[HN Gopher] Resources for chief technology officers, with the em...
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Resources for chief technology officers, with the emphasis on
startups
Author : szimpl
Score : 361 points
Date : 2021-02-27 13:37 UTC (9 hours ago)
(HTM) web link (github.com)
(TXT) w3m dump (github.com)
| kdeldycke wrote:
| Same here for Engineering Managers:
| https://github.com/kdeldycke/awesome-engineering-team-manage...
|
| With an emphasis on how to transition from developer to a
| management position.
| Gaessaki wrote:
| Would love to see similarly curated lists for other startup roles
| such as CMO, or CFO, if anyone has.
| riffic wrote:
| The great thing about 'awesome-' lists and open source in
| general is you can always start your own.
|
| not trying to be snarky, just a friendly nudge.
| poushkar wrote:
| Here is something similar for Tech Leads:
| https://techleadcompass.com/
| neatze wrote:
| Thank you!
| enduser wrote:
| Thank you for taking the time to make this. I was delighted to
| see some of your top choices, Jerry Weinberg and Eli Goldratt
| for example, and will be sharing this with several team mates
| who are working toward leadership.
| blakesterz wrote:
| Has anyone made/found a list from/for CISOs?
| jb1991 wrote:
| What exactly would be the audience for this? I'd be worried about
| someone coming in as a CTO who would actually need a list like
| this.
| koonsolo wrote:
| I, on the other hand, would be worried when a CTO claims (s)he
| knows everything already.
|
| The more experienced you are, the more you realize how little
| you know.
| yowlingcat wrote:
| While that's true, these articles don't teach you that much
| as a CTO. The most leveraged way to learn how to CTO is to
| work for a good one and keep the curiosity level high. The
| next way after that is to cultivate good relationships with
| CTOs you look up to and develop a mentor-mentee relationship.
| The next most leveraged way to learn how to CTO is to just do
| it.
|
| Ultimately, reading the material on these lists is a very
| small fraction of the job. Personally, I've already read most
| of the items on the last list years ago when I was earlier in
| my career and wanted to understand different historical
| organizational models. That's the right time to read this
| kind of stuff, because you can use it to pattern match and
| dig into what others around you are doing in an environment
| where you are not on the hook for their strategic mistakes.
|
| By the time you're actually doing it, this material will
| probably not be that much help. You'll be in the driver's
| seat, not the passenger's seat. You'll need to use driver's
| seat tools, not passenger's seat tools.
| koonsolo wrote:
| This is my personal opinion, so don't take it too hard. But
| your post triggers my BS alert.
|
| First of all, how many CTO's do you know? And how many of
| them are good?
|
| Second, is this "mentor-mentee" thing real, or just
| something business coaches and get-rich-quick gurus claim?
| Never seen it in the real world.
|
| I'm an old timer. Most of my experience comes from
| experience. Most of my intellect comes from books an
| articles written by people who know what they are talking
| about. Claiming that the latter is a waste of time seems
| very wrong advice to me.
|
| But maybe your mentor told you differently.
| staticautomatic wrote:
| Perhaps we should add "Don't say things like 'The most
| leveraged way to learn how to CTO'." to the list.
| yowlingcat wrote:
| > Perhaps we should add "Don't say things like 'The most
| leveraged way to learn how to CTO'." to the list.
|
| Please leave the unnecessary snarkiness for other forums.
| I could have said "The most leveraged way to operate as a
| technology executive" but that's rather wordy. More than
| happy to engage with any substantive critiques you have
| with my point of view. It's what has worked for me, and
| it's based on my own experience.
| staticautomatic wrote:
| My comment is both a substantive critique of how you
| communicate and a commentary on executive communication.
| yowlingcat wrote:
| > My comment is both a substantive critique of how you
| communicate and a commentary on executive communication.
|
| Once you strip out the pedantic remark, you haven't
| actually said anything. I think your actual silence
| speaks volumes and makes my point for me.
| staticautomatic wrote:
| If you think that's how leaders of companies should talk
| and that people who criticize you for talking like that
| should be written off as pedants then good luck to you.
| [deleted]
| skullgrid wrote:
| I have a pretty good relationship with my boss (not a
| CTO, but a member of the executive leadership at my
| company). I definitely do consider her a mentor to me,
| and I am certain that she considers me a mentee. Over the
| last few years she has explicitly gone out of her way to
| help me improve my leadership skills. Not saying that
| this is kind of relationship is common or not, but it
| does exist.
|
| I do agree with the overall content of your post, though.
| yowlingcat wrote:
| > I'm an old timer. Most of my experience comes from
| experience. Most of my intellect comes from books an
| articles written by people who know what they are talking
| about. Claiming that the latter is a waste of time seems
| very wrong advice to me.
|
| I wonder if you're making my point for me. As an old-
| timer, what you bring to the table that's more valuable
| than gold is hard fought experience -- not the things
| you've read. It's easy to read things, but to actually
| apply them and be responsible for their long-term
| consequences is rather different.
|
| To answer your other question, I know quite a few CTOs.
| In particular, there are two that I know very well
| because I worked for them on the ground-floor building
| $1B+ startups at the seed-series A stage. So much of what
| I know came from observing what they did, asking for
| help, asking them to explain how they came to certain
| conclusions or made certain major decisions. I wanted to
| take apart how they did things even if I wasn't
| responsible for them, so I could put it back together and
| understand how it works. Not only that, but I kept in
| touch with them afterwards and found them very valuable
| sounding boards for when I gave my first CTO gig a shot.
| koonsolo wrote:
| It's true that experience is harder to get than knowledge
| from reading. But I still think reading offers a huge
| amount of benefit that you cannot get from experience.
|
| One thing is that it opens up a world that is broader to
| your own. Another thing is that it can provide clear
| mental models that you probably won't figure out
| yourself, and that you can observe only after you know
| the theory.
|
| Let me give you a clear example.
|
| Early in my career I had to manage a junior. At the time
| I was reading The 7 Habits Of Highly Effective People. I
| applied the "stewardship delegation" from that book to
| the letter. It worked perfect. In my 19 year career, I
| apply it all the time, with great success (it also works
| on your kids :D).
|
| But nobody I know knows about it. I could have never
| learned one of the most important things, from experience
| alone.
|
| Even when you look at people like Bill Gates for example,
| they also still seem to get great value out of reading.
|
| Thanks for the conversation, and sorry for my snarky
| remark, I admit I was wrong judging you :)
| PragmaticPulp wrote:
| > Second, is this "mentor-mentee" thing real, or just
| something business coaches and get-rich-quick gurus
| claim? Never seen it in the real world.
|
| Have you ever learned from one of your more senior
| coworkers or peers? Worked alongside someone who showed
| you the ropes or helped you level up your skills? Then
| you've been a mentee.
|
| Have you ever taken time to guide new hires or junior
| coworkers in something you're familiar with? Provided
| advice to accelerate someone's learning? Then you've been
| a mentor.
|
| Mentor/mentee usually isn't an explicit declaration. It's
| a very valuable way to accelerate skills, though not the
| only way.
| koonsolo wrote:
| Sure I had those, but it's more explicit when you are one
| of the many programmers taking advice from a senior
| programmer.
|
| In the case of a CTO, since it's a unque role, you have
| to go outside of your company to get mentored. And that
| doesn't seem so straight forward to me. Because asking a
| colleague about a problem you are facing is way easier
| than calling someone and talking about your problem at
| your work.
|
| Maybe I'm ignorant about this topic, and maybe such
| things are more normal in US than here in EU. Such things
| go really against my nature, but I aslo never seen such
| relationship outside of the same company.
| yowlingcat wrote:
| > Maybe I'm ignorant about this topic, and maybe such
| things are more normal in US than here in EU.
|
| If you're ignorant about the topic, why not explore the
| other perspective with curiosity rather than gruffly
| dismissing it as provoking a BS sensor? Mentorship is an
| enormous part of the lifecycle of executive tenure of the
| ecosystem I participate in, which is the NYC startup
| ecosystem.
|
| I've observed that when my colleagues have built a deep
| relationship with their manager during their tenure,
| often times, they gain that mentorship permanently
| whether they stay at the company or not. The reason the
| mentor does it is because it's just another version of
| the old adage of paying it forward -- they know that a
| job they land in the future could come from one of their
| old reports; in fact, they might even end up working for
| one of their old reports!
|
| Investing time and energy into cultivating and keeping
| these relationships going is a large part of how my
| colleagues have continued to keep their career moving
| upward as they approach mid-career.
| koonsolo wrote:
| It seems my BS sensor went off too fast ;).
|
| I guess this mentality is common to startup scenes, but
| not really outside of that world.
| jc01480 wrote:
| Humility is a dwindling characteristic in modern times.
| eatonphil wrote:
| Nobody knows everything. :D I am constantly looking for
| engineering management resources to learn more or find new ways
| of thinking.
| tylersmith wrote:
| It's not a syllabus for a training program, it's a list of
| resources you might need at different times, as a refresher or
| supplement for areas where you're weaker than in other areas.
| agy wrote:
| I find CTO title without knowing at least company size
| ambiguous. Engineering managers, directors are more constant
| across companies. Is there a big difference between engineering
| manager with a team of 8 working on a product and CTO with the
| engineering team of 8? I would say no. I feel that the list
| will be helpful for those who want to learn more about
| engineering leadership and soft skills.
| ido wrote:
| What about someone _growing_ into the role of CTO? I run a tiny
| company (single-digit number of workers) & am de-facto the
| only "boss"/executive so I guess you can say I'm the CEO (I'm
| also an individual contributor - as I said, tiny).
|
| But I still need to sometimes _also_ do what a CTO would do in
| a bigger company, and if things go well and the company grows I
| may need to incrementally learn more and more of the themes
| above (up to the point where I hire a CTO to replace me in that
| role I guess).
| notretarded wrote:
| >But I still need to sometimes also do what a CTO would do in
| a bigger company
|
| Not really.
| [deleted]
| simonw wrote:
| I don't think I've ever met a CTO who wouldn't benefit from a
| list like this - or who would deny that it would be useful.
|
| The secret to getting good at management is to acknowledge that
| it is a huge, deep and learnable set of skills. The best
| managers I know are the ones who constantly seek to improve
| their skills, and "do the work" to improve.
| tpmx wrote:
| Makes me think of the two Lex Fridman podcasts with Jim
| Keller. The second one (last week) got quite fun/loose.
|
| It's clear that Jim is constantly reading/actively improving,
| sometimes doing kinda unusual things, like having a specific
| strategy for priming his REM sleep by thinking a lot about
| some current problem combined with some kind of meditation
| exercise.
| sponaugle wrote:
| "I don't think I've ever met a CTO who wouldn't benefit from
| a list like this - or who would deny that it would be
| useful."
|
| The most valuable thing for me, and I am a CTO, is exactly
| the reminder of the breadth of the list. Most of the areas of
| the list are things I am familiar with, but it is easy to let
| a few areas fall short. One of the key expectations of a CTO
| is broad expertise, which is a tall ask.
| tpmx wrote:
| > One of the key expectations of a CTO is broad expertise,
| which is a tall ask.
|
| Being a generalist + working in many separate areas will
| get you there. It does take time to build experience. I
| guess you can accelerate it slightly by reading books, but
| really, most of the lessons are best learned by doing, I
| think.
| mjul wrote:
| One of the most important skills is learning to communicate
| clearly.
|
| You need to give up details and be able to express the key
| concepts clearly on different levels of detail and
| business/technical understanding.
|
| Explaining this is something you will be doing again and again,
| so it is worth a lot of effort to get there.
|
| I recommend iterating until you have an A4 with the skeleton you
| need explain all this. It will include key
| stakeholders/users/integrations, key technologies/protocols, key
| services/components and the high-level system landscape with key
| internal and external systems.
|
| Notice that a good diagram for this mixes a lot of different
| views and formal notations.
|
| The key idea is that you should strive to provide a skeleton on
| which your audience can place their understanding and fill in the
| blanks that they are interested in based on you explanation.
|
| If you try to put everything there or follow a formal model like
| UML you will drown out the key concepts in the noise of the
| details.
| water8 wrote:
| BEWARE: There are a lot of investors that will try and take
| advantage of your skills to build their business with the promise
| of equity that isn't real or can be changed or diluted on their
| terms. DONT be fooled into taking more salary over equity.
| dreamer7 wrote:
| My biggest challenge as a CTO is that, by nature, I'm singular in
| focus. If I am developing something I find it hard to context
| switch and review other developers' work. The best strategy I
| have found so far is to block certain times in the week solely
| for reviewing everyone's progress.
| Waterluvian wrote:
| I'm interested in hearing more about the idea of being an
| effective CTO while focusing on also being a developer.
|
| I imagine it's necessary for small companies, possible for
| growing companies, and eventually impossible for sufficiently
| sized companies where the CTO role is at least 40 hours of your
| week.
| ido wrote:
| I personally find it to become the case with as little as 5-6
| developers under me (assuming they are good and I can trust
| them to program without needing me to step in and solve their
| problems of their own making on a regular basis).
|
| Also as someone nearing his late 30s I'm sometimes surprised
| how good some programmers are as young as late teens/early
| 20s! These rare talents mostly need me to prevent them from
| going into rabbit holes but when they are pointing in the
| right direction can produce amazing results.
|
| I am sure my time is better spent helping a few of these do
| better than what I'd get from just myself programming
| directly in the same amount of time (management is a
| multiplier on the team's productivity and that multiplier can
| easily get smaller than 1.0).
| water8 wrote:
| Managing a team is just like managing threads. Keep them as
| autonomous and lock-free as possible
| koonsolo wrote:
| Why don't you do it the other way around? Plan in some focus
| time to work when nobody can bother you, and for the rest be
| available for the team.
| sponaugle wrote:
| That is interesting. I'm a CTO, originally a CTO of a startup,
| now CTO of the much larger acquiring company. It is fascinating
| to see how different the CTO job can be across industries. I
| find my time is spent in almost the opposite direction, with
| the majority of it involving deep technical context switched
| rapidly.. and that really is the skill that I have need to
| refine the most - the ability apply high focus quickly. Cool to
| hear other stories.
| zingar wrote:
| Interesting, how did you develop that skill?
| zappo2938 wrote:
| Quite a few articles by Joel Spolsky but missing what I believe
| to be his most important, Things You Should never Do, Part I. [0]
|
| [0] https://www.joelonsoftware.com/2000/04/06/things-you-
| should-...
| bombcar wrote:
| Nowadays we don't just rewrite from scratch - we create
| entirely new languages to rewrite IN.
| ido wrote:
| Actually Joel did that too! Some visual-basic inspired
| language if I recall correctly.
| throwawayboise wrote:
| IIRC he did that to support something that wasn't otherwise
| possible at the time, having the same code base run in ASP
| and PHP (i.e. Windows and Linux).
| EugeneOZ wrote:
| I thought it's the list of awesome CTO persons and I was going to
| promote one I know... Looks like it's not.
|
| Upd.: and now it's renamed, of course.
| matsemann wrote:
| I like that it's short and somewhat curated, try to make it stay
| that way. Most awesome lists grow to be link dumps. For instance
| the awesome-js is over thousands lines long now, containing all
| sorts of random crap. It can be nice as a way to know what's out
| there, but when it contains 40 mvc alternatives in addition to
| react/angular and other big ones, it's just not useful.
| [deleted]
| cjblomqvist wrote:
| I believe the most important knowing if your list is either or,
| and ensuring it sticks to that. For awesome-JS it might be the
| directory path (then make sure that's what users get out of
| it), but for a list like this I totally agree one should not
| make it a register of everything out there.
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