Introduction

When I told my technology friends that I was writing a book about the first 100 days on the job as a Chief Technology Officer (CTO), I got the same response every time: “Why 100 days? It’s always a 90-day plan.” I’ve pushed the tried-and-tested plan up 10 days because there is an emotional connection to that number. It was also the first solid plan I witnessed when I came to America.

When my wife and I arrived in America in 2000, George W. Bush was running against Al Gore for president of the United States (POTUS). The race was in full swing, and it was two months from the November election. Televisions everywhere were lit up with debates, speeches, and ad campaigns. What struck me was how often they referred to their first 100 days in office. This first 100 days would set the tone for their full four years as president.

This inspired me to research the idea of the “first 100 days.” My model of the first 100 days, which you see here, is based on the extraordinary accomplishments of another POTUS, Franklin D. Roosevelt. He took office toward the end of what Milton Friedman called “the Great Contraction.” It was a period kicked offby the infamous stock market crash of October 1929, which left the American people nervous and susceptible to rumors of the coming financial disaster. This period saw unemployment rise from 3 percent to 25 percent.

Franklin D. Roosevelt took office on March 4, 1933, and what he would do in the first 100 days of office would shape his legacy and his country. He needed to implement, innovate, and inspire while supporting the pillars of leadership, teamwork, timing, and technology. He took offfrom the runway, tempering his flight with the help of smartly appointed advisors. During his campaign speech, he stated, “Throughout the nation men and women, forgotten in the political philosophy of the Government, look to us here for guidance and for more equitable opportunity to share in the distribution of national wealth…I pledge myself to a new deal.”

FDR’s pledge set him on the path to a remarkable first 100 days. While you’re not the president of a country, I find it inspirational to view your role as CTO as one of bringing remarkable change to the company you’re joining. You are approaching the company with the tools it needs to help it succeed not only while you are there, but for years after you leave. You are using your first 100 days to deliver on your reputation, which has preceded you.

Being a great CTO isn’t just about the first 100 days. It is about what you do before you get there, what you do while you’re there, and what you leave behind. It is about the steps you take to become the best possible CTO and the actions you complete to support your words. The first 100 days for a CTO, similar to those of our most inspirational leaders , are for reshaping, reforming, and rebuilding wherever you are able. As a CTO, you have the power to create changes that will heal and strengthen a company from within.

This book will serve to show you how to throw out the “norms” and approach the job from a different angle. We will discuss the relationship between the CTO and the CEO. We will discuss a select few ways to get where you need to be, both personally and within the company, and how to navigate the C-suite to foster only the best ideas. We will review your first 100 days and help you leave a presidential impression on the companies with which you work.

My Life Background

I grew up in South Africa. I knew from the time I was a child in the eighties that I loved computers. In school, we used to have a computer lab with BBC computers. Two of my best friends and I would go to the computer lab to practice coding on every break or free period. There was an incredible atmosphere of coding and what coding can bring to all of us. The good feelings I got from coding with my friends fostered my passion for computers and technology.

I remember being ten years old and being drawn to the glowing screens of arcade games. In South Africa, there were cafés, which would be closer to liquor stores in America. The owners wanted to distinguish themselves from other cafés, so they would bring in the latest and greatest arcade games. The kids loved it. I had a lot of fun watching other kids play Moon Patrol,

Ms. Pacman, Galaga, and Rally X, as I was never good at playing them myself. I found myself more fascinated by how the games worked than just by the hedonistic fun my friends got from it. I wanted to know how everything moved on the screen. I was always asking, “How?” How does it work? How did they make it move that way? Why does it act this way?

I remember going to a friend’s house where there was an Intellivision gaming console. I was entranced. His brother showed me a Walkman for the first time; Ultravox’s “Vienna” was the first song I ever heard on a Walkman. The sound was everywhere, and I was amazed. Being in that home was a pivotal moment for me. I wanted to know how it all worked. I asked my parents for a gaming console, but they were wary of kids’ fads. Instead of getting a console, I was sent to computer camp. I learned how to use an Atari 800, where I practiced computing with Logo. I was immediately hooked. My dad’s “evil plan” to draw me away from gaming consoles to computers worked.

My family helped me buy my first computer, but first I had to prove that I was serious about using it. I saved all the quarters I would have spent at the arcade in envelopes. When they noticed my devotion to working toward a goal over frivolous spending, I got my computer. It was an Atari 800 XL. I started coding in Basic almost right away. I learned the basics, and the first day I figured out how to add two numbers in Basic and store them in a variable. I had my eureka moment and ran down the street in unbridled happiness.

From there, I started coding two programs. One was a program to keep track of my pocket money. My dad wanted me to use accounting practices to track money, but I wanted to optimize that idea. I tracked how much money I would get, how much I would spend, what I would spend it on, and how much I had left. The program drew graphs using the information. The second program helped track the Top 40 songs on the radio. Back then, you had to listen to the radio every Sunday to hear the Top 40 most popular songs for that week. I had to quickly track the songs, where they were on the charts, and how they were moving. I started to predict which songs were going to move up to number one using this program. Needless to say, my predictions were hit and miss, but here’s the fun legacy that remains: I had more fun with my own Top 40 than with the one on the radio.

Unsurprisingly, I ended up majoring in computer science at university. It was here, in 1990, that I had my first encounter with the internet in the form of IRC. It was a chat app. Remember, in South Africa, we were part of the cultural boycott. We didn’t get music, shows, CDs, anything, due to apartheid. I felt disconnected from the world. My favorite band was U2, and they had boycotted South Africa. My world was computers, and everything exciting in computers was happening overseas. All my heroes were overseas, so IRC helped me feel more like part of a global computer enthusiast club.

I graduated with a bachelor of science and with honors, then went to work with the Council for Scientific and Industrial Research (CSIR), where I built and ran our first IRC server, built an NNTP server, which served as South Africa’s first Usenet server, and built out SSL relays and encryption device drivers. Eventually, a new company purchased our work, bought out my university scholarship—which had been granted by the CSIR— and brought me on board to work for them.

The new company, Nanoteq, was also located in South Africa and gave me an introduction to private startup enterprise.

I was pleased to be part of this air of possibility. At this time, South Africa was coming out of the apartheid regime. Most of my youth was characterized by the sanctions against South Africa. Computer magazines weren’t sent to our stores; everything felt like an extra effort in my youth. My favorite computer was the Atari, and even those stopped being exported to South Africa. Software was difficult to find, so I was drawn to open source, modems, and anything I could find. After living with these restrictions, the freedom I found in the startup to build anything and do anything was intoxicating. Being a part of that startup had a profound impact on my life.

The entrepreneurial spirit awoke in me. I had a front row seat watching this company build itself on the world stage of network security and data encryption. I already had a taste of coding and knew what I loved in that area; now I had a taste of entrepreneurship and knew I wanted to make the two meet.

I found a role model while working at Nanoteq. His name was Jaco Botha. In him I saw a glimpse of my future, of who I wanted to be as a leader in an organization. Finding someone to emulate, who is successful and has a lot to teach, grounded my career and would eventually shape my future endeavors.

Jaco embodied incredible engineering intellect and strength. I recognized the strain the business took on him, yet he projected incredible grace when working with us. He was inspiring us to do our best. He wasn’t our “buddy” at work, but he was a driving force that encouraged us to work our hardest without being too overbearing. I aspire to be that type of leader as a CTO and as an advisor to CTOs.

I married my wife around this time, and we began settling into life as newlyweds. Nanoteq was acquired by a private equity firm, which also acquired a German cryptographic organization called KryptoKom. We had an opportunity to move to a small border town in Germany called Aachen. As I was a key player in one of the projects being acquired, my wife and I decided to pack everything and move with a long-term view. We believed the world was our voice; South Africans were finally welcome to the world. It was an exciting time to be a South African postapartheid.

In 1998 we landed in Germany, and it was rough. Aachen felt like the final outpost for Germans at the Belgian and Dutch border, so the language and culture felt very closed to internationalization. You couldn’t order a pastry without perfect German at the bakery. Movies were all dubbed into German. There weren’t any English TV channels, and absolutely everything was in German. The first phrase I was taught in German was a protracted apology for not speaking German. We were young, naive, and scared, to a degree. While these were difficult times for us, I will cherish the three years we spent in Germany with all my heart.

The German company I joined was under tremendous pressure to release their newly acquired product. Regardless of this pressure, they were insistent on perfection. Our team really struggled. In fact, in the time I worked there, we hardly shipped any code I wrote because it wouldn’t do exactly what the company wanted it to do. Others would have released it already, but this company wanted to get to the next big thing right on its first release. I began to see flaws in this type of thinking. I learned the wrong way to go about producing software and handling technology. While it was extremely frustrating, it was an important learning opportunity I did not take for granted.

With me miserable at work and my wife lonely and bored in a country where she couldn’t legally work, we decided to relocate. I found a job with a biotech company in America, and we packed up and moved to San Diego.

When we moved from South Africa to Germany, a relocation service took care of our belongings. We did not have the same option during our move to America. We shipped a few boxes through the post office, and many of our things arrived broken. There was nothing mystical about our arrival in America.

However, my time at the biotech company incubated the entrepreneurial spirit that had begun all the way back in South Africa. My mentor from this company, who remains my dear friend today, showed me how to interact with others to generate the best possible outcome. The German company taught me what to avoid. Even if I didn’t realize it at the time, I was building something in myself that would become incredibly useful for my future.

Although I loved my mentor, I grew to dislike the work and my boss. The whole work environment began to bother me, so I began turning my attention toward the internal employees. There were about 150, and I started building tools and little scripts that would make their lives easier.

For instance, they struggled with daily sales reports. They had this massive ERP system that was built on Oracle, and they would need someone in IT to run the weekly sales reports for them. They sent the report to the VP of sales so he could see what was going on. I figured out how to hack the Oracle database schema so I could extract data in real time instead of on a weekly basis. I used a PERL library to build a web page and put some graphs on there.

I drew immense satisfaction from this organization. I felt like I was doing a bit more, like I was doing something important for the company. The VP of sales accidentally stumbled onto my work and was floored by it. The real-time sales dashboard I was able to create was shocking because I could get all the right information hidden deep inside their own system.

The pivotal moment for me here was discovering that the simplest tools can have the greatest impact on people. This is where I realized I wanted to highlight software that makes people happy by saving them time and creating simpler processes. This is when the entrepreneurial interest that was bubbling beneath the surface finally came to light. At that time, the term CTO wasn’t really a thing, but I knew that was the direction I wanted to go.

Becoming a CTO

I soon became a technical co-founder when a friend of mine proposed building a content management service that helped nonprofits gain a web presence. We built a gorgeous first page for these organizations so they could get up and running quickly. It was a novel idea for the time, and it was successful.

My co-founder focused on the business and the growth while I focused on the technology. From here, I had to build a team. I had to hire people. Through our efforts, it became a multimillion-dollar company. I started getting asked to be an advisor to other founders. I started understanding my role as a CTO. It was still a role that was coagulating into something, but I was at its genesis. I was a bit of an anomaly. There simply weren’t many of us in existence.

As I was still figuring out what my role as a CTO meant, I realized I encountered a difficult transition from coding to having a skill no one else had. In coding, everything is black and white. There is immediate feedback: it’s either true or false. I built things that everyone wanted. In the role of the CTO, I had to work on non-coding skills that I wasn’t sure other people would want.

It did something to my ego. As a technical co-founder, I literally opened a blank Vim session and started coding the product that would make this startup millions. With this expertise came a sense of entitlement, and I figured if I continued to do this, it would catapult me into the rest of my career. That is not what happened.

As you build your practice or your individual contributor skill, inevitably, you add people to it. These people need to be led. It’s not difficult to lead a small group, or to lead if you’re the smartest person in the room, but that model fails quickly as the group grows beyond that initial five or six people. Being the smartest in the room suddenly becomes a liability because the group can’t grow beyond your weakness.

I didn’t realize that I had begun accumulating skills that could be helpful to other people—not only to other CTOs, but to other founders and other CEOs. I started acquiring these skills on my own every day, and it was only in the later part of my time at the startup I helped create that I realized I could help other people.

I became a connector. I was a community builder as well as a technical expert. I was in love with the people, while my fellow CTOs weren’t as dedicated to them. This made me different in my community. I became an organizer of the local Ruby meetup group, and I started the Golang group with a friend. I realized that finding people to hire meant being part of a community. It seemed to come easy for me. I found my passion in building communities wherever I went.

Finally, in 2011, I decided I wanted to connect with other CTOs to learn from them and help myself be a better CTO to my startup. This was the birth of 7CTOs, a peer group created for CTOs to help each other. As of this writing, I am still actively building 7CTOs, which has grown to 300-plus members worldwide. Our doors are open to any and all CTOs, VPEs, and technical co-founders who want to find their tribes. Head over to 7ctos.com and apply!

Why I Wanted to Create This Book

I wanted to create this book to talk directly to you, the CTO. I know most CTO-types come from a programming background and, in many cases, have been programmers since an early age. You have built products and services all your life, and you are most comfortable working with technology. Similarly to you, I have known what I want to do from an early age; I am also a technical person.

I have learned, through working with many CTOs, that there are key characteristics that drive phenomenal CTO leadership. I want to share these characteristics with you and help you learn how to develop them. I want to help you understand the role and responsibilities of a great CTO. I want to show you how to own the role of the CTO and how to remind the CEO of your role. Most importantly, I want you to understand the real role of the CTO.

This book is split into three parts. In the first part, I look at what you can do to set yourself up for great CTO opportunities. In the second, I walk you through a 100-day framework for how to excel in your CTO role. In the final part, I take a look at some challenges you may have to deal with day to day and offer you some tools to help you navigate those. Throughout the three parts of this book, I will help you show up with your power and with your sense. If you can do this, you can flip things a little bit, where you can say, “How can I help your company? It’s not about me or who I am. It’s not about my commitment. It’s about my presence of mind, my management style.” You need to be curious about how you can join with the company’s uncertainty and navigate people through it.

I’ve seen positive outcomes from this mindset. At times, you will get high fives and amazing sessions; other times, you will have simply averted a disaster. Sometimes, the conversations will reveal more work to be done, and oftentimes, that work will fall on you. You want to weather the storm and survive it.

I want you to come away from this book with an understanding of how to have those difficult conversations. You have to be careful not to get resentful and passive-aggressive. Instead, you want to gently guide conversations to a solution. You want to provide overall value to the company, especially in the first 100 days. If you are relentless in positivity and providing continuous value, that will not only help you succeed with the company in front of you, but it will also give you the reputation you need to approach future companies.

I want you to come away from this book with a renewed confidence in yourself. I want you to know how to show businesses that you are there to do business and get results through a system of communication and innovation. Some companies may fawn over you and hold you to impossible standards; I want you to know how to help companies tone this down. While praise is great, you are not involved with the company to be put on a pedestal. You are present to help solve issues through team building and finding solutions. Therefore, you need to take back your power. Focus on the “why” of the company and be the person who takes the wheel.

I want you to come away from this book with a devotion to participating in the process that provides solutions to problems. This is the value that you bring, and I want you to know how to present that value to CEOs. Know what you can accomplish and what results you bring with you. That is the positivity. It is the compression of the coal that brings the diamond.