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7 Books Every Startup CTO Should Read

Putting technology infrastructure for a company together, selecting the proper tools and outlining the technical strategy, while also having skills in marketing and project management – all of this is in the handbook of a modern CTO.

A Chief Technology Officer is a top tech architect for a company or a startup, who manages the implementation of technology in accordance with business goals. Surely, he/she has to be a highly skilled person with a broad vision forward who is always learning.

As the coming of a new year always makes us draw conclusions and look for aspirations ahead, we continue our tradition of best CTO books selection. This time for CTOs.

They always have to optimize and maximize things, have to be creative and innovative, especially startup CTOs who begin with a blank canvas. So we’ve selected a versatile number of books every CTO should read, looking at technology from different angles and all written in recent years.

#1 Confessions of an Unintentional CTO / by Jack Kinsella

With first-hand experience of someone who started as web programmer and was promoted to a top-level position by trial and error, Jack Kinsella’s “Confessions of an Unintentional CTO: Lessons in Growing a Web App” is a great read. He also acknowledges that his book of advice about web applications based on real users and their problems, learned through through solving them and speaking to many software companies CTOs, came out as a “side effect” of his own job. It will appeal to solo entrepreneurs/programmers, tech officers, down to web developers.

must-read books for ctos

Review excerpt: “The book focuses on the issues that are most pertinent to the new CTO, such as ensuring data integrity, easing system maintenance, knowing what not to test, developing professional-grade accounting features for taxation reporting, sharpening an application’s ability to inform one of errors, and integrating SEO/analytics/online marketing right into the very foundations of a web application.”

#2 Continuous Delivery / by Jez Humble & David Farley

Full title: “Continuous Delivery: Reliable Software Releases through Build, Test, and Deployment Automation”. Jez Humble, the CTO of DevOps Research and Assessment LLC, and David Farley, the founder of Continuous Delivery Ltd., both with decades of experience in IT, share the principles and best practices of collaboration between developers, testers and delivery teams.

A wide range of topics including how to make software delivery a reliable process, so called “deployment pipeline” (an automated process to manage changes), the ecosystem and infrastructure, data configuration, testing capacities, risk management, etc. Plenty of handy info for any CTO, systems administrator, developer or tester.

must-read books for ctos continuous delivery jez humble

Review excerpt: “Whether or not your software development team already understands that continuous integration is every bit as necessary as source code control, this is required reading. This book is unique in tying the whole development and delivery process together, providing a philosophy and principles, not just techniques and tools.”

Customer comments excerpt: “Reading through this can be like a fire hose of ideas to improve your work flows. But to be successful, find just one thing in the chapter you can do to change your job for the better. Learn that one thing and do that one change until it becomes “the way” you do things. Then rinse and repeat.”

Watch Jez Humble’s talk about Continuous delivery

#3 Technically Wrong / by Sara Wachter-Boettcher

You probably didn’t expect this kind of book in our list. But think about this – when the Apple Health app launched, tracking vitamin intake, diet, exercise and all the health metrics, it didn’t track periods, which is pretty surprising considering the number of women who might find that useful. This is just one of the numerous examples of bias in today’s tech sphere which is supposed to be progressive.

If you’re either a CTO, or anyone else in tech industry, Sara Wachter-Boettcher offers the food for thought in her “Technically Wrong: Sexist Apps, Biased Algorithms, and Other Threats of Toxic Tech”. This book was published in October 2017 and tackles bias in digital products and unfairness in tech culture. From chatbots harassing women, social media platforms’ treatment of dead people, algorithms indicating more people of color, etc.

must-read books for ctos Technically Wrong / by Sara Wachter-Boettcher

Review excerpt: “No matter how we set the preferences, the results turn out the same. For all of technology’s supposed configurability, there’s a one-size-fits-all quality pushing conformity over individuality. Sara Wachter-Boettcher reveals how none of us should live up to the image our technology has of us. If a book on the technology industry ever deserved a standing ovation, this one is it.”

Customer comments excerpt: “If you work on the web, it’s your responsibility to read this book. You’ll look at your work and your decision-making in a whole new way.”

Listen to author interview about “Technically wrong”

#4 The Hard Thing About Hard Things / by Ben Horowitz

This book by a successful Silicon Valley guru Ben Horowitz refers to the managerial and strategic thinking side of a CTO. In “The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers” gives his honest and down-to-earth practical advice on running a startup and how to face the toughest problems. For example, what’s the psychology behind the decision to go bankrupt and how to extract positive things from it (illustrated by the story of Ben’s company LoudCloud acquired by HP for $1.6 billion).

The author speaks frankly and humorously about issues like how to fire a co-worker or a loyal friend, how to manage your psyche when the company is relying on you, how smart people can be bad employees, etc. As TechCrunch review points out, approaches and solutions in this book may not be for everyone, but sharing the experience of running a tech company may be helpful to any top manager or company leader.

must-read books for ctos The Hard Thing About Hard Things / by Ben Horowitz

Review excerpt: “Horowitz imparted valuable insight on hard lessons learned that apply to any manager, whether in the executive suite or not. It’s written in such an engaging and universally acceptable manner that no one could object. Who would realize that executives worry about things like initiating layoffs, hiring the right people, training, and minimizing politics, among others? A refreshingly honest take on the main success equation – The hard thing is getting it done.”

Listen to author interview about “Hard Things”

#5 Peopleware: Productive Projects and Teams / by Tom DeMarco & Tim Lister

Authors are principals of the consulting company Atlantic Systems Guild, specializing in the complex system building and emphasis on the human side. Both of them also lecture on tech ethics and corporate culture at US universities. Why does this book matter for CTOs? Those who work closely with software engineers know that most issues on projects come not from technical aspects, but from human. And this book has become a sort of classic in the IT project management world. This is its 3rd edition with 6 new chapters about new challenges.

must-read books for ctos Peopleware: Productive Projects and Teams / by Tom DeMarco & Tim Lister

Review excerpt: “When a book about a field as volatile as software extends to a third edition, be sure that the authors write of deep principle, of the fundamental causes, and not of the surface that everyone recognizes. And to bring people, actual human beings, into the mix! Excellent and rare.”

#6 Building Evolutionary Architectures / by Neal Ford, Rebecca Parsons, Patrick Kua

Published as recently as October 2017, the book “Building Evolutionary Architectures: Support Constant Change” by a trio of ThoughtWorks (global IT consultancy) actual CTO, tech architect and developer is of the newest examinations of the software development. This ecosystem is always changing, and you have to be on the lookout for new frameworks, tools, and paradigms. Lots of info is fresh and relevant, with the main emphasis on how to design proper technology, so this book may be useful in terms of this aspect of a CTO’s job.

must-read books for ctos Building Evolutionary Architectures / by Neal Ford, Rebecca Parsons, Patrick Kua

Review excerpt: “The timely book sits at the intersection of 2 key trends in the software industry. One is that engineers face increasing demand for delivery and quality, and the only way to address this is to build evolving architectures. The other one is that the role of the software architect is changing, as they are becoming members of product teams, instead of a separate group making decisions. The book not only addresses these points but is also full of pragmatic and insightful advice”.

Watch Patrick Kua’s talk about Evolutionary architecture

#7 The Startup Owner’s Manual / by Steve Blank

The impressive 600-page “The Startup Owner’s Manual: The Step-By-Step Guide for Building a Great Company”, first published in 2012, became the primary source of inspiration and instructions for literally thousands of entrepreneurs and startup owners. This book is great for any business owner, CEO, CIO, CTO, CDO and CMO, actually.

The book is highly practical: it includes over 100 charts and diagrams, over 70 checklists and a chapter on the 9 deadly sins of any startup. It explains in detail the “customer development method”, organizational tips, how to identify customers and make them buy your products. Oh, by the way, did I mention that Steve Blank is the founder of the Lean Startup movement?

must-read books for ctos The Startup Owner's Manual / by Steve Blank

Review excerpt: “A Bible for entrepreneurs to read and re-read. Take this book before you spin up, and save thousands of dollars and man hours in mistakes. Also, excellent amount of information for the newbie. I developed many applications, however I had zero idea on bringing them to the market. Like they say, it is never too late, so I’m reading it to unlearn what I’ve known and start all over again.”

Watch Steve Blank’s talk about “The Startup Owner’s Manual”

Final words

Of course, our selection of not only startup CTO books does not present the ultimate list, only you yourself know best what you need to read and what trends to follow. If you’re looking for alternative titles that might be useful for a CTO job, check out this larger list at Goodreads. If you have a suggestion to update our list or if we’ve missed any other good books, feel free to drop us a comment.

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Matt Warcholinski

Matt Warcholinski is the COO of Brainhub (a software house building awesome node.js web and mobile apps) who loves to build startups and play guitar.

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