I’m going to be straight with you—I never used to be a reader (or a writer). In fact, if my high school teachers saw me writing an article about a few of the top sales books of the hundreds of books I’ve read, they’d be astonished.

Yet, here we are.

After a number of years in the sales space (let’s not put a number on it), I realized that constant learning would be key if I wanted to continue to grow and succeed at my craft. This is when I really took it upon myself to become a reader and to evolve my skill-set.

The harsh reality is that sales organizations face an ever-changing landscape of challenges, but fortunately, many of the best answers have already been unearthed. Here I have put together my list of top sales reads that speak to the challenges modern sales organizations are facing.

Or, you could always skip the reading and tune in to my original podcast episode:

The 20 Best Sales Books

If you’re looking to add valuable sales books to your shelf, this is the only list you need. I’m more of a ‘living out of my suitcase and on the run’ kind of guy, so it pays to mention that 90% of these picks are available as audiobooks.

extreme ownership1. Extreme Ownership by Jocko Willink and Leif Babin

Jocko and Leif are ex-U.S. navy seals who learned valuable lessons in their experience on the most violent battlefield in Iraq. They faced insurmountable odds in securing a city that was deemed “all but lost.” Through true heroism, and true loss, they learned the true value of superior leadership at every level. In this book, they take the life or death lessons learned on the battlefield and apply them to the business world with surprising ease. One of the greatest takeaways is the principle of taking ownership over your actions, as people have an incredible tendency to pass blame when faced with challenging circumstances. Today, they work with some of the largest companies in the world, teaching business leaders the skills they need to lead and to win.

little red book of selling2. The Little Red Book of Selling by Jeffrey Gitomer

This book doesn’t waste any time, so neither will I with this summary. The Little Red Book of Selling is jammed full of key sales principles surrounding pitching and positioning yourself in front of a prospect, and it’s done in as few words as possible. This one’s a must for anyone that’s serious about selling.

secrets of closing the sale3. Secrets of Closing the Sale by Zig Ziglar

Would you believe me if I told you that the first sales training I received was from a case of cassette tapes? The voice on the other side of those tapes was none other than Zig Ziglar, one of the most famous sales trainers of all time. Through tried and tested methods, Zig shares his secrets of persuasion, and leveraging the power of questions and the imagination to push the sale. Time may have passed on some of the content in this one, but overall, there is still a lot of value to be had here. Great name (great Southern accent too), and great learnings all packed into Secrets of Closing the Sale.

the greatest salesman in the world4. The Greatest Salesman in the World by Og Mandino

This is a true classic, and a must read in the sales space. By Mandino’s suggestion, readers are supposed to take something like 10 months to read this title, but there is still some value there if you don’t want to give a year of your life to the book. Through analogy, Mandino teaches valuable lessons on the core philosophy of salesmanship and success through the story of a poor camel boy who achieves a life of abundance for himself. There are undoubtedly some powerful takeaways here, I strongly recommend giving this one a read.

how to master the art of selling5. How to Master the Art of Selling by Tom Hopkins

Still a standard for new sales hires in numerous organizations that I know of, How to Master the Art of Selling has been constantly updated and revised, making it as relevant today as it was the day it was published. This book dives into the reasons that sales can be such a great profession, and how you can leverage the most effective sales skills out there, a splash of creativity, and a strong belief in constant improvement to drive success and profitability.

perfect selling6. Perfect Selling by Linda Richardson

Although the cover may look like any other propaganda-packed sales book, this one is truly a gem. A major portion of this sales book is an emphasis on tactics to help you craft and deliver better presentations. You will also learn strategies to help you connect with customers, better explore customer needs, leverage your solutions more persuasively, resolve more customer questions and concerns, and act on the deal when the time is right. This is an end-to-end sales manual that you need to have on your shelf.

The 4 Four Disciplines of Execution7. The 4 Four Disciplines of Execution by Chris McChesney, Sean Covey, and Jim Huling

We’ve all experienced it… maybe we didn’t have a name for it, but we all know the toll it can take when all of the urgent and injected tasks begin eroding away on our days until we have little or no time left for strategizing and planning for tomorrow… it’s called the whirlwind. Fortunately, this book clarifies a proven strategy for combating the whirlwind, based on four simple disciplines. The disciplines are as follows: clarify your wildly important goal, determine the things that you're going to measure, get a scorecard on how you're going to measure it, and then make sure that you're holding people accountable. I can personally attest to the effectiveness of this strategy as I have installed this framework in my own life, as well as the Vendasta organization.

the psychology of selling8. The Psychology of Selling by Brian Tracy

The top 20% of salespeople make 80% of the money, and the bottom 80% make the remaining 20%, and this phenomenon can be explained through expectations. In sales, your expectations will limit your performance. The “fear of rejection” and “fear of failure” are some of the greatest blockers in making sales, and can be addressed by taking a glance into our own states of self-esteem. Tracy discusses strategies for removing our limitations, key areas to focus our efforts, as well as four key elements of strategic selling: “specialization, differentiation, segmentation, and concentration”.

mastering the complex sale9. Mastering the Complex Sale by Jeff Thull

Are you in the enterprise sales stream? The reality is that it is a very different sale when you’re working with a large, intricate enterprise prospect. You’re going to have multiple different decision makers with different agendas, you’re going to have to deliver a more compelling value proposition than ever before, you’re going to have to remove any remnants of the price driven sale, and you’re definitely going to have to provide professional customer guidance. This mandatory sales book will help you evolve as a salesperson, and help guide the long-term growth of your organization through proven tactics.

selling to big companies10. Selling to Big Companies by Jill Konrath

You don’t need the biggest boat to catch the biggest fish. But let’s face it, corporate decision makers aren’t answering your calls, and they definitely aren’t returning them. So, what can you do? With some similarities that can be drawn between this title and Jeff Thull’s work, Konrath also seeks to help salespeople solve the enterprise sales mystery. She delivers strategies surrounding account based sales and marketing action, tactics to position yourself as an invaluable resource ( not just another product-pusher), and everything else you need to differentiate yourself in a crowded market.

the art of war11. The Art of War by Sun Tzu

What innovation hasn’t come from a military background? I guess we may as well go ahead and add business to that bucket. Dating back 2,500 years, this book has revolutionized military warfare and thought across the globe. Further applications have been drawn for teachings in politics, sports, business, and everyday life. This book is much less about the logistics of warfare, and much more about winning in the game of wits, and how great leaders can leverage principles of motivation to steer their armies towards success. This is a must read for anyone in not only sales, but just business in general.

cracking the sales management code12. Cracking the Sales Management Code by Jason Jordan and Michelle Vazzana

So you were a cold-blooded killer on the sales floor, and now you’ve found yourself with a promotion and a new set of responsibilities; you’re a sales manager. This sales management book is grounded in the thought that sales has artistic attributes, but sales management is much more scientific. It may be true that not all things in the sales industry can be managed, but it is VERY important to separate those things beyond your control from those that will provide clear direction for your team. Cracking the Sales Management Code is designed to help sales managers establish key success metrics so that they can always keep one eye on success.

Selling is Everyone’s Business13. Selling is Everyone’s Business by Steve Johnson and Adam Shaivitz

Sales permeates every facet of an organization. Whether you’re a front-line sales rep or you’re trying to win over a boardroom, everyone has something to learn from the sales industry. Authors Johnson and Shaivitz are partners in a sales training company, so the lessons in this book come straight from the battlefield. One of the biggest lessons in this read is the separation between management and coaching. Oh, and get ready to discover the answer to the all-time sales question: how do you create a great salesperson?

pitch anything14. Pitch Anything by Oren Klaff

The message may be almost the same, but the way it’s delivered can change the world. Oren Klaff has used his personal framework for presenting ideas to collect $400M+ in funding for various ventures, so he might know a thing or two. With a sales application, Pitch Anything is a new take on delivering your value proposition, built around a “STRONG” framework:

  • Setting the Frame
  • Telling the Story
  • Revealing the Intrigue
  • Offering the Prize
  • Nailing the Hookpoint
  • Getting a Decision

Coaching Salespeople into Sales Champions15. Coaching Salespeople into Sales Champions by Keith Rosen

Another one for the sales managers out there. Using Rosen’s L.E.A.D.S. Coaching Framework, you can boost your teams performance, and you can do it fast. It’s all about building a coaching culture and instilling championship attitudes in your team. Unlock learnings that will help your team become more autonomous problem solvers, lessons on the power of observation for delivering more influential feedback, and how to achieve an organizational rhythm that will become synonymous with long-term ROI.

New Sales. Simplified.16. New Sales. Simplified. by Mike Weinberg

I’m famous for saying that I believe sales is going to change more in the next five years that it has in the past 50, and that’s what this top sales book is all about. You will find the answers on how to better leverage cross-platform touch-points through email, call, voicemail, social media, as well as steps to beat the infamous anti-salesperson reflex. New Sales. Simplified. takes a fun approach to highlighting some of the critical mistakes that most salespeople and managers make, along with a step-by-step process for driving more business than ever before.

Smart Calling17. Smart Calling by Art Sobczak

This one is all about how you use the phone. As it becomes easier and easier to do business across international borders, across oceans, and across the world, the phone is as important as it has ever been. The reality is that most salespeople hate cold calling and most sales people make some terrible mistakes when they are cold calling. I personally love cold calling, but this isn’t about me. This book outlines a technique that has been proven to minimize the impacts of fear and rejection for the salesperson. If you’re ready to start getting a lot more yeses on your calls and become a master prospector, then this one is a must-read.

The Seven Levels of Communication18. The Seven Levels of Communication by Michael J. Maher

There’s a dramatic difference between just speaking and speaking so that your audience understands you; and that’s communication. This book taps into the story of Rick Masters, a real estate agent who’s down on his luck until a mortgage professional who built a successful business without advertising or promotion takes him under her wing. Through the course of the book, he discovers the power of communication and the meanings of success and significance. Take the lessons of this personal sales book and learn how to build stronger relationships that can generate real referrals for you and your business.

How to Win Friends and Influence People19. How to Win Friends and Influence People by Dale Carnegie

I really couldn’t do a top sales reads list without at least one title from Dale Carnegie. After over 60 years in print, the lessons in this book are just as relevant today as they were the day it was written. Grounded in core principles of behavioural psychology, Carnegie’s classic has helped numerous people find success in business and in life. The book is broken into four major sections that are designed to help people of all walks of life to maximize their potential. The four sections are as follows:

  • 3 fundamental techniques for handling people
  • 6 ways to make people like you
  • 12 ways to win people over to your way of thinking
  • 9 ways to change people without arousing resentment

To Sell is Human20. To Sell is Human by Daniel H. Pink

Quickly becoming a modern classic, this sales book by Dan Pink is as much for the parent trying to convince their children to eat their brussel sprouts as it is for the modern salesperson. Pink explains how sales has evolved into everything that we do, and that sales isn’t a craft, but rather, the art and science of moving others. This is a must-read and is sure to change your perspective on selling, and what it truly takes to make a great salesperson.

Conclusion

What more is there to say? Pretty sure most of my high school teachers would be impressed that I was able to put together this many words in the first place, so why don’t we leave it right there.

Check out my show, the Conquer Local podcast, if you want to capture more great learnings and maybe even fend off greying a little longer than I did!