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 learn. Over the following years I studied and grew professionally. I learned both the theory and how to put it into practice. I had begun my journey to become a strategic CIO.

This book is the codification of all the knowledge I acquired, a playbook that I hope will be useful on your journey as you transition to a CIO or an IT leadership role. My context, like yours, is unique; the challenges you experience will differ from what I faced. However, if like me you have found yourself in an IT leadership position where you were unsure on your next move, then this book will provide you the guidance to help your orientation as you navigate the trials and tribulations of a life as a CIO.

Why Should You Care? The CIO Challenge

Becoming a CIO is a hugely rewarding role and one that is critical to nearly all modern businesses. Because of their unique position in the organization, CIOs understand the constraints and opportunities of the business as well as having knowledge of how to mitigate or capitalize on them. This makes them best placed to take a more active role in digital transformation projects, moving beyond implementing new technologies to spearheading organizational transformation and driving business value. However, it's still a relatively new role that's not very well understood by the rest of the business and the board; it is stressful and rapidly evolving. All of this is occurring within an environment of accelerated transformation, emerging technology, constant disruptions, rising customer expectations, against a backdrop of huge sociopolitical challenges. In short, a lot is expected from IT leaders and CIOs in this most turbulent of times.

The evolving expectations of the CIO to lead, disrupt and transform, run, mitigate risk, consolidate, and grow can appear to be contradictory based on the archetypes of IT leaders we have come to know. These contradictions form what Martha Heller calls the CIO Paradox as detailed in her book The CIO Paradox: Battling the Contradictions of IT Leadership (Routledge 2012):

• The "Innovator's Dilemma" paradox refers to the conflict of having to manage the balance between the requirement to stay operationally stable, secure, reliable, and compliant with the need to innovate, experiment, and take chances.
• The "Business-IT Alignment" paradox alludes to the need for CIOs to be technical experts as well as understand the business to ensure strategic alignment and coordination. This is difficult due to the complexity and rapid evolution of technology, the speed of business needs, and the time it takes to deliver technology.
• The "Digital Literacy" paradox relates to the challenges that CIOs face caused by other executives' ignorance of the consequences of technology choices and how it affects the company.
• The "Influence" paradox refers to the difficulty of acquiring authority to make decisions inside the business when they are often considered a service provider or an overhead.
• The "Blame" paradox speaks to the difficulty of CIOs accepting accountability for the outcomes of technological projects when they don't have complete control over decision-making. This is chiefly caused by asking CIOs to deliver defined scope or output rather than outcomes.

This set of conflicting forces is deeply embedded in the operating and mental models of organizations that have been formed within contexts that are no longer relevant today. The problem is that the purpose the system (the IT operating model) was designed for has changed. The old system is based on archetypes of CIOs that are mutually exclusive in that either they specialize in running efficient operations (the service provider, order taking, stable, secure, process-oriented) or they are focused on innovation (the disruptor, adaptable, innovative, lightweight governance, and fast). CIOs don't need to be innovators or operational; they need to focus on innovation and operational stability. They need to manage digital transformation, digital optimization, and operation efficiency. A good CIO can make or break a company. However, boards hire or promote technologists. What they need are strategic leaders who specialize in technology.

Taking Action: Becoming a Strategic Leader

Great CIOs are sought after; they are partners, cocreators, consultants, and advisors. They are business leaders first, ones that just happen to be accountable for the technology within an organization. They report to the CEO, have a seat at the top table, contribute, and sometimes lead an organization to digital transformation and strategic success. They achieve this by balancing and adapting to meet the variety of challenges they face. These are the core behaviors that they exhibit:

• Coauthor strategy.

  Great CIOs are not order takers. They coauthor strategy and focus on what matters, namely generating enterprise value. They can achieve this because of their deep knowledge of the business and operating models. They understand the context that the business operates in and the material factors that can affect the organization. They know what the business needs to do to be successful-where it will play and how it will win. They interpret where technology contributes and where it can lead.

• Focus on outcomes over output.

  It doesn't matter what you do if it doesn't make an impact. Great CIOs bridge the gap between business impact and technology output by focusing on what business outcomes are required for success, how technology can be used to achieve them, and how best to organize teams to execute them.

• Structure teams for intrinsic motivation.

  Great CIOs know that they are only as good as their team. Great CIOs excel in recruiting, developing, and retaining talent. They do this by ensuring teams are motivated to solve complex problems and deliver value. They achieve this by designing an operating model to support people's need for purpose, autonomy, and mastery.

• Focus on being agile, not doing agile.

  Great CIOs know that to bridge the paradoxes, they need to be adaptable. There is no single way of doing something. Agile is appropriate for some problems, whereas big upfront design is suitable for others. Failure is expected when exploring uncharted problem spaces but not when working in well-known and understood areas. Sometimes it's best to buy and sometimes it makes sense to build. Great CIOs adapt their methods and team dynamics depending on context.

• Manage the flow of work, not people.

  Great CIOs work on the system, not in it. They leverage their power to remove impediments and inspire teams with an aligned vision, using their strategic, social, and relationship skills to influence and lead in change and innovation. They manage the flow of work; they lead the people.

CIOs that show aptitude in these areas will have an impact greater than any other exec on business success. However, to get there you will need the right attitude. You will need to embrace a growth mindset. You need to continuously learn, adapt, and develop. Picking up this book is your first step on that journey.

What Will You Learn?

I am going to show you how I became a strategic CIO. I'll walk you through, step-by-step, how to create an IT strategy and a tactical plan to execute it. I will show you how to design an operating model to deliver results. You'll discover how to create an IT organization that is empowered and focused on solving customer problems and generating enterprise value. You'll learn to adapt your methods depending on the context of the problem you are facing. You'll understand the science behind what motivates teams and how to change behavior. You'll be taught how to think like a business leader and focus on impactful...