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.

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 →