16 Books to Help You Become a Better Sales Rep

From “SPIN Selling” to “The Giving Tree,” these books will boost your sales skills.
Brian Nordli
July 13, 2021
Updated: January 25, 2022
Brian Nordli
July 13, 2021
Updated: January 25, 2022

For most of sales’ existence, it was thought that successful sales reps either had it or they didn’t. “It” in this case meant the natural charisma and killer instinct to close deals and bring in business.

But that’s not true anymore.

Sales success today requires staying on top of the latest tactics, workflows and strategies to stand out in a crowded B2B SaaS landscape. It’s about building the right habits to maintain a full pipeline and the soft skills necessary to form lasting relationships. Instead of Always Be Closing,” the secret to success can be boiled down to a slightly less catchy phrase: “Always Be Learning.”

With hundreds of books to choose from, however, it can be difficult to know where to start. From tactical books like SPIN Selling to the children’s tale The Giving Tree, we’ve highlighted some of the most useful books — sales and otherwise — to help you become a better seller.

Must-Read Books to Boost Your Sales Skills

  • SPIN Selling by Neil Rackham
  • Gap Selling by Keenan
  • The Challenger Sale by Matthew Dixon and Brett Adamson
  • How to Win Friends and Influence People by Dale Carnegie
  • Emotional Intelligence for Sales Success by Colleen Stanley
  • Start With Why by Simon Sinek
  • Mindset: The New Psychology of Success by Carol S. Dweck
  • The Giving Tree by Shel Silverstein
  • Weekend Language by Andrew Craig and Dave Yewman
  • Just F*ing Demo! by Rob Falcone 
  • The Compound Effect by Darren Hardy
  • Eat Their Lunch by Anthony Iannarino
  • Never Split the Difference by Chris Voss and Tahl Raz
  • The Transparency Sale by Todd Caponi
  • Fanatical Prospecting by Jeb Blount 
  • Addicted to the Process by Scott Leese

 

Books on Sales Methodologies

SPIN SellingSPIN Selling by Neil Rackham

Former sales rep Neil Rackham’s four-part sales methodology has been a touchstone for sales reps since it was first published in 1988. Part of what makes the book so effective is how it simplifies the sales process down to four steps: SPIN, which stands for situation, problem, implication and need-payoff. Situation involves asking questions to understand where the buyer’s business is today and why they’re talking to you. Problem requires exploring what issues the customer is hoping to solve with your product. Implication digs into the impact that problem has on their business, and need-payoff questions lead the customer into drawing their own conclusions about your solution and how it can help them. Rackham provides a framework for asking each of those questions, as well as tips on how to nail the opening call and handle objections, making it a useful resource for any sales rep.

Buy: Bookshop, Amazon

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Gap SellingGap Selling: Getting the Customer to Yes by Keenan

Published in 2018, Gap Selling is one of the newest sales methodologies around. Keenan developed the framework to solve some of the issues he saw within sales organizations as a consultant over the past 10 years. The book encourages reps to take a problem-centric approach to sales rather than a solutions-oriented one. Keenan’s strategy hinges on an in-depth discovery process to understand and quantify the full scope of a customer’s current situation and their desired future state. That difference makes up the eponymous gap, which serves as the foundation for future sales conversations and the buyer’s motivation to buy. Gap Selling provides reps with a simple strategy that they can apply right away, but with nuances that will take time to master.

Buy: Bookshop, Amazon

 

The challenger saleThe Challenger Sale: Taking Control of the Customer Conversation by Matthew Dixon and Brett Adamson

Another book that encourages reps to re-think the buyer-seller relationship, The Challenger Sale posits that the best sales reps don’t just build a relationship with the buyer, they challenge them. Authors Brett Adamson and Matthew Dixon published the book in 2011 after interviewing multiple sales reps across the industry and the United States. Their approach reflects the fact that buyers are more reluctant than ever to purchase software, regardless of how much impact it can have on the company’s bottom line. The book details the skills, knowledge and strategies reps need to push back when they encounter objections and close a deal. At nearly a million copies sold, according to Dixon, the book has become a staple resource for many sales reps.

Buy: Bookshop, Amazon

 

Books to Boost Your Emotional Intelligence

how to win friendsHow to Win Friends and Influence People by Dale Carnegie

Sales success isn’t just about mastering various methodologies and frameworks, it’s also about relationships. On that front, few books have been as influential as Dale Carnegie’s How to Win Friends and Influence People, which has sold over 30 million copies. The book provides tips on how to become a better listener, build stronger relationships and handle arguments — all essential skills in sales. Whether you’re interested in connecting with your buyers or becoming a sales leader, there’s something in here for every rep.

Buy: Bookshop, Amazon

 

Emotional intelligence for sales successEmotional Intelligence for Sales Success: Connect With Customers and Get Results by Colleen Stanley

At its core, sales is about connecting with people. In Emotional Intelligence for Sales Success, Colleen Stanley highlights the role empathy and active listening play in the sales process. Throughout the book, Stanley, who’s president and founder of the consulting firm SalesLeadership, offers actionable steps to improve your emotional intelligence, tips for how to relate to and influence buyers, and advice on identifying when you’re stressed out. In 2020, Stanley also published a guide for sales leaders, Emotional Intelligence for Sales Leadership, in which she expands on ways that managers can develop and train their teams on the soft skills necessary to sales success.

Buy: Bookshop, Amazon

 

Start With WhyStart With Why: How Great Leaders Inspire Everyone to Take Action  by Simon Sinek

If you’re looking for a resource to help you become more persuasive with buyers or your sales team, then look no further than Simon Sinek’s Start With Why. Published in 2009, the book attempts to explain what makes some people more influential than others. As the name implies, the key rests in understanding your “why,” or the core reason for what you’re doing. Throughout the book, Sinek explores how that “why” influences people while also offering a framework for communicating with people and leading them. The book’s insights can be used for anything from sales to leading your own company.

Buy: Bookshop, Amazon

 

Mindset New Psychology of successMindset: The New Psychology of Success by Carol S. Dweck

If there’s one certainty in sales, it’s that you’re going to hear “no” a lot. Even the best sales reps have days filled with rejection. One of the keys to sustained sales success is in managing that failure. In Mindset, Stanford psychologist Carol Dweck breaks down the differences between having a fixed mindset (the belief that their abilities stay the same), and a growth mindset (the belief that abilities can be developed). Dweck argues that a growth mindset is key to success and outlines tips on how to start thinking differently.

Buy: Bookshop, Amazon

 

The giving treeThe Giving Tree by Shel Silverstein

You might be wondering why a children’s book is on this list, but there’s a lesson in its simple tale that any sales rep can learn from. In case you need a refresher, the story involves a boy who develops a relationship with a tree in which all he does is take from it until it is reduced to a stump. Amy Volas, founder of the sales recruiting firm Avenue Talent Partners, frequently returns to the book as a reminder that “when all we do is take in sales and in life, there is nothing left.” It’s a useful blueprint for relationship selling. After all, the best sales relationships are ones in which you give to buyers — advice, resources, connections — even if they aren’t going to buy from you.

Buy: Bookshop, Amazon

 

Books to Improve Your Communication Skills

Weekend LanguageWeekend Language: Presenting With More Stories and Less Powerpoint by Andrew Craig and Dave Yewman

If your sales presentations are full of terms like “leverage,” “seamless” and “synergistic,” odds are your customer’s eyes are glazing over. Weekend Language argues that reps should ditch the corporate-speak and start talking the way they do on the weekend at parties and with friends. In this case, that means in simple terms and engaging stories. Throughout the book, authors Andrew Craig and Dave Yewman offer tips and techniques to take your weekend storytelling prowess and apply it to your next sales presentation. If you’re looking for a way to freshen up your sales communication, give Weekend Language a read.

Buy: Bookshop, Amazon

 

Just Fing DemoJust F*ing Demo!: Tactics for Leading Kickass Product Demos by Rob Falcone

At a brisk 40 pages, Just F*ing Demo! gets straight to the point, so we will too. The book argues that people’s attention spans are dwindling, and they don’t have the time nor desire to sit through a full product demo. Rob Falcone offers a step-by-step guide to help you trim the fat and tailor your demo to your audience to keep them engaged.

Buy: Bookshop, Amazon

 

Books to Hone Your Skills From Prospecting to Closing

The compound effectThe Compound Effect: Jumpstart Your Income, Your Life, Your Success by Darren Hardy

Sales success, much like career success, boils down to developing the right habits and doing the little things day in, day out. The more a rep can keep up with daily activities to maintain a robust pipeline like posting on LinkedIn, prospecting and maintaining the CRM, the more likely they are to surpass their quota. The Compound Effect is a book about developing the habits necessary for career success. Over time, those small habits will compound and help you thrive, according to the author. Klue Account Executive Jacob Gebrewold said the book gave him the foundation to succeed as a rep and believes its a resource any rep can gain value from.

Buy: Bookshop, Amazon

 

Eat Their LunchEat Their Lunch: Winning Customers Away From Your Competition by Anthony Iannarino

There are three essential questions that every sales rep needs to get a buyer to answer before they’ll make a purchase — why change? Why now? Why you? Eat Their Lunch focuses on answering that third question, which in a crowded B2B SaaS industry, is more difficult than ever. In the book, Anthony Iannarino pulls on his own experience as a sales leader to help reps win those clients over to your side. The book focuses less on trashing your competitors and more on identifying who stands to gain the most from your product and coming up with a plan for each stakeholder in the company. Gebrewold considers the book the most powerful he’s come across in teaching him how to win deals over his competitors.

Buy: Bookshop, Amazon

 

Never Split the differenceNever Split the Difference: Negotiating as If Your Life Depends on It by Chris Voss and Tahl Raz

Few moments in sales require as much nerve and tact as the negotiation stage with the buyer. Concede too much or stand too rigid and the deal will collapse. Chris Voss knows a thing or two about what it takes to navigate this high-stakes environment and then some. As a former FBI hostage negotiator, Voss spent his career negotiating with kidnappers, bank robbers and terrorists to keep people safe. Throughout Never Split the Difference, Voss and co-author Tahl Raz share the skills and negotiating principles that can help anyone gain an edge in any deal-making scenario.

Buy: Bookshop, Amazon

 

The transparency saleThe Transparency Sale: How Unexpected Understanding and Understanding the Buying Brain Can Transform Your Results by Todd Caponi

When it comes to convincing someone to buy your product, there’s often a tendency to cover up the flaws and make it seem perfect. But in the age of information when product reviews are a click away, Todd Caponi argues that strategy isn’t going to fool anyone. The Transparency Sale says that the key to speeding up sales cycles is to eliminate the double-speak and half-truths and be honest at every stage of the sales cycle. That means being upfront about your product’s strengths and weaknesses, what features are in development, and what discounts you can offer. Volas considers the book a critical resource that will help you build better relationships with buyers.

Buy: Bookshop, Amazon

 

Fanatical ProspectingFanatical Prospecting: The Ultimate Guide to Opening Sales Conversations and Filling the Pipeline by Leveraging Social Selling, Telephone, Email, Text, and Cold Calling by Jeb Blount

Sales is a numbers game. The more you keep up with your prospecting — sending emails, cold calls and social media posts — the more chances you’ll have at meeting quota. That said, it also matters how you prospect. As the book’s title implies, Fanatical Prospecting is devoted to helping readers master the techniques they need to keep a full pipeline. From cold calling to texting to social media, the book has you covered. If your challenge is overcoming objections, then Jeb Blount also has you covered there with his other book, Objections.

Buy: Bookshop, Amazon

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Addicted to the processAddicted to the Process: How to Close Transactional Sales With Confidence and Consistency by Scott Leese

In Addicted to the Process, author Scott Leese focuses on giving reps the tools to master the transactional sale, which he defines as one with a short sales cycle, few stakeholders and high transaction volume. As a leading voice in sales and co-host of the Surf and Sales podcast, Leese details the habits, strategy and process that he believes will lead to consistent success. Leese has also published books to help reps make the leap to manager in From Rep to Manager, and advice for VPs in More Than a Number.

Buy: Amazon

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