How I went from Programmer to CEO in 3 years
I joined Goalist at the end of 2017 as a self-taught engineer with a creative writing degree. I’d built websites and apps before, but aside from decent programming fundamentals I didn’t actually know much about anything.
In January (2021) I was asked to be CEO of HumAIn, a subsidiary of Goalist.
Of course, there was a healthy helping of luck involved. There are also three other main behaviours that helped me grow, and gain enough trust to earn this wonderful opportunity.
1. Create Situations that Force You to Learn
I knew nothing when I joined in 2017 (that’s not entirely true, but it’s a Jon Snow reference). Thankfully, I was also aware of that fact. So fresh-out-of-college-me hatched a cunning plan in an attempt to learn as much as I could.
I was joining a startup, and startups are well known to be an environment where people have to “wear many hats”. With this in mind, before even starting work, I decided I would agree to work on literally anything for the first one year, no questions asked.
My thinking was that this would force me out of my comfort zone and would help me create a solid foundation of knowledge to build from.
So when they asked me to work on a Natural Language Processing AI task (for which I had no experience) I said yes, and requested that I have access to material to allow me to study it while I worked on the problem. It was new ground for the company as well, which had focussed on data crawling and cleaning until this point.
3 months later, this ended up being the first functioning AI in the company. I spent the first two months making completely noob mistakes, thinking I was doing well, and suddenly realising in a moment of panic that no, actually, the little AI was still not able to generalise.
Later, I was also asked if I could design a database for our new recruitment platform, Jopus. Did I have database design experience? No. What did I say? Sure.
Design a test to screen applicants without language bias? Okay!
You get the idea.
I want to highlight here, that pretty much everything I worked on during my “do everything” phase, had times when they were on the brink of failing, and yes many of them did fail.
When you screw up, tell (the right) people about it so that the team as a whole can limit the impact of the mistake and recover quickly.
Here’s where I noticed that I had had a lucky break.
Goalist has a strong value system. One of those values is “Share Bad News Immediately” and another one is “Take Action”. My lucky break was that, coincidentally, the organisation’s core values took into account that young, foolish folks like myself would make a bunch of mistakes.
Instead of creating a culture of blame, the organisation was using a very healthy work flow to handle mistakes. When you screw up, tell (the right)people about it so that the team as a whole can limit the impact of the mistake and recover quickly. We were able to apply the “fail fast — fail small learn and move on” idea within the company for the employees.
These two things ended up creating a growth algorithm that felt like it packed a year’s worth of experience into a few months.
The same principle applied to me taking on the responsibility of being the CEO of HumAIn as well. I’ll make many mistakes along the way, but if we can continue harnessing the power of the team to focus on recovery and continuous improvement I’m sure we’ll be able to pull through.
2. Use Empathy to help people grow
I quickly began to learn how little I could accomplish on my own. Being able to leverage the power of a team is much, much better and it follows that the “better” the people around me are, the more we can achieve as a team.
We may intuitively know what to improve in ourselves, but when it comes to other people, what is “better”?
There’s many schools of thought on how to encourage people to grow. My own opinion here is heavily shaped by Peter Senge’s “The Fifth Discipline”. The core of this book is about creating a learning organisation, and there’s a chapter on “Personal Mastery” which helped shape my thinking about encouraging people to grow.
Based on the principles in the book (on which I could write another article), I proposed that we should create a framework for employees to create personal visions and self-manage their progress towards those visions. Participation was voluntary.
The results were quite a patchwork. However, sitting down with everyone while being as unbiased as I could, and just acting like a sounding board and a question-asker for their dreams and goals helped me become better able to connect with them as people, understand their motivations, become better able to empathetically interact with them. By the end of it I was able to build a very personal connect with over half the company. The employees felt valued, and many of them used the framework to learn new skills or change unhelpful mental models.
So how did this help me become a CEO?
I believe the skill that I began to develop in these 1-on-1 self-improvement discussions held me in good stead later during projects with tight deadlines. Under pressure, resolving problems with constructive criticism needs to be balanced with empathy and understanding to keep the team’s morale high. Handling people like this even during times of stress further builds trust and makes people more open to learning and growth, making a stronger team.
3. Keep Asking “Why?”
People make decisions that I don’t understand. This seems to happen because:
- They have access to information I don’t know
- They are awesome, intelligent, and totally outclass me.
- They have made a bad decision
Given the opportunity, in each of the three situations there is great merit in learning more about the decision. It is particularly in this context that I’m advocating recursively asking “Why?” (yes, shamelessly. Harness your inner 5 year old).
I try to view the first two cases as cross-checking my own decision making process with others’ and learning about how I could replicate their process. Why do they have access to that information? Can I replicate their process to make better decisions myself? Asking “Why?” a few times can get another person to reveal frameworks and mental models that they have gained through years of experience.
The third case is often the first two cases in reverse — where I have information, or a thinking framework, that the other person does not. Asking “Why?” creates a chance to “debug” a colleague’s thinking without friction, uncover untested assumptions, and offer ideas or frameworks that may help them avoid similar bad decisions in the future.
It’s a very rare case that one “Why?” is sufficient. Both in my own answers to the “Why?” question, as well as those of others, both senior and junior, the answer to the first “Why?” is a well processed conglomerate of assumptions. Picking out things in each answer that don’t make immediate sense to me and asking about those in turn are what eventually lead to learning for me.
Curiosity is an extremely powerful tool, and I’m by no means a master of it. But it has been invaluable tool to improve myself and those around me, as well as way to actively prevent bad decisions from being made.
4. Luck
Luck deserves its own section in terms of importance in the story, but by definition it can’t be controlled, and doesn’t provide any applicable ideas to a reader. So I’m going to leave it without much elaboration, but I’m happy to share some stories in a separate post.
From my point of view, the points I’ve explained here played a concrete roll in increasing my actual capability (as well as what people perceived to be my actual capability) to deal with a variety of challenging and ambiguous situations. They are also things that worked in my specific situation and context to get me to where I am now. I believe that the ideas are applicable more generally, but I’d love to hear about other experiences as well.
Keep learning!
