What are Your Top Five?

In a job interview for a sales or sales leadership position, have you ever asked or been asked, “What are the top five books on selling that you’ve read and would recommend to your team?”? Probably not.? Is five too many?? How about the top three or the top two?? Doubt it.

What about, “Tell me about one book on sales you read? When did you read it? What did you get out of it? Would you recommend it?” Or something along those lines? I have asked those questions several times in the past.

But what’s the point of these questions?? Where am I going with this?? In my article, “Are you a Sales Professional?? Or just a salesperson,” I identified the four principles or qualities that define a sales professional as

1.????? Ongoing Learning and Adaptation

2.????? Application of Knowledge

3.????? Ethical and Professional Judgment

4.????? Complexity and Uncertainty

In my last article, “How to Practice Your Sales Profession,” I said,

“In each case (of the four listed above), you can learn from your own experiences and others’ experiences.

To learn from your own experiences requires you to focus on learning from your own experiences.? This sounds obvious, but very few are focused on it.? How often do you say or hear, “It’s just a numbers game,” to reinforce doing the same thing the same way?? Learning from your own experiences requires you to stop and analyze them – good and bad, successful and unsuccessful, productive and unproductive.? What was different or unique about this situation that led to this outcome?? How can I replicate the good outcomes and avoid the bad ones?? What did I do well?? What didn’t I do well that I could have done better?? What didn’t I do that I should have done?? These are just some of the questions you should ask yourself after each sales call or prospecting or outreach campaign.? Then, you need to take time to prepare for each sales call or outbound campaign to plan for how to apply what you have learned.?

How do you know if your analysis and conclusions are sound?? This is where sharing your experiences with others and learning from others’ experiences is helpful.? Two avenues are available to learn from others – internal or external to your organization.”

Ahh… okay, there it is.? Books on sales are one way one can learn from others’ experiences that are external to one’s organization.? There are other ways besides books, but I’ll save that for another article.?

So why top five instead of top ten or top three?? Well, five is the number of books on sales that positively impacted my selling and coaching that I would recommend.? I have bought a dozen or more additional books throughout my career, usually at an airport bookstore before I fly out of town.? But most of those were never finished because I didn’t think they were any good, and therefore, they got left behind somewhere and forgotten.

My guess is that very few salespeople most of us work with have read five or more books on sales.? Can someone have read zero books on sales and still be a good salesperson, or a top performer, or even a true sales professional?? Sure.? Can someone have read dozens of books on sales and be a terrible salesperson, a bottom performer, and not even close to a sales professional?? Absolutely.

So why ask the questions I stated earlier that I have asked before?? The questions usually come up as part of the broader conversation, and the answers can be insightful as to how a person thinks about their sales role within our specific section and the wider landscape of the sales profession.

As a player and coach, I believe in two things (among many others – but two related to this topic), and I want to see if a potential teammate agrees or thinks the same way. First, there is always room for improvement and stepping up your game.? Second, the game of sales (especially technology sales) is constantly changing and evolving, so much so that your current way of doing things becomes increasingly less effective over time.? As a coach, I want my team and my recruits to not only agree with these two points but to wholeheartedly accept and embrace them with an open mind, eager willingness, and strong desire not only to continue to win but also to win more and win better.

In my quest to continue to win, win more, and win better as a player and a coach, I have read five books that have impacted my skills and helped me evolve and improve my game.? Here, they are in order from oldest to newest.

The first one is an oldie but a goodie and has aged into a classic. It was published in May 1988, and I first read it in the early 2000s. We all know that selling is listening instead of talking or telling, but that wasn’t always known, and it probably came from Neil Rackham's book, “SPIN Selling.” At the time, it was a groundbreaking sales methodology book that introduced a research-based approach to selling complex, high-value products and services. The SPIN acronym stands for four types of questions that salespeople should ask to identify and develop customer needs: Situation (understanding the customer's current situation), Problem (identifying problems or pain points), Implication (exploring the consequences of those problems), and Need-Payoff (highlighting the benefits of solving the problems). Rackham's approach emphasizes the importance of asking the right questions to engage customers, uncover deeper needs, and build value, rather than relying on traditional sales tactics like closing techniques or hard selling.

This next one is the most popular answer to my question when I’ve asked it and probably the most widely read of the five books on my list.? What is your guess?? Yep – it’s “The Challenger Sale” by Matt Dixon and Brent Adamson published in November 2011.? The Challenger Sale is a sales methodology based on the idea that successful salespeople, known as "Challengers," engage with customers by challenging their thinking and teaching them something new about their business or market.? This approach is particularly effective in complex B2B sales environments (IT and tech) where customers are often overwhelmed with information and need guidance to make informed decisions. This method shifts the focus from building relationships to delivering valuable insights and leading the customer through the decision-making process.

The follow-up and sister book, “The Challenger Customer,” by the same authors, plus Pat Spenner and Nick Toman , published in September 2015, is less popular but was equally impactful for me.? This book explores the complexities of selling in B2B environments where multiple stakeholders are involved in purchasing decisions. It focuses on identifying and engaging "Challenger Customers" within organizations—those who are open to new ideas, willing to drive change, and capable of mobilizing support from other stakeholders. The book emphasizes the importance of building consensus among diverse buying groups and provides strategies for sales professionals to effectively influence these complex buyer networks. By targeting and equipping these internal advocates, sales teams can increase their chances of successfully closing deals and driving change within customer organizations.

“Gap Selling” by Keenan . , published in December 2018, was the most fun to read and listen to, given the author’s style.? Gap Selling is a sales methodology that focuses on identifying and closing the "gap" between a customer's current state and their desired future state. The approach emphasizes understanding the customer's existing challenges, problems, or pains and determining what they want to achieve or change. By identifying this gap, salespeople can position their product or service as the solution that bridges the difference, providing clear value and justifying the need for change. Keenan advocates for a consultative, problem-solving approach to sales, where the salesperson's role is to uncover the root causes of the customer's problems and demonstrate how their solution uniquely addresses these issues. The book provides practical strategies and techniques for engaging customers, diagnosing their needs, and driving sales outcomes by focusing on this gap.

Lastly and most recently is “The JOLT Effect” by Matt Dixon and Ted McKenna published September 2022.? Note that it is the same Matthew Dixon who co-authored “The Challenger Sale” and “The Challenger Customer.”? The JOLT Effect is a sales approach to help salespeople navigate situations where customers are hesitant or uncertain about making a purchase decision. The methodology revolves around the idea that the primary competitor in many sales situations is not another company and not the status quo but the customer's own indecision.? This methodology is particularly useful in modern sales environments where customers have access to vast amounts of information and often struggle with overthinking their decisions.

I have already shared some insights from “The JOLT Effect” in “The Obvious and Not-So-Obvious Reasons Prospects Don’t Buy” and “How High-Performance Sales Professionals Overcome Customer Indecision.”? I intend to share more insights from the other books in future articles.? Meanwhile, I have purchased and started listening to “The Innovative Seller” by Jake Dunlap, which my good friend and a quintessential sales professional, Mike Gleason , recommended.? If anyone else has any “must read” recommendations, please DM me or share in a comment to my post.