The Leadership Reader

I’ve started reading a lot more last year and that pace does not seem to be letting off. Right now I’m reading much of the core literature on leadership. I did the same back when I got into UX design and game design. It’s enjoyable material and it feels particularly relevant to me at this point in my career. I get my recommendations for these leadership books mainly from the Rands Leadership Slack.

When I talk to people about this, it sounds like it’s not very easy to figure out which books to read and where to start. Goodreads isn’t much help either. In the spirit of sharing my learning, I’ve ransacked my reading lists and composed this reader. I hope it will serve as a starting point for others. Expect it to be updated infrequently.

You can always grab coffee with me (dms open), if you want to talk about the stuff in these books.

Thanks Michelle for sharing her own reader recently and thanks Brian for prompting me to share this.

The books that I’ve read ordered by date read. Titles with an asterisk are must-read.

• Turn the Ship Around*, David Marquet
  One of the best books on management and a favorite in lots of places. Reads like a management novel but is a full guide on self-organization.
• Good Strategy Bad Strategy*, Richard P. Rumelt
  An introduction to strategy which contains a breadth of cases that will also keep the advanced practitioner from dozing off.
• The Coaching Habit*, Michael Bungay Stanier
  A short and actionable book about how to coach people.
• Never Split the Difference*, Chris Voss
  One of the best books on negotiation if you don’t mind the tone of voice (I don’t).
• Financial Strategy for Public Managers, Sharon Kioko
  A guide to financial statements and budgeting which everybody should know something about.
• What Got You Here Won’t Get You There*, Marshall Goldsmith
  About developing yourself, diagnosing your dysfunctions and fixing them that is comprehensive enough that most people will benefit.
• Reinventing Organizations, Frederic Laloux
  A bit of a slog but it does contain everything you need to know about the hierarchy-less school of management thinking.
• Developer Hegemony, Erik Dietrich
  A pragmatic retelling of Venkat’s Gervais principle and an interesting career perspective for software engineers.
• Managing Humans, Michael Lopp
  The cases are a bit caricatural but they still contain a huge amount of insight about software engineering management.
• The Principles of Product Development Flow*, Donald G. Reinertsen
  Essential and comprehensive mathematical treatment on how to exploit variability in your design/development projects.
• Notes on the Synthesis of Form, Christopher W. Alexander
  A different and fundamental perspective on design that is useful to anybody working in or around the field.
• Personal Kanban, Jim Benson
  A gentle introduction on how to employ Kanban for your personal productivity that scales up well.
• Extreme Ownership*, Jocko Willink
  Get past the military setting and you’ll find this book full of very useful principles for operational management.
• Lean UX, Jeff Gothelf
  Contains everything you need to know about how pragmatic organizations use UX right now but probably only very useful if you’re new to this stuff.
• The Dictator’s Handbook*, Bruce Bueno de Mesquita
  Essential guide to how power works in any organization.
• Science, Strategy and War, Frans P.B. Osinga
  The complete PhD thesis with everything in it about and from John Boyd. I’d say it’s a must-read but I don’t know who else would finish this.
• Certain to Win*, Chet Richards
  The condensed application to business of Boydian thinking and the foundational concepts of what agile is.
• The Responsible Company, Yvon Chouinard
  Read the other book instead.
• Tempo, Venkatesh Rao
  A somewhat unbalanced book that provides insights on Venkatesh’s approach to strategy and tactics in business.
• Dark Matter and Trojan Horses*, Dan Hill
  A quick read that contains some very useful concepts for thinking about organizational change.
• Subject to Change, Peter Merholz
  A useful primer on service design for managers from different fields.
• Let My People Go Surfing, Yvon Chouinard
  A lovely history of how Patagonia came to be and what the organization’s philosophy is about.
• The Seven Day Weekend, Ricardo Semler
  The original inspirational story of how businesses can be run differently.

The books I still have to read ordered by date added. Titles with an asterisk are top of pile.

• Coaching Agile Teams*, Lyssa Adkins
• The Ten Faces of Innovation, Tom Kelley
• Financial Intelligence for Entrepreneurs, Karen Berman
• Brotopia, Emily Chang
• The Practice of Adaptive Leadership, Ronald A. Heifetz
• Immunity to Change, Robert Kegan
• Build Your Dream Team, Candela Iglesias Chiesa
• Multipliers, Liz Wiseman
• Leadership Team Coaching, Peter Hawkins
• Scrum: The Art of Doing Twice the Work in Half the Time, Jeff Sutherland
• This is Service Design Doing, Marc Stickdorn
• Creating Great Choices, Jennifer Riel
• Primal Leadership, Daniel Goleman
• Flawless Consulting, Peter Block
• The Practitioner’s Guide to Product Management, Jock Busuttil
• Data Governance, John Ladley
• The First 90 Days, Michael D. Watkins
• Transform: A Rebel’s Guide to Digital Transformation, Gerry McGovern
• The Startup Way, Eric Ries
• One Mission, Chris Fussell
• Blue Ocean Shift, Kim. W. Chan
• Mastering the Complex Sale, Jeff Thull
• Radical Technologies*, Adam Greenfield
• Frame Innovation, Kees Dorst
• Agile Product Management with Scrum, Roman Pichler
• Agile Estimating and Planning*, Mike Cohn
• Organizational Patterns of Agile Software Development, James O. Coplien
• Against Management, Martin Parker
• The Future of Work, Thomas W. Malone
• Product Leadership, Richard Banfield
• Agile Retrospectives, Esther Derby
• Designing Data Intensive Applications*, Martin Kleppmann
• The Art of Action, Stephen Bungay
• Leading Teams, Richard J. Hackman
• Co-Active Coaching, Henry Kimsey-House
• The Secrets of Consulting, Gerald M. Weinberg
• Large Scale Scrum, Craig Larman
• The Lords of Strategy, Walter Kiechel III
• Scaling Teams, David Loftesness
• Product Development Performance, Kim B. Clarke
• Measuring & Managing Performance in Organizations, Robert D. Austin
• Managing to Learn, John Shook
• Toyota Kata, Mike Rother
• Leading Lean Software Development, Mary Poppendieck
• Impact Mapping, Gojko Adzic
• Digital to the Core, Mark Raskino
• Crossing the Chasm, Geoffrey A. Moore
• Actionable Agile Metrics for Predictability, Daniel S. Vacanti
• Finding the Space to Lead, Janice Marturano
• The Culture Map, Erin Meyer
• Management 3.0: Leading Agile Developers, Developing Agile Leaders, Jurgen Appelo
• Million Dollar Referrals, Alan Weiss
• Organizational Traps, Chris Argyris
• The Lean Startup, Eric Ries
• Agile Experience Design, Lindsay Ratcliffe
• The Manager’s Path*, Camille Fournier
• Team of Teams*, Stanley McChrystal
• When Cultures Collide, Richard D. Lewis
• Lean Enterprise, Jez Humble
• Crucial Conversations*, Kerry Patterson
• Radical Focus, Christian Wodtke
• Peopleware*: Productive Projects and Teams, Tom DeMarco
• Radical Candor*, Kim Malone Scott
• Intercom on Jobs to Be Done, Des Traynor
• High Output Management*, Andrew S. Grove
• Designing Together, Dan M. Brown
• Weapons of Math Destruction*, Cathy O’Neil
• Org Design for Design Orgs*, Peter Merholz
• Toyota Production System, Taiichi Ohno
• The Five Dysfunctions of a Team, Patrick Lencioni
• Your Strategy Needs a Strategy, Martin Reeves
• The Fifth Discipline, Peter M. Senge
• Design Sprint, Richard Banfield
• How to Thrive in the Next Economy, John Thackara
• UX Strategy, Jaime Levy
• The Hard Thing About Hard Things, Ben Horowitz
• User Story Mapping, Jeff Patton
• Sprint, Jake Knapp
• Succeeding With Agile, Mike Cohn
• The PDMA Handbook of New Product Development, Kenneth B. Kahn
• The Checklist Manifesto, Atul Gawande
• Remote, David Heinemeier Hansson
• Tribal Leadership, Dave Logan
• Design for the Real World*, Victor Papanek
• Kanban and Scrum — Making the Most of Both, Henrik Kniberg