Top Sales Reads to Drive Focus, Empathy, and Tactical Execution
As a sales leader, my list of favorite books may seem a bit unusual to most. Many sales professionals gravitate toward books on pitching, negotiation, and objection handling. As a cerebral seller, my favorite titles are ones that harmonize the science of sales with the concepts of focus, fulfillment, and execution. A healthy toolbox of tactics is definitely important (as you’ll see below). However, in sales as in life, understanding the personal and professional forces that affect parties on both sides of the transaction is critical to becoming a balanced and empathetic seller.
To Sell Is Human: Guess what?!? We’re ALL in sales now and no one understands that better than renowned author Dan Pink. Dan Pink is a master when it comes to describing not only how the sales profession has evolved over the past decades (and why), but also the ubiquity of “selling situations” we find ourselves in every day. From his famous “new ABC’s of selling” to tips for supercharging our product pitches to how the signs we read influence our behavior, To Sell Is Human is arguably the best book I’ve read in terms of distilling the sales profession down to a series of interactions, concepts, behaviors every single person can relate to. As Pink states about modern selling, “When simple, transactional tasks can be automated, and when information parity displaces information asymmetry, moving people depends on more sophisticated skills and requires as much intellect and creativity as designing a house, reading a CT scan, or, say, writing a book”. Indeed, selling has become a thinking persons game!
Thinking Fast and Slow: prepare to have your mind blown! While we all believe human beings (and buyers especially) are primarily logical and rational in our thinking, that couldn’t be further from the truth. In this bestselling book, Daniel Kahneman, Nobel Prize winner in Economics, outlines the two primary pathways by which we make decisions. The first system is characterized by automatic and instinctive judgments. Results like performing a 2+2 calculation or orienting yourself to the source of a sudden sound. The second system is slow and deliberate. This system is responsible for decisions made using logic and reason. For example, filling out a tax form or picking one child out of a group at a playground. While counterintuitive to most, it is in fact System 1 that rules the day! Our brains like taking shortcuts to preserve our mental energy and keep us safe. Understanding how these pathways work is critical to aligning your entire sales motion to how people make buying decisions. Once you do, you’ll be racking up those wins faster all while creating deeper levels of satisfaction for your customers!
Yes! 50 scientifically proven ways to be persuasive: the one that started it all for me! In this book Robert Cialdini (famous for the book Influence) and his co-authors present 50 short chapters outing social experiments that prove out different techniques for building trust, affinity, and inspiring action. Be warned though, this isn’t a book of Jedi Mind Tricks designed to get people to do things they don’t want to do. The examples presented are all based on the experiences we encounter in our everyday lives but rarely assign cause to. For example, the little notes in hotel room bathrooms designed to get you to hang up and reuse your towel or the tactics restaurant waiters use to increase their tips. The book is both educational, tactical, and a quick read. Highly recommend for anyone in sales.
Never Split the Difference – Negotiating as if Your Life Depended on it: many sales books regale you with stories of hard-fought deal victories and complex selling situations. Few do it by relating the experience to high-stakes international hostage negotiations, kidnappings, or bank robberies! But don’t let the gravity of the examples fool you. Author and former lead FBI hostage negotiator, Chris Voss, does an incredible job of taking insights learned from the study of human behavior, cognitive psychology, and neuro-linguistics and applying them to the types of negotiation situations most of us find ourselves in every day. From asking for a raise, getting and seat on a sold-out flight, and running customer discovery calls, Chris tackles it all. Not to mention, the stories he shares and the situations he’s found himself in over the years are pretty incredible!
Getting More – How You Can Negotiate to Succeed in Work and Life: Stuart Diamond presents a transformative approach to negotiation that emphasizes empathy and strategic thinking over traditional tactics. Diamond, a seasoned negotiator and professor at the Wharton School, argues that success in negotiations hinges less on aggressive bargaining and more on understanding the other party’s perspective, building rapport, and leveraging psychological insights. By offering practical advice and real-world examples, Diamond illustrates how negotiators can achieve better outcomes by focusing on what others value, adapting their strategies to varying contexts, and fostering genuine connections. The book challenges conventional negotiation norms and provides a refreshing, human-centered framework that can be applied to both professional and personal interactions.
The Sales acceleration formula: you’d be hard-pressed to find a sales leader in the SaaS startup space who hasn’t heard of Mark Roberge. Mark was the founding VP of Sales of Boston-based marketing automation provider Hubspot and helped take that organization from a tiny company to a global player. I was fortunate enough to connect with Mark in the early days of my third startup and hear firsthand some of the incredible insights he uncovered as he built his sales operation. Hubspot was a company stacked with super-smart M.I.T. alumni, and I loved both the cerebral and analytic approach they took to building their business. From start to finish, this book is full of high-value content.
As a lifelong learning and student of Sales, my reading list backlog continues to grow by the day with an extensive pile still waiting to be worked through. While I suspect round two of my favorite book list will be forthcoming, I’d love to hear from you!
Essentialism: Selling is all about focus and choice. The products and services we choose to sell, the customers we choose to sell them to, the approach we take to selling them, and the career choices we make along the way. Unfortunately, too often in work and life, people get caught up in what they feel they should want versus what they actually want. I saw this consistently during my time at Salesforce. Young, talented Sales professionals, wanting to get promoted into the segment above them because that’s what they felt most people around them wanted (even though they yearned for a different path). The other challenge is trying to do too many things instead of a few key things that matter. Less but better is the Essentialism mantra! Cut through the noise in both selling and career, identify what you really want, and how to get it. It also helps you figure out how to say no to things that won’t get you there. As evidence, the UK-born author presents his compelling personal story of dropping out of law school (i.e. what he thought he wanted) to move to America and follow his true passion.
Leaders Eat Last: No one harmonizes science and anthropology like my man Simon Sinek! If you’re interested in becoming the type of leader that leaves a lasting legacy and that people would fight to work with again, read this book. Sinek talks about different styles of leadership, presenting both qualitative and quantitative arguments for how to lead teams to greatness. He also goes deep into both the historical and physiological principles behind leadership and execution. Perhaps more than any other book, this one will help you identify the leadership trends and patterns that separate good organizations from great ones. The ones that, despite conventional wisdom, are able to execute consistently, punch far above their weight, and achieve extraordinary results!
The One Thing: This is the book I’m most famous for pushing on others. In fact, if you‘ve ever attended one of my executive dinners, you’ve likely left with a copy of this book as a parting gift. It’s no surprise that back at Salesforce, one of my awesome teams who supported the Boston region made me the custom T-shirt shown below!
In The One Thing, author Gary Keller does an outstanding job of illuminating the darkest corners of deceptively complex topics like prioritization, focus, habit, and willpower; all critical elements to peak sales performance. While the sentiments here are well-founded, the scientist in me particularly loved all the data and behavioral evidence Keller uses to support his arguments. You can’t go a chapter in this book without extracting some high-value insight about how you execute in your work or life and the recipe for achieving extraordinary results. But beware…actioning the insights from The One Thing are like going to the gym; easy to understand, hard to do. This stuff takes practice! Do yourself a favor and start now by reading this book.
And of course, if you’re looking for two books that bring together some of the best insights and perspectives from all of the above, check out my bestselling titles:
Sell the Way You Buy: A Modern Approach to Sales that Actually Works (Even on You!)
The Sales Leader They Need: Five Critical Skills to Unlock Your Team’s Potential
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Thanks for sharing David! I just ordered them all on Amazon. My favourite book this year is They Ask You Answer by Marcus Sheridan…the story of a fiber glass pool distributor in Warsaw, Virginia (population 1,500) that went from almost being bankrupt to the largest fiber glass pool MANUFACTURER from their content marketing efforts.
Thanks for sharing Jeff! Great to hear examples of a powerful content marketing strategy!
Dave, glad to on your newsletter and alwaye s love to hear what more insights you have – full of golden nuggets of wisdom. You gave me The One Thing a while back and it really changed the way I think about how I attack the day/week/year/life. I’ll take a look at the others as well!
Always a pleasure to help Mr. Cho and great to hear from you! All the best!
I’ve read never split the difference. Using those tactics, I was able to double my rate with an existing client, I also taught it to my wife, who was able to negotiate a 30% raise and literally got everything she asked for in a new contract. , and the best part was that both parties believed the deals were fair! I would 100% recommend.
Also, I usually suggest Predictable Revenue by Aaron Ross as a starting point for anyone wanting to understand Sales structures, especially SaaS-based businesses.