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Ask HN: Advice for a first time CTO?

4 points by websitescenes ↗ HN
I'm constantly learning and reading about technical leadership but I'm curious what experienced CTOs on Hacker News would say.

I've been CTO at E-DealerDirect for about 6 months now and so far my biggest challenge has been letting go of tasks as we scale. I'm used to hoarding work and I've had to constantly train myself to delegate.

Outside of that scenario, what else is important? What skills do I need to learn that I may not have now?

Thanks for your input, Hunt

3 comments

[ 3.4 ms ] story [ 15.6 ms ] thread
asprouse
Never underestimate the value of engineer training. Document your best practices and coding style. Diagram your software at a high level to show how different components interact. If you have any internally developed frameworks add documentation or at least an FAQ explaining why certain design decisions were made and examples of how to complete common tasks with the frameworks. It might sound like a big investment up-front but it doesn't have to be, start small and your materials will grow with your organization. Encourage your engineers to contribute if they had to figure things out on their own. Being able to point to these materials will help on-boarding and free up your time for high level tasks.
websitescenes
I've documented our stack and how things are connected but I've found it difficult to promote employee contributions. How do you incentivize contributions to documentation?
asprouse
I'll be honest it takes a bit of prodding at first and it's hard to do after the fact. I have found that it helps to ask for input from day one. For example if a user is setting up a dev environment for the first time set them up with your setup doc and tell them to take notes about any issues they have or things that should be clarified. The biggest incentive is knowing that your organization values employee feedback and will be receptive to changes they suggest.