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

by kanodiaashu on 12/29/23, 9:18 AM with 142 comments

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

  • by elmarschraml on 12/29/23, 10:06 AM

    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.

  • by pixelmonkey on 12/29/23, 11:45 AM

    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

    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!

  • by simonebrunozzi on 12/29/23, 11:32 AM

    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.

  • by rdli on 12/29/23, 2:59 PM

    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.)

  • by mobiuscog on 12/29/23, 10:37 AM

    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.

  • by CityOfThrowaway on 12/29/23, 9:49 AM

  • by rramadass on 12/29/23, 2:35 PM

    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

    2) Organizational Behaviour - https://en.wikipedia.org/wiki/Organizational_behavior

    3) Evidence-based Management - https://en.wikipedia.org/wiki/Evidence-based_management

  • by CountVonGuetzli on 12/29/23, 5:01 PM

    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)

    and

    The Art of Leadership, small things done well (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.

  • by mikey_p on 12/29/23, 8:24 PM

    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/

  • by svilen_dobrev on 12/29/23, 4:07 PM

    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-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_c...

    more on the topic:

    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

  • by budgi4 on 12/29/23, 11:10 AM

  • by WillAdams on 12/29/23, 1:29 PM

    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

    Contrast it with: 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-rev...

  • by EwanToo on 12/29/23, 10:25 AM

    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

  • by OliverJones on 12/29/23, 12:24 PM

    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.)

  • by rnjailamba on 12/29/23, 12:49 PM

    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.

  • by diegof79 on 12/29/23, 2:21 PM

    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.

  • by tgtweak on 12/29/23, 3:48 PM

    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.

  • by ipnon on 12/29/23, 3:26 PM

    "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 [1] https://lethain.com/eng-execs-primer/

  • by eddyzh on 12/29/23, 9:57 AM

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

  • by zoenolan on 12/29/23, 2:12 PM

    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/

  • by mysterydip on 12/29/23, 1:42 PM

    Game Thinking, by Amy Jo Kim: 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.

  • by oneplane on 12/29/23, 11:06 AM

    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 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.

  • by TheGuineaGhost on 1/5/24, 6:00 PM

    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.

  • by foxbarrington on 12/29/23, 3:46 PM

    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

  • by thiago_fm on 12/29/23, 10:08 AM

    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.

  • by elbi on 12/29/23, 1:14 PM

  • by kozak on 12/29/23, 9:51 AM

    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.

  • by ratg13 on 12/29/23, 10:19 AM

    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.

  • by tivert on 12/29/23, 8:11 PM

    Peopleware: Productive Projects and Teams

    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.

  • by stargrazer on 12/29/23, 12:29 PM

    Coincidentally, this showed up on my Twitter timeline just now:

    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.

  • by gwnywg on 1/2/24, 8:42 AM

    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.

  • by onion2k on 12/29/23, 10:57 AM

    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.

  • by jantypas2 on 12/29/23, 4:21 PM

    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.

  • by bigtechdigest on 12/30/23, 8:26 AM

    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

  • by Oras on 12/29/23, 11:47 AM

    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.

  • by AC_8675309 on 12/29/23, 7:12 PM

    If I were a CEO and my CTO asked that question I would start looking for a new CTO.

    Sorry, not a helpful answer...

  • by emmanueloga_ on 12/29/23, 9:57 AM

    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

  • by 0x54MUR41 on 12/30/23, 6:41 AM

    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

    [1]: https://news.ycombinator.com/item?id=38809998

  • by VPenkov on 12/29/23, 4:36 PM

    Just to add a bit to the excellent list this thread has collected:

    https://github.com/kuchin/awesome-cto

    Some hit-and-miss there but I discovered a lot of great advice.

  • by degradas on 12/29/23, 10:30 AM

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

  • by leandot on 12/29/23, 1:10 PM

    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.

  • by cientifico on 12/29/23, 9:50 AM

    There was this related post in hn that might help you.

    https://news.ycombinator.com/item?id=37971795

  • by mooreds on 12/29/23, 3:59 PM

    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.

  • by huqedato on 12/29/23, 11:10 AM

  • by huqedato on 12/29/23, 12:24 PM

  • by nemanja_codes on 1/1/24, 3:29 PM

    Have a look here:

    https://github.com/kuchin/awesome-cto

    Maybe I have few more useful links here:

    https://github.com/nemanjam/bookmarks

  • by wslh on 12/29/23, 9:59 AM

    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.

  • by koliber on 12/29/23, 3:11 PM

    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+.

  • by lifeisstillgood on 12/29/23, 1:11 PM

  • by jakderrida on 12/29/23, 2:42 PM

    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.

  • by TDiblik on 12/29/23, 12:53 PM

    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

  • by apples_oranges on 12/29/23, 10:32 AM

    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)

  • by feoren on 12/29/23, 7:47 PM

    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.

  • by jdalsgaard on 12/29/23, 1:05 PM

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

  • by mrtimo on 12/29/23, 3:07 PM

    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.

  • by jeanloolz on 12/29/23, 10:39 AM

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

  • by max_ on 12/29/23, 7:58 PM

    Check out Drew Houston's comment on HN from last year. [0]

    [0]: https://news.ycombinator.com/item?id=33595470

  • by pablobaz on 12/29/23, 11:38 AM

    Scaling People: Tactics for Management and Company Building

    This is a great book for larger team sizes.

    https://amzn.eu/d/hnEQvsV

  • by gorbachev on 12/29/23, 10:56 AM

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

  • by FourthProtocol on 12/29/23, 1:59 PM

    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)

    Keeping up to date on tech also important, especially at the tech lead/architecture level (https://www.wittenburg.co.uk/Work/Mentoring.aspx).

  • by sergioisidoro on 12/29/23, 9:55 AM

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

  • by krishadi on 12/29/23, 10:46 AM

    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`.

  • by brightball on 12/29/23, 5:14 PM

    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.

  • by emmelaich on 12/29/23, 11:22 AM

    Designing Data-Intensive Applications by Martin Kleppmann

  • by esseti on 12/29/23, 11:24 AM

    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

  • by coolThingsFirst on 12/29/23, 11:57 PM

    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.

  • by throwaway81523 on 12/31/23, 2:15 AM

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

  • by alberth on 12/29/23, 5:19 PM

    This is hugely dependent upon company size.

    CTO skills needed for a 10-person company is radically different than a 10,000-person company.

  • by Omroth on 12/29/23, 9:53 AM

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

  • by mattferderer on 12/29/23, 8:45 PM

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

  • by lnsru on 12/29/23, 11:08 AM

    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.

  • by RecycledEle on 12/29/23, 8:13 PM

    Do not read books or blogs.

    Learn to do every technical job in your company.

  • by jrflowers on 12/29/23, 10:32 AM

    The Butter Battle Book

  • by erikstarck on 12/29/23, 10:31 AM

    The Mythical Man Month and The Phoenix Project.

  • by pknerd on 12/29/23, 11:00 AM

    So, does a CTO need to know about:

    - Dev/ML/X Ops

    - System Architecture

    - DB design? etc?

  • by demon-code-999 on 12/29/23, 5:36 PM

    everyone is a CTO on linkedin

  • by graycat on 12/29/23, 9:13 PM

    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.

  • by smk_ on 12/29/23, 12:46 PM

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