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Ask HN: I don't enjoy being a CTO. Now what?
326 points by unhappycto on June 13, 2016 | hide | past | web | favorite | 219 comments
I recently joined a startup as their CTO and I'm hating it. They've been around a few years and have product market fit and now need technical leadership to grow the team and product.

It's my first senior management position, having been heavily code focused the last 12 years, with some small management as a senior/lead.

For my entire career I feel as though I've been working towards being the CTO and now I'm here I find it's not at all what I expected. It seems to be mostly about dealing with everyone's crap, trying to fight fires and constantly battling with the other managers and tech team to get things done. I haven't even written a line of code in months.

Over the past few years I've had a few gaps in my career where I have started my own business and been fully in charge of things. Those times were amazing although I never reached any level of sustainability. I thought perhaps being CTO in a startup would give me some of that same ownership, control and enjoyment but it just feels like another job. I actually feel a bit depressed by the whole thing which is a new sensation for me and my personality.

Am I expecting too much? Is it simply another job? What can I do to fix this or should I leave and get back to a coding job?

I'd love to hear from people with similar experiences!

PS. Sorry for the throwaway account but my main account has too much personal info for this topic!




tl;dr: in your situation many people go off and get an MBA. Don't do that. There's a reason there's only one CTO in HBS' 60,000 person alumni database (I am she.)

I was a very hands-on CTO for years after a decade of coding, and broadly enjoyed it. But as the teams I managed grew it became increasingly unfulfilling. When you're CTO, you're often excluded from business decisions which have a bigger impact on your team than any tech innovation, and the input you do have can be hard to relate to the shared business context of the CEO/COO/CFO.

So I went and got an MBA (Harvard).

Now I know exactly how to frame (and improve!) my non-technical contributions, have much more context on what "success" means, and have the credibility to really be a part of the senior team.

Unfortunately, there's no real place in the world for a highly technical business leader. You have to leave code behind at a certain point and spend your time on people/financial/planning issues. The ultimate end of that road is CEO, and not everyone wants to go there.

Also, I'd really misdiagnosed my malaise. What I'd been missing was not strategic input, but the opportunity to build things. To weave together inspiration and ideas into innovation and growth. I love building things and challenging assumptions, it fulfills me.

Now I'm off to start a new venture as a solo entrepreneur. The only truly successful technical leader is the founder, and that feels right. My last day at my day job is June 30th. :)


> Unfortunately, there's no real place in the world for a highly technical business leader.

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. Do you find that the issue here is that companies already at scale have separated concerns so highly that the management skills are more valued (so technical leaders go to startups / smaller places) or is this really just because us technical people like to build things more than manage things?

This is super interesting input - I think that on this answer, depends a lot of the future of companies, but also where technical folks can and should target. (Although you mention CEO which, I mean, that's a leadership role too hehe)


> 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. Ownership is ritually divided into COO/CTO/CFO, and of those CTO is linearly defined. Technical leaders are excluded from non-technical discussions by default, and norms are extremely hard to break.

^ This is why I recommend against great Engineers doing an MBA. There's just no role at Amazon/Google/etc. for that profile beneath the VP level, reporting trees for engineers/business branch at the second tier and never meet thereafter.

A different perspective is that in a sufficiently technical organization (ie: everyone, these days), technology is a giant black box to the rest of the leadership team. It's a big part of the budget and a massive component of success, yet completely opaque and unfamiliar to someone who rose up through sales/marketing/etc. In their minds, the CTO already has an outsize impact, and surrendering to them more scope is scary.


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 valuable skills. As many smart technical founders/leaders have crashed up against the corporate rocks of running a major division/initiative as business leaders failed due to distance from execution.

Right now though there's no role, and no opportunity, for a mid-tier (post-MBA) capital-E engineer. So there will be no MBA-toting, engineering-aware VPs.

Without business-fluent engineers (or engineering-fluent business folks) companies are deprived of interdisciplinary innovation. You get financial programs which ignore technical needs, and great inventions which don't have a market. Promotion which doesn't represent reality and deals which can't be executed.

Most of the frustration engineers have with business people is not that business folks can't do business well, but that they don't do so understanding the underlying technology.

And until there's a reason to want a techie MBA (or business-y Eng) at a sub-VP level, this isn't going to get better.


So why don't we, as an industry, talk to the Universities, and say that we really need a new program, let's say a TechMBA? (Or for marketing purposes, call it a TeMBA - that really rolls off the tongue :)

I'd think that there would be some interest around this from the universities, and business is really crying out for this too.

From the Uni viewpoint, it is another product they can leverage, whilst still using there in house competencies and also creating cross university synergies (HBS-MIT TeMBA)

For businesses, they get exactly the top management they need - even for non-tech companies - a CIO/CTO with solid tech skills and business skills is a sure winner.

P.S. Please forgive me for slipping in the word synergy. I truly believe it's a great word, with a great meaning, but has been flogged to death by the consulting industry.

{Edit} Actually, I like the idea of a TeMBA, I am going to start a AskHN: What would the syllabus be for a TeMBA?

{Edit 2} Here's the link:

https://news.ycombinator.com/item?id=11894955


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 with a school, they tend to have very close relationships.)


This is basically the APM program in Google. Google stopped hiring PMs without a technical background (either CS coursework, or professional experience as an engineer) in 2008, because they found that the PMs they did hire with no technical experience universally sucked.

They also have (had? it's been 2 years since I was there) an active rotation program between eng and PM roles, with the opportunity to transition permanently. A number of my friends did it; I'd seriously considered it, but my manager was willing to let me do PM-type roles without formally switching job titles.


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 behind a program like this, it would take off like nobodies business.

But I think we really need to get regular businesses (Davids, not Goliaths) behind this. And somehow, show them the benefits of a well rounded TeMBA graduate.


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?


This already exists: http://www.ntnu.edu/studies/mtiot . It probably exists in the US too.

The demand for them is crazy-high. Leadership roles in Norway are very rarely filled by hiring fresh graduates, but the consultancies lap them up.

It's an integrated 5-year master. They do engineering stuff the first three years, specializing in the third, and then they do two years of economics/business/leadership. It's very specialized, and to me it looks like they are OK at their chosen engineering discipline and OK at their chosen business discipline but not very well rounded. That's the sacrifices you have to make when you make a business/engineering combination but try to avoid making master-of-nones, I guess.

Their choices are (in each stage they can only chose one. 3. year available choices depends on 1/2. year choices):

1/2. year: CompSci/high-voltage/machine/marine

3. year: AI/digital economics/software/el. energy/heat & energy processes/production/marine projects and logistics/marine technical operations

4/5. year: economic optimization/project leadership/purchasing and supply/reorganization/investment and finance/innovation and entrepreneurship/HSE/strategy and business development


There is something similar in the US at Dartmouth (yes it has a slightly goofy name): http://engineering.dartmouth.edu/academics/graduate/innovati...

Basically they let you cross register with some Tuck Classes while doing research that is more self-directed than normal.

Source: I am in the program


Cornell has launched a program[1] that aims to be what you're describing here. There's also a Technology Management MBA from the University of Washington's Foster School[2], although it's more of a technology-oriented part-time MBA than a traditional MBA targeted at engineers.

[1] Cornell Tech MBA: http://tech.cornell.edu/programs/masters-programs/johnson-co...

[2] UW Foster Technology Management MBA: http://foster.uw.edu/academics/degree-programs/technology-ma...


> So why don't we, as an industry, talk to the Universities, and say that we really need a new program, let's say a TechMBA?

Its already been done, and there are a wide-number of tech-specialized MBA programs.


Lots of university have MBA-MEng joint program that will award 2 degrees upon completion. MIT's LGO program is such a program.


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.


Thanks - this is really interesting and thought provoking feedback.


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.


I think the difference between line of business software and companies that are actual software companies is so huge that it starts to make no sense to compare them.

I've worked on technology that goes out the door and contributes to the company's revenue stream, and I'd have been insulted if someone said I was in "IT". The cultural differences between that and truly working in the IT cost center is massive.

Most people who spend the careers working for banks and insurance companies never see the other side of the chasm.


In which case it's just one step removed. All products I have ever come across fix a pain point in one or more of the areas mentioned.


My take is that, at certain scale, the biggest problem is getting all the people to pull in the same direction. Technical leadership can define /how/ to pull, which can have a 10x multiplier if correctly implemented in the organization, but that implementation is a number of battles with messy human wills, which require psychology, not technology. As a CTO you may be able to hire directors who are good people pushers, to delegate most of that, or even perhaps a VP Eng if your company is big enough.


DelaneyM, your posts here, especially when combined, would make a pretty compelling article in their own right. Please consider writing them into a blog post and submit that to HN as well.


Thanks!

But the world (particularly our corner of it) is full of smarter people saying more interesting things. I feel like the best way I can contribute is not distracting readers from doing.


I think you underestimate yourself. Or overestimate other people :) There are plenty of uninteresting or non-useful comments posted everywhere, including on HN. Yours in this thread are both interesting and useful.


As a counterpoint, I use these distractions to center myself. There likely are smarter people saying more interesting things, but HN's feed also sometimes has things like "Java StringBuffer and StringBuilder performance". I would much rather read about a "TechMBA/TMBA/TemBA/STEMBA" proposal than about performance of utilities of strings in a language I don't use.


I second this! I would love to read a blog post - or a series of them - where you explain your thoughts in more depth.


It's funny how you hit the MBA nerve there. I've been considering going that route, but with the intention to get more involved with people from different backgrounds than anything else. I don't want the MBA to move away from my position as CTO, but to improve my abilities in other areas of the business and networking purposes. Would you still recommend not getting the MBA in that case?

This is all in preparation to take the entrepreneur route, while I can't simply take it right now.


An MBA provides only one thing: the opportunity to stop doing engineering.

Do you want to stop coding/building things, and instead build teams & business? Then do an MBA. There really is a lot to learn; it's not the irrelevant piece of paper it's often made out to be. The usual caveats apply (right school/program, work hard, etc.)

Do you want to be a higher-impact engineer? Don't do it. Apply to YCombinator, build more part-time projects, start a "sell stupid shit" on eBay company and learn the ins & outs of incorporation/taxes/financial tracking/etc.

Getting better at business & networking is a great idea, but an MBA for that alone is overkill.


> An MBA provides only one thing: the opportunity to stop doing engineering.

Holy smokes! If your statement is true, then here's me running in the opposite direction of that mba.

+1!


Think about it: MBAs learn non-engineering skills, so how could it possibly be otherwise. If you get an MBA and continue engineering work, then by definition you're not leveraging your MBA, and vice-versa. That's a huge simplification, of course and I don't completely agree with the OP, but that's the gist of her point.


There are exceptions to every rule, but I'd say within the context of "jobs at existing large employers of MBAs and/or Engineers" the true intersection of engineer & business is nonexistent.

(There are lots of places where it'd be advantageous to have both skills, but never necessary, which is my underlying thesis.)


It also provides access to an alumni network.


Not nearly as relevant/helpful it's often made out to be.

Executives are more helpful than most give them credit for. If you're a credible contact with real experience, and authentically ask someone for input or advice, most are happy to chat.

The thing about the vaunted "HBS network" is that if you're qualified to get in to HBS, you're extremely likely to be otherwise credible; those who wish they had access to the alumni network also tend to not have enough meat on their CV to get access either way.

I personally suspect that the most important networking aspect of an HBS degree is just humanizing executives and learning how to communicate with them. If you've got those two things down, actually connecting is much easier.


Interesting how you put it. The "devaluation of higher education" bit of this column struck a chord in me back then. It sort of lays out a similar point in a slightly different way:

http://web.mit.edu/krugman/www/BACKWRD2.html

Time will tell. :-)


> most important networking aspect of an HBS degree is just humanizing executives and learning how to communicate with them

So true! Probably this is the most important thing a good business degree provides.


Thanks for the reply. I had thought of doing an MBA a couple of years ago, albeit fleetingly. I don't think that will solve things in this current situation though :)

I also agree that perhaps my issue is more of building things rather than strategic input. After all, when building things for my own business is when I'm most happy so it's good to hear a similar conclusion.

Good luck with your new venture!


I'm also an HBS grad with a technical background (BS/MS comp sci + 7 years of coding before b-school). While I agree with most of your sentiments, I feel compelled to offer a slightly different view.

Regarding your comments around the CTO position, I think that is because HBS didn't pay attention to tech/startups until about 5 years ago (i.e.: Field 3, Startup i-lab, tighter recruiting with silicon valley). I'm guessing that in 10 years, we'll see more as the current batch of students mature in their careers and have the CTO position available to them. Additionally, most of the technical students in my class (myself included) decided to pursue the PM track for the very reason you highlighted -- to have a seat at the table when making significant business decisions. In my current role, I run product, engineering, and operations. I still code (python/flask/node/postgres) but I'm also responsible for the product roadmap and operations (supply chain, recruiting, call center efficiency). I have a direct impact on revenue/managing costs and driving results through the metrics we measure. More importantly, I work directly with the CEO and have even had the opportunity to present to the Board. I feel this wouldn't have been possible with an MBA.

tl;dr: An MBA can actually be helpful for technical folks. In looking holistically around product/operations/sales, the actual code is probably one of the less important things in achieving business goals. Take a PM track if you want to have broader impact outside of just dev work (but with the option value to continue coding if you like).


> Unfortunately, there's no real place in the world for a highly technical business leader.

So how do you account for Mark Zuckerberg, Elon Musk, Larry Page, and so on?

I think you meant to say "there's no place at Dronecorp for a highly technical business leader". It's logical that Dronecorp should hire Harvard MBAs who score high on agreeableness and are skilled at showing each other powerpoints.


See the last statement in the comment, "The only truly successful technical leader is the founder..."


Google and other well run companies have skilled technical people at all management levels.


I'd love to meet one, or see a job description for such a role.


When I was at Google my entire management chain had the title "software engineer" (except Alan Eustace, who officially had the title "VP of engineering" but had a hardware engineering background, and Larry Page, who had the official title of "CEO"). That was 6 levels up, including me. Amit Singhal (who was 3 levels above me and responsible for a department of 2000 people or so) was still titled "software engineer".


>So how do you account for Mark Zuckerberg, Elon Musk, Larry Page, and so on?

Is this a game of "which of those three does not belong"?

If so, too easy...


>Now I'm off to start a new venture as a solo entrepreneur. The only truly successful technical leader is the founder, and that feels right. My last day at my day job is June 30th. :)

Good move. All the best. I totally agree with this statement. For a technical person to become the founder gives the most amount of freedom. I have personally experienced this in my career. Working for corporates, I was often the tech lead of a project, with somebody else to manage the team, and particularly in Indian culture manager role assumes a relatively powerful role, and the tech person, is often frustrated. Even though you may feel, that it will be better off playing both roles, by oneself.

On this last point, I feel several tech people, although very able, often lack the confidence to play managerial roles. Have seen a friend who is CTO and very good, playing subordinate to his co-founder who is CEO. I feel he can play both roles, by himself and do it better. But can't help it, if he himself doesn't feel that way.

So, if you are feeling frustrated as a CTO, and want to have freedom while being able to get your hands dirty (programming, I mean). Being a founder, or even an equal co-founder should serve you well. If you can make it sustainable, nothing like it.

If you can make it sustainable, there is this risk of complacency. You may be too satisfied with just a lifestyle business. But that's another struggle & another story!


> Now I'm off to start a new venture as a solo entrepreneur. The only truly successful technical leader is the founder, and that feels right. My last day at my day job is June 30th. :)

Best of luck!


I'm an experienced CTO without an MBA but I largely agree. Having an MBA and continuing as a CTO employee doesn't make a lot of sense. I have a decent amount of business knowledge thanks to working at an accelerator, being an early employee at a successful start-up, and consulting.

However, most organizations want one thing from their CTO: deliver tech that fulfills the promise of what we sold. Sure, you'll have some product input, but in most cases you will be excluded from overall business strategy other than to answer "when can we have it?", or if you're lucky, "what are our options?"

This is true for a number of reasons, including:

- Maybe the CTO shouldn't be making strategic business decisions. If it's not a consumer start-up, the CTO is often not the most clued into the market, either for lack of access or because they're so busy managing the delivery of the solution.

- Stepping on toes. In a perfect world, no one would get threatened if you see something on someone else's turf and point it out as gently as possible. We don't live in that world.

Personally, I will most likely found my own company, knowing fell well that I will be the CEO and that my development tools will change to communication and money management. An MBA could be helpful for this but it's not essential, from what I've seen.


> Unfortunately, there's no real place in the world for a highly technical business leader.

I'm not sure I understand what you're saying here. As I understand it, the history of Silicon Valley was written by highly technical business leaders. They might not be writing code, but they're sure providing technical guidance - sometimes on a highly granular level...(e.g. famously Bill Gates micromanaging date/time storage in new language development when MS was a billion dollar company).

I contest that if you're highly technical, it's very difficult to step away from that knowledge (especially when you're seeing things going wrong). Not a bad thing?

Also - congratulations on becoming a founder! Best of success to you!


> You have to leave code behind at a certain point and spend your time on people/financial/planning issues

As an exceptional case, you can get into a large tech company like Google/Microsoft and thus enjoy a higher position while still being able to do what you enjoy (coding and technical stuff).

I was faced with this same dilemma when I quit my day job in a large multinational company and started freelance programming. As you said, there are career roadblocks in most companies when you are more technically inclined than managerial. Besides, there is no large employer like Google/Microsoft/etc. in my country, so freelancing is my only option.


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 become further removed from the actual execution?

Thanks for your comments here, as an engineer considering an MBA and general career trajectory, this has been really helpful.


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 your peers in the program and mentors.

If you want to be CEO of Cisco, suck it up and be a non-building technical leader. Eventually you'll be able to absorb or grow your scope into a profit-centre of the business (engineering is usually a cost centre), and if you excel at that you can climb the rest of the way. This is really the only end goal for which it makes sense to do an MBA.


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.


> Unfortunately, there's no real place in the world for a highly technical business leader.

You were at MS. How do you call Bill Gates if not highly technical ? :-)

That said, I understand what you mean.

> Also, I'd really misdiagnosed my malaise. What I'd been missing was not strategic input, but the opportunity to build things.

Isn't that exactly what Steve Jobs was doing for a living at Apple (or Pixar)?

Again I understand what you're saying, but maybe not all companies/positions are so well defined as you make it sound.


Bill Gates was a drop-out, not an MBA. Steve Jobs was a ... wait for it ... drop-out but also not technical. Steve Wozniack was the technical founder of Apple.

If you really want to understand Jobs' talent, think about what Apple did when he left and how they changed when he came back. The technology didn't change that much (sure, Unix, but that wasn't _that_ big of a deal). The key difference is how they sold computers. After Jobs' was forced out, Apple started to copy the MicroSoft strategy: make computers highly customizable. Needless to say, that didn't work for Apple. After Jobs' came back, Apple stopped that strategy and started selling 3 options: good, better, and best. IMO, that's the real key of Jobs' Apple turn-around. He made it easy for people to buy computers.

Anyway, from that perspective, Jobs was all sales/marketing and not even close to what you'd consider a CTO.


Given your technical background, be sure to involve someone with a strong sales/marketing point of view whether that's a cofounder, investor, or friend. Moreover make sure it's a relevant point of view. For example, someone with a great b2b pedigree won't necessarily add the most value if you're starting a consumer focused company. Most importantly, best of luck to you -


tl;dr: My first hire, and ideal cofounder, would be a really great CFO.

(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.


Tip: you should leave your contact details on your profile, in case one is reading this.


OT, but I greatly appreciate that you put your post summary at the top instead of at the bottom. I don't need a tldr summary at the end...

Was that a result of learning about executive summaries in your MBA program, or just something you picked up along the way?


Actually something I picked up in my summer at McKinsey.

For web content, we think of "above/below the fold". For executives/investors, the analogue is "above/below the [first screen of my blackberry | iPhone alert]".


I like this phrasing from Wikipedia:

"The inverted pyramid is a metaphor used by journalists and other writers to illustrate how information should be prioritized and structured in a text (e.g., a news report). It is a common method for writing news stories (and has adaptability to other kinds of texts, e.g., blogs and editorial columns)."


Looking at your linkedin background, I see you have some adtech experience. This is perhaps one of the few industries that could actually use this technical manager in the middle of the organization.

I'm building a martech company right now and this is exactly type of people I hope to gain, someone who knows how the tech really works while also understanding the needs of the business and our clients to make the right decisions. They don't need to code everyday but having a grasp of how ad serving works, how logging and reporting is done, how attribution occurs through cookies and other identification, etc. would all help to make them more informed and capable at producing value for our clients rather than turning products into undifferentiated mush that add no value, like the rest of the industry.

Or maybe I'm just that technical founder who will always have to mix the two disciplines and make the call myself - just wish there was a way to delegate this.


> Unfortunately, there's no real place in the world for a highly technical business leader.

Cough Elon Musk


Cough solo founder.

> The only truly successful technical leader is the founder,


Elon Musk wasn't even a founder at Tesla, let alone 'solo founder'. He joined as financier/chairman after R&D had begun and then took over as CEO some time after that.


Good point, but it's not meaningful to the GP's original point. Self-made billionaire financiers write their own ticket, whether they are technical or not is merely a footnote.


+1!


A study of gifted people (probably relevant to a lot of people here) found that people who run, manage and/or start companies are the most satisfied with their careers: https://www.diva-portal.org/smash/get/diva2:281434/FULLTEXT0... and that gifted people in most other fields (law, medicine, etc.) as professionals are mostly good at what they do but indifferent about it. Start a company is great advise.


Congrats on taking that leap of faith.

Essentially in the same boat as you and agree on the value of the MBA is in communications.

While arguably technical business leaders can significantly help organizations, businesses just don't see that way.

I've made the shift to the business side and don't do any coding at all. More time is being spent planning, analysis, presentations and building relationships.

I'm also set to start a new venture on my own as solo founder. Good luck!


Just wanted to say thanks for the anecdote and good luck.


> Unfortunately, there's no real place in the world for a highly technical business leader.

There certainly is, but I'll concede there might not be in a random startup.

For a counterexample, John Carmack seems to have done well for himself as Oculus CTO, even coding interesting things by himself:

https://news.ycombinator.com/item?id=10273235


> Now I'm off to start a new venture as a solo entrepreneur. The only truly successful technical leader is the founder, and that feels right. My last day at my day job is June 30th. :)

Hey I'm off to start a new venture as a solo entrepreneur as well, my last day is June 30th, and I think we live in the same city. Neat!


>there's no real place in the world for a highly technical business leader.

Bill, Larry and Sergei, Musk and Bezos did ok


All of those people are founders.

My thesis is that there's no place in the world to be hired as an engineer w/ an MBA (which is comparably compensated to and inaccessible to "just" engineers or "just" MBAs), and no place within traditional hierarchies.


Ah - got you. Though I could counter with Satya Nadella who had a degree in Comp Sci and an MBA before joining Microsoft.


But he hadn't been a practicing engineer, and never worked in an engineering or technical capacity at Microsoft.


Bezos is not highly technical. Very smart, and grasps concepts very quickly, but not highly technical by any stretch.


I wasn't sure about that one and googled him a bit. He actually seems more tech than you might imagine. Apparently bachelor's degree in EE/CS from Princeton, where he was Phi Beta Kappa, worked as a programmer, wrote part of the original Amazon code in C and there was this on Quora:

>At Blue he reads every technical memo released to the company. He also participates in weekly reviews, and the more data-rich the presentation the better. He'll stop and analyze every plot and gives feedback to the point you think he knows more about the subject matter than the actual presenter.


4 exceptional cases aren't much of proof of anything..

It's like saying racism and equality is resolved because Obama is president.


I'm not sure if it isn't the majority of leaders of major tech companies aren't technical. Rometty at IBM also did computer science, Zuckerberg was writing networking and ML software at school. Tim Cook might be an exception.


Again, mostly founders.

Tim Cook though is my personal hero, and probably the truest counterexample. IMHO he's the most influential intersectional tech/business innovator of the past decade, and that includes Jobs. Only Hiroshi Mikitani comes close.

(Seriously, Tim: call me!)


Sure, but you're citing the most outlying of outliers as examples.


Any idea what your new venture will be?


Oh sure.

Software eats fulfillment, basically.

Currently FBA (http://services.amazon.com/fulfillment-by-amazon/benefits.ht...) is a 3B$ business without any competitors. There are good reasons for that: it's capital-intensive, technically/operationally/managerially challenging, and can only really be learned by doing.

I've just finished architecting & implementing a 30k package/day distribution system from scratch, I know I can do better. FBA is a surprisingly low bar to clear (they're mathematically/structurally constrained), and the industry hasn't really improved since the 90's. And with the right structuring it can be mostly funded through debt & advance receipts.

Basically, I'm going to pick up where FlexPort (https://www.flexport.com/) leaves off (literally! Ha, logistics joke!) Except in an even less sexy vertical. :)


Depending which verticals you're trying to target, and who you think your end customers will be, there's a much larger shadow market for these kinds of services, currently being well served by a combination of "pure" logistics companies (UPS, FedEx, DHL, etc) and the largest contract manufacturers (Foxconn, Flextronics, Jabil, Sanmina, Pegatron, Quanta, Compal, and a couple more). If you haven't already researched this area, I think it would be a good way to spend a couple weeks.


Integrated supply chains are incredibly complex once you get to that level, and not really candidates for a new entrant. The big logistics players you list go after those contracts rabidly, and newly signed contracts have payoffs measured in decades.

It's a massive industry, nearly 1.8T$ this year. (Yeah, that's a T.) I'll be happy with carving out my little 50B self-serve niche before digging into integrated supply chains. :)


I would have thought UPS - and similar companies - would be considered competitors, which are no small fries! But, perhaps I'm looking at the wrong layer of the onion? And perhaps the layer you're referring to/hoping to operate in is n degrees removed from that. In any case, good luck!

+1!


tl;dr: different markets & different needs

It's not hard to get a dedicated fulfillment service once you've hit a decent size (say ~10k/day). But it's a very intensive sales process with long-term commitments.

They also tend to be both opaque and hard to integrate with other systems. Most use end of day EDI (yes, the 30yr old standard), some of the more "modern" ones have multiple drop times/day.

So major fulfillment providers (not UPS, which doesn't do fulfillment; but FedEx/Rakuten/etc.) are both inappropriate for fast-growing, flexible or seasonal loads, and don't support innovation in customer service for eCommerce companies.

FBA is a much more modern (and extremely successful!) service, but is only cost-effective if you're selling on Amazon. Their 3rd-party, non-branded service is not only prohibitively expensive but feature-light and under-developed.


As the ex-CTO of an ecommerce startup, I really hope you succeed and wish you the best of luck.

There's plenty of us, little guys that need logistics/fulfillment and the options just suck. There's a huge space between starting (when you can do it yourself with UPS/equivalent or even standard post) and when you hit a few thousand packages per day (when Fedex and similar is a decent option).


What were your biggest challenges with standard post solutions?


The main one is that, at least with the providers I used (three, including Fedex) there was no api and no way to interface with their systems automatically, everything had to be done through archaic websites with a usability designed before the dot com boom or by phone. During busy times (christmas shopping, for example), we had several interns dedicated exclusively to handle sending the info (number of packages, destinations...) to the supplier and printing the shipping labels.

I think that when you reach the thousands of packages per day, you are offered those services, but as a small setup with 'only' hundreds of packages, the only option was to do it manually. We had a simple system to handle orders, inventory, manufacturing... It would have been a breeze to integrate an api with it to print the labels automatically to give the guys actually preparing the packages.

We didn't get a lot of issues that usually pop up when talking ecommerce (scammers, false orders), we didn't even get many returns (I only remember a couple of cases) but we did get a few packages that disappeared in transit with no explanation or, obviously, a refund. The process to report those was horrible, similar to cancelling a mobile phone contract and in most cases we had to simply write-off the package and send a new one to the customer (actually, we are waiting for the resolution of a case when a package worth a few thousand euros was lost, we might actually get back that money).

Another thing that was annoying, although I know it's understandable, is that to start getting discounts they require a volume that, as a new company or sole trader you are simply not going to get. Paying the normal rate for Fedex, for example, makes packages quite expensive when you are talking international (and the fact that I live in an island with a population of less than 10M people doesn't help). We basically kept shipping costs to a minimum by eating into our profit margin. We got less money, but helped improve the sales.


This is an awesome idea and I wish you the absolute best of luck with it. As a software engineer in a startup that does our own logistics/fulfillment/warehousing/etc, I can say I'd love to see more modern products in this area.


? The mid/senior leadership of the best known companies hires all thr available techie MBAs. There are few CTOs because a 50K employee company only has 1 CTO. Others are CEO, COO, CIO.

A mid/senior person at a big company is similar to a CxO at a small company.


> The mid/senior leadership of the best known companies hires all thr available techie MBAs.

This is false, and also misses the point.

I went through two recruiting cycles at HBS (Harvard Business School), which is one of the largest (~1000/yr) and most representative business schools. I did not see a single position advertised which required actual engineering experience. I was also one of three people (in 1000) who had a job before school which required writing code.

There were plenty of companies which would have loved to hire a solid engineer, but the job they'd be hired into would neither require nor use those skills. I could certainly go work in Product Management at Google, for instance; but why would I want to? My better path to VP at Google would be as a coder (if I wanted to be a VP at Google).

> There are few CTOs because a 50K employee company only has 1 CTO. Others are CEO, COO, CIO.

There is 1 CTO in the HBS alumni database. There are more than 36,000 CEOs. CEO-CTO is probably ~2:1 in the real world.

ps: data mining the HBS Alumni database is fascinating, btw!


Strongly doubting the assertion that it is easier to become a Google VP as a coder than a product manager. Product managers are responsible for the product and its P&L which is much more suited as training ground for VP than being a coder, in my opinion


A better 1:1 comparison is PM vs lead Engineer. They're at similar levels in the hierarchy.

There are idiosyncratic and systematic ways to consider this statement.

My personal belief is that it would be an easier path because I know myself to be very good at building products and supporting engineers, and relatively less interested in market research & networking.

In a more general sense, it's pretty easy to get a rough count of the number of product-oriented VPs at Google on LinkedIn, then count how many have PM backgrounds and how many came up through engineering (divided by the ratio of PMs to engineering managers). I did that analysis two years ago when I was considering Google, and it came up strongly on the side of engineer.

I'd be particularly interested to know if this has changed since, or if internal/better data suggests otherwise!


I suggest that once you get to the senior manager level on both tracks they generally start to merge as both become less focused on technical minutiae and more focused on product planning and execution. Eng directors [outside of pure research areas] have to be as market/business savvy as PM directors, for sure.


That's very likely true, but it doesn't say much about the relative access each has to a VP office.


You are saying Google has a lot of VPs without MBA and no product leadership experience, without any prior experience of having P&L responsibility, strictly engineering experience? Perhaps, but I am skeptical. I'd like to see the data on that.


If you restrict it to product VPs, it was true as recently as 2014.

The set of Google VPs has a representative sample on LinkedIn. Prove me wrong.


All the VPs who came through engineering that I found did so after having been early employees at one of the top tech companies. I buy that. But if you are going to climb the ladder now, I doubt you can do it through engineering at Google


I don't think HBS would be the best dataset to use though:

1. The CTO position probably didn't exist until the 90s so you'd need to restrict your dataset to something more recent

2. HBS doesn't generally attract tech people. All of the people that I know that went to HBS(~20) work in finance/consulting/non-profit. Some came from a tech background. Stanford may be a better choice. That was the vibe I got when I attended MBA info sessions at HBS and Stanford. Columbia had sort of a mix.


+1!


Your career is both fascinating and inspirational. Best of luck with your new venture.


+1!


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 where the CTO (my boss) was in your exact position (in fact, if it weren't for your style of writing - English was very obviously his third or fourth language - I would almost bet money that you were him, your stories are that eerily similar) and it was a miserable experience. $CTO was an otherwise brilliant coder who was on his first cto-gig outside of 'team leader'. Outside of work, he was a great guy - warm, personable, funny. At work, he resented not being able to code in many different ways, often with the team bearing the brunt of his misery. He'd often make decisions for others to implement, then second (or third) guess himself days or weeks later, insist we throw out all the work, and start again. He'd often be irritable, make rash decisions, have temper flare-ups, ask for feedback then get upset when he got it, etc. It was a bad scene for all involved, but the dude was a walking personification of the Peter Principle. He would have been infinitely happier remaining a coder, and his team (myself included) would have been infinitely happier with a CTO comfortable in a leadership position.


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 more control than I currently do. Perhaps that is a problem with me and if I simply took control and treated it like my own business I could change things enough to suit me more. But is that a good decision for the business? I'm not so sure. What's the point in changing things so much that the business suffers?

Anyway, your points about your previous boss really resonate with me right now. I'm finding myself increasingly frustrated and dreading meetings because I feel that frustration is coming across to the rest of the team.


The fire-fighting thing sticks out to me a bit, in part because it's caused me pain in the past and in part because you keep mentioning it. I might venture a guess that one of the underlying issues that's really getting to you is not the lack of actually writing code, per se, but that you have always had environments where you can get lost in deep focus or flow, and now your brain is being actively rewired to support continual rapid context switching. This is uncomfortable and unfamiliar and your brain is rebelling against this new environment.

I've never had a CTO title, but I've been in many similar positions.

In case you decide to stick it out for a while, I would suggest several easily implemented opportunities immediately:

(1) Establish an #engineering-support channel in Slack and a Triage calendar in Google Calendar. Put your team members on a rotating schedule to triage any engineering fires that the business has.

The Calendar should pipe into the Slack channel at 9 am every day. For a few weeks, send an "@channel please remember $engineer is your point of contact for today." By then the rest of the business should get the idea. Instruct your team that you trust them to decide which issues need to be addressed immediately and which ones need to go into the queue, but if they have any questions they can escalate to you. Also explain you understand that context switches are expensive, and you are totally okay if this causes a productivity hit on their given triage day.

It doesn't mean you won't be interrupted with real fires, but it does keep the less urgent ones from creating a context switch for you. Include yourself in the schedule, and you can send the message to your team "we're all in this together" instead of "hey I'm too good for this nonsense."

(2) The Business guys will respect your calendar, and if they don't, you have leverage to call them out on it because The Calendar is sacred in the business world. Block out 2 or 3 hour chunks throughout your week to work on hard problems. You drive a lot more value this way than with the fire fighting, anyway.

(3) The Calendar also works for time with your family. Daughter's Ballerina Recital? Block out 4pm-8pm on your calendar as soon as your hear about it—"Blocked—At Home"—and again, leverage if somebody wants to interrupt you with a fire.

(4) Train everyone on how to add each others' calendar to their own calendar view; this seems obvious to engineering, but less engineering-minded people may not know they can do that.


Before you quit, you should consider using your willingness to quit as leverage to try to improve the situation. This is not an easy thing to do, but if it succeeds it can pay enormous dividends down the line, and you have little to lose by trying it first. Contact me privately if you'd like more info or coaching on this. (My qualifications: I've been CTO of two semi-dysfunctional startups.)


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.


Here's the problem with that reasoning. As OP implies she has enjoyed leading/managing within her own companies. Before my company was acquired it was thrilling to perform these duties even though it was more grueling. So it's not necessarily a matter of not being cut out for that kind of work.


You know, maybe it makes me sound bad but I do enjoy leadership on a smaller scale and where I am ultimately in control. I know one-man bands don't get very far (usually) and some people management is expected even in your own business. I guess my point here is that yes, you're right I have enjoyed leadership previously and thought the step up would be similar but it's not.


I read it more as the OP had their own company where they were in charge of making decisions AND executing them, and there's no real indication of managing employees. I suspect they enjoyed the execution. If they don't enjoy dealing with people's crap and putting out fires, senior management of any reasonably large group is probably not for them - and that's absolutely okay.


Right, I wonder if this person ever understood what the job of CTO is. Yes it's "dealing with everyone's crap", it's a management position. Yes you haven't written code in months, it is a management position.


The main problem I'm seeing with this kind of topics is this notion that "management" and "coding etc." are on the same vertical. That as an end result of a successful career as a professional is to move into management.

Well, that's just bonkers.

I used to be a coder. Now I'm in management and I've learned, the hard way, that management is it's own specialty ... and that the best managers don't see them self's as "above" their team, but the "team coordination & external communication" specialist of the team. The only reason for the extra pay is the expectation that a manager take the brunt of the "external" crap (aka. having responsibility for the team) so that the rest of the team don't have to and can keep working. Which means that just as you need knowledge and experience to be a good coder, you need knowledge and experience to be a good manager. I find the notion of going from "best in your field" back to being "the green guy" at the height of your career as utterly crazy.

But that's just me.


My very large company has 5 lanes. Purely technical is at the far right, purely management is at the far left. Our CTOs do not spend the majority of their career in the company in either lane and that seems to have worked out okay. I don't think people are particularly encouraged to stay in the management lane either.


Interesting. Can you put some descriptive labels around the three "middle" lanes as well? I'm trying to figure out the distinction that would make someone 25% management, 75% technical, vs 50/50


On the other hand, as a coder, working with a manager with little or no code experience is ineffective and frustrating. Having a manager who can wrap her head around complex architectures, and argue/negotiate for one strategy over the other is extremely important. Yes, so are team skills, but I wouldn't call the the path from coding to manager coders fundamentally flawed.


If you are a hacker, then try to just hack the suckiness out of the job.

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.


Hey, I aimed that ^ comment at OP, but someone else responded, and I just sent them the workbooks. So I just want to let you all know, the offer is open to anyone who contacts me.

The only thing I ask is don't mass share the files I send to you. Send to your friends or whatever, just don't put them up on megashare or some shit like that.

(I know that that will happen, but at least I tried :)


By the way, for others coming to this thread late, I'm off to bed, so if you don't hear from me in a few hours it's because I'm sleeping. But I will send out the files to anyone that's interested, I'm just on my mobile at the moment so I don't have the files at hand. But I'll send them out to anyone who requests them in about 5 hours or so :)


Learning is painful, and it's tempting to just go back to your comfort zone. You dont really learn much in your comfort zone, and learning often feels a bit uncomfortable. Check out the Ideas behind "growth mindset" for more about this [1].

You mentioned the idea of management being about cleaning up crap and dealing with people instead of writing code. A few thoughts on that. There is a lot of people and management work involved in making code pay off for an organization at scale. Code by itself doesn't offer any value. It has to be in production, it has to be used by the customers, it has to be something that adds value for the customers. And it has to be managed in a way that the code is delivered before the competition gets a chance to sink you. Also code doesn't write itself, teams of people do, and those teams need to be built and maintained and recruited and taught. Making all of those things happen involves people relationships and soft skills. Your job is to make those things happen smoothly, guide and grow the engineering teams, prevent the fires, and establish the relationships that make that all happen smoothly and scalably.

It's a different set of skills from writing code, but it can be learned if you apply yourself to it and recognize the value it'll provide to your organization if you do.

[1] https://www.ted.com/talks/carol_dweck_the_power_of_believing...


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 people.

If you're a technical CTO, and want to code more than manage/build a team, then hire/promote a VP of Engineering with strong soft skills to grow/manage your team. If its the reverse, hire/promote a VP of Engineering who's technically stronger.

If you're constantly being pulled into engineering battles, hire/promote an architect you respect to negotiate.

If you're running engineering meetings (ipm's, retros, etc), hire/promote a SCRUM master or equivalent.

If you're battling sales, operations or marketing, hire a Director of Product Management with solid communication skills. That person will 'fight' your battles (and probably love it!).

If you're putting out fires in production, hire/promote a Director of QA. They'll work on designing systems to catch those bugs.

If your infrastructure goes down a lot, hire/promote a senior devops engineer.

On the engineering/coding front, I find it super helpful to rotate into teams and pair one-on-one with engineers. You get exposure to their day-to-day code battles/challenges/environments, the tech decisions at the lowest levels, the ability to code/manage daily and respect with your team. You can then prioritize stories/epics to fix problems that you see across your organization that plague a technical team like debt, environments, knowledge gaps, etc.

Don't step away, stay positive and solve for the organization you want to lead.


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!


> I haven't even written a line of code in months.

CTOs generally don't write code. But, in a typical startup designations don't matter so much. How different is your current role from the one you were offered during the negotiations?

> I thought perhaps being CTO in a startup would give me some of that same ownership, control and enjoyment but it just feels like another job.

Do you feel connected to the overall vision of the company? If you did, then you should look at the things you're unhappy with as bumps on a road worth traveling.

Since you do have the ownership (through your designation), you have power to change things that bother you. It's only when you start making visible impact, you will start truly belonging.

Finally, I would urge you to talk to other senior folks in the company openly about what's bothering you. Maybe you are missing another perspective that they will be happy to share with you.


You are absolutely correct, I need to talk with the other senior folks and this question here was my way of hearing some thoughts before going through that process.

> Do you feel connected to the overall vision of the company?

If I answer honestly, then no, not really. I think it's an interesting idea that will end up making a lot of money but no, the central 'theme' of the business doesn't touch any interests or passions of mine. The role came about via my network and I was much more interested in moving into the role of CTO than the product. Writing that out like this makes me realize that was a big mistake.


The challenge of leadership is that of leading people, not of writing code. Dealing with people can be messy, frustrating, and depressing, but it's what needs to be done.

As a CTO, I code about 30% of the time, but I expect that to go down as our company grows. Much of the time I deal with people who were offended that so-and-so shot down their new design, or they think their career is being harmed because they can't rewrite the entire product in Clojure, or senior management is freaking out because of one minor bug that hits an important customer.

If you can see a path to where you want your company and team to be in a few years, then stay and try to move down that path. It is very rewarding to see tangible progress in your product and your team. If you want to be coding all day, find another job.


That's life. The higher you go, the more crap you have to eat so those who deal with executing can execute without distractions. If you don't want to eat crap, you have to stay at a lower level (team lead/distinguished engineer/r&d labs)

On the other hand, being that high should indeed get you ownership and control, if you don't have it question your relationship with the CEO/rest of the company. You should own and be responsible for all the technical stuff, that is the upside of eating all the crap you can eat.

On a related note, if you are a good coder, you can and should schedule some time to do pair programming with the team to stay on top of things and actually write some code. But only as long as you are more of a help than a hindrance.


So.. about that non-eating crap low level job, any open position for me? :)


Depends on your skillset, but indeed we are hiring devs for our Madrid office. We are not ready for remote yet. We pride ourselves, among other things, in eating all the crap at the top.

Required Skills: C#.

Caveat: We want people that like learning new technologies, as we do use some other tech stacks other than .NET's. We will train you if you don't know it yet, as long as you are interested and capable.


Could you help me relocate? Inside EU. I don't know C# very well, but I worked with F# and also learned about some 110 other languages (https://klibert.pl/articles/programming_langs.html) and never considered stopping to learn new ones.

(Mostly just testing if it's really that easy ;-))


Sent you an email.


Exactly. As they say, crap travels downhill.


I'm surprised that no-one has suggested getting a VP Eng alongside you.

http://avc.com/2011/10/vp-engineering-vs-cto/


I can't up vote this enough, this absolutely true.

This is the same arrangement I have at my company (me the CTO), I can focus on the code, architecture, devops and the VP Eng. can help build the team, work out personal troubles with the developers. Obviously there needs to be a good relation between the two for this to work.


Indeed, or even just an Engineering Manager to deal with the day to day management activities.


I think part of the problem is that we often see CTO as the holy grail for the technical side of things, where that is the final stop in a linear career path. DEV > SR. DEV > ARCHITECT (maybe) > TECH LEAD > DEV MGR > VP/DIR > CTO

If you love coding and solving problems, you may find yourself less fulfilled farther down that line.

We're also talking about titles that end up being somewhat arbitrary and non-transferrable once we take companies of different sizes into account. CTO of a 10 person startup might translate to Tech Lead in an enterprise software business. CTO at a startup might still get to write code (I know many that do), whereas CTO at a company with a couple hundred developers might not even see code.

If you aren't happy, find somewhere that you can do what you enjoy doing. If this is truly your first senior management position, it might be clear that senior management isn't for you - or this isn't the organization that you should be in a senior management position. You could certainly find Sr Mgt or CTO roles where coding is part of the everyday routine.


Key question is WHY did you take up this job in the first place? Do you really believe in the mission of this company or just the CTO title and a lucrative pay attracted you here. If you truly believe in the mission of the company, you're doing the right thing by taking all crap and making progress towards end goals. You are probably not coding because your time is better spent doing what you're doing now. Will you make more difference to the world if you went back to the coding role?


I have to agree. In my experience some of the best managers have been the ones who shielded their employees from bullshit, taking the brunt, making sure we can keep moving quickly towards completing the goals.


This is one of the main goals of a tech manager: "some of the best managers have been the ones who shielded their employees from bullshit". If a manager of a tech group isn't doing that, they're failing at their job, and likely have some form of attrition problems, quality issues, feeling of uncontrolled chaos, etc.


> It seems to be mostly about dealing with everyone's crap, trying to fight fires and constantly battling with the other managers and tech team to get things done. I haven't even written a line of code in months.

Welcome to management! You're dealing with the crap so your people can do their job. If you get to code a few weeks a year then you're lucky.

If you really don't enjoy it, go find something else. There are a lot of highly technical jobs that should prove a real challenge.


Sounds exactly like the CTOs job. I think too often the folks in SV abuse the CTO title when they really mean senior architect or engineer.

I'll offer advice but it comes from someone with no experience:

Take this opportunity and grow from it. So it's not the job you wanted or expected; you can still find a way to be successful. Really get to know the teams, figure out who has the emotional and intellectual capacity to deliver for you, and reward those folks. Good luck!


> I think too often the folks in SV abuse the CTO title

I believe part of it is overall title inflation, which makes it confusing for some people to understand what the actual role is and what you will be doing.


I feel ya! So my experience is not exactly the same, but I really get where you're coming from... About a decade ago was the last time that I touched any code as part of my dayjob. I was a web developer for 6 years, and I've been either a project manager or product manager for almost 10 years...and funny enough, for the latter couple of years as a dev. I yearned to move to a position where I sat between the "tech" teams and the "business" teams. I thought this was a natural progression up. I was told that I had a knack for explaining complex and technical things in easy-to-digest way for non-techies. So I tried the non-dev route. Fast-forward some time, and I've changed companies a couple of times since then, and without looking almost a decade has passed. My current and last job has led me to the most disappointing moments of my professional career. I won't say depression but feels pretty close to it. In my case i think it feels like nowadays I'm not building anything. The feeling that I used to get as a developer was that I was building something. I totally get that building something means different things between someone who sits at a desk and churns out code vs. people who build essential things such as wells and irrigation systems for some struggling third world country...nevertheless, at the end of my days as a "coder" i still felt like I introduced something into this world; I had such a sense of accomplishment, even if my salary didn't express that. In the last decade, I'm lucky enough to have had something to take my mind off things: in essence, my family. If it wasn't for my wife and daughter to fill my days with joy (and yes the usual family ups-and-downs, but hey, its still a distraction!)...if it wasn't for my family, surely I would have slipped into a deep depression. What makes things tough - now - is that after almost a decade of not touching code, its that much harder to "go back into codding", at least as a dayjob. Ok, I'm stopping now because this is mere blathering (and i should just post on my own).

...Suffice it to state: YOU ARE NOT ALONE with the remorse you feel with direction of your professional career! The only tiny bit of advice I can provide to you: find a healthy mix of non-work-related distractions in your life AND jump around to different companies. The fact that you have such great experience is something some relevant company will find useful; you simply need to tell them your goals, and hope things align.

Good luck!


As CTO of a mid-sized insurance company, I spend less than an hour per week writing code. My job is to lead the architecture and infrastructure teams in meeting company objectives. It is not my job to personally deliver solutions.

CTO is all about leadership. If this doesn't work for you then I suggest your "what next?" is a return to Lead Architect or Lead Developer roles at another company.


I took up a job as CTO after being a lead developer and junior partner at a bunch of startups. OMG what a punishment.

I've now resolved to just go out on my own because it's too painful working for anyone else in this curious position of great responsibility but not enough power.


Was the money even good?


This is one of life's conundrums. Work hard at getting really good at doing something you love doing, and then stop doing it. My advice would be to find someone or some people that are the adjacent jigsaw pieces to you - a set of skills you don't have, maybe it's the stuff that was missing previous times you ran your own businesses – and then start a business with these people where you can carry on doing the thing you love. For me, I had to do it with someone who had all the networking and new business skills that I so painfully lack.


It sounds like your biggest annoyance is the fire-fighting. These kinds of fires don't just "happen". They're not forces of nature, they're forces of man. Either directly or indirectly, but always the source of it.

Usually a failure of process, expectations management, or both.

You've mentioned feeling a lack of control. Is that lack of control over the fires being set in the first place or a lack of control over being able to appropriately handle the arsonists? Have you clearly identified the arsonists in your case?

Is the arsonist the CEO; by making insane external sales or Board promises?

Are the arsonists your customers; by making product/pricing/support demands that render the overall value proposition of your company moot; i.e. getting you to focus too many resources on basically charity work to "get their logo"?

Are the arsonists your team members; by having a strained relationship with best-practices, consistency, reliability, velocity, productivity, etc.?


I highly recommend following Camille Fournier's blog, she writes/speaks extensively about being a technical leader and CTO. Priceless lecture especially that it comes from someone very experienced.

Check out this post about transitioning to hands-off position http://www.elidedbranches.com/2016/04/ask-cto-navigating-han...


There's a story that Woz tells about how he was feeling as though he was being pushed in to management as Apple grew and the anxiety, etc., that caused him. Eventually he realized (and/or someone pointed out) that he didn't have to follow the role changes and could remain in a hands-on engineering role.

I've worked with a few people along the way who were senior enough and wise enough that they easily could have found themselves a management position if that's what they wanted. But they either had tried it and decided it wasn't for them, or they just knew they would be happier coding and maybe doing some mentoring of the junior staff.

tl;dr: Transitioning to management may be the 'normal' career path, but why do it if it makes you unhappy?


Somebody has to do these things. They can be done more or less well. This has a big impact on your company's success and on the happiness of your team. Those are the only good reasons to endure the hardships.

You're coming to understand what executives do and how that's necessary in a company, at least until humans find better ways of working together. This isn't something you really see clearly when you're the CEO because you're above the fray. And this isn't something you see when you're an individual contributor if the executive of your group is doing his or her job well.

People are paid in part based on how poorly a job can be done. The CTO is a role where real catastrophes are possible. It's a job the rest of the business often doesn't understand well, managing a team the rest of the business understands even more poorly. It's easy for bad choices to do a lot of damage to a company over a long period.

If you're the rare individual who can bridge both worlds and do this job well, then it's likely your company and your team won't find anyone who can do this better. And if they have to look, it's quite possible they'll find someone who does it a lot worse, makes your team miserable, and drives the company into the ground.

The reason to do the job is to make the company successful and to make the lives of those on your team better. If you believe enough in the company's mission, the other executives, and your team, then you'll figure out the rest.

Humans can endure a lot of hardship if it fits within some context we find worthy. It's not an easy job. But if it's a worthy cause then carry on.


As a CTO myself, i see there is a lot of vagueness in the whole role of CTO. Almost all other roles in an organization are well-defined and have clear goals and responsibilities. The role of the CTO varies so widely between each organization, it is something that has to be specified clearly when going through the hiring process or even when starting a startup.

Why does this happen? I have found it has a lot to do with the investors and management team. I've seen the definition of the CTO varies as far as "The CTO should be the technical evangelist, super SEO." all the way to, "The CTO is in charge of Product and delivery."

IMHO giving CTO titles to the "evangelist, super SEO" undermines the role, because that role does not warrant either "Chief" or "Officer" in their title.

----

As far as myself, i retain the CTO title because am the owner of the technology; in that i make sure that technology is all the things we are trying to achieve as a business; looking beyond the current implementation and plan out how we need to build the product over the coming years. This goes alway down to components required, system architecture, external interfaces and how we can do things better, faster, cheaper. I also write pieces of the code and help out in engineering task as needed. This keeps my competency in day to day ENG high. Involvement with ENG tasks and coding is what keeps my sanity.

If someone asked me if i liked my role as CTO i would say yes but there is all the things you listed (fight fires and battling with managers and tech team).


The best translation I ever heard for "CTO" was "Chief Talking Officer" (from someone who had been "promoted" into the position.

Several different jobs can be assigned the title CTO but they are all technical leadership positions, not direct execution. The company should be getting leverage from your position -- you should be enabling the growth of the company, by being th external technical face of the company, by helping direct technical development internally, by representing the technical / architectural issues in the management team, or by defining the technical direction based on the exec team's decisions on company direction. Different companies need different mixes of these. BTW it's often a way to retire a founder without losing their technical input, or to keep them from meddling :-).

In your case you were hired on, so they wanted you to use your technical expertise to help guide the company (or keep the tech from getting into trouble -- but even on the execution side, that's the VP of Engineering's job).

So if it turns out this isn't what you really like doing, there's no harm in that: you should find something you would enjoy more, and help the company find someone else to do the job they need doing.


By and large, you are describing people management. It is quite about dealing with crap. I don't mean that as a complaint, merely a fact.

Good managers take crap so others don't have to.

Ideally, we get good enough to prevent the crap from happening in the first place. But it is most certainly the job. It's entirely understandable if you find it's not for you.


Maybe its too big a company? "Around a few years" sounds like they have a sizeable staff. So a CTO position there would be very different from a CTO at a new startup. Pretty much like you describe it. A management position, heavy on the 'officer' and lighter on the 'technical'. Managing a team of technologists make you responsible for making the right decision. Too many folks think CTO means you 'get to' make technical decisions. No, you're actually responsible for making sure the right ones get made. Which means listening to your competent team, understanding what they tell you, and reconciling that with the business.


A CTO's role should be technical leadership. If a major part of your role is dealing with everyone's crap and putting out fires, I wouldn't necessarily consider that technical leadership.

I've been in a similar situation, and for me, the right solution was having the right people under me that I could trust to fight the fires.

You should be deciding how the fires are fought, but your team should fight them. At least some part of your day should be available for steering your team/organization/product.

(But code, not so much. :)


I've been in the same position. Was first to join a couple of founders, built the first few iterations of the application, small group, great fun, lots of challenges, lots of code. As funding came, team grew I became the CTO officially. But then the fun stopped. Technical decisions which were meant to be mine were dropped on me by one of the founders despite my objections (most if not all proved to be mistakes). In the end I stepped down and we invented a new role where I'd be in charge of innovation. That worked well. The CTO who replaced me run away himself after a short while and after that we were CTO-less.

Thing is there are many forms to the CTO role and different people see that role in different eyes. To me the CTO is a technical leadership position. You are meant to decide the technical strategy of the business. Decisions from which servers to use, to what language to how things are done, architecture from the top down, etc. Someone mentioned about the VP of Eng. role which I can't agree more - That role is there to support you with the crap. That person needs to be more manager than tech. He is there to make sure your time is dedicated to the core of your position. Not everybody saw this roles as I did which is why I was happy to stand down than try to fight it. I was there from day 0 to acquisition about 7 years later.


I have the opposite problem, which is that I think I would enjoy and be good at a CTO type role, but since I don't have a personal background as a coder, I'm not sure how to move toward it. Almost all the job listings I've seen require a CS degree and a decade+ of experience as a developer. Startups, in particular, seem to believe that CTO = lead coder.

I've managed websites for years, overseeing design and development teams, setting product roadmaps, negotiating contracts, even testing and debugging websites and server configuration. I understand the stack of technologies that make up a website, although I have not written web applications myself. The little bit of code I've written is on the margins: shell scripts, one-off JS widgets, etc.

I'm not bad at managing people, and I enjoy it. I'm not bad at managing peer and executive relationships, and I enjoy it. These are the sorts of things that a lot of developers seem to really dislike about elevating into CTO.

So: is it possible to land a CTO role without being a experienced and expert code-writer? Or am I thinking of the wrong thing?


Well, if we believe the Fred Wilson post that someone linked to above [0], what you're looking for is a VP of Engineering position, not a CTO role.

[0] http://avc.com/2011/10/vp-engineering-vs-cto/


In our culture we always strive for a "better" job. Better jobs pay more, and have more societal prestige and status. In our culture we associate better jobs with being managers. The higher up the management chain you are, the better job you have and the more important you are and the more money you get. (and more money is always better too). If you can make it to CEO you can make 1000x the lesser workers who do not have as good a job.

Is that a valid cultural paradigm? Are management jobs always "better"? Should they get paid more because they are so much better and more desirable positions to have?

Sometimes this attitude seems like a remnant of a feudal age where the management positions were held by nobility (our betters). Certainly some of the pay inequalities are now forming the basis for civil unrest.

The craftsmen are the true heart of the companies production and IMO the rest of the team should be focused around supporting the craftsmen rather than the craftsmen focused on supporting the management. (regardless of your product)

I think our culture is a little broken.


Find out what you REALLY want. Find your motives. Find the underlying essential motivation. That's much deeper than coding or not handling crap. Those are superficial symptoms, not what makes you move.

Find a good professional coach that can help you with finding this out. Pay money for it. You probably can spend several thousands $$$ on this. Not that it needs to be that expensive, but $1000-$2000 is easily spent.

If you quit this good paying job, while it may actually have the opportunity to bring you to your dream job, it's worth staying there long enough to get your things together.

http://simainternational.com/coaching/strategic-life-career/ This is a link to SIMA, about motivational assessment. There are more methods. This is just a starter, but it may be right for you. Be sure to find an experienced coach.


I just read something along the same lines on the way to work this morning:

https://medium.com/code-like-a-girl/why-i-left-management-th...

The author was in a similar spot, and chose to go back to the tech track.

Her takeaways were:

What gives you energy and what drains you? How do you feel accomplishment? What drives and excites you?

Answering those three questions honestly will give you a better idea on what kind a role would best fit you.


Answering those three questions can be really difficult. You probably have a big blind spot there. A professional coach can take that away.


You can also look at the CTO role as slightly different style of hacking; you program with teams, training, and planning in addition to setting technical direction and leadership. Many CTOs design and code as well (I do) as a senior-senior designer or architect, but you should think about the meta-programming as exciting on its own. Many senior level architects love to train and lead teams technically, and a CTO often focuses on these things. Senior level architects also curate the technology and design, which CTOs also often own. It's a great role, though it sounds like you may need to grow into parts of it. I suggest that it's totally worth it.

There are various ways to cast the role too; many organizations also have a VPE (or VPD) and other mid-level leaders. These roles can allow some flex in what a CTO is responsible for, though ultimately the role is responsible for direction in technology.


I've been Tech Evangelist, Chief Technologist, and CTO in the past few years, both at large and small companies.

I think it's wrong to generalize - a CTO experience can be good or bad depending on several factors. It is entirely possible that you could be VERY happy in a similar situation, but with a different company.

Usually CTOs can be divided into engineering types, and outward-facing types. The former is hands on, codes, handles the engineering team, or at least has a strong bond/influence with the VP of Engineering. The latter is more in touch with customers, does more public speaking activities, and tries to condense feedback and requests in a way that the VP of Engineering can translate it into the product. Right now I'm the outward-facing type. I am enjoying it, mostly because the two co-founders are great individuals and leaders.

Let me know if you have questions - I would be happy to try to answer.


You wanted to be the lead developer and you got CTO. You can be both in a very small startup, but CTO is a management position, not a coder. Maybe you should find a job you'll enjoy more and leave. Or find another CTO to replace you and become lead developer, but that could lead to awkward relationships inside the company.


as a CTO you're not just an employee of a company, but also one of its leaders. you have control over what you do. if you don't like the day to day process, change it.


As a technical leader, the biggest hurdle I faced personally was understanding how to measure and improve myself in the right ways.

While success in an engineering role can generally be described as "write good code" (with all the nuances therein), technical managers are measured on totally different things, and it isn't obvious how to improve most of them.

When I transitioned and realigned myself to these things, my outlook changed, and I started really enjoying leadership roles:

* Embrace the idea of being hands off technically. I have never seen a hands on technical manager that worked out well - politics will always come into play. Instead, encourage friendly inter-team debate, which you can coach and steer into a healthy dynamic to make the right decisions. Feel satisfaction that the team you build creates better engineering than you could alone.

* Focus on helping your team lead fulfilling careers and lives. See in them what they could become in 10 years and help them achieve it, even if it sometimes conflics with your short term interests.

* Build amazing products - The leader is way more instrumental in this than often credited.

* Create a great team environment that people want to be a part of.

* Get a seat at the business table - you should absolutely be a big part of the product roadmap. Done right, eventually you should have sales/customer teams coming to you for advice and input like 'Customer X wants Y, what do you think?'

* Create great communication flow - make sure everyone else knows how important your team is, and help your team see how what they do contributes, and how the market/product is changing and why.

On your comment about fighting fires and other managers - you can change this. These things make any job unpleasant. I strongly recommend reading The Phoenix Project to get some ideas from an IT perspective - it can easily be read in a weekend and addresses exactly these common problems.


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.


My advice is to realize that you are hired as a leader in the organization. Use your leadership to change what needs to change so that the company succeeds. An important factor for the success of the company (as long as you are still hired there) is that you are doing what you love doing and what helps the company, because it'll make a big impact. If you like writing code and write 2 lines of code, it'll raise the morale of the team and get them motivated to work more.

What I am trying to say is assume your leadership and do what you want to be done. If the company likes it, then great. It is a win-win situation. If not, then next steps are clear.


I have a similar problem... and similar to DelaneyM

In 2007, I got my MBA in Finance, which is the worst time to get one at the beginning of great recession.

Anyways, I taught my self to code in 08-10 and somehow convinced people to pay me to code!

After being unemployed for so long in 2009-2010, I was happy to move down this coding career path cause the money was so easy.

But only in the last year or so I have come to realize (after all the money wore off), I have no desire to be CTO or a coder, I'm having a hard time being a coder, lol.

I'm a entrepreneur, that knows how to code, is my new catch phrase. I have a enough leadership and communication skills I'm just wasting those talents when I'm just a heads down coder.


Fighting fire is no reason to be sad of if you are in control. I recently quit because I was fighting too many fires, was underpaid and was not in control of things.

I'm not sure about your pay structure, but if you are a CTO you definitely have power to change things. I think you should do that. If computing is what you love there is no better place than to be a CTO. You may review code, even write some modules and dictate how things should be done. And you should do it so that the system is stable with less fire. If you are not capable of doing so, you should hire someone who is capable of doing just that.

Email me if you want to talk privately.


> It seems to be mostly about dealing with everyone's crap, trying to fight fires and constantly battling with the other managers and tech team to get things done

Welcome to any senior/management/executive position ever.


I partly disagree:

It doesn't have to be that way. That is a sign of shitty management.

But the reality is, there are a lot of shitty managers out there, therefore it is the norm.


CTO is a coding role. Also, coding roles are less valuable than CTO roles.

If you like the money, keep the money and do your job well.

If it's not about the money, get a coding role somewhere and know that your goal is to be a great coder, not to work up the company ladder.

Being a coder is great, but realize that different jobs have different work and different values attached to them. Make sure what you want to be and what you do are aligned correctly so that you get what you actually want.

It seems like what you think you want, what you are working towards, and what you are really doing aren't aligned.


I work for a company and the CTO submits PRs for two projects, and does some QA testing, and helps guide my team's R&D software. It is a medium sided company. For him it is a chance to lead the future of the company while still writing code and he embraces it fully, albeit he is very busy, but you can tell he gets energized by the way he plays the role. This would not be possible without the right company culture. However as CTO you are probably the best suited person in the company to shift culture toward this, if you wanted.


Thought provoking. I read it earlier today, dropping in to add my two cents. I've been toggling between roles that either fits into 'product manager' or 'product developer'. That included a short stint as a startup founder.

IMHO (and experience) an A1 CEO/product/sales/business-guy can't be an A1 CTO/tech lead/research-guy and vice-versa. My operating keyword in this argument is 'A1'. This is counterintuitive to our natural inclinations.

Edit: Typo


Well, the issue with coding is that in theory a good CTO makes way more money.

I am dealing with the same problem, though I am not sure what makes me happy exactly. I think sometimes we get into this carrier path thing and just move forward through inertia. Things are good on paper, but in reality you feel like crap.

I don't know, I am slowly trying to move away from my current job. I am planning to use savings to buy websites, the idea kind of excites me, which is a great feeling to have.


Maybe this transition comes too soon but moving from coding in to management is a normal progression. It is another job , but in general it values the same qualities you should have as a coder: Understanding the dynamics of the situation and finding the best solution to get the job done. As CTO you should have the flexibility to find other people to help in the things you hate the most and focus on the fun parts.


> For my entire career I feel as though I've been working towards being the CTO and now I'm here I find it's not at all what I expected. It seems to be mostly about dealing with everyone's crap, trying to fight fires and constantly battling with the other managers and tech team to get things done. I haven't even written a line of code in months.

Please tell me you are trolling.


I think you're finding exactly what it seems you're finding; the CTO role is not for you (as it isn't for me either.) It is exactly what you're experiencing; dealing with bullshit, trying to get people to do things, get people to find common ground, etc.

If you're not enjoying it you should go back to being a lead developer. You may make less money but you'll be happier.


There's not a lot to say other than: find a mentor now.

Start cold-emailing CTOs in the same portfolio as your company. They'll be happy to help.


Correct me if I am wrong. But it sounds to me you are still struggling between a coding job and a full time management job. And to be fair, i think this is what you would be expecting for most of management position in lots of the companies.

You mentioned you have done some small management as senior/lead. Then think back, which part do you enjoy when you were there.


> trying to fight fires

Your leadership should help people avoid that fire fighting.

> I haven't even written a line of code in months.

That's a good sign for a CTO.


I did it for 11 months, and I hated it too, so I quit. Now I'm figuring out something that'll make me happy. :)


gdb wrote a brilliant post about his experience that you should definitely read: https://blog.gregbrockman.com/figuring-out-the-cto-role-at-s...


Maybe seek out a VP Engineering role at a smaller company. To me VP of Eng is usually more hands-on technical vs CTO which is more strategic like applying technology to business and big picture.

Not sure how old you are but a CTO role might make more sense later in life.


My experience is that VPE takes on more of the day to day management stuff and CTO takes on figuring out how to apply technology to solve business problems.

OP sounds like they want a VPE to work alongside.


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 :)


hey. meh, general rule: listen to your gut and follow it. It's that simple ;)


How do you advance to leadership roles?

I try to pursue it when it seems like it appears in companies I'm around but it feels mostly like crapshoot.

My other best guess is start my own company, which I think about all the time.


>> It seems to be mostly about dealing with everyone's crap, trying to fight fires and constantly battling with the other managers and tech team to get things done.

That's 99% of what management is.


Great question and some useful advice. What online forum/community is the best match for this type of question? Maybe it's too niche, but it would be nice have one.


LinkedIn, with a fake profile if you want to stay anonymous. Stack Exchange is a good place, but find the right sub. Then Reddit. Enough places to find advice.


I've been in those shoes and still feel a bit of that. Would love to chat and share some personal notes if you want to reach out - dangoldin@gmail.com


I would just leave unless there is some major financial incentive in your contract that you don't want to give up (hundreds of thousands or more).


Honestly, it's not far off from a typical CTO role. Being CTO is about connecting the technology side of the company with the vision and business goals of the company, and making sure the two match. There are great ways to structure the technology and build out the product that don't contribute to the business goals or even the vision of the startup (and can even be opposed to it), and there are sometimes less-than-ideal ways of building the technology of a company that get it where it needs to be when it needs to be there.

The CTO's job is about half technology and half business when it's a small startup. As the startup grows, you can't possibly make every technology decision, and so your job is more about getting the right people in place who can make the best technology decisions on your behalf as long as you keep them appraised of what the business needs are driving each of their decisions. And because getting those people in place and managing those people is almost all on the business side, your role becomes more about active business management while maintaining an in-depth awareness of the technology so that you can step in and correct course as necessary.

These are all just generalizations of course, as every startup is different. I imagine if you're the CTO of a startup that caters to software developers and code, you probably get to continue devoting some portion of your time to coding. Even in other startups, I've seen a lot of CTO's (myself included) get to actually do some code occasionally, but it's more like once every 1 to 3 months, which sounds about in line with what you're doing.

I think the CTO role you desire does exist, but it's in a specific, somewhat narrow stage for a startup. It sounds like you desire to be a co-founding CTO of a very early-stage (possibly idea-stage) startup. I think your desired traits for the responsibilities of a CTO can also continue to exist years into a startup's operations if the startup remains bootstrapped and self-funded.

From my experience (both with bootstrapped and venture funded startups), when a startup takes venture funding and forms a board, the CTO role becomes more about managing expectations, facilitating understanding of the technology to the depth needed to those who need to understand it to make the proper business decisions, and more importantly, contributing to and making the business decisions that require the knowledge of the technology that only you bring to the leadership and management team. The smae change in responsibilities happens to bootstrapped startups that become big enough, but the change is more organic and occurs over a longer period of time (which actually makes sense when you consider that venture funding is intended to make non-organic growth occur over a faster timeframe).

More cynically, I guess this management of expectations and facilitation of communication could be described as "dealing with everyone's crap," but really, it's probably what the startup needs. If you truly think it's not what the startup needs, then speak up! You are the CTO after all, and that's now part of your job to make sure the company is making progress. But recognize that the business side of a startup is as important (often more important depending on what the startup does, how it's funded, what it's milestones are, etc.) as the technology side, so make sure you understand the importance and motivations of what everyone else is trying to accomplish in the company before dismissing their actions wholesale.


Some amazing comments on this thread, thank you everyone. Reading through as fast as I can and will respond soon


No, you're not expecting too much.

This sort of thing happens surprisingly often-- the typical solution is to approach the CEO/board and seek a transition: quietly open a search for a new CTO and you find something that matches your passion. It's better for everyone: startups are no place for people without deep passion.

hope this helps!


Welcome my friend.


>PS. Sorry for the throwaway account but my main account has too much personal info for this topic!

If I was a CEO or founder, I would of course tolerate this kind of thing.


you should try meditation ^_^


Isn't it crazy, you spend so many years training and building your experience to become great at your job. So much so that you get rewarded with a promotion to management. A position you are given no training for. It is a hard transition and most people have difficulty with it.

First of all, congrats on the promotion.

You need to ask yourself, was coding what made you leap out of bed in the morning or was it that you were building something?

If it was coding then you need to go back to your old role. Please repeat to yourself this is not a failure despite what popular media and the start-up bro culture tells you. If you find a job and role that you love you are beating 90% of the workforce and win at life!

If it was building then you might still be able to make this CTO role work, just in a different way than you are used to.

Forget about technology, you are now a people manager. People are now your tools to build something. Fighting fires and dealing with everyone's crap is usually a sign of some kind of micromanagement. Have you placed yourself in the middle of everyone's decision making process? Are you their road bock for getting stuff done? This is often a result of giving your team tasks to do instead of goals.

Activities describe how people spend their time, whereas goals are the results that they seek.

Give each team member a goal and some kind of structure on how they can make their own decisions to achieve their goal. For example you can tell everyone any decision that takes less then half a day to implement they can decide. Anything that takes more time than that they should discuss with you. Your goal is to set their goal and then get out of their way. You need to run interference between them and distractions from other parts of the company. Check in with them regularly to mentor and coach them to achieve their goal. Can you empower team leads below yourself to do some of the mundane management? When I worked for a performance management company I posted this over on Quora on goal setting. https://www.quora.com/Whats-the-difference-between-a-goal-an... Setting a goal changes the conversation from them coming to you with problems to coming to you with ideas and solutions.

One lesson I learnt when dealing with other managers, departments and up the line is that you have to over communicate. Everyone is mad busy in a start up and they will not remember what you discussed and all agreed last month. You almost need to market yourself, your team, goals and achievements to get their buy in. Run some regular workshops to get further buy in from them.

Your depression may stem from the feeling that you are not doing a good job more than the role itself so keep that in mind.

I have gone through the painful transition myself from doer to manager and I have made all the mistakes :) Design and marketing is my area, not tech. Happy to answer any questions you might have alan at spoiltchild.com

Alan


Did you really think being CTO means writing a lot of code? :D


I came up with a story that intuitively shows the difference of doing the seemingly exact same thing on different levels when I lived in the SF Bay Area - where I had ants in almost all apartments I lived in during the summer.

The story is about KILLING ANTS.

(Note: I lived in mostly peaceful coexistence with "my" ants - they had their roads through my living room and I ignored them, unless they started to crawl around my food. So no need to get upset, no excessive ant-killing took place in the development of this example.)

-----------

You kill a few ants in your kitchen. You can do that with your thumb or any object. However you do, it is a physical interaction between you and the ant(s). To kill more you repeat the same physical action. Killing one ant: one thumb press. Killing one hundred: one hundred thumb presses.

So the critical skill and the concrete action you will be doing throughout your ant-killing career is the "thumb press". Or if you use poison your skill is thumb pressing the spray can to distribute the poison.

-----------

Let's jump a few layers.

You become so good you attract the attention of the California governor. He puts you in charge of ant-killing in California.

-----------

QUESTION:

Will you do the same thing you did before, only more of it? A billion "thumb presses" instead of a few hundred?

Of course not!

You will never see or even touch a single ant yourself in your new job.

Instead of with ants you now work with a) humans, b) lawyers, c) regulations, d) logistics, e) statistics(!!!). You need to hire thumb-pressers, you need to organize poison - tons of it. You need to distribute the poison. You have to create maps and tell the middle managers where they should send their troops. You need to deal with absentees, internal politics, laws regulating work hours and poisons, people who were poisoned by your ant-killing troops because they misused the poisons. You need to collect numbers: Where were ants seen in the state? How many before the killing, how many after a week, a month, a year? Were the measures effective?

-----------

Compare the skills you need to control - kill - ants in your apartment or house with the skills you need to kill ants in ALL houses all over the state or country.

It SOUNDS like it is the same task - "kill ants". But human language is deceptive - 100% context dependent. "Scale" changes a problem completely.

If your ant-killing employees see any benefit at all in seeing you too kill an ant occasionally it is purely subjective "he's one of us", objectively each hour you yourself spend killing ants means you don't do your actual job of managing. It helps when you have past(!) experience - but joining your workers now really means that a) your are not doing your job or b) the problem still is low-scale (small startup - or, in the case of ants, even though you are responsible for ant-killing in the state there only are a handful of houses where there is anything to do).

-----------

Or another example, moving soil: If you need to move a tiny bit of earth you can use your hands. If it's a little bit you use a shovel - already you will no longer touch the soil directly. If you need to move even more soil you use an excavator - you now are even farther from the actual soil, and you need to know a lot about the machine, organize diesel fuel, spare parts, etc. If you need to move a vast amount of soil you get to the same problem as above, you don't even see the soil any more, you direct an organization, people, logistics, statistics, etc.


Nice simple analogy


[Not the right community for discussion and you can't delete old hacker news posts so let me nip this in the bud.]


If you do nothing but write code all day every day, you're not providing leadership, not managing, and not helping to others to develop their skills.


just take a nice vacation for a few months. ill fly in to do your job in exchange for 50% of the salary. after you've made up your you can either come back or not (and ill be a rich mofo muhahaha). the lesson being: if you get such a position and then complain about it being no fun then you are the problem. its an honor to be the boss. it makes a lot of money. if its no fun, well cleaning toilets for $5 an hour is no fun either but people do it anyways.


Can you re-architect the product from scratch? This should be doable if the raw building blocks (modules etc.) are properly designed and easily incorporated into a new design. If this is not the case, then all the more reason to rewrite the code!


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 wonder, did they really rewrite or refactor. Did they chuck out every single last line of code at once, or transitioned it slowly? Do they no legacy code left at all?


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.


OP not enjoying the CTO role doesn't mean he/she should waste company resources for their own amusement.

http://www.joelonsoftware.com/articles/fog0000000069.html


Read carefully: I said only rewrite if the code structure is bad. If the code structure is good, then re-architecting can amount to restructuring only the top-level parts.

It can give OP a better feel for how the code is designed, and give them more opportunity to change things in a more structured way in the long term by repeating the process (rather than just fighting fires every time).


Code structure provides very little business value.

Ten year old battle tested spaghetti is more valuable than any benefits a complete re-write would provide.


From my experience, if the following two conditions are met, you should continue. if not you should quit:

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.




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