Ask HN: I don't enjoy being a CTO. Now what? • Hacker News Board

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

#151

Post by tat45 » Mon, Jun 13, 2016, 4:58 PM UTC

I was a manager and a lead technical analyst (basically a CTO with a much narrower scope than a full company). I now refer to the nine years I spent doing this so-called "work" as The Lost Years, because I wrote very, very little code and my skills dried up.

There are some people who enjoy it. But I found it to be exactly as unfulfilling you described it, for much of the same reasons (spent too much time fighting management fires and not enough time solving technical problems), and it ultimately drove me back to being a software developer. Thank goodness my skills hadn't atrophied completely, but I'm definitely behind my cohort in terms of expertise, and I spend too many cycles regretting the lost time I could have spent growing my skills.

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

#152

Post by DelaneyM » Mon, Jun 13, 2016, 4:58 PM UTC

rorykoehler wrote: post #148

DelaneyM wrote: post #74

Earlier quoted context omitted.

> While I certainly see evidence of this in the workplace, I also see that this kind of leader would be exceptionally valuable to any organization. You'd think!! I have a few theories as to why this is so: The most charitable interpretation is that, since technically competent business leaders are so incredibly rare (set aside that every engineer thinks they can do it), there's no design pattern for that leader. Owne…

I always viewed tech as a tool to improve the other aspects of the organisation. What are you doing with tech if you are not improving either operations, marketing or finance?

It could also be your product.

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

#153

Post by giaour » Mon, Jun 13, 2016, 5:02 PM UTC

DelaneyM wrote: post #93

tamana wrote: post #89

Earlier quoted context omitted.

Why would a techie want a MBA job below VP level? Most don't want to be advertising account managers or business analysts either. Does that matter?

tl;dr: If there's no reason to get an MBA as a promotion-track engineer, then not only will none of your promoted engineers will have MBAs, none of your promoted MBAs will have practical experience being a great engineer. They wouldn't, of course. And that's really the problem. If you don't have mid-level technical managers with MBAs, you don't get to promote/hire VP-level technical MBAs. An MBA does teach a lot of v…

You might be right about the startup world, but there is a massive demand for techie MBA/business-y Eng at the sub-VP level in big tech companies with tiered management. That sounds like exactly the skill set you would need to manage a division or org of one of the big 5.

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

#154

Post by roymurdock » Mon, Jun 13, 2016, 5:13 PM UTC

nekopa wrote: post #139

DelaneyM wrote: post #125

Earlier quoted context omitted.

This needs to be solved demand-side, not supply-side. If you graduated a class of TechMBAs right now they wouldn't have any jobs to use their new skills. Flip it around: if Google opened up a new role for "Active engineers with MBAs", and presumably a few others followed suit, a top school or two (GSB/HBS/CBS/etc) would create the curriculum & recruiting plan to fill it. (Most likely Google could do this together wit…

Is this not a classic chicken-egg scenario? I think if you graduated a class of TeMBAs right now, they would have jobs just because of the MBA side of the equation. And, I think they would kick-ass in what ever job they take because of their tech skills. Even stooping as low as to say that their Excel skills would rock because they know how to masterfully program macros. But WOW , yes, if someone like Google got behi…

An MBA doesn't really confer any skills that couldn't be acquired from 6 months of actually working/managing at your target company - it's seen as more of a networking tool, and a way for someone to hit the reset button and shift into a different field, or to get a raise within a traditional consulting/corporate migration path.

So I have to agree with DelaneyM that the crux of the issue is demand-side: where is the need for specific managerial jobs that require a baseline technical understanding (to estimate timelines, speak intelligently about the product with clients, etc.) as well as basic business skills (negotiation, project management, strong network for potential clients) that is worth the salary that an individual who just invested $200k and 2 years worth of time will be asking?

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

#155

Post by DelaneyM » Mon, Jun 13, 2016, 5:14 PM UTC

giaour wrote: post #153

DelaneyM wrote: post #93

Earlier quoted context omitted.

tl;dr: If there's no reason to get an MBA as a promotion-track engineer, then not only will none of your promoted engineers will have MBAs, none of your promoted MBAs will have practical experience being a great engineer. They wouldn't, of course. And that's really the problem. If you don't have mid-level technical managers with MBAs, you don't get to promote/hire VP-level technical MBAs. An MBA does teach a lot of v…

You might be right about the startup world, but there is a massive demand for techie MBA/business-y Eng at the sub-VP level in big tech companies with tiered management. That sounds like exactly the skill set you would need to manage a division or org of one of the big 5.

Demand & applicability != opportunity.

Maybe it's chicken & egg, maybe it's a Unix philosophy applied to organizational design (https://en.wikipedia.org/wiki/Unix_philosophy#Do_One_Thing_a...), but there is virtually no true demand for an engineering MBA.

I'm happy to be proven wrong with a counter-example of a posted job description. Try to find one example of a hybrid position with more potential and better pay than a corresponding pure engineering role.

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

#156

Post by Joeri » Mon, Jun 13, 2016, 5:17 PM UTC

unhappycto wrote: post #79

lwhalen wrote: post #32

What I'm about to say may be considered harsh, but I promise I don't mean it to be. Quit. Just leave. Go back to coding. It's obvious you don't enjoy management, there's no shame in admitting that. Rather than inflict your misery on the rest of the team, get back to your wheelhouse where you can be happy, your team can be happy, and ultimately your company (current or future) can be happy. I have worked in a job wher…

Thank you for this, it's the way my mind has been leaning but it's good to hear. I realize my original post makes it sound like I had no idea what being a senior manager might involve which is just not true. I understand a lot of fire fighting and dealing with problems is par for the course I just didn't know if I'd enjoy doing that or not. How are you supposed to know until you try? :) I also felt like I'd have way…

A manager should set the course, provide the means and assist in navigating the rough patches, but they shouldn't be at the helm shouting instructions at the people climbing the sails. A manager who tries to take control typically leads to frustration for everyone involved.

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

#157

Post by a13n » Mon, Jun 13, 2016, 5:20 PM UTC

amelius wrote: post #84

reboog711 wrote: post #20

Earlier quoted context omitted.

Over the years; I have found very few valid business reasons to re-write a code base that is still supporting the relevant business. As a CTO, there is a good chance the poster would not be materially involved in such an effort. From a business perspective; something that works is more important than something that is well architected.

Tell that to the Facebook team who recently rewrote their entire front end codebase using React.

I was also at FB when they hit File > New Project on their iOS app which IIRC drives more revenue than anything else at the company.

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

#158

Post by embwbam » Mon, Jun 13, 2016, 5:21 PM UTC

I had a similar experience. I'm a great coder with good communication and leadership skills. In 2009 I co-founded a hip startup in the TV space. I had experience as a senior / architect prior to this, but this was my first time as CTO, let alone any management position.

I LOVED the first year. I was solving difficult problems, working productively, coding like crazy, learning a lot about business and startups. But it was just me and a contractor or two.

In the second year we were growing and I started to recruit. I didn't really like finding people, but I loved creating a great culture and productive environment, so it wasn't bad. I found some great people to hire and continued to be the lead dev. I started to experiment with process and getting teams to run themselves.

By year three we had 12 devs, and multiple teams. I was spending a lot of time cleaning up after unwise decisions and trying to implement process to keep us productive. Our apps and team got big. I loved being in flow and coding so much, I would drop the ball on management tasks to finish features I was shipping. I was involved in too many things: product decisions, partner deals, traveling, and our customer development research (we were floundering and making the wrong product at this point).

I hated it. Every time I procrastinated something I got more stressed and depressed. I tried changing my role to lead dev, but it was a mess and I left.

After wandering around and experimenting with different things for years, I think I've figured some things out. I'm contracting with multiple long-term clients. The skills and network I earned doing my startup have been great for finding work. I only take projects where I can have a high level of ownership and creativity (no team to deal with). I have been able to work with fun technology across multiple disciplines (in the last year: React, Haskell, Elm, iOS, Swift, Clojure, among others).

I do mess around with my own ideas sometimes, but I realized that what I really love is to create products, and I don't like management, or selling things I've created. So I'm most effective creating products with/for other people who are taking the business risk.

Not sure if there's anything in there you can use, but good luck! Figure out what you love to do, keep experimenting. I hated being a CTO too. There's no shame in figuring out it's not right for you, but it IS hard to allow yourself to go down in status. For me it was this big ego thing holding me back. Don't make that mistake :)

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

#159

Post by unhappycto » Mon, Jun 13, 2016, 5:28 PM UTC

sfmelton wrote: post #128

I love being a CTO. You can design the technical organization you want to lead. If you are unhappy, change the design of your organization. It takes time (and money), but totally worth it. I think the key when you achieve product market fit is filling the roles in your technical organization with stronger leaders than you, and stepping out of those management positions. Plus, you can learn from and partner with these…

This is a great response, thank you. Unfortunately for me, it's unrealistic as we simply don't have the budget to hire all these people.

I see a future over the next couple of years where I have someone great in each of those positions but it will be a long, hard journey to get there.

This whole thread has given me a lot to think about and I wish I could personally thank everyone. However HN is limiting my responses so it might take a while!

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

#160

Post by msgerbush » Mon, Jun 13, 2016, 5:33 PM UTC

DelaneyM wrote: post #150

msgerbush wrote: post #147

Earlier quoted context omitted.

This is obviously a personal question, but as someone looking to transition from an engineer to more of a technical business leader, what would you consider the most direct and fulfilling path? It sounds like the ultimate goal is becoming a CEO/entrepreneur, but do you think the"increasingly unfulfilling" years as a CTO are necessary/unavoidable? How do you continue to get the sensation of building things, as you bec…

It depends on whether you want to end up in macro or micro business. If ultimately you want to be an entrepreneur, then try to sign on as an early/founding engineer with a qualified and capable business team. You'll learn most of what you need to do it yourself by proximity. Alternatively, consider one of the better incubators/accelerators as a way to draw a living salary while executing over time with support from y…

Great, that's exactly what I suspected, but nice to hear from someone who's been through it already. Thanks, again, and good luck with your new venture.