From Think like a CTO by Alan Williamson

If you aspire to be a CTO or are working as one, this book is for you. The CTO position is not well defined and this book will help you prepare for or carry out work as a CTO. It will also help you (the CEO, CFO, or COO) decide what sort of professional you want to hire as a CTO and what their job should be.

Read on to find out more.

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What is a CTO?

The Chief Technology Officer is one of the most exciting and rewarding roles a technologist can take on in their career.   The position can define a company, open up new opportunities, create new product lines, improve workflow and have a huge impact across all departments.

I am going to make a big assumption here that, given you are reading this book, you already have a good idea of what a Chief Technology Officer is.  Yet, I would suspect that if I was to collect everyone who is reading this book for their description of what a CTO is, we would get as many different perspectives as there are readers.   This huge variety in interpretation is what makes this role not only challenging but exciting at the same time.

The closest counterparts, Chief Executive Officer (CEO) and Chief Financial Officer (CFO), are very well-defined roles, with their areas of responsibility clearly understood: the CEO leads the charge and the CFO writes the checks!   Okay, a little disingenuous but the point is that these roles are universally accepted, compared to the ambiguity around the CTO role. The CTO definition gets morphed and pulled depending on the organization, with dramatically ranging responsibilities from company to company.  At a very high level, the CTO is responsible for the technology vision and execution of a company.

If this was a game of chess, we have the Chief Executive Officer (CEO) as the King and the Chief Financial Officer (CFO) as the Queen—which is the most powerful piece on the board, being allowed to move in any direction and for as many squares as desired.   This is true in business too with the CFO being involved in every decision, as that involves either bringing money into the company or out.  Where does that leave the CTO?

As anyone that has seriously played chess, knows there is a whole world of strategy that underpins what on the surface seems to be a simple board game.  Watch any professional player as they agonize for hours over a single game.

I like to think of the CTO as the Rook (the castle), the next most powerful piece, as they provide the support for the rest of the pieces to move around the board, clearing paths into the distance, to move freely.

Figure 1. The Rook

Yet with all this power and responsibility, it is a role that most are unprepared for, with many not realizing just how much there is to it, especially in today’s modern architecture.  Not only does the role oversee the research, developing and implementation of the company’s technology, it also covers the execution, licensing, compliance and continued security monitoring of the production environment.   In a world of always-on-always-connected networks, linked devices of all shapes and sizes, office, home and remote workers, the challenges facing today’s CTO are way beyond what the CTO’s of the 80’s and 90’s faced. If that isn’t enough, we work in an industry that continually reinvents itself, undergoing seismic changes in our tools and processes every 5 years.

Whether you are a seasoned CTO, new in the role, taking over from someone else, or a CEO trying to determine if you need a CTO (yes is the answer to that by the way), there is a lot more to this position than most realize.  It doesn’t matter the size of the company, from a 2 person start-up, right up to an organization with thousands of employees, the responsibility is wide.

This book was born from the need to fill a space in learning to prepare both the company and the individual for the role of Chief Technology Officer.   It springs from many years of experience in the field working with companies of varying size (from startup to Small to Medium Business—typically no more than $100M revenue), serving as either full-time CTO or interim-CTO for portfolio companies within and outside of the private equity space.

These companies have a wide range of activities, with little overlap.  But they all had the same requirement when it came to their CTO: someone to envision, lead, implement and maintain the product technology for the company.

When I took on my first CTO role, I had no idea what was expected of me.   I asked around all my contacts, reached out to existing CTO’s and spoke at length to many trusted sources as to what I needed to do to succeed.   What was clear, it was a way bigger responsibility than I first imagined.  I had a lot of learning I had to do—and quickly.  I made a lot of mistakes, mainly down to not knowing what I should be doing.  What I needed then was a guide, i.e. this book.

Who is this book for?

If you fall into any of the following categories, then you are reading the right book.

  1. You are an experienced technologist wanting to make that next step in your career to CTO.
  2. You are serving as CTO for the first time and you want to be sure you are doing everything you can.
  3. You are a seasoned CTO and your company is growing rapidly and you are being asked to do things that you simply have no idea how to respond to.
  4. You are taking over from a previous CTO, with the executive team looking to you for big revolutionary changes.
  5. You are a CEO/CFO who is looking to see if you need a CTO (and the sort of things they would do for you) and how to hire for this role.

Depending on your company size, some of the chapters will not be relevant.  They may be more appropriate for another time of your career or the company’s evolution.  However, even if that is the case, it does no harm for you to dip into the chapter and see what it would entail if there was an organization change and suddenly you were faced with managing that area.  Besides, it is good to be able to offer moral support to those who are maybe dealing with it, and sympathize with their struggle.

This book will answer some of the questions you may have asked yourself, but dare not ask your CEO for fear of looking like you don’t know what you are doing.  After all, they hired you to take care of everything that they cannot, so they need to have the confidence that they hired the right person for the job.

Each chapter will visit a major area of responsibility and take a deep dive into those areas and outline the considerations you should be mindful of and strategies to manage each.   That said, this is not a technology cookbook, I am not going to recommend Java over C#, or Amazon over Azure, or cloud vs data center.

Instead, I will give you the considerations that you should remember while making these enterprise level decisions, as the decision you are making could have long lasting effects, even well after you leave the role.  I will be offering small case-studies throughout to help illustrate the decision process.   Each decision you make, will be in the context of what the company needs and what resources you have at your disposal.  There is no right or wrong, and a decision that is based on data and not gut instinct is always defendable.

This book will open your eyes to the areas of responsibility that a CTO may face in their career and give you the necessary skills to evaluate, understand and execute for a successful outcome within the context of your company.

Being the best CTO you can be

The CTO role is constantly changing with new challenges to be conquered each and every day.   It is why I love the job: boredom is inherently factored out from day one.   This means that you need to keep relevant.  We’re in one of the most fast paced industries possible, with new and exciting technologies popping up every day.  How do you choose which to follow and which to ignore?  How do you stop yourself from getting too dated?  How much are you expected to know?  What level of detail are you expected to know?  These are the questions we technologists ask ourselves all the time.   But when you are deciding these for a whole company, the consequences are far reaching.

We all suffer from imposter syndrome – the feeling that we don’t really know what we are doing and someone else always knows better.  This is completely natural and more prevalent in the tech space given how fast things evolve.   Every time you read some news about the latest and greatest innovation, it puts doubt that you are not keeping up or you are failing your team or company.   Let me assure you that this feeling will not go away and you should learn to live with and embrace it.   I will give you some techniques here as a CTO that you can use to make sure you don’t feel you are falling behind or backing a technology that will be out of date next year.

The book is filled with practical examples, illustrating the point at hand, complete with lots of real-world stories of the challenges that CTO’s have faced and conquered.   As part of my role at the MacLaurin Group, and now at the private equity firm, New Harbor Capital, I work with CTO’s across many different industries in the private equity space, lifting them up, mentoring them, advising them on specific issues/problems they are facing.

Many of the problems I have been brought in to assist could have been prevented with better planning and a little knowledge that something like that could have happened in the first place.   The vast majority of this book is curated from these encounters, real issues, facing real CTO’s, as well as my own experience growing a number of technical teams as full time CTO.

What this book aims to do is to be a lot more specific to the areas that typically fall under the remit of this desk of the Chief Technology Officer.  Since the role isn’t as well defined as some of the more established executive roles, it is largely what you or you company want it to be.  A CTO can make themselves completely invaluable to a company if they see the opportunity they have to make the company run like a well-oiled machine.

So whether it’s just you, or you are faced with running a group of 100 engineers, let’s discover just what it takes to be a successful CTO.

Check out the book here.