Details of a Great CTO From Someone Who Has Never Been One Before

I'm probably risking a lot in terms of opportunity and job prospects in releasing this, but at the same time, any person who finds their way to this post actually cares about getting to know who I am. Please know that I respect the gesture immensely and have hope that if you've come this far, my opinions have a good chance of being understood rather than used against me.

Anyways... I've never been a CTO, but I've gotten to know and work with a few by now who have understandably had different strengths, backgrounds, and focuses.

The first CTO I worked with was amazingly both business and technology savvy and did no coding whatsoever. Another played the role of every C level position you could think of. He was the only guy in the 6 person company who pitched investors, focused on sales, and committed code. The guy even did the shopping for all the snacks and drinks in the office. I'm trying to convey that I understand a CTO's roles may vary, and that my distinction of his/her competency is not entirely dependent on whether programming is involved.

One CTO I worked with was oh so very incapable in my opinion that he is legitimately driving talent away. Previously, he was never a developer, worked with developers indirectly and above multiple levels, and had previously never demonstrated technical competency or interest.

His merit literally came from being the CEO's neighbor/buddy, being a big wig as a VP of Product (Big-Wig-Corporate-Title GALORE! Quora thread to the rescue for a defition on the title), showing off with cringy techie stickers like "I love APIs" on his laptop (true story), and spewing buzzwords that he didn't really know all over the place to other people with similar d-bag power who definitely didn't know wtf those words meant. My takeaway from this? Talk and marketing goes a long, long way in the real world. I digress.

I'm going to take this moment to vent on a few of my gripes with a bit of detail:

  • Being there only to complain and point fingers than to be a part of the decision and discussions within the dev team. Not failing together with us but always focusing on grabbing credit for accomplishments.

  • Thinking everything is easy and wanting things done yesterday without caring to take the time to understand the complexity and drawbacks of decisions and problems.

  • Considering the number of lines of code as the best and only way to gauge contributions and enthusiasm.

For God's sake, CTO is an acronym for Chief Technology Officer!

From a scale of 1-5, with 1 being slightly involved/focused on (at least more than nothing) to 5 as a must, I think that a CTO's responsibilities and relationships between his/her development team should include as much of the following as possible:
  • 5/5 - Knowing how to code his/her way out of a paper bag. Like, literally have him/her solve this (code is in Go):
func main() {  
    enterPaperBag()
}

func enterPaperBag(){  
    for true {
         // you're stuck, GTFO.
    }
}

I will bet my bitcoin, altcoins, and my sub-par-but-still-capable mining rig that my CTO couldn't do this.

  • 5/5 - Be a part of the meetings/discussions/tasks that the development team is involved in as much as possible. This includes a few things such as retrospectives and sprint planning.

  • 3/5 - Try to contribute to the technology space via mentoring and talks/panels/discussions whenever possible. Collaborate with other people in the same space. Ex. Do a blog post on a problem you faced with your team and how you tackled it.

  • 5/5 - Take time to understand the decisions surrounding the technologies used in the product stack, its advantages and disadvantages.

  • 5/5 - Promote growth within the team in the form of training, involvement in conferences, etc. Encourage your devs to attend a conference, at least be there to provide some kind of opportunity for growth.

  • 5/5 - Acknowledge your team and place a real focus on rewarding them if possible. If there are constraints with that, at least make it clear.

Hmm. Way more 5/5 than I thought.

Let me also add that I am aware that there are other details and responsibilities that I left out which may relate to other parts of a business, such as sales, kissing investors' butts, finding more investor butts to kiss, trying to change the world, working with the engineering team, doing "big picture" stuff, and so on.

While I've DEFINITELY written things in which I've gone back to after a few years and went, "what the hell was I thinking, I had no idea what I was talking about!", I really hope that one day, if I ever have the fortune and pleasure of being a CTO, that I will look back at this and have as little shit to say about myself as possible. We'll see.