job, and it hit me like a bucket of ice-cold water. It wasn't that I had imposter syndrome. I just didn't know what to do.

Back in January of 2015 I received an offer from Iglu.com, an online travel agent for the cruise and ski markets, to become its first IT director. I wanted a change from Wiggle.co.uk, where I had been the first full time developer working along the founder, development manager, and most recently an enterprise architect. The new role was a step up, but I was confident in my technical ability. After all, it was only another form of e-commerce, and I was comfortable with that. But I wasn't prepared for a role as the most senior leader in IT and one that was part of the exec group—one that not only needed to lead and inspire an IT department, ensuring day-to-day reliable operational running, but one that had a pivotal role in contributing to the organization's digital transformation. It was a role that required me to be a business leader as well as a technical leader. I realized I had a lot to ...