5 Books on Sales Every Leader Should Read

If you want to grow and scale your business, you need to get sales working right. These five books will help.

When I founded my technology company, I thought I was brilliant at sales. I had closed several million-dollar deals at the company I worked at previously and was a rockstar. I figured it would be easy to find a few projects each month to feed the team we built and grow the business quickly.

I was wrong. I quickly began to struggle with finding good quality leads, and the leads I did find would stall and go dark or pull out at the last minute. The lack of sales quickly began to hinder the company’s growth, and I began to question my skills and value as a CEO.

I did what any effective business leader should do when they are stuck. I hired a coach. She helped me see that my problem was not my skills, my smarts, or my motivation; it was my strategy and process. To get effective and predictable sales, you need a system and a framework. Once I had these in place, there was no stopping us.

Here are five key books that I read early in that process that really changed the way I thought about sales and selling. If you’re looking to grow and scale your business and need more and better sales, I highly recommend these books.

1. To Sell is Human - by Dan Pink

I always start here. So many leaders say that they don’t like sales or that they don’t want to be perceived as a slimy salesperson. Boloney. Everyone sells to everyone every day of their lives. We just don’t always call it sales or think of it as selling. Get over it.

The sooner we realize and embrace that selling is a natural and fundamental process in our everyday lives, the sooner we can embrace the role and excel at it. Pink deconstructs our stereotypical notion of the pushy salesperson and shows selling is a natural and necessary skill for anyone, not just business people. He makes it approachable and palatable. Do I dare say, even honorable?

2. Challenger Sale - by Matthew Dixon and Brent Adamson

Matt and Brent break down what really works in sales organizations. Backed by real research and copious data, they looked at several different types of salespeople who drive performance in high-growth companies. What they find is a little surprising and counter-intuitive.

While individual performance will often go to the lone wolf salesperson who treks out into the world alone to stalk their prey and bring home the kill, the best sales organizations are made of challenger salespeople. These are the people who are consultative and help the client navigate the sales process.

The key is they are willing and able to challenge the prospect’s thinking and help consider new perspectives and criteria they may not have thought of initially. These challenger salespeople are not only highly effective, but they also work systematically using a process and tools that are repeatable and trainable. If you want to build a sales system and a sales team, this book is a must-read.

3. Traction: A Startup Guide to Getting Customers - by Gabriel Weinberg and Justin Mares

Not to be confused with the EOS book Traction, Weinberg and Mares outline the 19 key ways in which growth companies generate leads. This includes everything from SEO and SEM, tradeshows, affiliate programs, and gorilla marketing. It’s a useful and comprehensive list.

I have clients read through the strategies and evaluate them on three key criteria. First, what do you have content and materials for? Second, what do you like doing and are good at? And finally, which channels are your target customers likely to be using and open to a buying conversation? Find two or three that score well on all of these, and you’re off to the races with a few new lead-generation techniques.

4. New Sales. Simplified - by Mike Weinberg

Weinberg breaks down the complex and overwhelming process of selling into three basic steps. First, select the right targets. Second, create effective sales weapons. And third, plan an effective attack. While simple, most companies get these steps wrong. They fail to define their ideal targets. They create lackluster selling materials. And they go to market with a hope and a prayer, rather than a plan.

This book walks through all of these steps and gives tons of ideas and suggestions for how to make your sales process not only more effective but easier to build and manage. The goal here is to have a system you can use consistently and repeatedly to generate predictable revenues and scale your business. This book does it.

5. Spin Selling - by Neil Rackham

I read this book years ago when I first started my technology company. Until then, I sold based on rapport and luck. This book gave me a framework to think about the sales process and conversation and helped me understand the buying process and how I could structure it into a simple set of stages.

Rackham outlines the SPIN (Situation, Problem, Implication, Need-payoff) approach and gives you clear and easy-to-remember queues for each stage. By making sure you’re working through the key questions, you will increase your chances of success and quickly kill leads that are not ready or not a fit for your solutions.

Sales is a natural and necessary skill for any business person. However, if your job is to find leads and close deals, you need to become an expert. These books are a great starting point and will give you the foundations for becoming a high-performance sales superstar.

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