Bookshelf

The books that shaped how I think about the gap between how organizations officially work and how they actually work.

Grouped by the four territories I write about. Recent books first; the foundations underneath them after. A short note on each says why it earned its place.

AI & Technology

On what it actually takes to turn AI and technology into enterprise capability.

Recent

  • Co-Intelligence: Living and Working with AI

    Ethan Mollick · 2024

    The most practical account I have read of what working alongside AI looks like day to day — and why the official process is usually the last thing to catch up.

  • Power and Prediction: The Disruptive Economics of Artificial Intelligence

    Ajay Agrawal, Joshua Gans, Avi Goldfarb · 2022

    Explains why AI pilots succeed and enterprise adoption stalls: the value sits in redesigning the system around the prediction, not in the model itself.

  • Competing in the Age of AI

    Marco Iansiti, Karim R. Lakhani · 2020

    Makes the case that the operating model, not the algorithm, is the real competitive unit — which is exactly where most transformation programs never look.

  • The Coming Wave

    Mustafa Suleyman, Michael Bhaskar · 2023

    A sober reminder that governance is not a compliance afterthought. Containment is a design problem, and most organizations have not started designing.

Enterprise Transformation

On why large programs stall, and how work really flows through an organization.

Recent

  • Transformed: Moving to the Product Operating Model

    Marty Cagan · 2024

    Names the gap between adopting the vocabulary of product and actually changing how decisions get made. Most transformations stop at the vocabulary.

  • Wiring the Winning Organization

    Gene Kim, Steven J. Spear · 2023

    Gives language to something I have watched for years: performance is decided by the wiring between people and teams, not the talent inside them.

  • Team Topologies

    Matthew Skelton, Manuel Pais · 2019

    The org chart describes reporting lines; this book describes how work actually moves between teams. That second picture is the one that matters.

  • Sooner Safer Happier

    Jonathan Smart, Zsolt Berend, Myles Ogilvie, Simon Rohrer · 2020

    An honest catalogue of the anti-patterns large enterprises fall into when they try to become agile by decree.

  • Flow Engineering

    Steve Pereira, Andrew Davis · 2024

    Practical mapping techniques for making invisible work visible — the first step to closing the gap between the plan and the operating reality.

  • Product Operations

    Melissa Perri, Denise Tilles · 2023

    Treats the plumbing between strategy and teams as a discipline in its own right. Most organizations leave that plumbing to chance.

Foundations

  • The Principles of Product Development Flow

    Donald G. Reinertsen · 2009

    Still the most rigorous book on why queues, batch size and cost of delay quietly decide outcomes that dashboards never show.

  • Developing Products in Half the Time: New Rules, New Tools

    Preston G. Smith, Donald G. Reinertsen · 1997

    Decades old and still right: speed is an economic decision, and most organizations never price it.

  • Leading Lean Software Development: Results Are Not the Point

    Mary Poppendieck, Tom Poppendieck · 2009

    A reminder that results come from the system leaders build, not the targets they set.

  • Scaling Lean & Agile Development

    Craig Larman, Bas Vodde · 2008

    The best early treatment of why scaling agility is an organizational-design problem, not a process-rollout problem.

  • The Lean Startup

    Eric Ries · 2011

    Validated learning applies inside large enterprises at least as much as in startups — they are simply better at hiding what they have not learned.

  • Balancing Agility and Discipline: A Guide for the Perplexed

    Barry Boehm, Richard Turner · 2003

    An early, grown-up refusal of dogma: the right method depends on the real risk profile, not the fashionable one.

  • Agile Management for Software Engineering

    David J. Anderson · 2003

    Applied the Theory of Constraints to software management long before flow became fashionable.

  • Software in 30 Days

    Ken Schwaber, Jeff Sutherland · 2012

    Written for executives rather than teams — useful for showing leaders what changes on their side of the table.

  • Agile Software Development

    Alistair Cockburn · 2001

    Treats software as a cooperative game between people, which is still the most accurate description I know.

  • The Software Project Manager's Bridge to Agility

    Michele Sliger, Stacia Broderick · 2008

    A humane guide for the people whose roles change most in a transformation, and who are usually least supported through it.

Leadership & Organizations

On informal networks, invisible leaders, and the systems beneath the organization chart.

Recent

  • Humanocracy

    Gary Hamel, Michele Zanini · 2020

    The closest book I know to my own thesis: bureaucracy is the official organization, and it is quietly taxing the real one.

  • Right Kind of Wrong: The Science of Failing Well

    Amy C. Edmondson · 2023

    Separates intelligent failure from the preventable kind. Organizations that cannot tell them apart stop telling the truth about both.

  • Empowered

    Marty Cagan, Chris Jones · 2020

    What leadership looks like when teams are trusted with problems instead of handed features.

  • The Motive

    Patrick Lencioni · 2020

    Another Lencioni fable, this one about why leaders take the job. Motive determines which uncomfortable work gets done and which gets delegated away.

Foundations

  • The Five Dysfunctions of a Team

    Patrick Lencioni · 2002

    The book that proved a fable can carry a serious idea. It shaped how I chose to write The Tower of Progress.

  • Tribal Leadership

    Dave Logan, John King, Halee Fischer-Wright · 2008

    Maps the informal tribes that actually run organizations — the ones that never appear on the chart.

  • The Culture Game: Tools for the Agile Manager

    Daniel Mezick · 2012

    Treats culture as something you can see and work with, not a slogan on the wall.

  • The Servant Leader

    James A. Autry · 2001

    An early, practical case that leading through service is a performance strategy, not a soft one.

  • Collaboration Explained

    Jean Tabaka · 2006

    Facilitation as a leadership skill — the quiet craft behind most decisions that actually stick.

  • Personal Kanban: Mapping Work, Navigating Life

    Jim Benson, Tonianne DeMaria Barry · 2011

    Visible work starts with your own. Leaders who cannot see their own queue rarely see anyone else's.

CTO Field Notes

On the practice of technology leadership inside complex enterprises.

Recent

  • The Engineering Executive's Primer

    Will Larson · 2024

    The most honest book on what the senior technology role actually involves once the title is on the door.

  • Staff Engineer: Leadership Beyond the Management Track

    Will Larson · 2021

    Describes the invisible leaders of engineering organizations — the people who hold systems together without formal authority.

  • The Staff Engineer's Path

    Tanya Reilly · 2022

    Practical about the unglamorous glue work that keeps complex technology organizations from quietly falling apart.

Foundations

  • Agile Product Management with Scrum

    Roman Pichler · 2010

    A clear account of the product owner role before it became a job title without authority.

  • Agile Excellence for Product Managers

    Greg Cohen · 2010

    A useful bridge for product managers moving from document-driven to team-driven work.

  • The Power of Scrum

    Jeff Sutherland, Rini van Solingen, Eelco Rustenburg · 2011

    A short business novel that makes the case for Scrum through story rather than ceremony.

  • User Stories Applied

    Mike Cohn · 2004

    Requirements as conversations rather than contracts — still misunderstood two decades later.

  • Agile Estimating and Planning

    Mike Cohn · 2005

    Planning as a way to learn, not a promise to defend.

  • Specification by Example

    Gojko Adzic · 2011

    Shared examples close the gap between what the business means and what gets built.

  • Getting Started with Kanban

    Paul Klipp · 2011

    A short, practical starting point for making work visible on a single team.

The Tower of Progress cover

And my own attempt

The Tower of Progress: Leading Through Transformation

A leadership fable about the invisible leaders who keep organizations working despite broken systems.

Explore the book →