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Ask HN: What are good books/blogs to read for a first time CTO?
523 points by kanodiaashu 10 months ago | hide | past | favorite | 142 comments
Planning my first startup as CTO, what resources should I go through for sure.



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.


And maybe CTO means “the founding programmer of a new startup” in which case my advice would be to stop reading and start coding :-)


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.


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.


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.


Too reductionist.

You must "sharpen the saw".

This takes many forms including adequate learning / training for self improvement as well as investment in your tooling that will pay dividends on delivering faster or with higher throughput.

These are second and third system effects that require intention to monitor or measure but the effect is real.


Of course nothing is black and white, but if you have limited time/money then you want to get to ramen profitability fast and you simply don’t have time for business model canvases, the perfect employee option scheme, a scalable k8s setup or a perfect CI/CD pipeline.

There’s so much stuff that feels important and valuable, but so little of it really cannot wait until after your wheels are off the ground.

When you read postmortems of startups that didn't get enough customers, often it’s this stuff that actually went wrong. Too much time spent on other stuff than “build something” and “that people want”.

To my experience, it’s difficult to resist all that good advice that’s all over the internet, books, accelerator programs and the like, and saving it all for later. People will tell you “you should get $PETPEEVE right from the start” for every imaginable pet peeve (all the way from legal stuff to unit tests to SEO) and they’ll be very convincing. Trying to resist this is not reductionist, it’s super hard.


It is survivorship bias. Because the companies get to a point where unimportant things are important and you spend years in that second phase, the learnings are upside down. „If only we would have solved technical problem X from day 1 we would have so much less hassle in the years to come.“ Except that solving problem X on day 1 instead of shipping what the company did might have killed the company. I see this in a lot of second time founders, where startup 1 was successful - „this time I‘ll really avoid my mistake X.“


Sure. But the point was that if you're a team of 1 engineer, even if your title is CTO, time spent learning "how to be a CTO" when you don't have any team whatsoever is time not spent building the prototype that needs to demonstrate $XX value/growth by YYYY-MM-DD in order to survive.

Learning is always encouraged, but you should be learning to solve the problems you're about to face. Learning to solve problems which aren't going to be obstacles in the near or mid future isn't helping you in your immediate circumstances. Sometimes the immediate circumstances aren't much of a concern, but when they are, you need to be sure you're learning with that in mind.


Any advice is going to be reductive when measured against the reality of building a startup. While learning and continuous improvement are table stakes, I think the GPs advice is much better to get first-time founders overall. "Sharpening the saw" is likely to feed perfectionist tendencies, or send them into dopamine learning loops online. There's a reason that "bias for action" is treated as a highly valuable trait in founders.


I'd say the time for sharpening the saw was before you started the company. The next opportunity to invest into best practices / long-term is when the company actually has some traction.


The entire point of sharpening the saw is that it is continual though. It doesn't have to be a major investment or long-term, in fact it explicitly references "Daily Self-Renewal". I believe the original comment branch just meant don't worry about "what's applicable to the CTO".


And honestly, pre product-market fit my advice would be not even coding, but iterating in an extremely scrappy way (read: Google Sheets, Jupyter Notebooks, no-/low code, handwritten invoices) until you have people paying for your product and not churning after the first month. Everything else comes secondary. For every company that didn‘t manage to scale their tech and teams fast enough, there‘s 100 that die by „building and they will come“ a polished app with great UX through 4 ecosystems that get launched to deafening silence.


Tbf I believe this depends a lot on the product category. Uber could do this in their first few months but eg Retool couldn’t.


Obviously some ideas can’t be tested without writing some code, but it’s more of a mindset than a strict playbook–many programmers (myself included) tend to bias towards wanting to write code and avoid sales conversations until the thing feels “done”. Tech message boards are littered with programmers trying to justify why their app has to have a full polished build that will take a year before they can begin selling it.

When you get in the habit of asking yourself, before building, how you can learn the most about what people want with the least amount of code, clever ideas often come to mind.


Heh I was going to mention Google sheets. Great database that doesn't scale, but before you're close to worrying about that you have a lot of answers.


this is perfect advice which i can't agree with enough. that is unless the founders insist on a flawless UI... then you are in for a world of pain

never understood why teams of literally 1 or 2 devs are always forced to try attempt to acheive the visual quality of apps like instagram, whatsapp, etc


> never understood why teams of literally 1 or 2 devs are always forced to try attempt to acheive the visual quality of apps like instagram, whatsapp, etc

For the same reason those kinds of places have more managers than workers… it’s a vanity project.


Haha, for sure. I wrote about that contrast here a few years ago: https://www.mooreds.com/wordpress/archives/2555


His productivity will shoot trough the roof, when it moves into deleting code.


:-)


> 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

One word of caution: Engineers and EMs read these newsletters and even management books, too.

It’s not hard to see when your leadership is just parroting things they read from a book or newsletter and trying to pass it off as if they had deep leadership experience. Engineers are good at seeing through cargo cult leadership.

I suggest that if you embrace a practice found in a book or a newsletter, be transparent about the source. Encourage people to read more about it in the book or newsletter where you found it. Don’t try to pass it off as a management technique you invented or pulled from deep background experience, because it feels disappointing to the team when someone realizes their CTO is just parroting things from a newsletter or blog and trying to hide the source.

Also, don’t get into the mindset that having read a lot of books or blogs or podcasts or newsletters is a substitute for experience. Some of the worst leaders I’ve had were those who would lord their book knowledge over everyone as though it made them the confident expert on everything, while we could all clearly see that the extents of their knowledge started and stopped with what was contained in the books they read. Books contribute bits and pieces and give suggestions to add to your corpus of knowledge, but if you treat them like definitive, all-encompassing sources of wisdom then it’s going to be clear to people that you don’t really know what you’re doing. Be honest and stay humble.


That's a very good point. A "CTO" can mean any mix of managerial, leadership and technical responsibilities.

It is my assumption that a CTO is usually coming with technical background already except when he/she is a cofounder and they got technical domain as a result of division of responsibilities. But I am suspicious of startups where none of the cofounders come from technical background.

That leaves managerial and leadership. IMO, if you are a CTO, managerial is something you can hire other people to do for you as your technical organisation grows and leadership is something you should really be focusing on.

You can have flourishing technical organisations with the CTO being a poor manager but a good leader but very unlikely with a CTO with good management but poor leadership skills.


Even if you're effectively 'just' a tech lead of a small team, like I am, it's still a very different job than being a tech lead of a small team in a larger company. You are at the top level of the small group, so you end up being involved in a lot more non-tech things than you think you would be.

Your peers are not other engineers and engineering managers like you would be in most situations, but marketers, product people, designers, PMs and so on. Who is the founder and ultimate authority (CEO) and if you are a co-founder or not also really changes things. A founder CTO is also very different from a non-founder CTO. Co-founder conflicts is a huge thing to manage, (see https://flocrivello.com/co-founding-considered-harmful/ ) because at a small size even as a non founder, you're pretty close to it. You should decide upfront if you're going to approach the job as another effective founder or employee and communicate that to founder at the start as part of a conversation.

I made the transition from staff eng to eng manager to CTO at a small startup, and each one is still a very different job even though the skill sets transfer greatly. I code way more at the startup than I did as an eng manager too. Several things I would suggest:

1. You're an exec, even if your company is tiny, and how it works is different than being a manager. Concepts like the 'first team' https://www.michaelvizdos.com/resources/first-team and 'getting on the balcony' matter way more than when you're in a purely product & eng organization: https://www.bettermanager.co/post/move-away-from-the-dance-f...

2. Don't be shy about getting exec coaching, and having the company pay for it. We did that and it was very helpful.

3. Read Radical Candor (updated edition!!!), but also read it with a bit of a grain of salt, realizing the title and advice was chosen because the writer wanted to balance their general high agreeableness with a counterweight that goes too far for the typical person IMO, which the writer writes about that exact dynamic in the second edition.

2a. Learning to be properly direct is super essential, especially at small sizes where its more make or break based on how emotionally deluded you are. The people you are working with need be able to handle you being real with them too. If they cannot, move on, it's that important.

4. Expand your skill set, do everything technical. If you're a backend engineering manager, expand your stack to all parts of the business. That means the back end, the front end, data, analytics, observability, devops, AI models, performance tracing, etc. I started as a mobile eng with previous backend experience, and I wish I expanded sooner so the company had those things on lock sooner, especially in the data analytics side. Engineers hate analytics, embrace it fast to counteract that tendency.

5. Gergely, Will Larson, etc are good resources, but also note they come from what I call the "Uber strain", and thus structure a lot of their experience and advice based on formative years working at Uber. I also worked at Uber when they were there and I recognize a bunch of Uber-isms in their writing.

A good chunk of what they talk about is how to be successful at a place like Uber. Something I've realized later with them is that other companies can be pretty different, and what they espouse sometimes might not match. But on the other hand, Uber's work culture came from previous strains of silicon valley tech culture, especially google's due to the top engineers being from google and setting up their promo system to match googles (vs lets say apple) and the knock on effects of that. Something about that place made people get really good at understanding what is needed to succeed in tech leadership and write about it, I guess it's kind of a paypal mafia effect.


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!


That sounds like a really awesome workplace you built there. Nice job.


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!


Glad to hear it was helpful!


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.


Yes, so much is contextual and it's really hard to get that from books. But conversations, whether with peers or a coach, can help you because they have that context.


On that subject, Someone I knew used to use the bartech cto network. But I'm not sure if it still exists, as I now can't find any trace of bartech online. There is this page: https://discourse.bartechcto.net/login but it seems to be invite only.


How/where did you find former CTOs to talk to?


The slack community in https://randsinrepose.com/welcome-to-rands-leadership-slack/ has a pretty good number of CTOs and other leaders.


Plus one for this. There's a #startup-cto channel there that is full of good folks to chat with.


This looks interesting, thanks!


I guess it was easy for me. Before becoming CTO at VMware, I was Senior Technology Evangelist at AWS, and was very well known in the Cloud Computing space. I met a ton of startups and larger companies, mostly on the technical side, so I knew a lot of people.

I also helped many of them a lot during my years at AWS, and most of them were very eager to give me a hand / provide advice.


I mentioned this in another comment but ctolunches.com is a group of engineering leaders that I have participated in from time to time.

7 CTOs is another one that I have heard of but haven't participated in.


...you just found one and talked to him.


not always a him


"They/Them" would be appropriate if we didn't know the person's gender or if they were specifically non-binary. However, in this case, we do know that this specific person is "he/him" thanks to the username and public profile, so the comment parent to yours was appropriate and your comment less so.

(Your comment is less appropriate because the analogy would be if you said: "Nice to meet you, Jim. Not all people in your position are men, though.")


I'm a he/him, but I take no offense if people think I'm a she/her, given that my first name (Simone) can be both feminine and masculine, depending on the culture/background. (I'm Italian, in Italy it's only masculine)


Nor a she. Hope no offense is taken by such a small matter



I'm pretty sure you can safely call him a him in this case.


When does Simone become something else?


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 - 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.


I can't tell if this is typical hn pedantry or genuine misunderstanding, so I'll point out that I was not referring to "some entity named Simone", I was referring to the particular Simone in this very comment thread, for whom we have strong evidence about preferred pronouns.

> 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.

Physician, heal thyself.


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.)


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.


*non-core


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.


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.


People are notoriously bad at identifying what actually led to their success. Career advice authors even more so.


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).



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


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.


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/


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


A CTO can't have friends in their department?


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.



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...


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


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.)


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.


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.


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.


"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/


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


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/


Hello, fellow CTO Craft member!


Howdy :)


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.


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.


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.


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


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.



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.


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.


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.


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.


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.


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.


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.


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


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.


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

Sorry, not a helpful answer...


Great CEO here, firing your first time CTO for asking for advice on something they've never done before


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.


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


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


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.


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...


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.


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

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)


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.


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.


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

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


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.




Have a look here:

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

Maybe I have few more useful links here:

https://github.com/nemanjam/bookmarks


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.


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+.



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.


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


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)


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.


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


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.


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


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

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


Scaling People: Tactics for Management and Company Building

This is a great book for larger team sizes.

https://amzn.eu/d/hnEQvsV


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


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).


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


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`.


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.


Designing Data-Intensive Applications by Martin Kleppmann


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


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.


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.


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


This is hugely dependent upon company size.

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


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


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


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.


Do not read books or blogs.

Learn to do every technical job in your company.


The Butter Battle Book


The Mythical Man Month and The Phoenix Project.


I've had The Phoenix Project recommended before. Listening to the Audio Book now - hoping it's good.


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.


So, does a CTO need to know about:

- Dev/ML/X Ops

- System Architecture

- DB design? etc?


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.


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.


everyone is a CTO on linkedin


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.


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


And those who can do are often terrible teachers.




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