The CTO's Reading Trellis

The CTO's ability to face the onslaught of novelty lies not in their ability to stay on top of trends, but rather in the mental models they've crafted from which all their knowledge flows.

It is 1980. It is a Saturday afternoon and my Dad and I are at the local hardware store. Like an Ace Hardware or Home Depot. We are walking the isles. Very slowly.

I am pouting. I’m too young to share my dad’s fascination with the variety of tools, materials, and doodads filling the shelves. But he ignores me. Slow as a tortoise. Touching tools. Rotating screws. Searching for clues on the future problems he might solve with all these new inventions.

This is a familiar ritual for us. But it is also excruciating for the mind of an 8 year old. Eventually I will make my displeasure known and tug at him impatiently. He is patient with me.

By the time we get back into the car, he will turn to me and say, "One day, you’ll run into problems that need the right tools to fix them. But to fix them, you need to know what tools are available. Even better, if you learn about the tools first, you’ll be able to spot problems before they even happen!"

These words shaped my world. Because soon I would fall in love with computers and become a prolific programmer. Learning the tools so I could code my way through all sorts of problems I was solving.

The hardware store ritual has evolved into a new one that has had a profound impact on my career as CTO. The perusal of tools has been replaced by the reading of books and the creation of my Reading Trellis that I want to tell you more about.

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Announcement: I’ll be in NYC (10/24) and Chicago (10/28). Message me if you’d like to join a small group of us for dinner. CTO’s only please. Separate checks.

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The CTO isn’t someone who knows everything

Remember when you were reading Bitcoin: A Peer-to-Peer Electronic Cash System? We were all trying to make sense of how blockchain worked. Why? Because in 2020 our CEOs and VCs were all talking about the blockchain gold rush.

Oh that wasn't you huh?

How about when we all started reading Emergent autonomous scientific research capabilities of large language models because our CEOs woke up one morning in 2023 with a new appetite for AI?

Or did you even know about Attention Is All You Need when it came out in 2017?

Or did you actually read Ethereum: A Next-Generation Smart Contract and Decentralized Application Platform by Vitalik Buterin (2013), or maybe The Graph: Decentralized Query Protocol by Yaniv Tal, Jannis Pohlmann, and Brandon Ramirez (2017)?

And let’s not forget 5G and Beyond: A Future of Convergence by Qualcomm Technologies (2020), Federated Learning: Collaborative Machine Learning Without Centralized Training Data by Google AI (2017), or InterPlanetary File System (IPFS): A Peer-to-Peer Hypermedia Protocol by Juan Benet (2014), and on and on and on ..

Have I made my point yet?

I'm not talking about all the books you should have read by now, the YouTube channels you should be subscribed to, the socials you should be following or the podcasts you should be listening to.

To know everything is too hard. There are too many discoveries. Too much research. It is impossible to stay on top of it. And if you’re trying, to truly comprehend what is being explained adds weeks and months to your cognitive digestion.

And it makes you a super ineffective CTO.

The CTO isn't someone who needs to learn from experience

I’ve often reflected on how my skills have been shaped by the unique path I’ve walked. Sure, I’ve built and sold a company—a solid success by most standards. But I’ve never had to knock on doors for venture capital to keep my startup alive.

Does this mean that because I don't have that experience, I can't do that?

I’ve been the CTO for early-stage companies, guiding them through the chaotic early years to become stable, thriving businesses. But I haven’t been the CTO leading an army of 400+ engineers.

Does this mean that because I don't have that experience, I can't do that?

What does that say about my capability as a CTO? I’d argue it says nothing about whether I could lead a large engineering team or stand in front of a room full of VCs, passionately making my case for funding.

Our hiring systems are designed to fixate on keywords and on past roles that imply certain capabilities. They’re wired to assume that experience in one specific context equates to competence in another, ignoring the nuances of what someone is truly capable of, given the right opportunity.

The Peter Principle, introduced by Laurence J. Peter, suggests that people tend to rise to their “level of incompetence” in hierarchical organizations¹. Essentially, past success in a role doesn’t necessarily predict success in a more complex or unrelated role, especially if the skills required are different.

Just because you led a small team doesn’t mean you can’t lead a large one, and past experiences may not be indicative of how you perform in a new, scaled environment.

So if you're a CTO who doesn't "know everything" and you also don't have the "necessary lived experience", what is there to do?

The CTO makes sense of things by drawing from a wide range of interpretation methods

A truly wise person is not someone who knows everything, but someone who is able to make sense of things by drawing from an extended resource of interpretation schemes. This stands in harsh contrast to the common but not-so-wise belief that we need to learn from experience. It is much better to learn from the experiences of others – especially when this experience is reflected on and turned into versatile “mental models” that can be used in different situations.

- How to Take Smart Notes. One Simple Technique to Boost Writing, Learning and Thinking ~ Sönke Ahrens

For most of my life, I viewed reading as the process of memorizing isolated facts. My eyes would laser-focus on pages, scan with frenetic energy, extract phrases from sentences, and cram them into my memory banks.

It wasn’t until I discovered the Zettelkasten method for knowledge management² that my relationship with reading completely transformed. The shackles linking the act of reading to the task of knowledge gathering were broken.

I no longer see reading as a means of accumulating knowledge. Instead, I view it as the ritual of crafting my own trellis—a lattice-like structure designed to support my own mental models, my own ideas, and my own thinking.

Imagine a trellis where climbing plants and vines intertwine the lattice to grow upward and spread out. The beauty of the plant, the intimacy of the flower. These are not the words you read. These are the thoughts you seed. The contexts you create and connections you make. The beauty that is your own mind with it's power to see patterns and parallels that no one else could find.

Just like that kid in the hardware store. I don't care to remember the tool I held in my hand. I care about the thoughts it evoked and the new paths that were created when I felt new questions floating in my brain.

Now when I read, I look for the principles behind the ideas being presented. I make my own connections, wrestle with contrarian concepts, and find the patterns that excite me.

In short, I don’t rely on authors to provide the facts that will shape my life. I see them as inputs for the trellis I’m constructing. From this trellis, I will grow and support my own ideas.

Introducing the CTO's Reading Trellis

The CTO’s strength in navigating the constant flood of new developments comes not from staying current with trends, but from the mental models they’ve built, which shape and guide all their knowledge.

The CTO’s Reading Trellis is the foundation for creating those mental models.

It consists of:

1. The Method

2. The Matrix

3. The Features

Let’s go through the Method first. Then we will describe how we build the Matrix. Once we have the Matrix we will know which books, that we call Features, we need to use to train our brains.

The Method

1. Pick a block from the matrix preferably starting from the top left.

2. Read the book making notes of everything that catches your eye. I talk about how to maintain a CTO Notebook if you want to use that method.

3. Once you’re done, go through your notes, think deeply about them and find new contexts and connections with other notes you’ve made.

4. Write about your new thoughts and watch the flowers grow around your mental models.

5. Pick your next book from the CTO’s Reading Trellis.

Go through all 20 books of the CTO’s Reading Trellis.

The Matrix

The CTO’s Reading Trellis is a matrix. On the X-axis I place the CTO Sentinels™ - the four emerging properties of a healthy technology organization.

• Speed of Tech Delivery, Organizational Adaptability, Shield Against Threats, Fuel Sales

On the Y-axis I place the 4 quadrants of Emotional Intelligence and I throw in Fiction for good measure.

• Self-Awareness, Self-Management, Social Awareness, Relationship Management, Fiction

This forms the core of the lattice on which I will build the trellis.

Let's take a look at the following question: what self-awareness (Y1) is necessary to be able to build technology quickly and efficiently (X1) in an organization? To me that book is clearly The Effective Executive by Peter F. Drucker since it helps the CTO recognize their personal strenghts and weaknesses in productivity and decision-making. It especially help leaders identify how their behaviors impact the efficiency of tech delivery.

How about when we combine Fiction (Y5) with Shield (X3)? There could be many choices here, but to me a standout favorite is the book Cryptonomicon by Neal Stephenson. It explores themes of cryptography and security. It engages CTOs in considering the complexities of protecting information in a technological context.

The Features

Just like we use Features for training Models in machine learning, we look at these books as input data to help train our own mental models.

I won't go into endless repetition here because I think you get it. Based on this formula, I would like to present to you the list of “features” I think every CTO should read to build their own mental models.

1. The Effective Executive by Peter F. Drucker

Speed x Self-Awareness

This book helps CTOs recognize their personal strengths and weaknesses in productivity and decision-making. By enhancing self-awareness, it enables leaders to identify how their behaviors impact the efficiency of tech delivery.

Alternatively, check out “Flow: The Psychology of Optimal Experience” by Mihaly Csikszentmihalyi, which explores achieving peak productivity through deep focus, or “The Principles of Scientific Management” by Frederick Winslow Taylor, which discusses efficient work methods based on scientific analysis.

2. Deep Work by Cal Newport

Speed x Self Management

It teaches techniques for focused work and time management. CTOs can improve their self-discipline, leading by example to boost their team’s productivity and speed up tech delivery.

Alternatively, check out “Essentialism: The Disciplined Pursuit of Less” by Greg McKeown, which emphasizes focusing on what truly matters, or “Indistractable: How to Control Your Attention and Choose Your Life” by Nir Eyal, which provides strategies for maintaining focus.

3. The Five Dysfunctions of a Team by Patrick Lencioni

Speed x Social Awareness

The book uncovers common issues that hinder team performance. Understanding these dysfunctions enhances a CTO’s social awareness, enabling them to address team dynamics that affect delivery speed.

Alternatively, check out “Emotional Intelligence” by Daniel Goleman, which delves into how emotional intelligence affects team dynamics, or “Crucial Conversations: Tools for Talking When Stakes Are High” by Kerry Patterson et al., which offers techniques for effective team communication.

4. Accelerate by Nicole Forsgren, Jez Humble, and Gene Kim

Speed x Relationship Management

Based on extensive research, this book offers strategies for managing teams and processes to achieve high-performance technology delivery, emphasizing the importance of strong relationships and collaboration.

Alternatively, check out “The DevOps Handbook” by Gene Kim, Jez Humble, Patrick Debois, and John Willis, which provides practical guidance on implementing DevOps practices, or “Continuous Delivery” by Jez Humble and David Farley, which explores reliable software release strategies.

5. The Phoenix Project by Gene Kim, Kevin Behr, and George Spafford

Speed x Fiction

This novel illustrates real-world IT and DevOps challenges. It provides insights into improving tech delivery through engaging storytelling, making complex concepts relatable.

Alternatively, check out “The Unicorn Project” by Gene Kim, which offers another insightful narrative on DevOps and software development challenges, or “Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency” by Tom DeMarco, which discusses productivity through storytelling.

6. Leadership and Self-Deception by The Arbinger Institute

Stretch x Self Awareness

It encourages leaders to examine their own biases and behaviors. Self-awareness gained from this book helps CTOs design organizations that avoid pitfalls stemming from self-deception.

Alternatively, check out “Ego Is the Enemy” by Ryan Holiday, which examines how ego can hinder effective leadership, or “Insight: The Power of Self-Awareness in a Self-Deluded World” by Tasha Eurich, which focuses on developing self-awareness for better leadership.

7. The Practice of Adaptive Leadership by Ronald Heifetz and Marty Linsky

Stretch x Self Management

Offers tools for personal adaptability in leadership. CTOs learn to manage themselves effectively while steering organizational design in changing environments.

Alternatively, check out “Leadership on the Line” by Ronald Heifetz and Marty Linsky, which discusses navigating the challenges of leading change, or “Switch: How to Change Things When Change Is Hard” by Chip Heath and Dan Heath, which provides strategies for implementing change.

8. Team of Teams by General Stanley McChrystal

Stretch x Social Awareness

Demonstrates how interconnected teams function. Enhances a CTO’s understanding of social dynamics essential for designing flexible and responsive organizations.

Alternatively, check out “The Culture Code: The Secrets of Highly Successful Groups” by Daniel Coyle, which explores building strong team cultures, or “Collaborative Intelligence: Using Teams to Solve Hard Problems” by J. Richard Hackman, which examines enhancing team effectiveness.

9. Reinventing Organizations by Frederic Laloux

Stretch x Relationship Management

Explores innovative organizational models that prioritize relationships and self-management, guiding CTOs in creating empowered and collaborative workplaces.

Alternatively, check out “Holacracy: The New Management System for a Rapidly Changing World” by Brian J. Robertson, which discusses a novel approach to organizational structure, or “The Starfish and the Spider: The Unstoppable Power of Leaderless Organizations” by Ori Brafman and Rod A. Beckstrom, which explores decentralized organizational models.

10. The Goal by Eliyahu M. Goldratt

Stretch x Fiction

Through a business narrative, it introduces the Theory of Constraints. Helps CTOs think critically about process optimization and organizational design.

Alternatively, check out “Critical Chain” by Eliyahu M. Goldratt, which applies the Theory of Constraints to project management, or “The Machine That Changed the World” by James P. Womack, Daniel T. Jones, and Daniel Roos, which examines the principles of lean production.

11. Thinking in Systems by Donella H. Meadows

Shield x Self Awareness

Teaches systems thinking, enabling CTOs to understand the complexities within their organizations and anticipate internal and external threats.

Alternatively, check out “Systems Thinking: Managing Chaos and Complexity” by Jamshid Gharajedaghi, which offers insights into designing complex systems, or “An Introduction to General Systems Thinking” by Gerald M. Weinberg, which provides foundational concepts in systems theory.

12. The Obstacle Is the Way by Ryan Holiday

Shield x Self Management

Introduces Stoic principles for turning challenges into opportunities. Helps CTOs maintain composure and resilience when facing threats.

Alternatively, check out “Meditations” by Marcus Aurelius, which presents Stoic philosophy on overcoming challenges, or “Man’s Search for Meaning” by Viktor E. Frankl, which explores finding purpose through adversity.

13. The Black Swan by Nassim Nicholas Taleb

Shield x Social Awareness

Discusses the impact of rare, unpredictable events. Enhances a CTO’s awareness of potential risks that could threaten the organization.

Alternatively, check out “Antifragile: Things That Gain from Disorder” by Nassim Nicholas Taleb, which discusses thriving amidst uncertainty, or “The Signal and the Noise: Why So Many Predictions Fail—but Some Don’t” by Nate Silver, which examines probability and forecasting.

14. Leaders Eat Last by Simon Sinek

Shield x Relationship Management

Helps a CTO shield their organization by teaching how fostering strong relationships can build a culture of trust and collaboration. This enhances team resilience and protects the organization from internal and external challenges.

Alternatively, check out “Turn the Ship Around!” by L. David Marquet, which presents a model for empowering leadership.

15. Cryptonomicon by Neal Stephenson

Shield x Fiction

Explores themes of cryptography and security. Engages CTOs in considering the complexities of protecting information in a technological context.

Alternatively, check out “Snow Crash” by Neal Stephenson, which explores themes of virtual reality and data security, or “Neuromancer” by William Gibson, which delves into cyberpunk and artificial intelligence.

16. Start with Why by Simon Sinek

Sales x Self Awareness

Encourages leaders to identify and communicate their core purpose. Aids CTOs in aligning technology initiatives with the company’s mission to drive sales.

Alternatively, check out “Drive: The Surprising Truth About What Motivates Us” by Daniel H. Pink, which examines intrinsic motivation, or “The Purpose Economy” by Aaron Hurst, which discusses how purpose drives business success.

17. Measure What Matters by John Doerr

Sales x Self Management

Introduces OKRs for setting and tracking goals. Helps CTOs manage their objectives effectively to support sales growth.

Alternatively, check out “High Output Management” by Andrew S. Grove, which offers management insights from Intel’s former CEO, or “The Lean Startup” by Eric Ries, which introduces lean methodologies for business innovation.

18. The Innovator’s Dilemma by Clayton M. Christensen

Sales x Social Awareness

Explores how companies can miss market shifts. Enhances a CTO’s awareness of innovation opportunities to fuel sales.

Alternatively, check out “The Innovator’s Solution” by Clayton M. Christensen and Michael E. Raynor, which provides strategies for creating and sustaining growth, or “Crossing the Chasm” by Geoffrey A. Moore, which discusses marketing disruptive products to mainstream customers.

19. Never Split the Difference by Chris Voss

Sales x Relationship

Provides negotiation techniques and communication skills. Essential for CTOs to manage relationships with clients and stakeholders to enhance sales efforts.

Alternatively, check out “Getting to Yes: Negotiating Agreement Without Giving In” by Roger Fisher and William Ury, which is a classic guide on principled negotiation, or “Influence: The Psychology of Persuasion” by Robert B. Cialdini, which explores the principles of influencing others.

20. The Circle by Dave Eggers

Sales x Fiction

Examines the intersection of technology and consumer behavior. Stimulates thought on how tech products can influence and drive sales.

Alternatively, check out “1984” by George Orwell, which examines themes of surveillance and societal control, or “The Net Delusion: The Dark Side of Internet Freedom” by Evgeny Morozov, which critiques the impact of the internet on society.

Build Your Own Reading Trellis

Here’s how you can build your own Reading Trellis.

Ask yourself: what am I into? Or what do I want to learn more about? Put that on the Y-axis of a spreadsheet.

Then ask yourself: what is expected of me to be powerful in this world? Put that on the X-axis of the spreadsheet.

At the intersection of each of these words, find the book that Google or ChatGPT suggests you read. Do a little research. Follow your gut.

An example

Here’s a different Reading Trellis I built because I was getting concerned that I was falling behind on some major technologies as I was the CTO of e-commerce, consumer focused company.

X-Axis (CTO Focus Areas): Customer Experience Enhancement, Operational Efficiency, Data-Driven Decision Making

Y-Axis (Emerging Technologies): AI, Blockchain Technology, IoT

This image links to a Google Sheet I created for you.

What book did you decide to read next?

With the Reading Trellis, we are less concerned about what we’re reading. In the compression of time and the eternal urgency we operate in, it is often a dreadful choice to decide what to read next.

Don’t dread it.

Just read whatever your heart desires. Even better use the CTO’s Reading Trellis to pick your next book. Know that what you’re going to read isn’t the thing. It’s feeding your mind with new questions. Creating new gaps for you to step into.

And at a time that is most surprising to you, you will face a question that seems to have no clear answer, and you will step into it with your very own constructed thoughts. Thoughts that have been growing on your trellis. Beautiful, inspired and complete.

Throw a healthy dose of humility and curiosity into all your conversations and you will be unstoppable.

If you’re interested in joining a weekly book club with me to get through these books, send me a message.

Etienne

1. Peter, Laurence J., and Raymond Hull. The Peter Principle: Why Things Always Go Wrong. William Morrow & Co., 1969.

2. Luhmann, Niklas. Kommunikation mit Zettelkästen: Ein Erfahrungsbericht. Westdeutscher Verlag, 1981.