My favorite books for dysfunctional organizations from a formerly dysfunctional leader

Why am I passionate about this?

I’ve always been interested in finding new ways for organizations to operate. When I was early in my career, I always had a habit of questioning the conventional wisdom of policies and procedures. I always want to know if the actions that we’re doing are delivering the results that we’re expecting. This led me on a journey to understand how teams function and to go beyond the easy answers.


I wrote...

Operations Anti-Patterns, DevOps Solutions

By Jeffery D. Smith,

Book cover of Operations Anti-Patterns, DevOps Solutions

What is my book about?

Operations Anti-Patterns, DevOps Solutions shows how to implement DevOps techniques in the kind of imperfect environments most developers work in. Part technology tutorial, part reference manual, and part psychology handbook, this practical guide shows you realistic ways to bring DevOps to your team when you don't have the flexibility to make sweeping changes in organizational structure.

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

The books I picked & why

Book cover of Turn the Ship Around! A True Story of Turning Followers into Leaders

Jeffery D. Smith Why did I love this book?

Technology is rarely the problem in most organizations. It’s people, processes, and how the two come together to create a web of dysfunction.

I loved Turn the Ship Around because it takes you on a journey from start to finish and sprinkles the lessons for change throughout that journey. The book taught the importance of empowering leadership throughout an organization.

As leaders we can do more harm than good by accidentally hording the power of decision making. This book will teach you to undo that mistake.

By L. David Marquet,

Why should I read it?

3 authors picked Turn the Ship Around! A True Story of Turning Followers into Leaders as one of their favorite books, and they share why you should read it.

What is this book about?

"Leadership should mean giving control rather than taking control and creating leaders rather than forging followers."

David Marquet, an experienced Navy officer, was used to giving orders. As newly appointed captain of the USS Santa Fe, a nuclear-powered submarine, he was responsible for more than a hundred sailors, deep in the sea. In this high-stress environment, where there is no margin for error, it was crucial his men did their job and did it well. But the ship was dogged by poor morale, poor performance, and the worst retention in the fleet.

Marquet acted like any other captain until, one…


Book cover of Thinking in Systems

Jeffery D. Smith Why did I love this book?

Our work environments are complicated. We don’t always recognize how something seemingly unrelated can have a huge impact on another item or task way downstream.

Being able to think and view the world through the lens of systems opens your approach to solving problems both technical and human. Reading this book helped me make the connection that change control policies were the cause of our increased failure rates.

These sorts of unlikely relationships are what thinking with a systems mindset allows you to create. 

The book does a thorough job of taking you through the language of systems, diagramming systems, and walking you through some real-world examples. It’s the perfect tool for your career toolbox.

By Donella Meadows,

Why should I read it?

5 authors picked Thinking in Systems as one of their favorite books, and they share why you should read it.

What is this book about?

The classic book on systems thinking, with more than half a million copies sold worldwide!

This is a fabulous book. This book opened my mind and reshaped the way I think about investing. Forbes

Perfect for fans of Kate Raworth, Rutger Bregman and Daniel Kahneman!

The co-author of the international best-selling book Limits to Growth, Donella Meadows is widely regarded as a pioneer in the environmental movement and one of the world's foremost systems analysts . Her posthumously published Thinking in Systems, is a concise and crucial book offering insight for problem solving on scales ranging from the personal to…


Book cover of Making Work Visible: Exposing Time Theft to Optimize Work & Flow

Jeffery D. Smith Why did I love this book?

It’s amazing how invisible work can destroy the productivity of a team.

This book teaches why it’s critical to make your work visible. It has a bend towards agile working environments, but it can honestly be used anywhere with a little bit of adaptation.

The author uses the idea of a “time thief” to help illustrate her point and to help you, the reader, conceptualize just what this lack of visible work is costing you.

By Dominica DeGrandis,

Why should I read it?

1 author picked Making Work Visible as one of their favorite books, and they share why you should read it.

What is this book about?

Today's workers are drowning: nonstop requests for time, days filled to the brim with meetings, and endless nights spent heroically fixing the latest problems. This churn and burn is creating a workforce constantly on the edge of burnout.

In this updated edition, IT time management expert Dominica DeGrandis reveals the real crime of the century time theft, one of the most costly factors impacting enterprises in their day-to-day operations.

Through simple solutions that make work visible, DeGrandis helps people round up the five thieves of time and take back their lives with time-saving solutions. Chock-full of exercises, takeaways, real-world examples,…


Book cover of Rework

Jeffery D. Smith Why did I love this book?

I love Rework because it’s a business book that is straightforward in its language and approach.

It’s economical with its page count and once it makes a point it moves on. And there are a ton of great points in this book. 37 signals has always had a unique approach to work and managing their company. While the book has an entrepreneurial mindset in its approach, the lessons are applicable to any leader.

If you’re the type of person that isn’t happy with the “standard” approach to how things are done, this book is for you.

By Jason Fried, David Heinemeier Hansson,

Why should I read it?

2 authors picked Rework as one of their favorite books, and they share why you should read it.

What is this book about?

A radical new business book from business trailblazers Jason Fried and David Heinemeier Hansson that offers a reappraisal of business best practice - advocating stripping everything back to bare essentials. With its straightforward language and easy-is-better approach, Rework is the perfect playbook for anyone who's ever dreamed of doing it on their own. It will COMPLETELY change your approach to work.

Every once in a while, a book comes out that changes just about everything. This is one of those books. Ignore it at your peril' -- Seth Godin, New York Times bestselling author
'Inspirational...REWORK is a minimalist manifesto that's…


Book cover of Deep Work: Rules for Focused Success in a Distracted World

Jeffery D. Smith Why did I love this book?

Not all the problems of an organization belong to other people.

Sometimes you’re part of the problem. One of the issues people struggle with is managing their increasing workloads and maintaining a high level of quality. Deep Work helped me understand how much focus we need to get into the flow and produce at a high-level.

If you’re someone who feels like they’re always nibbling at the edges of productive work, but never quite getting into a deep flow of things, then this is the book for you. 

By Cal Newport,

Why should I read it?

8 authors picked Deep Work as one of their favorite books, and they share why you should read it.

What is this book about?

Many modern knowledge workers now spend most of their brain power battling distraction and interruption, whether because of the incessant pinging of devices, noisy open-plan offices or the difficulty of deciding what deserves your attention the most. When Cal Newport coined the term 'deep work' on his popular blog, Study Hacks, in 2012, he found the concept quickly hit a nerve. Most of us, after all, are excruciatingly familiar with shallow work instead - distractedly skimming the surface of our workload and never getting to the important part. Newport began exploring the methods and mindset that foster a practice of…


You might also like...

American Flygirl

By Susan Tate Ankeny,

Book cover of American Flygirl

Susan Tate Ankeny Author Of The Girl and the Bombardier: A True Story of Resistance and Rescue in Nazi-Occupied France

New book alert!

Why am I passionate about this?

Susan Tate Ankeny left a career in teaching to write the story of her father’s escape from Nazi-occupied France. In 2011, after being led on his path through France by the same Resistance fighters who guided him in 1944, she felt inspired to tell the story of these brave French patriots, especially the 17-year-old- girl who risked her own life to save her father’s. Susan is a member of the 8th Air Force Historical Society, the Air Force Escape and Evasion Society, and the Association des Sauveteurs d’Aviateurs Alliés. 

Susan's book list on women during WW2

What is my book about?

The first and only full-length biography of Hazel Ying Lee, an unrecognized pioneer and unsung World War II hero who fought for a country that actively discriminated against her gender, race, and ambition.

This unique hidden figure defied countless stereotypes to become the first Asian American woman in United States history to earn a pilot's license, and the first female Asian American pilot to fly for the military.

Her achievements, passionate drive, and resistance in the face of oppression as a daughter of Chinese immigrants and a female aviator changed the course of history. Now the remarkable story of a fearless underdog finally surfaces to inspire anyone to reach toward the sky.

American Flygirl

By Susan Tate Ankeny,

What is this book about?

One of WWII’s most uniquely hidden figures, Hazel Ying Lee was the first Asian American woman to earn a pilot’s license, join the WASPs, and fly for the United States military amid widespread anti-Asian sentiment and policies.

Her singular story of patriotism, barrier breaking, and fearless sacrifice is told for the first time in full for readers of The Women with Silver Wings by Katherine Sharp Landdeck, A Woman of No Importance by Sonia Purnell, The Last Boat Out of Shanghai by Helen Zia, Facing the Mountain by Daniel James Brown and all Asian American, women’s and WWII history books.…


5 book lists we think you will like!

Interested in decision making, sustainable development, and cognition?

10,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about decision making, sustainable development, and cognition.

Decision Making Explore 80 books about decision making
Sustainable Development Explore 30 books about sustainable development
Cognition Explore 37 books about cognition