20(ish) Leadership Books That Actually Work

I’m busy writing a book on leadership and the mindsets of people that take the initiative. 

I’ve read over 100 books in 18 months around as part of the research

There were some very useful ones, a bunch that immediately found their way onto the charity pile, a couple that went in the bin, and one that I’ve hate-kept (will explain later). 

So if you are interested in that niche bookshop section here’s my short list of recommendations.

I’ve found that these books fall into 6 buckets and I've shared a few of the best ones in each category (because I promised Peter).

Bucket 1: Hagiographies 

(Biographies & Corporate Histories)

These are hero’s journey stories that focus on the who and the what, but tend to gloss over the how. 

They are studies of business icons that are often plagued by survivor bias, so you see the path of the winner, but not the thousands of other people who did the exact same thing and went bankrupt.

They are case studies of one.

The majority of business books are of this type, they are fun to read, but often provide limited insights. 

These ones did though.

Top 3ish Hagiographies

1. The Challenge Culture: Why the Most Successful Organizations Run on Pushback by Nigel Travis  Nigel Travis is the former COO of Blockbuster (a company he watched implode after he left) who went on to become the CEO of Dunkin’ Brands. To ensure Dunkin’ didn’t suffer the same fate, Travis introduced a ‘challenge culture’, an environment where employees are encouraged to safely push back against leadership. It’s a good biography, and it also comes with hugely practical ideas and principles to ensure your business or teams don't become corporate echo chambers. 

   
   

2. Up the Organization: How to Stop the Corporation from Stifling People and Strangling Profits by Robert Townsend As the CEO of Avis in the 1960s, Townsend famously transformed the business by launching the world’s first challenger brand with the iconic "We Try Harder" campaign. Townsend was a radical character and he shares his opinions on a wide variety of business topics. The original book featured an appendix titled “Guerrilla Guide for Working Women”, which  was an impressive relic of mid-century mansplaining that newer editions have understandably cut.
   

3. Turn the Ship Around!: A True Story of Building Leaders by Breaking the Rules by L. David Marquet It's fascinating to pull shared business principles from un-business-like environments. L. David Marquet was a U.S. Navy Captain tasked with commanding the worst-performing nuclear submarine in the fleet. By completely abandoning the military's traditional top-down command structure and pushing decision-making authority down the chain, he turned the worst ship into the best. It's the ultimate case study on moving from a ‘leader-follower’ to a ‘leader-leader’ structure.
   

4. Acquired Podcast: Every Company Has a Story by Ben Gilbert & David Rosenthal OK, not a book. If you have a long drive ahead of you and there’s no way to take notes and learn, you might as well pretend you’re doing something productive. This is a series of entertaining (and very long) deep-dives into the origin stories of corporate giants. Great example of Hagiographies: fun stories, even if you walk away with almost nothing you can actually apply to your own business. 

Bucket 2: Autopsies 

(Seeking trends from historical performance)

These books look backwards at a selection of successful companies or leaders in the hope of uncovering a valuable correlation behind their success.

They feel scientific and robust because they use charts, metrics, and comparisons, but correlation does not necessarily mean causation. 

It's a classic statistical trap:

Ice cream sales and shark attacks are highly correlated, but you're not going to be attacked by a frenzied shark just because you’re eating an ice cream. 

Good to Great by Jim Collins is the most famous example of these books, but of the 11 companies he highlighted as being “built to last”, two had disappeared and only two outperformed the S&P 500 average over the next 6 years.

There’s no way these books can dig deeply enough and have a wide enough dataset to be statistically significant so read them with a huge handful of salt. 

These are the ones I found most convincing.

Top 3 Autopsies

1. The Challenger Sale: How To Take Control of the Customer Conversation by Matthew Dixon & Brent Adamson Based on a study of thousands of sales reps across industries they sliced the sales force into five distinct personality types. Only one group, “The Challengers”, consistently deliver when deals get complex and consultative. These are the people who actively debate the customer and take control over the conversations. It’s written for sales teams, but it’s a transferable blueprint for any team trying to push new ideas and make things happen.
   

2. Eating the Big Fish: How Challenger Brands Can Compete Against Brand Leaders by Adam Morgan A look at how whole companies can adopt a challenger mindset to disrupt entrenched, resource-rich market leaders. It provides an excellent roadmap for doing more with less by breaking industry rules. Also I’m sensing a lot of beef between the two consultancies that sprang up around these first two books and trademarking of the word ‘Challenger’ to defend their ideas.
   

3. The Captain Class: The Hidden Force Behind the World’s Greatest Teams by Sam Walker A guy with a great surname trawled the most successful sports teams in history to see what made the win and found they all had a certain unconventional type of character as a captain. There is a massive caveat: all very successful sports people are almost psychotically fixated on their goals, so unless your office culture requires a terrifyingly intense, hyper-competitive focus on zero-sum games it’s not a great guide. It’s entertaining and I found quite a few useful insights from the peripheral stories of people that didn't quite hit Walker’s top tier. Like everyone who has written one of these books, Sam Walker has also started a consultancy. 

Bucket 3: How-Tos 

(Rules, Manuals, Guides & Self-Help)

This is another big chunk of the bookshelf. 

They are often all pants, no trousers. 

They’ll give you the tactics often without the principles, and without understanding the why you can’t excel at the how. 

They can be useful when you have a specific issue you need to solve (which I didn’t have with this project), so these examples are just the very general ones I found useful.

Top 3ish How-Tos

1. The Lean Startup: How Constant Innovation Creates Radically Successful Businesses by Eric Ries Everybody with a start-up has read this book, but the ideas are transferable to anyone trying to get a new idea of the ground whether its a whole business, a product or just a project. It's a scientific method for managing uncertainty by focusing on building a ‘Minimum Viable Product’ and testing assumptions against real user behaviour, the framework prevents you from wasting months building things nobody actually wants.

2. Good Inside: A Practical Guide to Becoming the Parent You Want to Be by Dr Becky Kennedy This is an excellent approach to emotional intelligence and empathy specifically written for parents. The core idea is that people are fundamentally "good inside," and bad behaviour is just a misguided expression of deeper, unmet needs. It is an absolute revelation if you have children, but the psychological underpinnings are entirely transferable to the workplace. Managing a defensive, burned-out colleague requires almost the exact same active listening, boundary-setting, and emotional regulation skills as calming a kid throwing a tantrum in a soft play.

Bucket 4: Scholarly Breakthroughs

Usually written by the scholars who uncovered the ideas, they take one psychological or economic phenomenon and explore it deeply.

They can really shake up your understanding of a slice of the world. 

It is often a very particular slice, so you need to read a fair few of these to build up a usable and wide and useable set of ideas.

So, from a string list here are my recommendations.

Top 3 Scholarly Breakthroughs

1. Mindset: Changing The Way You think To Fulfil Your Potential by Carol Dweck 

   Dweck discovered that there are two ways of thinking: those with a fixed mindset (who believe talent and intelligence are static traits you are born with) and those with a growth mindset (who believe abilities can be developed through effort and strategy). Having a growth mindset is key to continued learning and improvement and the good news is that growth mindset itself can be learned.
   

2. Grit: Why Passion and Resilience Are the Secrets to Success by Angela Duckworth Duckworth found that raw talent and high IQ are wildly overrated predictors of long-term achievement and instead, the ultimate differentiator is what she calls "grit" (and I call for no particularly good reason "bouncebackability"), which is a blend of long-term passion and persistence. 
   

3. Thinking Fast And Slow by Daniel Kahneman The human brain is a marvel of evolutionary engineering that is also profoundly glitchy. Kahneman breaks thinking into two systems: System 1 (fast, intuitive, and prone to bias) and System 2 (slow, deliberate, and incredibly lazy). It’s a dive into cognitive illusions that cause smart people to make catastrophically bad decisions.

Bucket 5: Big Ideas Journalism

These are often beautifully written books. 

They take the ideas of the Scholarly Breakthrough books and bodge a few of them together to present a slightly wider and engaging way to look at the world. 

Once these authors have an idea they have a tendency to explain everything through this single lens, which leads to oversimplification of complex systems.

There are chock loads of good examples of these books, so here’s the ones that were most useful for this project.

Top 3 Big Ideas 

1. Hidden Potential & Think Again by Adam Grant 

   Adam Grant is an organisational psychologist who also writes big ideas books. Think Again focuses on the skill of unlearning and changing your own mind, while Hidden Potential provides a framework for identifying and cultivating talent in people that traditional systems overlook. 
   

2. The Advantage: Why Organizational Health Trumps Everything Else In Business by Patrick Lencioni 

   Lencioni is famous for writing The Five Dysfunctions of a Team, a book built around one decent idea that he bulked out by inventing conversations with imaginary people in a fictional corporation. After a couple more weird business fables, he consolidated all of his theories into this single, non-fiction volume which is a whole load better. If your company is culturally toxic you will fail, so here’s how to avoid that outcome.
   

3. Factfulness: Ten Reasons We're Wrong About The World - And Why Things Are Better Than You Think by Hans Rosling Rosling dismantles our collective, pessimistic biases about the state of humanity, using hard data to prove that the world is in vastly better shape than the news leads us to believe. It is well-written and refreshing, then right at the end there’s a twist in the story that will make you very emotional. I did not expect that.  

Bucket 6. Principles 

These are books that look at strategies, or are just made to make you think differently. 

Because they focus on underlying systems, their insights are transferable, adaptable, and timeless.

They teach you metacognition (how to think), not just what to think. 

Top 3 Principles 

1. A More Beautiful Question & the Book of Beautiful Questions by Warren Berger  

   I liked the book so much I bought the sequel, which is also good. The core idea is that in a fast-changing world, answers become obsolete quickly, but asking the right questions is a superpower. It's all about navigating the journey from "Why?" (challenging the status quo) to "What if?" (uncovering possibilities) to "How?" (execution). You’ll learn to be a Questionologist.
   

2. Any of His Books - Dave Trott

   Dave Trott is a legendary advertising copywriter who tells allegorical stories in a beautiful style. Each week he writes a blog article and then after a while squeezes some of the best ones into a book. He shares real-world examples of creativity and innovation, constantly challenging his readers to think differently and look at problems laterally.

• Principles: Life and Work by Ray Dalio This is a meaty tome, from the founder of Bridgewater Associates. The first half is a heavy dose of self-mythologising as Dalio charts his own rise. But once you wade through the billionaire ego trip, the second half offers a number of valuable ideas and principles for decision-making.
  

Sick Bucket: The Book I Hate-Kept

The book that personally annoyed me the most is Radical Candor. 

Radical Candor: How to Get What You Want by Saying What You Mean by Kim Scott

Scott was an early hire at both Google and Apple, and is someone who is completely unaware of her privileged survivor bias. The book is a tedious humblebrag that repackages well-established management insights as revolutionary. The central idea, of a 2x2 grid balancing ‘caring personally’ with ‘challenging directly’, is a psychological framework that she pretty much claims as her own idea. The other big problem is that a large proportion of the people who have read the book (or scanned the title) now use this terminology to be weaponised arseholes. 

The End

Sources: See above