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Ask HN: Going from CTO to Developer?

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Re: Ask HN: Going from CTO to Developer?

#42
post #27

I'm an ex CTO. I ran the company as basically 2ic for 5 years before I quit. Before I quit they offered me profit share which was stupid because profit can easily change. I do not regret leaving at all from a mental health perspective. I was losing my friends, family and myself. I do regret leaving because afterwards I'm just a loser developer, lumped in with the guy that moves the button left a bit, when before I wa…

Very possible outcome for OP too.

The weakest part is usually the human factor and the need to bucket someone into a few categories like "rock star" or "loser" or "slightly better than unskilled labor" or "nerd engineer".

Have been in a similar situation and sadly found unless your peers have truly understood what you've done and how, they'll filter your suggestions or insight through whatever bucket they've placed you in.

Re: Ask HN: Going from CTO to Developer?

#43
post #25

I flinch whenever I see people talking about "being a CTO", because there's really no such thing. The title doesn't really mean anything. In startupland, three possible (and possibly overlapping) meanings of the title are: 1. The corporate officer title a founder that isn't the CEO gets because they're on the board, purely as recognition of their seniority ("why is this person on the board?" "because they're the CTO.…

Surprised to see such a cynical and negative comment from such a well known account. CTO at early stage startup is often the most important person in the company, technical delivery/execution, hiring, early decisions on which frameworks, integrations, helping with sales, etc.

The obvious cynicism aside, what you said doesn’t really contradict point #1. All those responsibilities can be taken by any IC in pre-seed/seed startups (except the wrongly stated “most important person on the company”).

Re: Ask HN: Going from CTO to Developer?

#44
If you want to go back to IC role, that should not be a problem anywhere really.

If you are tired of "all the responsibilities, management, etc" then you will probably not follow that path anymore, you tried and it's not for you.

However, if you ever decide to follow that path again, be advised, boards/founders want to hire C-level people who have a proven track of building successful organizations through good and bad times. Having even a single occurence that signals you were "tired of all the responsibilities, management, etc" will disqualify you.

Re: Ask HN: Going from CTO to Developer?

#45
post #13
post #8

I'd love to hear about the other direction. What kind of skillsets or prep can a problem solved do to transition into more leadership roles? Is it primarily getting an MBA? Getting lucky?

No need for an MBA. You can make your own luck here: start by taking on voluntary leadership roles such as mentorship, or running initiatives within your company (setting up an informal team to codify source code management practices, that kind of thing). Make sure your own management know that you are interested in this path. The book The Manager's path has excellent advice on ways you can prepare yourself for manag…

> start by taking on voluntary leadership roles such as mentorship, or running initiatives within your company (setting up an informal team to codify source code management practices, that kind of thing).

This I have been successful with at multiple companies. Often bringing a complete shift in development practices / headcount allocation strategies. I've setup multiple teams and initiatives at my current FAANG employer as an L3/L4. My most recent one was a library which is being used by extremely high priority projects with VP-level visibility.

> Make sure your own management know that you are interested in this path.

This is where I have been extremely unsuccessful. I explained that at some point in the future I wanted to be at the Director or VP level. One of the higher level employees that I was discussing this with laughed at me (she also did the same about my library and other initiatives only later to applaud when our VP thanked me for landing them).

My manager and skip level manager are advising to "take your time" and "you may not actually want that" and similar things. They say to focus on L+1 which I do understand as a priority but what I am really trying to communicate is:

1. Long term I'd like to be higher level leadership

2. I don't know if the skills I am learning right now will put me on this path

3. I want to in the short term work on high impact projects and in the long term build the muscles needed so that when I say "I'd like to be a director" no one laughs at those ambitions

Re: Ask HN: Going from CTO to Developer?

#46
post #40
post #37

Earlier quoted context omitted.

As an eng manager, I always make it super clear (many times) when new engineers onboard they're always welcome to say "this doesn't make sense" ask for more details. Sometimes (maybe even often) they're right. I also enourage them to "assume good intent" from other devs and managers. Fundamentally no one manager knows everyone and no one engineer is right about everything.

Yea, the problem is that bad managers likely end up being bad because they don't have this humility.

I don't think it's really a question of humility. it's more about placing the highest value on the functioning of the team. once your overriding goal is 'not looking bad', and 'escaping blame', that goal, which should be primary gets completely lost.

Re: Ask HN: Going from CTO to Developer?

#47

Earlier quoted context omitted.

Surprised to see such a cynical and negative comment from such a well known account. CTO at early stage startup is often the most important person in the company, technical delivery/execution, hiring, early decisions on which frameworks, integrations, helping with sales, etc.

The obvious cynicism aside, what you said doesn’t really contradict point #1. All those responsibilities can be taken by any IC in pre-seed/seed startups (except the wrongly stated “most important person on the company”).

Sure, but then that IC, if executing correctly should just leave and found their own startup. And true, sales/building the right thing is often #1.

Re: Ask HN: Going from CTO to Developer?

#48
post #13

Earlier quoted context omitted.

No need for an MBA. You can make your own luck here: start by taking on voluntary leadership roles such as mentorship, or running initiatives within your company (setting up an informal team to codify source code management practices, that kind of thing). Make sure your own management know that you are interested in this path. The book The Manager's path has excellent advice on ways you can prepare yourself for manag…

> start by taking on voluntary leadership roles such as mentorship, or running initiatives within your company (setting up an informal team to codify source code management practices, that kind of thing). This I have been successful with at multiple companies. Often bringing a complete shift in development practices / headcount allocation strategies. I've setup multiple teams and initiatives at my current FAANG emplo…

Only advice I can give you is pick your team/company very carefully. Choosing the right team can open up promotion opportunities that other teams might not have. Half the battle is putting yourself in the right situation. Also, big promotions commonly go to people that have lasted a long time in some organization. I saw people at FAANG spend a decade in one organization, then finally get recognition and ended up a few levels higher in a quick fashion. The people you spoke to were laughing because the high ups probably got there very early, there is no path to their level because the cake is baked, that company doesnt have growth opportunity.

Re: Ask HN: Going from CTO to Developer?

#49

Earlier quoted context omitted.

The obvious cynicism aside, what you said doesn’t really contradict point #1. All those responsibilities can be taken by any IC in pre-seed/seed startups (except the wrongly stated “most important person on the company”).

Sure, but then that IC, if executing correctly should just leave and found their own startup. And true, sales/building the right thing is often #1.

Agreed.
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