Five must-read leadership books in 2023 that have stood the test of time

I'm a self-confessed, recovering nerd.

Much of what I learnt about leadership came from hard-earned, personal experience. But none of it would've stuck if not for amazing mentors. Many have patiently guided me through my many mistakes.

Other 'mentors' appear to me on pages of well-thumbed books.

Books that I come back to year after year, as I calibrate my own leadership journey and contextualize the lessons that I've had the opportunity to learn.

For 2023, I've compiled a list of these books that have stood the test of time for me.

Authors that have seen me through running my first-ever team retreat, all the way to co-founding and running a global SaaS company today.

(Scroll to the end if you want a tl;dr)

What about the latest and greatest books?

There are plenty of amazing books on leadership that have been written recently.

But I wanted to put together a list of the true diamonds, that have been a source of inspiration and learning for me over and over again.

Each time I dip into these books, I draw fresh insight. Insight that contributes directly to the issues at hand for me. Whenever I think of gifting a book to a new or experienced leader, I gravitate toward those on this list.

For the first time in one place, here are the five leadership books that have stood the test of time for me.

1. High Output Management - Andrew Grove

Andrew Grove was born in Hungary, and survived the Nazi occupation there before migrating to the United States at the age of 20. He joined technology giant Intel on the day of its incorporation as employee number 3, and eventually went on to be the company’s third CEO.

Mr Grove orchestrated the transformation of Intel from a manufacturer of memory chips into the world's dominant producer of microprocessors for PC, servers, and general-purpose computing. In doing so, he grew Intel from $4B to $197B, making it the world’s 7th largest company at that time with 64,000 employees.

This is easily the oldest book on the list - it was written in 1983, almost 40 years ago. But even when you read it today, it feels like it could have been published last week. Here are just a sample of concepts that stand out for me:

• Objectives and Key Results (OKRs). He introduces the concept of OKRs, a system of focusing effort on the same important issues throughout an organization. It’s no secret that Google, the Gates Foundation, and a diverse range of other high-performing organizations have adopted this management system to great success.

• Task-relevant maturity. “Micro-managing” has become a bad word. Leadership courses and training programs routinely advise against managing how something is achieved, and focus instead on what is to be achieved. However, Mr Grove argues for a more nuanced approach. Tighter control when a person has low task-relevant maturity (ie is new to the job), and looser control when they have high task-relevant maturity.

• Managerial leverage. Managers contribute to organizations through “leveraging” their time - spending small amounts to have large impact through three main activities: 1) information gathering, 2) decision making, 3) “nudging” others. Do it right, and you get positive high leverage actions: delegation with supervision, training and influencing processes with unique skills or knowledge. Do it wrong and you get negative high leverage actions: delaying decisions, meddling, abdication, and unnecessary interruption.

Other artefacts of modern management: performance reviews, being deliberate about meetings, matrixed reporting lines, and others, are all laid out in this book and remain extremely relevant today.

2. Five Dysfunctions of a Team: A Leadership Fable - Patrick Lencioni

The genius for me about this book was the use of fable.

In ancient storytelling tradition, abstract concepts and dilemmas are brought to life through flowing narrative. It is easy to read: where it could otherwise have been pedantic and laborious, the prose instead moves at a fast pace while issues and how they are resolved feel eerily familiar.

Like other books on this list, even though this was published in 2002 - a whole 20 years ago - the adventures of fictitious Kathryn Petersen and her company Decision Tech sound like they could easily be the boardroom of many companies today.

Today, the five dysfunctions are well-known:

These dysfunctions are deliberately organized in a hierarchy - solving the bottom layers unlock your ability to solve the upper layers.

The tricky part is navigating through the pyramid.

For example, how do you know you’ve established enough trust to start addressing the need to have healthy conflict in a team?

Once you’ve facilitated healthy conflict, what can you do to create the conditions for team members to disagree and commit?

The fact that there are no easy answers to these questions speaks more to the fine art of leadership and the uniqueness of each team than to the ineffectiveness of the framework.

Where the fable format really shines is that just by reading the plot and empathizing with the characters, I found myself automatically diagnosing situations on teams I’ve been on, and finding inspiration for new ways of handling challenges that arose.

For being a book that sets your creativity free to tackle thorny issues in your team every time you read it, it deserves a spot on this short list.

3. First, Break All the Rules - Marcus Buckingham and Curt Coffman

The idea that you can take something as intangible as management practices and employee engagement, and find a robust, statistical relationship with tangible business outcomes like productivity, profitability, and customer satisfaction was unheard of.

Until this book.

Published in 1998, the authors looked at interviews with more than 80,000 managers and 1,000,000 employees to try and tease out the secrets behind high performance at work.

Some of the key insights have now become canonized in good management doctrine, such as:

• People join companies, but leave managers. Messrs Buckingham and Coffman found that the impact of direct managers mattered the most in employee engagement and productivity, rather than company policies, perks, and benefits. In fact, almost 70% of the difference between why someone is engaged or disengaged can be explained by their manager.

• Manage to people’s strengths, not their weaknesses. It’s tempting to focus performance and development conversations around what someone needs to improve upon, or where they fell short. It’s more important to understand what that person is great at, and why. Figuring out how to help them be best in the world at something unleashes exponentially higher performance, and automatically creates high levels of engagement. Figuring out how to ensure their blind spots don’t damage performance is the second order of business.

• Define outcomes, and remove blockers to achieve them. Once you’ve identified a person’s unique talent, and have equipped them with the necessary training and coaching to achieve initial success, it’s time to get out of the way. Dogmatically following Standard Operating Procedure is more likely to ensure average performance rather than making high performance possible.

4. Thinking Fast and Slow - Daniel Kahneman

What’s a psychology book doing in a list of leadership books?

Personally, I’ve found that the most important thing about getting leadership right is getting the psychology of those you’re leading right.

Everything from setting processes, to motivating performance, to figuring out learning styles, depends on understanding how your people think and respond to situations placed in front of them.

Even though this is the most recent book in this list (published in 2011), it is a helpful summary of decades of research from one of the most respected psychologists in the world.

Yes, I said “summary”.

Yes, the book is 499 pages.

Yes, Prof Kahneman did win the Nobel prize.

The delineation into System 1 - fast, intuitive - and System 2 - logical, deliberate - thinking isn’t really new or groundbreaking.

But the impact that these have on predictable biases in our thinking, and how we end up making poor decisions, is uniquely Kahneman.

A very small snapshot of my favorite concepts from the book:

• Cognitive ease is how easy it is for System 1 thinking to override System 2. That is our default state in the workplace. Putting healthy fruit snacks openly in the office pantry for example, rather than a bowl full of M&Ms, takes advantage of cognitive ease to nudge healthier snacking behavior.

• The Availability heuristic causes us to feel better about our answers if we can recall them more easily. For example, this is the tendency of sales managers to overstate price as a deciding factor in their deals if they lost the last 3 accounts to cheaper competitors, even if the vast majority of deals were lost because of a missing critical product feature.

• Prospect theory and how we are much more distressed at losing $100 than gaining the same $100 causes us as individuals to be risk averse by default. When this rolls up to the organization, especially large organizations, it is far easier and psychologically more rewarding to protect the status quo, rather than take risks to capture new gains.

As leaders, I’ve not found it possible to stay aware of all of these psychological hacks and how to counter them at all times. But this book helps a baseline level of fluency in them, so that we can make better decisions more consistently over time.

5. Drive: The surprising truth about what motivates us - Daniel Pink

Often we can see the potential in our team members, but have trouble figuring out how to access it.

Sadie may be highly resourceful when it comes to figuring out the best itineraries for team building activities, and executes them well. But somehow her projects keep missing deadlines and going over budget.

Justin is an excellent communicator and conveys ideas succinctly and persuasively to internal stakeholders. But put him in front of a client and suddenly he’s tongue tied.

Ivy shows flashes of brilliance, going on whirlwind coding sprees where she takes 2 weeks to build features that took others on the team months. But in between these flashes are idle periods where she drops the ball on simple maintenance tasks.

Why?

Mr Pink gets into the science of human motivation in this book, as relevant today as when it was published in 2009.

The “carrot and stick” model of encouraging performance, so often employed in the workplace, is fundamentally flawed.

Human motivation is primarily intrinsic, from within. Extrinsic motivators - money, promotion - only work for simple, repetitive tasks.

He boils intrinsic motivators down to three basic elements:

• Autonomy - the ability to direct our own lives

• Mastery - the desire to get better at something that matters to us

• Purpose - the yearning to do something in service of something larger than ourselves

These are the basic building blocks of leadership. The framework Mr Pink introduces here is practical and simple enough for us to check in with it regularly, to see how well we’re connecting our team to each of these 3 elements of motivation.

Key takeaways summary

For a quick tl;dr, here are highlights from each of these books:

• Think of management like a mathematical function. To get better, break it down to the component parts and work on each one.

• Work to build trust first and foremost to build effective teams. Direct that trust productively to create constructive conflict, collective commitment, and individual accountability to drive results.

• A critical task of a manager is to uncover the unique strengths of each person on our team, and find ways to polish them. Let go of dogmatic process once results start to come.

• Be aware of the biases and shortcuts that our brains are most likely to fall into, and regularly find ways to build mechanisms around ourselves to ensure these don’t degrade the quality of our decision-making.

• For optimal performance, focus on creating an environment where our team is intrinsically motivated. Continually check back to ensure we are allowing them Autonomy, Mastery and Purpose.

What are the books on your must-read list?