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5 Books That Will Change the Way You Lead Forever

A great leadership book is a small miracle. By the end of it, you not only see the world differently, but you also see yourself differently. And as a result, you're better able to create meaningful change both at work, and in your life.

Here are the five leadership books that have influenced me the most, both as a coach and as a person who runs her own business. Without them, I can honestly say I’d not only be a different person, but also not nearly so good at what I do.

I hope you’ll give them a look.

Written in 1990, just one year after the world wide web was invented, and several years before anyone really knew what it was or what it could do, Senge was seemingly able to predict the world of complexity, uncertainty and ambiguity we all cope with in the twenty-first century. How was he able to do this? I assure you, he’s not psychic. Rather, he’s a system thinker. In fact, he was and remains to this day, one of the world’s leading voices on system leadership theory (thus making him a hero of mine).

How it will change you.

Senge does away with “…the illusion that the world is created of separate, unrelated forces”, but is instead the product of interconnections and interdependencies of people, processes and interactions. If you’re a regular reader of this blog, and this sounds familiar, it’s because I write about it a lot.

Once you accept this notion, your perception of the world will change. You’ll see how underlying structures (or systems) generate patterns of behavior that create the results you see in your life and business. You’ll seek to understand yourself and your coworkers. You’ll commit to getting really good at your job, and the practice of leadership. You’ll understand the value of co-creation and team learning. And because of this, you’ll be better prepared for whatever the future throws at you.

Best Quote: “Structures of which we are unaware hold us prisoner.”

First published in 1999, I think this is the most underrated self-help book of all time. What makes it so powerful is that Hudson takes the mystery out of the good-old midlife crisis. Rather than painting it as something silly or embarrassing (as let’s face it, many of us believe it to be), he shows us that questioning the meaning of our existence is both normal and necessary throughout the years between 35 and 65.

How it will change you.

About 90% of the clients I work with are experiencing some kind of midlife crisis (whether they actually name is as such or not). Midlife ennui is one of the leading causes of feeling stuck, and if not addressed in a thoughtful way, it can lead to all kinds of self-destructive behaviors.

After reading this book, you’ll understand that midlife is a time for contemplation, preparation and reinvention. If done correctly, the midlife crisis is a powerful thing. Rather than feeling you’ve somehow led yourself astray, you’ll understand that it’s your responsibility to reconsider and re-evaluate your life from time to time. You’ll know that feeling unsettled and dissatisfied is simply part of your exploration. In rising to the challenge of reinvention, you’ll be released your cynicism, powerlessness, isolation and hopelessness, and step into the life you want.

Best Quote: “Creative adult life requires the birth of many new dreams, the possibilities of many new adventures, and the excitement of risk taking.”

If you like this book, also try: How to love your midlife crisis, a blog post by me.

Most of us think that coaching means telling. After all, we’ve all watched or been subject to a basketball coach or a soccer coach or a figure skating coach telling, telling, telling. This is what I want. This is what you need to do. This is what I think about you. That’s all well and good in the sports world, but when we take these practices to work, well, things stop working as well as they might.

At the core of Stanier’s work, is a well-timed, simply stated question.

How it will change you.

Well, for starters, you’ll start asking questions; good ones, and at the right time and place. Rather than telling employees what’s up, you’ll ask, “What’s on your mind?” You’ll ask them to focus on their real issues. You’ll ask them what else they might be able to do or say when facing a particular issue or situation. You'll ask them what they really want. This is real coaching because you’re training your team to think strategically, systematically and, for themselves.

Most importantly, you’ll learn to tame what Stanier calls “The Advice Monster”.

Best Quote: “…the Advice Monster leaps out of the darkness and hijacks the conversation. … In short, even though we don’t really know what the issue is, or what’s going on for the person, we’re quite sure we’ve got the answer she needs”.

If you like this book, also try: The Advice Trap, Stanier’s new book which will be released on February 29th (leap day!).

by Alexander Osterwalder and Yves Pigneur

In the aforementioned world of complexity, uncertainty and ambiguity we all now live in, business models are emerging and evolving more rapidly than ever before. And frankly, it’s all a bit confusing and at times, even overwhelming. Osterwalder and Pigneur offer a practical guide, using illustrations, worksheets and real-life examples to help you develop a business model for any kind of organization. And, the whole thing fits on a single page, a worksheet they call a “Canvas”.

How it will change you.

You’ll start to think systematically about your business model. What are the inputs? What are the outputs? How is value created? And what are the resources, processes and interactions required to deliver it?

And, then you’ll learn to think as a designer. You’ll ideate, experiment and iterate. And eventually, you won’t feel so confused and overwhelmed.

Best Quote: “…the scale and speed at which innovative business models are transforming industry landscapes today is unprecedented… it’s high time to understand the impact of this extraordinary evolution.” (Okay, this quote is fairly pedestrian, but the truth is, this isn't a particularly quotable book. What it lacks in flowery words, it more than makes up for with actionable ideas.)

If you like this book, also try: Value Proposition Design, Testing Business Ideas and Business Model You, by the same authors.

Book 5: A Beautiful Constraint, by Adam Morgan and Mark Barden

When I was a start up CEO, I used to tell my design and dev teams that “creativity loves constraint”. It was a phrase I picked up somewhere, and though my colleagues hated it when I said it, it always turned out to be true.

Morgan and Barden begin with the premise that constraints are beautiful because they force us to be more creative. And that creativity just might be what gives us our competitive edge.

How it will change you.

Three simple words: We can, if…

You have a vision. But, there are many obstacles to achieving that vision. After reading this book, you will knock down those obstacles one by one using the phrase, “We can, if…”

I use this methodology with most of my clients. It works with both business and personal issues, and it is very, very powerful. Life changing in fact. My favorite days are “We can, if…” days.

Why? Because it focuses you on the right question, it evokes a sense of responsibility, and it is inherently optimistic by being about answers and not problems.

Best Quote: “By making a constraint beautiful, we mean seeing it as an opportunity, not a punitive restriction, and using it as a stimulus to see a new or better way of achieving our ambition.”

If you like this book, also try: The War of Art by Stephen Pressfield and Big Magic by Elizabeth Gilbert.

Bonus Book: The Unstuck Leader

by Me

So yes, I too have written a book. And seeing how influenced I’ve been by this particular group of authors, if you like the ideas above, you’ll probably like my book too. (Yes, yes, I know I'm being exceedingly cheeky by including it in such illustrious company, but it's my blog so here it is.)

How it will change you:

You’ll become more self-aware and resilient, allowing you to live in a world of complexity, uncertainty and ambiguity and still have the capacity to make quality decisions. You’ll learn to identify the underlying systems and structures that are adversely affecting the business as a whole. And you’ll learn to commit to leadership as a practice and to build a network of likeminded leaders.

In short, you’ll learn not only how to do the things that great leaders do, but also how to become the kind of person who does the things that great leaders do.

Best Quote (if I do say so myself): “Unstuck Leaders leave room for surprise, serendipity, uncertainty, fear and discover. Because the truth is, our imaginations are far too limited to dream of everything that’s possible for us.”

If you like this book, also try: Subscribing to my email newsletter (green box at top right of your screen on desktop, or under this post on mobile). I promise I'm not a spammy nightmare. One per week, and that's it.

The Unstuck Leader book is now available.
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