Ask HN: I don't enjoy being a CTO. Now what?

Take a mental step back, and look at the business as a large computer, everyone's crap as bugs, fires as serious bugs and dealing with other managers as a high level architectural/resource allocation problem.

Then get to hacking! Refactor the program (your role and tasks) until its running smoothly (i.e. you're happy) then start adding features. Learn to apply (not so shiny) new technologies (management methods, time management, people management). Set up a test suite to compare what you want to what you actually get. Red - Refactor - Green. (Seems like all your tests would be a solid red at the moment:)

Do top down and bottom up analysis - make specs for what you want as a CTO, and make specs for what you'd want (as a programmer) from an ideal CTO.

Set up your own performance benchmarking suite with the metrics that matter to you: Fun factor, coding opportunities, battle to relax ratio, etc...

Just make sure to stay ethical, DRY and most of all, keep it interesting and fun. No black hat hacking when dealing with people.

(Oh, and if you know parallel programming, start a new thread called $JOB_SEARCH to run concurrently while you do all this)

P.S. I've trained (successfully) quite a few new managers, specifically highly experienced technical staff that move into new positions of management. The most recent one I did was for a global telco hardware provider. I can send you some of my workbooks (for a 3 day course, covers the main basics about moving into management and being happy and great at it) if you want to hit me up - email is in my profile. I pinkie swear I won't out your real profile, or you can just set up a throwaway email if you're really worried.

(When I frame myself as a technical leader, there's a quick assumption that I don't grok sales/marketing. If I introduce myself as a "Harvard MBA & angel investor", there's an immediate conclusion that code is beyond me... Nice to know that, when both are presented, the engineer wins. :) )

That said, sales is one of the easiest areas to hire for. I respect sales very much, most of my co-founders in the past have come from sales and I've learned a lot from them. But enterprise salespeople pay for themselves, have less/no expectation of equity, and expect to bounce from job to job every year. At some point I'll need a sales leader to manage a sales team (subdivide industries/regions, hire/fire, etc.) But that's not a founder-level role.

The biggest thing I need is going to be a great CFO. I'm getting into the logistics business (software eats fulfillment?), which is pretty capital-intensive. Debt is a better instrument for this than equity, but I have neither the time nor the temperament to secure that.

I'm broadly anti-VC, but may end up pitching primarily for the credibility with lenders & institutional investors.

1) Are you ok with not coding and just have a technical vision and dealing with people constantly ?

2) Does the CEO respect technical part of the project ? that means he doesn't think that he can imagine anything and then the CTO will do it with his team.

Let me explain each point:

The first one: as a CTO most of your time is spent on:

- [Hiring] this part will probably take 20% to 30% of your time. you have to interview them technically and be able to sell your company and motivate them.

- [Communication] Communicating with the CEO and other key roles: this is everyday, you have to be involved in every decision concerning the product. and you should be able to explain clearly why you are against or for a feature in the product (this one takes maybe 30% to 40% of your time!)

- [Technical] Macro architectural decisions, code revision, etc.this is paradoxically the easiest part ! it should not take more than 20% of your time.

- [Management] Making sure that developers are motivated enough, talking to technical team every morning and trying to understand their feelings and vision and deciding if they are in line with the culture of your team. this part should take 20% of your time. if it takes more than that, that means that you didn't do the hiring very well. so you should spend your energy on firing and hiring again.

The second one: Does the CEO understand that technical decisions are vital for the project so he has to include you on any business decision ?

If yes, then it is a good news. but if the CEO is that old school guy who thinks that any idea can be implemented by engineers and the CTO is the responsable for any non respected deadline then just run. quit, don't even try to change his/her mindset cause you cannot. usually it is really easy to figure out that the CEO respects technical part or he just pretends to respect.

Hope that helps :)

PS: Most people (myself included) cannot dive into code and dealing with people at the same time. When I am coding I don't even here what people is telling me. so I cannot be good at management. that's why I think that a CTO should not code at all.

Cough Elon Musk