16 ms·

Ask HN: What are good books/blogs to read for a first time CTO?

523 points by kanodiaashu 3y ago

Planning my first startup as CTO, what resources should I go through for sure.

gwnywg 3y ago
Other people said it already that CTO may mean different things depending on context. From my exp CTO in small startup is marketing tool and it does not mean real "the CTO". In small org CTO is simply "do it all in no time" type of job, that includes hands on coding, infrastructure, but also hiring, overseeing and managing people. You also need to understand code lifetime and methodology of your choice, how to use it to provide good enough time estimates. And all of this will lead you to be probably replaced once organization grows.
TheGuineaGhost 3y ago
A Chief Technology Officer (CTO) is a top executive responsible for an organization's technological needs as well as its research and development (R&D). This role typically involves overseeing the development of technology to be sold to customers or used internally. The CTO also aligns the company's technology strategy with its business goals, ensures that technological resources meet the company's short and long-term needs, and leads the technology or engineering department. Additionally, they stay up-to-date with new technological developments and may also be involved in management decisions beyond the scope of their department.
CityOfThrowaway 3y ago
Peopleware is a classic https://www.amazon.com/Tom-Demarco/dp/0932633439/?nodl=1&dplnkId=34275b21-f2f0-4a43-b988-42ec9cd61865 https://www.amazon.com/Tom-Demarco/dp/0932633439/?nodl=1&dpl...
cientifico 3y ago
There was this related post in hn that might help you. https://news.ycombinator.com/item?id=37971795 https://news.ycombinator.com/item?id=37971795
kozak 3y ago
If it's just a "planning my first startup" stage and not an existing enterprise of some non-zero size, I'd suggest starting from the book "The Lean Startup" by Eric Ries and other general "startup mentality" information sources. For a tech-minded CTO, it's especially important to have that correct "startup mentality" to avoid big mistakes from the start.
Omroth 3y ago
The Meta Cast (Bob & Josh) is very useful for getting an insight into team management.
sergioisidoro 3y ago
An Elegant Puzzle: Systems of Engineering Management, by Will Larson
emmanueloga_ 3y ago
I’m reading the O’Reilly book on terraform. The end appendix has a great list of books to read for a CTO. Also planning to check the author other book, “Hello, startup” (see [1]). 1: https://www.ybrikman.com https://www.ybrikman.com
eddyzh 3y ago
It's old but a mythical man month is where dev management books realy started.
wslh 3y ago
Assumming you have worked as software engineer I recommend to talk with other CTOs, product people, and/or senior engineers (peer groups) and have concrete problems you would like to solve in mind. What kind of startup you want to build and in what field? Knowing more details about the challenges you will face help to narrow the focus to specific knowledge and skills.
deleted 3y ago
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elmarschraml 3y ago
Depends a lot on your situation: Does "CTO" mean you are the tech lead of a small (single team) engineering organization? Then everything written for staff engineers applies. E.g I've heard good things about "Staff engineer's path" by Tanya Reilly. Does "CTO" mean you are leading an org that is too large to be hands-on with tech, and need to build an effective structure and culture? Then I second the recommendation for "an elegant puzzle" by Will Larson. Or does "CTO" mean that you switched from being an engineer to managing a team of engineers? Then everything for new managers applies, for starters I'd recommend "Becoming an effective software engineering manager" by James Stanier, or "Engineering management for the rest of us" by Sarah Drasner. For some good general material, I'd also recommend the resources that Gergely Orosz makes available for subscribers to his "pragmatic engineer" newsletter. Those are templates for the kind of documents and processes you will most likely need - if you're new to the role, you will not go too wrong by using them, and if you want to create your own they are excellent starting points.
- skrebbel 3y ago
  And maybe CTO means “the founding programmer of a new startup” in which case my advice would be to stop reading and start coding :-)
  - 946789987649 3y ago
    There's always time to read, you can't only code. E.g. I run a lot so I get through a hell of a lot of audio books.
    - ysavir 3y ago
      I don't think the parent comment means only code, never learn. I think their intention was to not worry too much about the "CTO" title and instead focus on building the product at hand.
      - skrebbel 3y ago
        Yep. When building a startup you’ll find a lot of well-meaning people (in books or in person) who really do nothing but distract you. YC got it right, you should make something people want. Everything that’s not either making something or finding out what people want is just going to slow you down.
thiago_fm 3y ago
As a CTO you'll work a lot with people, the best resource you can get is related to people. Get a mentor, read books about dealing with people in the most optimal way for you and the business (closing deals, negotiation, psychology etc). Also learn how to develop people. There are a few books on this, but nothing beats experience and being reflective about it. Every situation is specific and it's up to you to strategize how to develop people in your team, finding out what are the right buttons to push.
ratg13 3y ago
Given that you have provided no information about your industry, the size of your company or team, your background, or any relevant information that could be used to help, literally any book could be a good fit for you. Your best bet is to see if your company is willing to pay for you to take some Dale Carnegie classes (Specifically the ones on Effective Communication). It will help you more than anything technical.
EwanToo 3y ago
If this is the first time you'd to be responsible for budgets, working with the board, finance teams, HR, etc, then I'd recommend a general business management book like "The Personal MBA" to give you an introduction to the concepts and language that those teams will use. The Personal MBA: A World-Class Business Education in a Single Volume https://amzn.eu/d/dTAp1GF https://amzn.eu/d/dTAp1GF
degradas 3y ago
Will Larson has a lot of excellent material and an upcoming book specifically targeted for engineering executives. Check out https://lethain.com/tags/executive/ https://lethain.com/tags/executive/ and https://www.oreilly.com/library/view/the-engineering-executives/9781098149475/ https://www.oreilly.com/library/view/the-engineering-executi...
erikstarck 3y ago
The Mythical Man Month and The Phoenix Project.
- Izmaki 3y ago
  I've had The Phoenix Project recommended before. Listening to the Audio Book now - hoping it's good.
  - Izmaki 3y ago
    A couple of hours of listening in here, it feels a lot like "The Five Dysfunctions of a Team" - a made-up story about a made-up company with made-up problems that are simple and self-contained enough to have solutions, and where colleagues are able to work together, despite turbulence. It's hard to relate to, honestly. It's likely that the target audience is just not "me", but I think somebody with very limited experience dealing with operations would enjoy it. Questions like "why is IT Change Management important" and "how do we prevent people from making mindless changes in production on a Friday afternoon". If you know this already, so far this book is nothing but a "good story about work" - if anybody ever miss this part of life.
  - deleted 3y ago
    [deleted]
jrflowers 3y ago
The Butter Battle Book
apples_oranges 3y ago
I would suggest reading 2-3 books from your tech domain, I mean the tech stack your startup will be using, and maybe 2-3 more about your niche (for example if you are in online advertising, read books about advertising in general and online in particular)
mobiuscog 3y ago
Whichever books you read - some great suggestions in the comments so far - please treat them as advice, and not religious texts. So many managers and higher fail terribly at being effective because they believe all they need to do is encourage/enforce the practices in the books on the engineering teams, and that is the path to failure and the death of morale. Take the books as guidance, but listen and engage with your reports (and their reports) to find the problems that need to be solved. Don't dictate or drive people, let them use their expertise in the direction you lead.
- ksplicer 3y ago
  People are notoriously bad at identifying what actually led to their success. Career advice authors even more so.
  - liquidpele 3y ago
    I’d imagine mostly because, at least with some jobs, a dead parrot could be successful because the success was tied to other things (luck, founder connections, a few great sales/devs, etc).
jeanloolz 3y ago
Managing Humans: Biting and Humorous Tales of a Software Engineering Manager
krishadi 3y ago
On a side note, when I had my startup and was the CTO, a lot of advice I got and also what I ended up realising was that my priority and goal was to build an amazing `Tech Team`.
gorbachev 3y ago
Books can help, but if I was you, I'd try and find a good mentor.
onion2k 3y ago
Technical founders are not CTOs. At least, not for a long time. A CTO role defines the strategic vision for the org. You'll have a vague idea of that as a founder but until you nail the product and where it fits in a market it won't really matter too much. Focus on executing and getting traction instead.
pknerd 3y ago
So, does a CTO need to know about: - Dev/ML/X Ops - System Architecture - DB design? etc?
- rwmj 3y ago
  IMHO they ought to have a developer background. That doesn't mean they need to be an expert in DBMS design or whatever, but they should know enough to know when one of their reports is talking BS. I once worked for a CTO who threw out all our Linux systems and replaced them with Solaris (early 2000s) because "Linux couldn't scale", at the behest of our database architect who was basically just trying to increase his own empire and budget. One of the stupidest and most costly decisions, that also demoralised the rest of the team.
- Izmaki 3y ago
  My expectation as a lead-role in DevOps is that my CTO understands what I am saying, if I were to present a business case to him for evaluation or raise a concern with the company tool stack. Shortly put I want somebody with decision making powers to also have the knowledge to make those decisions. I don't need them to be able to implement any of the changes, but I need them to be able to know why the change needs to happen and what business value it does or does not give.
oneplane 3y ago
At a startup phase, I'm not sure there is anything that is strictly speaking a "CTO" task, except the paperwork. And once you get big enough for it to matter, the same rule applies as for a CEO: the CxO you need for your first million is a different one you need for your 100 million and different yet again for your first billion. There is of course a GitHub list for this: https://github.com/kuchin/awesome-cto https://github.com/kuchin/awesome-cto and perhaps the best way to find out what you need is to check things off of that list that don't actually have anything to do with what you're actually working on. Role names generally have very little meaning on their own, it's all about context.
lnsru 3y ago
You need to book communication and/or good sales course. As CTO you’re into politics, not into tech. Ability to communicate clearly and steer the conversation is your skill number one. Tech background is nice to have, but not really useful. You will hire people for that.
budgi4 3y ago
Accelerate https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 https://www.amazon.com/Accelerate-Software-Performing-Techno... Team Topologies https://www.amazon.com/Team-Topologies-Organizing-Business-Technology/dp/1942788819 https://www.amazon.com/Team-Topologies-Organizing-Business-T... Making Work Visible https://www.amazon.com/Making-Work-Visible-Exposing-Optimize/dp/1950508498 https://www.amazon.com/Making-Work-Visible-Exposing-Optimize...
huqedato 3y ago
https://zachgoldberg.com/ctohandbook https://zachgoldberg.com/ctohandbook - that's a good start
emmelaich 3y ago
Designing Data-Intensive Applications by Martin Kleppmann
esseti 3y ago
The effective manager - how to manage people The mom test - how to discover product The EOS (Traction and Co) - how to manage the company and give direction to the vision of the company
- paulcole 3y ago
  I think EOS is great and that every startup should use it, but have a feeling that most HN readers will detest it because of Not Invented Here syndrome. It’s too tempting to think “How hard can it be to figure out how to run a meeting, set goals, etc.?” And then end up spending the time that should’ve been spent having meetings and working towards goals on all the minutiae and cruft that somebody else has worked out in the past.
simonebrunozzi 3y ago
I've been a CTO a couple of times (VMware, startup), I don't think I'm a good one (I am better as an individual contributor, rather than as a manager), but I have one piece of advice for you: ignore books, or use them as secondary source of truth. You should instead TALK to long-time or former CTOs and ask them for advice. You won't find that advice in any book. It's invaluable.
- rwmj 3y ago
  How/where did you find former CTOs to talk to?
  - _jal 3y ago
    ...you just found one and talked to him.
    - nsoldiac 3y ago
      not always a him
      - fdsalkjvlkjlkj 3y ago
        I'm pretty sure you can safely call him a him in this case.
      - _jal 3y ago
        When does Simone become something else?
        Jtsummers 3y ago
        Simone as a feminine or masculine name depends on the language and country. Simone in French is feminine, and in Italian (so a reasonable interpretation here given the last name) is masculine. In the US (and, from what I've seen, other English speaking countries) the name is brought in from French and generally considered feminine (barring being in an Italian community, I've met a couple Simone <Italian last name> men, but often the name becomes Simon after a generation or two in the US for men like how Roberto or Juan will become Robert or John for Spanish-language immigrant families). https://en.wikipedia.org/wiki/Simone_(given_name)#Simone https://en.wikipedia.org/wiki/Simone_(given_name)#Simone - Pick any of the Italians off the list and they're almost certainly men, most of the non-Italian Simone's are women. Of course, it's still safer to look them up if you don't actually know the person in question and want to use he or she.
pablobaz 3y ago
Scaling People: Tactics for Management and Company Building This is a great book for larger team sizes. https://amzn.eu/d/hnEQvsV https://amzn.eu/d/hnEQvsV
RorieD 3y ago
[flagged]
pixelmonkey 3y ago
I was CTO of a startup from pre-seed stage ($0 raised, bootstrapping) thru Series A + B stages ($millions raised, scaling). I then promoted a senior engineer to the CTO role, around the time that we had ~20-30 engineers organized into sub-teams with engineering leads. As part of that, I ran an engineering management book club internally for the new CTO and engineering leads (which was also open to any engineers to join). I then published that reading list as a neatly organized blog post. The team wrote web / SaaS / analytics software in Python and JavaScript, deployed on Linux + AWS, using lightweight planning tools like GitHub and Notion. It was also a fully distributed team long before the pandemic. Over time, the company (Parse.ly) gained hundreds of enterprise customers and established itself via profitable growth in a straightforward SaaS business model. In 2021, less than a year after this blog post was published, the company was acquired by one of the largest open web internet companies (Automattic, creators of WordPress.com). "Managing software teams: the definitive reading list" https://amontalenti.com/2020/11/28/definitive-reading-list https://amontalenti.com/2020/11/28/definitive-reading-list The blog post is organized into a few sections, each featuring a few relevant books: - Management as a high-leverage activity - Product marketing and product management - Debugging dysfunctional product cultures - The psychology of deep work - Fully distributed teams - Programmer mindset and philosophy It's easy to skip around to find a good starting point or make your own (smaller) reading list. Hope that helps. Good luck!
- dopamean 3y ago
  That sounds like a really awesome workplace you built there. Nice job.
- elamje 3y ago
  Hey Andrew! Thanks for sharing all the resources and giving me guidance a few years ago. Still very thankful for a few of your posts and pointing me to read Venture Deals, all made me a much better CTO and founder. Hope your current journey is going great!
  - pixelmonkey 3y ago
    Glad to hear it was helpful!
Oras 3y ago
For a startup, focus on shipping faster. The only thing that matters in a startup is finding the product market fit. If you don’t get to this point, the startup will die. So spending time optimizing the performance or arguing which code formatting standards to follow is just a waste of time and resources.
huqedato 3y ago
https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507 https://www.amazon.com/INSPIRED-Create-Tech-Products-Custome... https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/149197379X/ https://www.amazon.com/Escaping-Build-Trap-Effective-Managem...
OliverJones 3y ago
Read about what to do: _The Fifth Discipline_ by Peter Senge. A bit dated by now, it's still good stuff about "systems thinking" . And you'll need a lot of deliberate systems thinking in your job, and you'll need to teach others to think that way. Read about what not to do: _The Ultimate Question_ by Fred Reichheld. This book is about the notorious Net Promoter Score. (Would you recommend HN to a friend? Would you? Would you?) Reading it will give you insight into how bonehead MBAs with Cs in their marketing classes can convince leadership they've come up with a good way to measure customer satisfaction. (Net Promoter Score works fine for competitive businesses selling commodity products -- rental cars to individuals for example -- but not for many places where it is now used.)
stargrazer 3y ago
Coincidentally, this showed up on my Twitter timeline just now: https://github.com/kuchin/awesome-cto https://github.com/kuchin/awesome-cto - A curated and opinionated list of resources for Chief Technology Officers and VP R&D, with the emphasis on startups and hyper-growth companies. Someone else beat me to the link.
smk_ 3y ago
Those who can't do, teach. Don't read. Do.
- rjtavares 3y ago
  And those who can do are often terrible teachers.
rnjailamba 3y ago
Mindset and leadership (explore other titles by Gerald M. Weinberg as well) - An Introduction to General Systems Thinking - Becoming a Technical Leader: An Organic Problem-Solving Approach So that you have a good answer to "when will it be ready" - Software Estimation: Demystifying the Black Art - Agile Estimating and Planning People management - The Manager's Path: A Guide for Tech Leaders Navigating Growth and Change - High Output Management Besides Mythical Man Month already mentioned in other comments.
TDiblik 3y ago
Depends on what you're into: romance: i would suggest "Looking for Alaska" by John Green or "Pierre et Luce" by Romain Rolland fantasy: The Way Of Kings by Brandon Sanderson or "Blackout" by Marc Elseberg life advice ig?: "The Algebra of Happiness" by Scott Galloway ... never been a CTO xd
jdalsgaard 3y ago
Not a book or blog per se, but: https://datatracker.ietf.org/doc/html/rfc1925 https://datatracker.ietf.org/doc/html/rfc1925 -- The Twelve Networking Truths.
leandot 3y ago
You’ve been chosen to be a CTO, this usually means that you either did well in the company or were hired because of a good track record. So keep doing this + keep things simple, plan ahead, learn from colleagues, share knowledge. Stay humble, confess mistakes, ask for genuine feedback and advice. Books and blogs have a limited anecdotal value (sometimes it is high but the effort is also high). I’ve learned more from individual HN comments and actual work experience and mistakes than any book.
- tailspin2019 3y ago
  I mean this is decent advice, but slightly odd given you could easily have plugged your site here AND actually given the OP what they asked for :-) Maybe it’s some reverse psychology thing. Ok I’ll do it, you evil genius… https://hackernewsbooks.com https://hackernewsbooks.com PS CTOs aren’t always chosen, many are self-appointed as founders or co-founders (possibly in this case too). Chosen implies you’ve been subject to external assessment, self-appointed is a different matter altogether (ie. you may be extremely aware of possible knowledge/experience gaps that you need to quickly fill). To add my own suggestion, I think High Output Management by Andy Grove is an excellent resource (not just for CTOs)
  - leandot 3y ago
    That is a very interesting line of thinking, my comment was kind of the opposite - I find that after reading a couple of good books on a certain topic, the rate of learning goes down rapidly compared to the steady amount I get from HN comments and experience. About hackernewsbooks - it's not mine since many years and I am not affiliated with it, I am just the one who built it and sold it. It's still nice though.
    - tailspin2019 3y ago
      I didn’t mean to give you a hard time - I think you’re right about the limited returns on reading after a while! It just seemed a shame not to mention hackernewsbooks since it is probably a good resource for the OP :) It makes more sense though if you have sold it! Congrats on that.
lifeisstillgood 3y ago
Simply put: https://grugbrain.dev/ https://grugbrain.dev/
elbi 3y ago
https://datatracker.ietf.org/doc/html/rfc1925 https://datatracker.ietf.org/doc/html/rfc1925
WillAdams 3y ago
Jerry Kaplan's _StartUp_ is a classic which shows the dark underbelly of deal-making and press-release creation, and why we can't have nice things if they aren't being made so as to ensure the profit of a dominant player: https://www.goodreads.com/book/show/1171250.Startup https://www.goodreads.com/book/show/1171250.Startup Contrast it with: https://www.folklore.org/MacBasic.html https://www.folklore.org/MacBasic.html and the early history of VisualBASIC (and wonder how things might have played out had the Mac had a nice development environment out the gate) and for management interactions see: https://www.joelonsoftware.com/2006/06/16/my-first-billg-review/ https://www.joelonsoftware.com/2006/06/16/my-first-billg-rev...
mysterydip 3y ago
Game Thinking, by Amy Jo Kim: https://gamethinking.io/ https://gamethinking.io/ Coincidentally, a quote from Ycombinator CEO Garry Tan on their site: You’ve got to find your own window of opportunity. Game Thinking is your instruction manual.
FourthProtocol 3y ago
I'm somewhat surprised that strategy is only mentioned once (at time of writing). Strategy is vital for any leadership role. Sun Tsu is a classic, but can be difficult to assimilate. There are many resources on Wikipedia. Often overlooked is dealing with power and politics (https://www.wittenburg.co.uk/Work/Politics.aspx https://www.wittenburg.co.uk/Work/Politics.aspx) Keeping up to date on tech also important, especially at the tech lead/architecture level (https://www.wittenburg.co.uk/Work/Mentoring.aspx https://www.wittenburg.co.uk/Work/Mentoring.aspx).
zoenolan 3y ago
As others have said, joining a community has been helpful to me. I would recommend CTO Craft. You get to hear what issues others are dealing with and how they solve them. https://ctocraft.com/community/ https://ctocraft.com/community/
- tudorizer 3y ago
  Hello, fellow CTO Craft member!
  - zoenolan 3y ago
    Howdy :)
diegof79 3y ago
The best advice is probably to learn as much as you can from different sources but also keep a pragmatic point of view that helps to select the things that apply to your situation. Very often, new leaders follow a recipe without paying attention to the organization's problems. (check the book “The First 90 Days” by Watkins; it may give you ideas to organize your initial approach). As someone who went from engineering to product design, I observe that CTOs without a product vision are challenging to work with. For example, at a previous company, a CTO tried to implement the hard rule that every UI component should be in the shared UI library. But, even when I was leading the design system, that rule didn’t match how a product design process works. It caused delivery slowdowns and a degradation of the UX. I can bring up other examples, and the typical pattern is a leader looking at only one aspect or two without balance. Try to go beyond engineering and learn more about business and product design, which will help you prioritize engineering decisions. Some product-related books: Inspired by Cagan and Well-Designed by Kolko. Beyond engineering and product, as a C-level executive or director, people and hiring will be your primary concern. There are many management books, and I don’t have any particular to recommend (all of them will provide tools, but none is perfect: The Advantage and The Five Dysfunctions of a Team by Lencioni, The Phoenix Project by Gene Kim). I also enjoy taking ideas from biographical stories like Creativity Inc. by Ed Camull or Creative Selection by Ken Kocienda. Finally, a book I found funny and cynical but depicts big corps very well is “Management Stripped Bare” by Jo Owen.
rramadass 3y ago
Doing short courses (executive training) might be better. Assuming you have the Technical Domain side covered, my suggestion would be to focus on the following; 1) Behavioural Psychology - https://en.wikipedia.org/wiki/Behaviorism https://en.wikipedia.org/wiki/Behaviorism 2) Organizational Behaviour - https://en.wikipedia.org/wiki/Organizational_behavior https://en.wikipedia.org/wiki/Organizational_behavior 3) Evidence-based Management - https://en.wikipedia.org/wiki/Evidence-based_management https://en.wikipedia.org/wiki/Evidence-based_management
jakderrida 3y ago
I imagine whatever agency or branch that's employing you should provide the specialized training you need. I doubt they'd publish or share the most important practices for security against those you're Counter-Terrorist Operations are targeting from staying ahead of you with that knowledge.
rdli 3y ago
I think the #1 thing when you become part of an exec team is that you should be optimizing for the _business_, and not your function. The working assumption is that you will keep your function executing and delivering, but what is really hard is helping to figure out what the right decisions are for the business. Should we invest more in product or sales? What if there’s a huge top of funnel problem — what can we do about it? Your job is to bring that technology perspective to the discussion. I’ve been an exec, founder, CEO, and board member at various stages of successful (IPO) /unsuccessful companies (acqui-hire) companies. And the common thread at every stage is that the most successful companies had management teams that worked well together to optimize for the business. So instead of spending your energy on reading / learning more about tech, I’d recommend you spend your energy learning more about business (I’d probably start by asking the CEO & the rest of the mgmt team for advice on what to learn.)
- mooreds 3y ago
  This is phenomenal advice. You might, for example, recommend outsourcing non-corrosive functionality rather than building it in house, if you feel that is better for the company. You should do this even if it leads to layoffs for your department, because, again, your goal should be a thriving business, not a thriving engineering department and a lackluster business. Source: I did recommend and lead this course of action once (the outsourcing, not the layoffs). Company is still using an outsourced solution.
  - mooreds 3y ago
    *non-core
- wlonkly 3y ago
  This is one of the points made in Patrick Lencioni's "The Five Dysfunctions of a Team", which I've always found a valuable read. A warning, though: it's a "business fable", where he gets his point across by telling a fictional story. Business writers tend to be pretty terrible fiction writers so it's corny, but it also makes it a pretty light read.
mrtimo 3y ago
I teach an MBA class on a similar subject. The students like a book called "Adventures of an IT leader". It's a fun read that students with work experience can relate to. And students without work experience can learn a lot from.
koliber 3y ago
This might be a bit contrarian, but don’t read engineering oriented books. Read up on selling, marketing, and product design. These are the things that will help you make better decisions about what you will build. My bet is that you got the technology parts covered, and the management things will start to matter once you have a team of 8+.
ipnon 3y ago
"An Elegant Puzzle" by Will Larson[0] is revelatory when it comes to leading a software engineering team. There is a solution to every organizational problem I've encountered in companies from single digits to thousands. That book alone, along with its intentional and organized bibliography is one of the best investments you can make in a tech career. Even without context on the size of your company, Larson's new "The Engineering Executive's Primer"[1] will surely make a valuable introduction too. [0] https://press.stripe.com/an-elegant-puzzle https://press.stripe.com/an-elegant-puzzle [1] https://lethain.com/eng-execs-primer/ https://lethain.com/eng-execs-primer/
hardkorebob 3y ago
[dead]
foxbarrington 3y ago
You might find my survival guide for founders who depend on devs to get things done useful. It covers topics like how not to lose key information if a dev leaves, preventing endless rebuilds and framework switching, keeping devs busy vs. keeping them productive, and ensuring product builds don't go off the deep end. As an example, here's the chapter on estimates: https://superstruct.tech/blog/estimates https://superstruct.tech/blog/estimates
tgtweak 3y ago
Given the diversity of the "CTO" role in terms of responsibilities and scale - what you should be reading will vary depending on your current size, composition, industry and your own personal experience level. One I find no trouble recommending regardless of these however is High Output Management by Andy Grove (of Intel). Not a new book, but chalk full of what I consider absolute truths when it comes to optimizing middle management (which is predominantly your role as a CTO, once the org reaches 50+ people and your direct reports all have direct reports). The fact it is still very relevant to organizational challenges today when it was written 40 years ago is a testament to this. It is a shame there are so few books that focus on this very-ignored (and honestly largest) segment of management and arguably where you get the most traction as a company. I've yet to meet two CTOs that share the same skillset or strengths, or who work in the same org structure. I would recommend doing some executive courses and trainings (with our other execs) to learn some common language and techniques/methodologies around team management and execution - this has been the thing which helped me most in embracing a CTO role (even one with other CTOs from separate business units reporting into). It is ironic but the best blend for a high level CTO is actually people and organizational skills moreso than pure technical aptitude. You need to be able to fact check your people and ask the right technical questions and understand the fundamentals of technical debt and TCO analysis, but honestly you'll be using your people/organizational skills and trying to hire people that know the technology better than you for the most part.
mooreds 3y ago
This isn't a book or blog, but I recommend two different communities: CTOlunches.com, which is an in-person group that meets for lunches around the world. It also has an active mailing list, with hundreds of engineering leaders there. The rands leadership slack (Google for it) is an invite only slack with thousands of engineering leaders across the world. Great for asynchronous conversations across a wide variety of topics; they even have an anonymous q and a channel.
svilen_dobrev 3y ago
Camille Fournier: the manager's path Eye-opener (worst take away / for me - you can't be friends with devs-under-you anymore. Or with anyone techie it seems. Probably depends on company-founders' culture - if small and new - or politics - if older and/or bigger) some more of hers here: https://skamille.medium.com/an-incomplete-list-of-skills-senior-engineers-need-beyond-coding-8ed4a521b29f https://skamille.medium.com/an-incomplete-list-of-skills-sen... Also.. you can't be everything. Choose your poison (or if it has been pre-chosen, find out what it is sooner than later), hire other people for other stuff: https://www.allthingsdistributed.com/2007/07/the_different_cto_roles.html https://www.allthingsdistributed.com/2007/07/the_different_c... more on the topic: https://news.ycombinator.com/item?id=20642423 https://news.ycombinator.com/item?id=20642423 And... think/assess very-very well - all-the-time - How much trust you have got.. and for what. YMMV. Sometimes "CTO" is only a parrotizing label for investors to flock on. Sometimes it's for real. have fun
- Solvency 3y ago
  A CTO can't have friends in their department?
  - mooreds 3y ago
    I think it is really tough for execs to have friends in the same department, not just the CTO. Sometimes the business has needs that conflict with people's needs/desires and a good exec should choose the business.
jantypas2 3y ago
I don't know if I qualify for a CTO though people call me one (people have called me names since I was a kid but Mom always said to ignore them...) But let's tuck at that first word -- "Chief". In many cultures Chief meant the one who held the final responsibility for whatever went bad. They were also the ones who had to negotiate with opposing forces. With that in mind, learn your opposing forces and what can go wrong. Ask the dreaded Marketing tribe for their books and learn shamanic things like how long it takes to get something into the media or a retail store. Negotiate with someone in nursing to learn the mystical art of dealing with angry people you are actually trying to help. You will learn more from a nurse or a clothing buyer than you will learn from the best coding book.
VPenkov 3y ago
Just to add a bit to the excellent list this thread has collected: https://github.com/kuchin/awesome-cto https://github.com/kuchin/awesome-cto Some hit-and-miss there but I discovered a lot of great advice.
CountVonGuetzli 3y ago
After doing the first-time CTO thing three years ago in an established company with over 100 engineers, I think these two are the minimum required reading: An Elegant Puzzle: Systems of Eng Management (https://lethain.com/elegant-puzzle https://lethain.com/elegant-puzzle) and The Art of Leadership, small things done well (https://www.amazon.com/Art-Leadership-Small-Things-Done/dp/1492045691 https://www.amazon.com/Art-Leadership-Small-Things-Done/dp/1...) There are a lot more that were helpful to me, but those two encompass most of the important concepts and skills already in a usefully synthesized way, at least for me.
brightball 3y ago
Are you funded and hiring or are you building? If you’re building, I’ll echo other commenters…stop reading and go code. For just about any advice I’d say go read Rework, in between coding sessions.
alberth 3y ago
This is hugely dependent upon company size. CTO skills needed for a 10-person company is radically different than a 10,000-person company.
demon-code-999 3y ago
everyone is a CTO on linkedin
AC_8675309 3y ago
If I were a CEO and my CTO asked that question I would start looking for a new CTO. Sorry, not a helpful answer...
- Rastonbury 3y ago
  Great CEO here, firing your first time CTO for asking for advice on something they've never done before
  - AC_8675309 3y ago
    You are taking a massive corporate risk by bringing in someone who doesn't know what they are doing. I would be equally worried if I was the director of engineering and had to work with this person. Ditto if I was a lower level engineer. If I had to guess the poster is actually talking about engineering and confusing it with technology ... which is a whole different problem.
feoren 3y ago
Learn about your industry. Learn about the problem. Learn as much as you can about the problem your company is trying to solve. Learn industry jargon. You already know enough about the tech; just focus on the subject matter itself.
max_ 3y ago
Check out Drew Houston's comment on HN from last year. [0] [0]: https://news.ycombinator.com/item?id=33595470 https://news.ycombinator.com/item?id=33595470
tivert 3y ago
Peopleware: Productive Projects and Teams https://www.amazon.com/Peopleware-Productive-Projects-Teams-3rd-dp-0321934113/dp/0321934113/ref=dp_ob_title_bk https://www.amazon.com/Peopleware-Productive-Projects-Teams-... It's a classic, and also a pretty easy read. If you're in technology and haven't read it yet, you should.
RecycledEle 3y ago
Do not read books or blogs. Learn to do every technical job in your company.
mikey_p 3y ago
Must listen: The Idealcast with Gene Kim I can't stress just how good this podcast is, all of the guests are excellent. Here's a brief highlight of my favorites: - Michael Nygard, SVP of Enterprise Architecture, Sabre - brilliant breakdowns of how to approach software problems conceptually - Dr Steven Spear - tons of excellent stuff from years of studying Japanese management techniques - Elisabeth Hendrickson - has been studying testing and QA for decades, tons of great insights - Scott Havens - incredible breakdown of the inventory management system of jet.com, acquired by Wal-mart and now powering walmart.com https://itrevolution.com/podcast/ https://itrevolution.com/podcast/
mattferderer 3y ago
Underrated new book not mentioned here - Think Like a CTO by Alan Williamson
graycat 3y ago
To several of the authors here, "thanks, I needed that". I have the software written, and it appears to run as intended. Now, doing computer systems management, silly stuff; main problem, getting past bad documentation, e.g., was just up all night working with video adapters, device drivers, display resolution, font scaling, HDMI, display port, flickering cursors, etc. Since the documentation was so bad, I did take some notes on the more important things I learned, e.g., by the TIFO (try it and find out) Method. The results are not perfect but are good enough for now. I can delay more until the business is growing nicely (if it ever does). That is, for now concentrate on giving people "something they want" and put video issues way down on the TODO list. But a concern: If such silly technical stuff does go well, then I could be going live on the Internet fairly soon. Then some of the issues might be: (1) publicity and getting the first users (2) getting advertisers (3) billing and accounting So, from this thread and a few hours at Google this week, I just concluded: For nearly all that stuff, nearly every business has to do it. So, there are well polished options for how to do it, and I can put it low on the TODO list for now. For what to do if the business starts to grow, I saw some of that at FedEx and elsewhere. Right, as in this thread, focus on providing "what people want", the work, and the revenue. E.g., if I get a lot of users, then that should help getting some advertisers. Then will need billing and accounting, and, uh, there is no shortage of people who can provide such services for me -- getting the revenue is the hard part; given the revenue, it stands to be easy to work with an accounting service! Or, for a lot "I don't know how to do it, but there are plenty of people who do." In particular, for management and in particular engineering management, I've seen, been in, and done some of it and conclude now that my business will be nicely successful before I will have to look into the theories of it. In particular, I saw several cases of guys really eager to work hard, occasionally all night, get good stuff done, with no credit from any management. For the core technical stuff, my efforts have some of that, and it should be a business advantage, uses some of my experience and Ph.D. in applied math, I would say beats AI, and easy for me -- early on in the effort I wrote up the math in Knuth's math word processing TeX. Then used the write up when I wrote the code (Windows, IIS, .NET, ASP.NET, ADO.NET, platform invoke, etc.). So, the core technical stuff is done, not even on the TODO list! On with the rest with the balances as often in this thread.
coolThingsFirst 3y ago
You are focusing on the wrong thing, your #1 goal should be building a business that people want to pay for. Everything else is secondary.
0x54MUR41 3y ago
I would like to add a book called "Think Like a CTO" [0] by Alan Williamson. The author has experiences as a CTO in different companies. He also give a lot of advice. The book is not only applicable for CTOs, but also other leadership roles. It discusses various topics from team management to technology decisions. edit: the book was already mentioned by mattferderer [1]. [0]: https://www.manning.com/books/think-like-a-cto https://www.manning.com/books/think-like-a-cto [1]: https://news.ycombinator.com/item?id=38809998 https://news.ycombinator.com/item?id=38809998
bigtechdigest 3y ago
Neither a book nor a blog, but I'm building a newsletter that aggregates the latest articles from company engineering blogs. I think you might find it useful: http://bigtechdigest.substack.com http://bigtechdigest.substack.com
throwaway81523 3y ago
Tom DeMarco, "Peopleware". It says don't have open plan offices (iirc). That's good enough for me.
nemanja_codes 3y ago
Have a look here: https://github.com/kuchin/awesome-cto https://github.com/kuchin/awesome-cto Maybe I have few more useful links here: https://github.com/nemanjam/bookmarks https://github.com/nemanjam/bookmarks
Hernandesalvir 3y ago
[dead]

523 points by kanodiaashu 3y ago

Planning my first startup as CTO, what resources should I go through for sure.

Other people said it already that CTO may mean different things depending on context. From my exp CTO in small startup is marketing tool and it does not mean real "the CTO". In small org CTO is simply "do it all in no time" type of job, that includes hands on coding, infrastructure, but also hiring, overseeing and managing people. You also need to understand code lifetime and methodology of your choice, how to use it to provide good enough time estimates. And all of this will lead you to be probably replaced once organization grows.

TheGuineaGhost 3y ago

A Chief Technology Officer (CTO) is a top executive responsible for an organization's technological needs as well as its research and development (R&D). This role typically involves overseeing the development of technology to be sold to customers or used internally. The CTO also aligns the company's technology strategy with its business goals, ensures that technological resources meet the company's short and long-term needs, and leads the technology or engineering department. Additionally, they stay up-to-date with new technological developments and may also be involved in management decisions beyond the scope of their department.

CityOfThrowaway 3y ago

Peopleware is a classic https://www.amazon.com/Tom-Demarco/dp/0932633439/?nodl=1&dplnkId=34275b21-f2f0-4a43-b988-42ec9cd61865 https://www.amazon.com/Tom-Demarco/dp/0932633439/?nodl=1&dpl...

cientifico 3y ago

There was this related post in hn that might help you. https://news.ycombinator.com/item?id=37971795 https://news.ycombinator.com/item?id=37971795

kozak 3y ago

If it's just a "planning my first startup" stage and not an existing enterprise of some non-zero size, I'd suggest starting from the book "The Lean Startup" by Eric Ries and other general "startup mentality" information sources. For a tech-minded CTO, it's especially important to have that correct "startup mentality" to avoid big mistakes from the start.

Omroth 3y ago

The Meta Cast (Bob & Josh) is very useful for getting an insight into team management.

sergioisidoro 3y ago

An Elegant Puzzle: Systems of Engineering Management, by Will Larson

emmanueloga_ 3y ago

I’m reading the O’Reilly book on terraform. The end appendix has a great list of books to read for a CTO. Also planning to check the author other book, “Hello, startup” (see [1]). 1: https://www.ybrikman.com https://www.ybrikman.com

eddyzh 3y ago

It's old but a mythical man month is where dev management books realy started.

wslh 3y ago

Assumming you have worked as software engineer I recommend to talk with other CTOs, product people, and/or senior engineers (peer groups) and have concrete problems you would like to solve in mind. What kind of startup you want to build and in what field? Knowing more details about the challenges you will face help to narrow the focus to specific knowledge and skills.

deleted 3y ago

[deleted]

elmarschraml 3y ago

Depends a lot on your situation: Does "CTO" mean you are the tech lead of a small (single team) engineering organization? Then everything written for staff engineers applies. E.g I've heard good things about "Staff engineer's path" by Tanya Reilly. Does "CTO" mean you are leading an org that is too large to be hands-on with tech, and need to build an effective structure and culture? Then I second the recommendation for "an elegant puzzle" by Will Larson. Or does "CTO" mean that you switched from being an engineer to managing a team of engineers? Then everything for new managers applies, for starters I'd recommend "Becoming an effective software engineering manager" by James Stanier, or "Engineering management for the rest of us" by Sarah Drasner. For some good general material, I'd also recommend the resources that Gergely Orosz makes available for subscribers to his "pragmatic engineer" newsletter. Those are templates for the kind of documents and processes you will most likely need - if you're new to the role, you will not go too wrong by using them, and if you want to create your own they are excellent starting points.

skrebbel 3y ago
And maybe CTO means “the founding programmer of a new startup” in which case my advice would be to stop reading and start coding :-)
- 946789987649 3y ago
  There's always time to read, you can't only code. E.g. I run a lot so I get through a hell of a lot of audio books.
  - ysavir 3y ago
    I don't think the parent comment means only code, never learn. I think their intention was to not worry too much about the "CTO" title and instead focus on building the product at hand.
    - skrebbel 3y ago
      Yep. When building a startup you’ll find a lot of well-meaning people (in books or in person) who really do nothing but distract you. YC got it right, you should make something people want. Everything that’s not either making something or finding out what people want is just going to slow you down.

thiago_fm 3y ago

As a CTO you'll work a lot with people, the best resource you can get is related to people. Get a mentor, read books about dealing with people in the most optimal way for you and the business (closing deals, negotiation, psychology etc). Also learn how to develop people. There are a few books on this, but nothing beats experience and being reflective about it. Every situation is specific and it's up to you to strategize how to develop people in your team, finding out what are the right buttons to push.

ratg13 3y ago

Given that you have provided no information about your industry, the size of your company or team, your background, or any relevant information that could be used to help, literally any book could be a good fit for you. Your best bet is to see if your company is willing to pay for you to take some Dale Carnegie classes (Specifically the ones on Effective Communication). It will help you more than anything technical.

EwanToo 3y ago

If this is the first time you'd to be responsible for budgets, working with the board, finance teams, HR, etc, then I'd recommend a general business management book like "The Personal MBA" to give you an introduction to the concepts and language that those teams will use. The Personal MBA: A World-Class Business Education in a Single Volume https://amzn.eu/d/dTAp1GF https://amzn.eu/d/dTAp1GF

degradas 3y ago

Will Larson has a lot of excellent material and an upcoming book specifically targeted for engineering executives. Check out https://lethain.com/tags/executive/ https://lethain.com/tags/executive/ and https://www.oreilly.com/library/view/the-engineering-executives/9781098149475/ https://www.oreilly.com/library/view/the-engineering-executi...

erikstarck 3y ago

The Mythical Man Month and The Phoenix Project.

Izmaki 3y ago
I've had The Phoenix Project recommended before. Listening to the Audio Book now - hoping it's good.
- Izmaki 3y ago
  A couple of hours of listening in here, it feels a lot like "The Five Dysfunctions of a Team" - a made-up story about a made-up company with made-up problems that are simple and self-contained enough to have solutions, and where colleagues are able to work together, despite turbulence. It's hard to relate to, honestly. It's likely that the target audience is just not "me", but I think somebody with very limited experience dealing with operations would enjoy it. Questions like "why is IT Change Management important" and "how do we prevent people from making mindless changes in production on a Friday afternoon". If you know this already, so far this book is nothing but a "good story about work" - if anybody ever miss this part of life.
- deleted 3y ago
  [deleted]

jrflowers 3y ago

The Butter Battle Book

apples_oranges 3y ago

I would suggest reading 2-3 books from your tech domain, I mean the tech stack your startup will be using, and maybe 2-3 more about your niche (for example if you are in online advertising, read books about advertising in general and online in particular)

mobiuscog 3y ago

Whichever books you read - some great suggestions in the comments so far - please treat them as advice, and not religious texts. So many managers and higher fail terribly at being effective because they believe all they need to do is encourage/enforce the practices in the books on the engineering teams, and that is the path to failure and the death of morale. Take the books as guidance, but listen and engage with your reports (and their reports) to find the problems that need to be solved. Don't dictate or drive people, let them use their expertise in the direction you lead.

ksplicer 3y ago
People are notoriously bad at identifying what actually led to their success. Career advice authors even more so.
- liquidpele 3y ago
  I’d imagine mostly because, at least with some jobs, a dead parrot could be successful because the success was tied to other things (luck, founder connections, a few great sales/devs, etc).

jeanloolz 3y ago

Managing Humans: Biting and Humorous Tales of a Software Engineering Manager

krishadi 3y ago

On a side note, when I had my startup and was the CTO, a lot of advice I got and also what I ended up realising was that my priority and goal was to build an amazing `Tech Team`.

gorbachev 3y ago

Books can help, but if I was you, I'd try and find a good mentor.

onion2k 3y ago

Technical founders are not CTOs. At least, not for a long time. A CTO role defines the strategic vision for the org. You'll have a vague idea of that as a founder but until you nail the product and where it fits in a market it won't really matter too much. Focus on executing and getting traction instead.

pknerd 3y ago

So, does a CTO need to know about: - Dev/ML/X Ops - System Architecture - DB design? etc?

rwmj 3y ago
IMHO they ought to have a developer background. That doesn't mean they need to be an expert in DBMS design or whatever, but they should know enough to know when one of their reports is talking BS. I once worked for a CTO who threw out all our Linux systems and replaced them with Solaris (early 2000s) because "Linux couldn't scale", at the behest of our database architect who was basically just trying to increase his own empire and budget. One of the stupidest and most costly decisions, that also demoralised the rest of the team.
Izmaki 3y ago
My expectation as a lead-role in DevOps is that my CTO understands what I am saying, if I were to present a business case to him for evaluation or raise a concern with the company tool stack. Shortly put I want somebody with decision making powers to also have the knowledge to make those decisions. I don't need them to be able to implement any of the changes, but I need them to be able to know why the change needs to happen and what business value it does or does not give.

oneplane 3y ago

At a startup phase, I'm not sure there is anything that is strictly speaking a "CTO" task, except the paperwork. And once you get big enough for it to matter, the same rule applies as for a CEO: the CxO you need for your first million is a different one you need for your 100 million and different yet again for your first billion. There is of course a GitHub list for this: https://github.com/kuchin/awesome-cto https://github.com/kuchin/awesome-cto and perhaps the best way to find out what you need is to check things off of that list that don't actually have anything to do with what you're actually working on. Role names generally have very little meaning on their own, it's all about context.

lnsru 3y ago

You need to book communication and/or good sales course. As CTO you’re into politics, not into tech. Ability to communicate clearly and steer the conversation is your skill number one. Tech background is nice to have, but not really useful. You will hire people for that.

budgi4 3y ago

Accelerate https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 https://www.amazon.com/Accelerate-Software-Performing-Techno... Team Topologies https://www.amazon.com/Team-Topologies-Organizing-Business-Technology/dp/1942788819 https://www.amazon.com/Team-Topologies-Organizing-Business-T... Making Work Visible https://www.amazon.com/Making-Work-Visible-Exposing-Optimize/dp/1950508498 https://www.amazon.com/Making-Work-Visible-Exposing-Optimize...

huqedato 3y ago

https://zachgoldberg.com/ctohandbook https://zachgoldberg.com/ctohandbook - that's a good start

emmelaich 3y ago

Designing Data-Intensive Applications by Martin Kleppmann

esseti 3y ago

The effective manager - how to manage people The mom test - how to discover product The EOS (Traction and Co) - how to manage the company and give direction to the vision of the company

paulcole 3y ago
I think EOS is great and that every startup should use it, but have a feeling that most HN readers will detest it because of Not Invented Here syndrome. It’s too tempting to think “How hard can it be to figure out how to run a meeting, set goals, etc.?” And then end up spending the time that should’ve been spent having meetings and working towards goals on all the minutiae and cruft that somebody else has worked out in the past.

simonebrunozzi 3y ago

I've been a CTO a couple of times (VMware, startup), I don't think I'm a good one (I am better as an individual contributor, rather than as a manager), but I have one piece of advice for you: ignore books, or use them as secondary source of truth. You should instead TALK to long-time or former CTOs and ask them for advice. You won't find that advice in any book. It's invaluable.

rwmj 3y ago
How/where did you find former CTOs to talk to?
- _jal 3y ago
  ...you just found one and talked to him.
  - nsoldiac 3y ago
    not always a him
    - fdsalkjvlkjlkj 3y ago
      I'm pretty sure you can safely call him a him in this case.
    - _jal 3y ago
      When does Simone become something else?
      - Jtsummers 3y ago
        Simone as a feminine or masculine name depends on the language and country. Simone in French is feminine, and in Italian (so a reasonable interpretation here given the last name) is masculine. In the US (and, from what I've seen, other English speaking countries) the name is brought in from French and generally considered feminine (barring being in an Italian community, I've met a couple Simone <Italian last name> men, but often the name becomes Simon after a generation or two in the US for men like how Roberto or Juan will become Robert or John for Spanish-language immigrant families). https://en.wikipedia.org/wiki/Simone_(given_name)#Simone https://en.wikipedia.org/wiki/Simone_(given_name)#Simone - Pick any of the Italians off the list and they're almost certainly men, most of the non-Italian Simone's are women. Of course, it's still safer to look them up if you don't actually know the person in question and want to use he or she.

pablobaz 3y ago

Scaling People: Tactics for Management and Company Building This is a great book for larger team sizes. https://amzn.eu/d/hnEQvsV https://amzn.eu/d/hnEQvsV

RorieD 3y ago

[flagged]

pixelmonkey 3y ago

I was CTO of a startup from pre-seed stage ($0 raised, bootstrapping) thru Series A + B stages ($millions raised, scaling). I then promoted a senior engineer to the CTO role, around the time that we had ~20-30 engineers organized into sub-teams with engineering leads. As part of that, I ran an engineering management book club internally for the new CTO and engineering leads (which was also open to any engineers to join). I then published that reading list as a neatly organized blog post. The team wrote web / SaaS / analytics software in Python and JavaScript, deployed on Linux + AWS, using lightweight planning tools like GitHub and Notion. It was also a fully distributed team long before the pandemic. Over time, the company (Parse.ly) gained hundreds of enterprise customers and established itself via profitable growth in a straightforward SaaS business model. In 2021, less than a year after this blog post was published, the company was acquired by one of the largest open web internet companies (Automattic, creators of WordPress.com). "Managing software teams: the definitive reading list" https://amontalenti.com/2020/11/28/definitive-reading-list https://amontalenti.com/2020/11/28/definitive-reading-list The blog post is organized into a few sections, each featuring a few relevant books: - Management as a high-leverage activity - Product marketing and product management - Debugging dysfunctional product cultures - The psychology of deep work - Fully distributed teams - Programmer mindset and philosophy It's easy to skip around to find a good starting point or make your own (smaller) reading list. Hope that helps. Good luck!

dopamean 3y ago
That sounds like a really awesome workplace you built there. Nice job.
elamje 3y ago
Hey Andrew! Thanks for sharing all the resources and giving me guidance a few years ago. Still very thankful for a few of your posts and pointing me to read Venture Deals, all made me a much better CTO and founder. Hope your current journey is going great!
- pixelmonkey 3y ago
  Glad to hear it was helpful!

Oras 3y ago

For a startup, focus on shipping faster. The only thing that matters in a startup is finding the product market fit. If you don’t get to this point, the startup will die. So spending time optimizing the performance or arguing which code formatting standards to follow is just a waste of time and resources.

huqedato 3y ago

https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507 https://www.amazon.com/INSPIRED-Create-Tech-Products-Custome... https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/149197379X/ https://www.amazon.com/Escaping-Build-Trap-Effective-Managem...

OliverJones 3y ago

Read about what to do: _The Fifth Discipline_ by Peter Senge. A bit dated by now, it's still good stuff about "systems thinking" . And you'll need a lot of deliberate systems thinking in your job, and you'll need to teach others to think that way. Read about what not to do: _The Ultimate Question_ by Fred Reichheld. This book is about the notorious Net Promoter Score. (Would you recommend HN to a friend? Would you? Would you?) Reading it will give you insight into how bonehead MBAs with Cs in their marketing classes can convince leadership they've come up with a good way to measure customer satisfaction. (Net Promoter Score works fine for competitive businesses selling commodity products -- rental cars to individuals for example -- but not for many places where it is now used.)

stargrazer 3y ago

Coincidentally, this showed up on my Twitter timeline just now: https://github.com/kuchin/awesome-cto https://github.com/kuchin/awesome-cto - A curated and opinionated list of resources for Chief Technology Officers and VP R&D, with the emphasis on startups and hyper-growth companies. Someone else beat me to the link.

smk_ 3y ago

Those who can't do, teach. Don't read. Do.

rjtavares 3y ago
And those who can do are often terrible teachers.

rnjailamba 3y ago

Mindset and leadership (explore other titles by Gerald M. Weinberg as well) - An Introduction to General Systems Thinking - Becoming a Technical Leader: An Organic Problem-Solving Approach So that you have a good answer to "when will it be ready" - Software Estimation: Demystifying the Black Art - Agile Estimating and Planning People management - The Manager's Path: A Guide for Tech Leaders Navigating Growth and Change - High Output Management Besides Mythical Man Month already mentioned in other comments.

TDiblik 3y ago

Depends on what you're into: romance: i would suggest "Looking for Alaska" by John Green or "Pierre et Luce" by Romain Rolland fantasy: The Way Of Kings by Brandon Sanderson or "Blackout" by Marc Elseberg life advice ig?: "The Algebra of Happiness" by Scott Galloway ... never been a CTO xd

jdalsgaard 3y ago

Not a book or blog per se, but: https://datatracker.ietf.org/doc/html/rfc1925 https://datatracker.ietf.org/doc/html/rfc1925 -- The Twelve Networking Truths.

leandot 3y ago

You’ve been chosen to be a CTO, this usually means that you either did well in the company or were hired because of a good track record. So keep doing this + keep things simple, plan ahead, learn from colleagues, share knowledge. Stay humble, confess mistakes, ask for genuine feedback and advice. Books and blogs have a limited anecdotal value (sometimes it is high but the effort is also high). I’ve learned more from individual HN comments and actual work experience and mistakes than any book.

tailspin2019 3y ago
I mean this is decent advice, but slightly odd given you could easily have plugged your site here AND actually given the OP what they asked for :-) Maybe it’s some reverse psychology thing. Ok I’ll do it, you evil genius… https://hackernewsbooks.com https://hackernewsbooks.com PS CTOs aren’t always chosen, many are self-appointed as founders or co-founders (possibly in this case too). Chosen implies you’ve been subject to external assessment, self-appointed is a different matter altogether (ie. you may be extremely aware of possible knowledge/experience gaps that you need to quickly fill). To add my own suggestion, I think High Output Management by Andy Grove is an excellent resource (not just for CTOs)
- leandot 3y ago
  That is a very interesting line of thinking, my comment was kind of the opposite - I find that after reading a couple of good books on a certain topic, the rate of learning goes down rapidly compared to the steady amount I get from HN comments and experience. About hackernewsbooks - it's not mine since many years and I am not affiliated with it, I am just the one who built it and sold it. It's still nice though.
  - tailspin2019 3y ago
    I didn’t mean to give you a hard time - I think you’re right about the limited returns on reading after a while! It just seemed a shame not to mention hackernewsbooks since it is probably a good resource for the OP :) It makes more sense though if you have sold it! Congrats on that.

lifeisstillgood 3y ago

Simply put: https://grugbrain.dev/ https://grugbrain.dev/

elbi 3y ago

https://datatracker.ietf.org/doc/html/rfc1925 https://datatracker.ietf.org/doc/html/rfc1925

WillAdams 3y ago

Jerry Kaplan's _StartUp_ is a classic which shows the dark underbelly of deal-making and press-release creation, and why we can't have nice things if they aren't being made so as to ensure the profit of a dominant player: https://www.goodreads.com/book/show/1171250.Startup https://www.goodreads.com/book/show/1171250.Startup Contrast it with: https://www.folklore.org/MacBasic.html https://www.folklore.org/MacBasic.html and the early history of VisualBASIC (and wonder how things might have played out had the Mac had a nice development environment out the gate) and for management interactions see: https://www.joelonsoftware.com/2006/06/16/my-first-billg-review/ https://www.joelonsoftware.com/2006/06/16/my-first-billg-rev...

mysterydip 3y ago

Game Thinking, by Amy Jo Kim: https://gamethinking.io/ https://gamethinking.io/ Coincidentally, a quote from Ycombinator CEO Garry Tan on their site: You’ve got to find your own window of opportunity. Game Thinking is your instruction manual.

FourthProtocol 3y ago

I'm somewhat surprised that strategy is only mentioned once (at time of writing). Strategy is vital for any leadership role. Sun Tsu is a classic, but can be difficult to assimilate. There are many resources on Wikipedia. Often overlooked is dealing with power and politics (https://www.wittenburg.co.uk/Work/Politics.aspx https://www.wittenburg.co.uk/Work/Politics.aspx) Keeping up to date on tech also important, especially at the tech lead/architecture level (https://www.wittenburg.co.uk/Work/Mentoring.aspx https://www.wittenburg.co.uk/Work/Mentoring.aspx).

zoenolan 3y ago

As others have said, joining a community has been helpful to me. I would recommend CTO Craft. You get to hear what issues others are dealing with and how they solve them. https://ctocraft.com/community/ https://ctocraft.com/community/

tudorizer 3y ago
Hello, fellow CTO Craft member!
- zoenolan 3y ago
  Howdy :)

diegof79 3y ago

The best advice is probably to learn as much as you can from different sources but also keep a pragmatic point of view that helps to select the things that apply to your situation. Very often, new leaders follow a recipe without paying attention to the organization's problems. (check the book “The First 90 Days” by Watkins; it may give you ideas to organize your initial approach). As someone who went from engineering to product design, I observe that CTOs without a product vision are challenging to work with. For example, at a previous company, a CTO tried to implement the hard rule that every UI component should be in the shared UI library. But, even when I was leading the design system, that rule didn’t match how a product design process works. It caused delivery slowdowns and a degradation of the UX. I can bring up other examples, and the typical pattern is a leader looking at only one aspect or two without balance. Try to go beyond engineering and learn more about business and product design, which will help you prioritize engineering decisions. Some product-related books: Inspired by Cagan and Well-Designed by Kolko. Beyond engineering and product, as a C-level executive or director, people and hiring will be your primary concern. There are many management books, and I don’t have any particular to recommend (all of them will provide tools, but none is perfect: The Advantage and The Five Dysfunctions of a Team by Lencioni, The Phoenix Project by Gene Kim). I also enjoy taking ideas from biographical stories like Creativity Inc. by Ed Camull or Creative Selection by Ken Kocienda. Finally, a book I found funny and cynical but depicts big corps very well is “Management Stripped Bare” by Jo Owen.

rramadass 3y ago

Doing short courses (executive training) might be better. Assuming you have the Technical Domain side covered, my suggestion would be to focus on the following; 1) Behavioural Psychology - https://en.wikipedia.org/wiki/Behaviorism https://en.wikipedia.org/wiki/Behaviorism 2) Organizational Behaviour - https://en.wikipedia.org/wiki/Organizational_behavior https://en.wikipedia.org/wiki/Organizational_behavior 3) Evidence-based Management - https://en.wikipedia.org/wiki/Evidence-based_management https://en.wikipedia.org/wiki/Evidence-based_management

jakderrida 3y ago

I imagine whatever agency or branch that's employing you should provide the specialized training you need. I doubt they'd publish or share the most important practices for security against those you're Counter-Terrorist Operations are targeting from staying ahead of you with that knowledge.

rdli 3y ago

I think the #1 thing when you become part of an exec team is that you should be optimizing for the _business_, and not your function. The working assumption is that you will keep your function executing and delivering, but what is really hard is helping to figure out what the right decisions are for the business. Should we invest more in product or sales? What if there’s a huge top of funnel problem — what can we do about it? Your job is to bring that technology perspective to the discussion. I’ve been an exec, founder, CEO, and board member at various stages of successful (IPO) /unsuccessful companies (acqui-hire) companies. And the common thread at every stage is that the most successful companies had management teams that worked well together to optimize for the business. So instead of spending your energy on reading / learning more about tech, I’d recommend you spend your energy learning more about business (I’d probably start by asking the CEO & the rest of the mgmt team for advice on what to learn.)

mooreds 3y ago
This is phenomenal advice. You might, for example, recommend outsourcing non-corrosive functionality rather than building it in house, if you feel that is better for the company. You should do this even if it leads to layoffs for your department, because, again, your goal should be a thriving business, not a thriving engineering department and a lackluster business. Source: I did recommend and lead this course of action once (the outsourcing, not the layoffs). Company is still using an outsourced solution.
- mooreds 3y ago
  *non-core
wlonkly 3y ago
This is one of the points made in Patrick Lencioni's "The Five Dysfunctions of a Team", which I've always found a valuable read. A warning, though: it's a "business fable", where he gets his point across by telling a fictional story. Business writers tend to be pretty terrible fiction writers so it's corny, but it also makes it a pretty light read.

mrtimo 3y ago

I teach an MBA class on a similar subject. The students like a book called "Adventures of an IT leader". It's a fun read that students with work experience can relate to. And students without work experience can learn a lot from.

koliber 3y ago

This might be a bit contrarian, but don’t read engineering oriented books. Read up on selling, marketing, and product design. These are the things that will help you make better decisions about what you will build. My bet is that you got the technology parts covered, and the management things will start to matter once you have a team of 8+.

ipnon 3y ago

"An Elegant Puzzle" by Will Larson[0] is revelatory when it comes to leading a software engineering team. There is a solution to every organizational problem I've encountered in companies from single digits to thousands. That book alone, along with its intentional and organized bibliography is one of the best investments you can make in a tech career. Even without context on the size of your company, Larson's new "The Engineering Executive's Primer"[1] will surely make a valuable introduction too. [0] https://press.stripe.com/an-elegant-puzzle https://press.stripe.com/an-elegant-puzzle [1] https://lethain.com/eng-execs-primer/ https://lethain.com/eng-execs-primer/

hardkorebob 3y ago

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foxbarrington 3y ago

You might find my survival guide for founders who depend on devs to get things done useful. It covers topics like how not to lose key information if a dev leaves, preventing endless rebuilds and framework switching, keeping devs busy vs. keeping them productive, and ensuring product builds don't go off the deep end. As an example, here's the chapter on estimates: https://superstruct.tech/blog/estimates https://superstruct.tech/blog/estimates

tgtweak 3y ago

Given the diversity of the "CTO" role in terms of responsibilities and scale - what you should be reading will vary depending on your current size, composition, industry and your own personal experience level. One I find no trouble recommending regardless of these however is High Output Management by Andy Grove (of Intel). Not a new book, but chalk full of what I consider absolute truths when it comes to optimizing middle management (which is predominantly your role as a CTO, once the org reaches 50+ people and your direct reports all have direct reports). The fact it is still very relevant to organizational challenges today when it was written 40 years ago is a testament to this. It is a shame there are so few books that focus on this very-ignored (and honestly largest) segment of management and arguably where you get the most traction as a company. I've yet to meet two CTOs that share the same skillset or strengths, or who work in the same org structure. I would recommend doing some executive courses and trainings (with our other execs) to learn some common language and techniques/methodologies around team management and execution - this has been the thing which helped me most in embracing a CTO role (even one with other CTOs from separate business units reporting into). It is ironic but the best blend for a high level CTO is actually people and organizational skills moreso than pure technical aptitude. You need to be able to fact check your people and ask the right technical questions and understand the fundamentals of technical debt and TCO analysis, but honestly you'll be using your people/organizational skills and trying to hire people that know the technology better than you for the most part.

mooreds 3y ago

This isn't a book or blog, but I recommend two different communities: CTOlunches.com, which is an in-person group that meets for lunches around the world. It also has an active mailing list, with hundreds of engineering leaders there. The rands leadership slack (Google for it) is an invite only slack with thousands of engineering leaders across the world. Great for asynchronous conversations across a wide variety of topics; they even have an anonymous q and a channel.

svilen_dobrev 3y ago

Camille Fournier: the manager's path Eye-opener (worst take away / for me - you can't be friends with devs-under-you anymore. Or with anyone techie it seems. Probably depends on company-founders' culture - if small and new - or politics - if older and/or bigger) some more of hers here: https://skamille.medium.com/an-incomplete-list-of-skills-senior-engineers-need-beyond-coding-8ed4a521b29f https://skamille.medium.com/an-incomplete-list-of-skills-sen... Also.. you can't be everything. Choose your poison (or if it has been pre-chosen, find out what it is sooner than later), hire other people for other stuff: https://www.allthingsdistributed.com/2007/07/the_different_cto_roles.html https://www.allthingsdistributed.com/2007/07/the_different_c... more on the topic: https://news.ycombinator.com/item?id=20642423 https://news.ycombinator.com/item?id=20642423 And... think/assess very-very well - all-the-time - How much trust you have got.. and for what. YMMV. Sometimes "CTO" is only a parrotizing label for investors to flock on. Sometimes it's for real. have fun

Solvency 3y ago
A CTO can't have friends in their department?
- mooreds 3y ago
  I think it is really tough for execs to have friends in the same department, not just the CTO. Sometimes the business has needs that conflict with people's needs/desires and a good exec should choose the business.

jantypas2 3y ago

I don't know if I qualify for a CTO though people call me one (people have called me names since I was a kid but Mom always said to ignore them...) But let's tuck at that first word -- "Chief". In many cultures Chief meant the one who held the final responsibility for whatever went bad. They were also the ones who had to negotiate with opposing forces. With that in mind, learn your opposing forces and what can go wrong. Ask the dreaded Marketing tribe for their books and learn shamanic things like how long it takes to get something into the media or a retail store. Negotiate with someone in nursing to learn the mystical art of dealing with angry people you are actually trying to help. You will learn more from a nurse or a clothing buyer than you will learn from the best coding book.

VPenkov 3y ago

Just to add a bit to the excellent list this thread has collected: https://github.com/kuchin/awesome-cto https://github.com/kuchin/awesome-cto Some hit-and-miss there but I discovered a lot of great advice.

CountVonGuetzli 3y ago

After doing the first-time CTO thing three years ago in an established company with over 100 engineers, I think these two are the minimum required reading: An Elegant Puzzle: Systems of Eng Management (https://lethain.com/elegant-puzzle https://lethain.com/elegant-puzzle) and The Art of Leadership, small things done well (https://www.amazon.com/Art-Leadership-Small-Things-Done/dp/1492045691 https://www.amazon.com/Art-Leadership-Small-Things-Done/dp/1...) There are a lot more that were helpful to me, but those two encompass most of the important concepts and skills already in a usefully synthesized way, at least for me.

brightball 3y ago

Are you funded and hiring or are you building? If you’re building, I’ll echo other commenters…stop reading and go code. For just about any advice I’d say go read Rework, in between coding sessions.

alberth 3y ago

This is hugely dependent upon company size. CTO skills needed for a 10-person company is radically different than a 10,000-person company.

demon-code-999 3y ago

everyone is a CTO on linkedin

AC_8675309 3y ago

If I were a CEO and my CTO asked that question I would start looking for a new CTO. Sorry, not a helpful answer...

Rastonbury 3y ago
Great CEO here, firing your first time CTO for asking for advice on something they've never done before
- AC_8675309 3y ago
  You are taking a massive corporate risk by bringing in someone who doesn't know what they are doing. I would be equally worried if I was the director of engineering and had to work with this person. Ditto if I was a lower level engineer. If I had to guess the poster is actually talking about engineering and confusing it with technology ... which is a whole different problem.

feoren 3y ago

Learn about your industry. Learn about the problem. Learn as much as you can about the problem your company is trying to solve. Learn industry jargon. You already know enough about the tech; just focus on the subject matter itself.

max_ 3y ago

Check out Drew Houston's comment on HN from last year. [0] [0]: https://news.ycombinator.com/item?id=33595470 https://news.ycombinator.com/item?id=33595470

tivert 3y ago

Peopleware: Productive Projects and Teams https://www.amazon.com/Peopleware-Productive-Projects-Teams-3rd-dp-0321934113/dp/0321934113/ref=dp_ob_title_bk https://www.amazon.com/Peopleware-Productive-Projects-Teams-... It's a classic, and also a pretty easy read. If you're in technology and haven't read it yet, you should.

RecycledEle 3y ago

Do not read books or blogs. Learn to do every technical job in your company.

mikey_p 3y ago

Must listen: The Idealcast with Gene Kim I can't stress just how good this podcast is, all of the guests are excellent. Here's a brief highlight of my favorites: - Michael Nygard, SVP of Enterprise Architecture, Sabre - brilliant breakdowns of how to approach software problems conceptually - Dr Steven Spear - tons of excellent stuff from years of studying Japanese management techniques - Elisabeth Hendrickson - has been studying testing and QA for decades, tons of great insights - Scott Havens - incredible breakdown of the inventory management system of jet.com, acquired by Wal-mart and now powering walmart.com https://itrevolution.com/podcast/ https://itrevolution.com/podcast/

mattferderer 3y ago

Underrated new book not mentioned here - Think Like a CTO by Alan Williamson

graycat 3y ago

To several of the authors here, "thanks, I needed that". I have the software written, and it appears to run as intended. Now, doing computer systems management, silly stuff; main problem, getting past bad documentation, e.g., was just up all night working with video adapters, device drivers, display resolution, font scaling, HDMI, display port, flickering cursors, etc. Since the documentation was so bad, I did take some notes on the more important things I learned, e.g., by the TIFO (try it and find out) Method. The results are not perfect but are good enough for now. I can delay more until the business is growing nicely (if it ever does). That is, for now concentrate on giving people "something they want" and put video issues way down on the TODO list. But a concern: If such silly technical stuff does go well, then I could be going live on the Internet fairly soon. Then some of the issues might be: (1) publicity and getting the first users (2) getting advertisers (3) billing and accounting So, from this thread and a few hours at Google this week, I just concluded: For nearly all that stuff, nearly every business has to do it. So, there are well polished options for how to do it, and I can put it low on the TODO list for now. For what to do if the business starts to grow, I saw some of that at FedEx and elsewhere. Right, as in this thread, focus on providing "what people want", the work, and the revenue. E.g., if I get a lot of users, then that should help getting some advertisers. Then will need billing and accounting, and, uh, there is no shortage of people who can provide such services for me -- getting the revenue is the hard part; given the revenue, it stands to be easy to work with an accounting service! Or, for a lot "I don't know how to do it, but there are plenty of people who do." In particular, for management and in particular engineering management, I've seen, been in, and done some of it and conclude now that my business will be nicely successful before I will have to look into the theories of it. In particular, I saw several cases of guys really eager to work hard, occasionally all night, get good stuff done, with no credit from any management. For the core technical stuff, my efforts have some of that, and it should be a business advantage, uses some of my experience and Ph.D. in applied math, I would say beats AI, and easy for me -- early on in the effort I wrote up the math in Knuth's math word processing TeX. Then used the write up when I wrote the code (Windows, IIS, .NET, ASP.NET, ADO.NET, platform invoke, etc.). So, the core technical stuff is done, not even on the TODO list! On with the rest with the balances as often in this thread.

coolThingsFirst 3y ago

You are focusing on the wrong thing, your #1 goal should be building a business that people want to pay for. Everything else is secondary.

0x54MUR41 3y ago

I would like to add a book called "Think Like a CTO" [0] by Alan Williamson. The author has experiences as a CTO in different companies. He also give a lot of advice. The book is not only applicable for CTOs, but also other leadership roles. It discusses various topics from team management to technology decisions. edit: the book was already mentioned by mattferderer [1]. [0]: https://www.manning.com/books/think-like-a-cto https://www.manning.com/books/think-like-a-cto [1]: https://news.ycombinator.com/item?id=38809998 https://news.ycombinator.com/item?id=38809998

bigtechdigest 3y ago

Neither a book nor a blog, but I'm building a newsletter that aggregates the latest articles from company engineering blogs. I think you might find it useful: http://bigtechdigest.substack.com http://bigtechdigest.substack.com

throwaway81523 3y ago

Tom DeMarco, "Peopleware". It says don't have open plan offices (iirc). That's good enough for me.

nemanja_codes 3y ago

Have a look here: https://github.com/kuchin/awesome-cto https://github.com/kuchin/awesome-cto Maybe I have few more useful links here: https://github.com/nemanjam/bookmarks https://github.com/nemanjam/bookmarks

Hernandesalvir 3y ago

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