5 ms·

Resources for chief technology officers, with the emphasis on startups

446 points by szimpl 6y ago

dreamer7 6y ago
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 6y ago
  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 6y ago
    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 6y ago
      Managing a team is just like managing threads. Keep them as autonomous and lock-free as possible
      - Schwolop 6y ago
        I like this. Hadn't heard it before, but it's succinct and as it happens, I agree!
- koonsolo 6y ago
  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.
  - bpodgursky 6y ago
    I think these are both valid approaches for different company sizes. If it's a team of 3-4, you're primarily an IC, who also CTO's. If it's a team of 10-15, it's the opposite.
- sponaugle 6y ago
  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 6y ago
    Interesting, how did you develop that skill?
    - sponaugle 6y ago
      The biggest accelerator, at least for me, was having a child. As anyone who has children know, the first few years are a long sequence of tasks interspersed with small breaks. If you want to get anything done, you have to be able to do it in small increments. On the hobby side for instance, I worked at keeping a running note log with my projects so I could walk in and actually make progress on a project when I only had 10 mins free. I carried a notebook with 'thought areas' that needed some thought applied, and if my daughter was sleeping I might crack it open and look at one of the problems and work on it. The ability to do real, forward progressing complex work in small chunks has made a huge difference in both my personal life and my professional one. I suspect it will also be helpful as I get older, because eventually great memory skills fade!
      - Schwolop 6y ago
        I second this. Ok, I'm on the Manager schedule now. How do I still make things? Having kids puts you on the Manager schedule (interruptions are to be expected and blocks of time without pre-scheduled interruptions are rare) whether you like it or not.
zappo2938 6y ago
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-never-do-part-i/ https://www.joelonsoftware.com/2000/04/06/things-you-should-...
- bombcar 6y ago
  Nowadays we don’t just rewrite from scratch - we create entirely new languages to rewrite IN.
  - ido 6y ago
    Actually Joel did that too! Some visual-basic inspired language if I recall correctly.
    - throwawayboise 6y ago
      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 6y ago
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 6y ago
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 6y ago
  [deleted]
- cjblomqvist 6y ago
  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.
Gaessaki 6y ago
Would love to see similarly curated lists for other startup roles such as CMO, or CFO, if anyone has.
- riffic 6y ago
  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.
blakesterz 6y ago
Has anyone made/found a list from/for CISOs?
jb1991 6y ago
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 6y ago
  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 6y ago
    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 6y ago
      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.
poushkar 6y ago
Here is something similar for Tech Leads: https://techleadcompass.com/ https://techleadcompass.com/
- enduser 6y ago
  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.
- neatze 6y ago
  Thank you!
kdeldycke 6y ago
Same here for Engineering Managers: https://github.com/kdeldycke/awesome-engineering-team-management https://github.com/kdeldycke/awesome-engineering-team-manage... With an emphasis on how to transition from developer to a management position.
water8 6y ago
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.
mjul 6y ago
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.
haolez 6y ago
I'm a CTO of a non-startup company and I've found one or two articles useful. Thanks!

446 points by szimpl 6y ago

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 6y ago
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 6y ago
  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 6y ago
    Managing a team is just like managing threads. Keep them as autonomous and lock-free as possible
    - Schwolop 6y ago
      I like this. Hadn't heard it before, but it's succinct and as it happens, I agree!
koonsolo 6y ago
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.
- bpodgursky 6y ago
  I think these are both valid approaches for different company sizes. If it's a team of 3-4, you're primarily an IC, who also CTO's. If it's a team of 10-15, it's the opposite.
sponaugle 6y ago
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 6y ago
  Interesting, how did you develop that skill?
  - sponaugle 6y ago
    The biggest accelerator, at least for me, was having a child. As anyone who has children know, the first few years are a long sequence of tasks interspersed with small breaks. If you want to get anything done, you have to be able to do it in small increments. On the hobby side for instance, I worked at keeping a running note log with my projects so I could walk in and actually make progress on a project when I only had 10 mins free. I carried a notebook with 'thought areas' that needed some thought applied, and if my daughter was sleeping I might crack it open and look at one of the problems and work on it. The ability to do real, forward progressing complex work in small chunks has made a huge difference in both my personal life and my professional one. I suspect it will also be helpful as I get older, because eventually great memory skills fade!
    - Schwolop 6y ago
      I second this. Ok, I'm on the Manager schedule now. How do I still make things? Having kids puts you on the Manager schedule (interruptions are to be expected and blocks of time without pre-scheduled interruptions are rare) whether you like it or not.

zappo2938 6y ago

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-never-do-part-i/ https://www.joelonsoftware.com/2000/04/06/things-you-should-...

bombcar 6y ago
Nowadays we don’t just rewrite from scratch - we create entirely new languages to rewrite IN.
- ido 6y ago
  Actually Joel did that too! Some visual-basic inspired language if I recall correctly.
  - throwawayboise 6y ago
    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 6y ago

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 6y ago

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 6y ago
[deleted]
cjblomqvist 6y ago
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.

Gaessaki 6y ago

Would love to see similarly curated lists for other startup roles such as CMO, or CFO, if anyone has.

riffic 6y ago
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.

blakesterz 6y ago

Has anyone made/found a list from/for CISOs?

jb1991 6y ago

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 6y ago
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 6y ago
  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 6y ago
    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.

poushkar 6y ago

Here is something similar for Tech Leads: https://techleadcompass.com/ https://techleadcompass.com/

enduser 6y ago
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.
neatze 6y ago
Thank you!

kdeldycke 6y ago

Same here for Engineering Managers: https://github.com/kdeldycke/awesome-engineering-team-management https://github.com/kdeldycke/awesome-engineering-team-manage... With an emphasis on how to transition from developer to a management position.

water8 6y ago

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.

mjul 6y ago

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.

haolez 6y ago

I'm a CTO of a non-startup company and I've found one or two articles useful. Thanks!