12 Books To Kickstart Your Leadership Skills

Looking for books to read this fall? Here are some highlights from my 2016 reading. Please take a look and enjoy! You’ll find insight on networking, how to learn valuable super skills, become more productive and find biographies of highly successful leaders.

How Do You Read So Many Books?

Reading books is a priority for me so I make time for it on a daily basis. My minimum is 30 minutes of book reading per day. My connection with books goes way back. In fact, I had a part time job in a public library as a teenager. If learning, growth (and yes, entertainment) interest you, then find a way to make time for books.

1. The Education of Millionaires: Everything You Won’t Learn in College About How to Be Successful by Michael Ellsberg


After listening to this book twice on Audible, I bought to read in Kindle format. It’s an excellent book. The book presents two arguments. First, that higher education in the U.S. (and to some degree elsewhere) is dysfunctional and overpriced and no longer the only path to living the good life. The second argument, forming the majority of the book, is an explanation of key business success skills: sales, marketing, networking and more.

Rating: 5/5



2. The Last Safe Investment: Spending Now to Increase Your True Wealth Forever by Bryan Franklin and Michael Ellsberg

The Last Safe Investment

This ambitious book seeks to take on the financial industry and describe a better way. In some ways, the book is structurally similar to “The Education of Millionaires.” The authors start by describing a large scale system they describe as broken (i.e. the financial services industry) and then propose solutions. There are interesting concepts here such as the Happiness Exchange Rate and Super Skills. In some cases, I found that there was no quite enough examples and evidence to back up the book’s points. There is still much to be gained from reading this book.

Rating: 4/5

3. The Productivity Project: Accomplishing More by Managing Your Time, Attention, and Energy by Chris Bailey

The Productivity Project

What strategies and techniques actually work in productivity? That’s the premise of Bailey’s book. It’s an excellent book that covers both tactical points and big picture issues (e.g. taking care of your mind and body make a big impact). The author’s website is also an excellent resource of articles that combine serious and playful explorations of productivity (e.g.¬†5 huge lessons I learned binge-watching Netflix for a month and 10 huge productivity lessons I learned working 90-hour weeks last month).

Rating: 5/5

Tip: Curious to learn more about this book? Read my book review of The Productivity Project.


4. Networking with the Affluent Paperback by Thomas Stanley

Networking With The Affluent

Networking is one of the most powerful skills to develop, yet many people struggle with it. Ever heard the tip to “give value to your network” and wondered what exactly that means? In this book, Stanley gives you plenty of practical examples. For example, write to elected officials to support causes that people in your network care about (assuming you have a similar position). Even better, refer customers to people in your network.

Note: the book is aimed at sales professionals and professional services providers (e.g. imagine you are an accountant looking to building your practice with affluent clients). With a bit of creative thought and reflection, you can apply much of the book’s insights to your career even if you are not in sales.

Tip: Readers ask me how to make the most of conferences. Check out this resource: “How To Get The Most Value From Conferences In 6 Steps

Rating: 4.5 / 5 (The book’s dated examples are sometimes tiresome. Don’t let that stop you from obtaining valuable insights!)

5. Give and Take: Why Helping Others Drives Our Success by Adam M. Grant


Earlier in 2016, I had the opportunity to see Grant speak at the Rotman School of Management in Toronto. Grant’s work shows why being a giver in life and business improves productivity and performance. Grant’s dedication to field research sets this book apart from many books written by professors. The final section of the book covers how to apply the book’s insights.

Rating: 5/5



6. Originals: How Non-Conformists Move the World by Adam Grant

Originals Adam Grant

What does it mean to make an original contribution? Grant shows that novelty and logic is not enough to bring a new idea to life. Sometimes you have to take an indirect approach. As I grow my platform and see more of the world, creativity is a growing concern for me. It was well worth it to read this book. Oh, Facebook COO Sheryl Sandberg wrote the forward.

Bonus: Check out Grant’s TED talk The surprising habits of original thinkers.

Rating: 5/5



7. The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses by Eric Ries

The Lean Startup

What does it take to create a successful product and business with a minimum of wasted time and money? That’s the question that Ries explores in the book. I like that he refers to his own startup experience in developing the book. If you are interested in finding out more about tech startups and their approach to innovation, this is the book for you.

Rating: 4/5 (I found some of the book’s concepts difficult to apply. However, there is a community of fans and consultants who can help you apply the book’s concepts!)



8. Eleanor Roosevelt Vol 1 & 2 by Blanche Wiesen Cook

Eleanor Roosevelt Vol 1

I picked up theses books after I saw that Ryan Holiday recommended them. Wow! What an interesting life – full of change, activity and overcoming disappointments. Did you know that some insiders encouraged ER to run for President in 1940? ER did not hold public office yet she wielded tremendous influence through her network, publishing and activism. These books took weeks to read – it was well worth the effort.

My favourite Roosevelt biography remains The Rise of Theodore Roosevelt by Edmund Morris. His boundless energy, work ethic and accomplishments remind me to keep working away at my goals.

Note: Volume 3 in the series, covering 1939-1962, is expected for release later in 2016. I may well read on my end of year vacation.

Rating: 5/5

9. The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter by Michael D. Watkins

The First 90 Days

Executives and managers starting a new job face special challenges to get up to speed. In this book, you will learn how to make the most of your early days in a new role. Watkins emphasizes the importance of listening and learning before you start to make changes. You can read this book in a weekend: short, to the point and helpful.

Rating: 5/5 (Project Managers: think about applying this book’s concepts when you start a new project especially if you are working with a new team).



10. Born for This: How to Find the Work You Were Meant to Do by Chris Guillebeau

Born For This Book Cover

I have followed Guillebeau’s work for years with great interest. In some ways, he is an inspiration for the work I do on this website (see: 279 Days to Overnight Success which inspires me to continue my work). In this book,¬†Guillebeau explores how to find a career that suits you. To get you started, there are some helpful resources on the Born For This book website such as how to start a side hustle.

Rating: 4/5 (I think his earlier book “The $100 Startup” was stronger. If you’re looking for tips on how to make it big in the Fortune 500, this is not the book for you.)

Tip: Curious about Guillebeau’s annual conference, “The World Domination Summit”? Read my article Field Report from the World Domination Summit.

11. Becoming The Boss : New Rules for the Next Generation of Leaders by Lindsey Pollak

Becoming The Boss Book Cover

You’ve been promoted! Now what? That’s some of what you’ll learn in Pollak’s book. I like that she targeted her approach to the Millennial generation though much of the book will apply to others. Most career management books for this generation focus on the first job, so it is great to see this broader perspective.

Rating: 4/5




12. The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stanier

The Coaching Habit

The best leaders develop their staff. You can’t accomplish that if you never listen and treat your staff like a pair of hands. In his timely new book, you will learn the fundamental coaching skills. Want the ultra-brief version? “Listen more and ask more questions.”

Rating: 4/5

Hat Tip: Today’s post is inspired by James Clear’s book article: Book Summaries: Popular Books Summarized in 3 Sentences or Less.



Question For The Comments:

What book have you read this year to grow your leadership skills?

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