Being a CTO at a small startup with 2-3 people was exciting. Titles didn’t matter, they had no weight except when pitching to investors. All that mattered back then was how fast you could put together a working prototype together.
When I was promoted to CTO at a much larger company that’s when I struggled. One of the biggest challenges was actually the title itself. In my case, I went from being a productive engineer to worrying about how others viewed me at the company and if I was living up to expectations. Your classic case of Imposter syndrome .
How long did it take me to overcome my imposter syndrome? About two years! and a lot of sleepless nights. Luckily for me I had a good mentor with a lot of patience. I still don’t feel comfortable on some days but I’ve learned to trust that usually means your heading in the right direction.
Looking back there were a few pointers I wish I knew beforehand that I want to share.
Technical CTO or Manager CTO
The biggest problem with the CTO title is that no one really defines the role for you. The reality is the job changes as the needs of your company change.
If you are confused about what to do next, ask yourself what your organization is lacking and head in that direction. For me, we needed talent so I focused heavily on recruiting one quarter. When we brought in competent engineers I focused on mentorship and performance. Then one quarter I was back working on technical side of things.
The reality is your role will change with the company so there isn’t a guidebook on being successful in this role.
Don’t Lead by Title
Don’t refer to yourself using your title. I have found titles are good for rewarding hard work but have little meaning in modern organizations.
Introduce yourself as a “team lead” or “leading the engineering teams at X company”. I still remember introducing myself during a meeting with a client. I was quickly met by a sarcastic “Whoa, we’re talking to a CTO!". It leaves a weird awkwardness which is not really needed in the first place.
It’s better to ditch the title early and talk to people on the same level. I would even go as far as removing it from your business card.
It sounds simple enough but it’s hard to drop your ego if you have one. The faster you can forget about your title the quicker you can get on with real work!
People Pleasing
I do and still often like to please people. This has helped me succeed quickly in my early career as a software developer as I would take on large amounts of work to please upper management.
When you become responsible for people this strategy quickly backfires on you. I was lucky enough to get direct feedback from a peer and course correct early.
If you don’t know what people pleasing looks like here are a few signs:
- You settle for mediocre because you don’t want hurt an engineers feelings.
- You try to make excuses for low performers and lower their bar compared to the rest of the team.
- You find yourself running around trying to please an engineer that is upset with your company culture.
Heed this warning, if you are too nice you don’t communicate direct feedback your team members desperately need to improve. Worse, you keep a disruptive team member in your company longer.
Mind Games
Jealously, fear, anxiety, I have these all and my mind still messes with me. However, if you can push through the discomfort and accept failure as a learning experience you quickly adapt and don’t get easily phased when there’s problems.
Conclusion
Congratulations on the promotion, your challenge in the new role will be yourself! My advice, keep calm and try things that make you uncomfortable, this is the best way to learn and the quickest way to build a hard skin.