top of page
  • Writer's pictureMike Hanna

5 Surprising Books with Powerful Sales Lessons

We’re going to have a little fun with this blog post today, looking at some books that are a real throwback. They’re not best selling books on sales or sales management. Drumroll please…They’re picture books you might remember from when you were a kid. But as it turns out, they have some timeless lessons about sales. So software sales professionals with kids or grandkids, take note next time you’re reading any of these classic stories—because they have some fundamental insights about the sales process.

If You Give a Mouse a Cookie and the Power of Upselling

We all know how it begins...he’ll ask for a glass of milk. When you give him the milk, he’ll ask for a straw. When you give him a straw...and so on, until it circles right back to the cookie. Upselling is one of the best ways for a business to generate income. In some verticals such as online retail, upselling can increase revenue between 10-30%, while generating as much as 75% of of total revenue; in comparison to the cost of a new customer acquisition, upselling is 68% more affordable. Upselling can easily become part of a software sales model as well, not just at the actual point of sale but over the course of the relationship. There may be ancillary products or services your company can offer as a client expands into new territories or different verticals. So if you’re giving a client a cookie, be ready with that glass of milk...and then the straw.

The Runaway Bunny and Overcoming Objections

The Runaway Bunny is written by the same author who penned Goodnight Moon, and it has a similarly endearing cozy look. It’s the story of a bunny who (guess what) keeps trying to run away, but his mother always thinks of a way to catch him. If he sails away, she’ll be the wind to blow him back to shore. If he turns into a flower, she’ll turn into a gardener. Mama bunny just doesn’t give up, and she always has a quick rejoinder that relates to the bunny’s objection—until finally, the little bunny just decides to come home for a carrot. Overcoming objections in the software sales process is a true mixture of art and science, emotional appeal and reasoning skill. Being adept at handling objections can be the difference between closing more sales and constant frustration. Expert objection handlers know their clients very well (they do their research on the company and the market) and can handle one objection after another until that client gets to the proverbial carrot.

The Very Hungry Caterpillar and the Sales Process

This is one of the most endearing children’s books of all time. It’s the story of (as the title says) a very hungry caterpillar. He methodically works his way through several food items. On Monday he eats through one apple. On Tuesday he eats through two pears. On Wednesday he eats through three plums. There’s a plan and a pattern, until he gets to Saturday, when he eats through a whole tone of junk food and retires with a stomach ache. In software sales, having a proven process yields better results. Some companies (in all areas of sales) see as much as an 18% increase in revenue growth once they implement a sales process. Such a process can increase efficiency, allocate responsibility, facilitate more accurate forecasting, ensure more accountability with each individual software sales rep, and allow for improvement on a standardized process that all reps are using. Stay hungry, reps...but stick to the plan. Things can derail if you go for chocolate cake, ice cream, pickles, Swiss cheese, salami, candy, and pie all in one day.

The Little Engine That Could and Persistence

This is the story of a little locomotive who is asked to pull a train over a large hill. As she does it, she repeats to herself over and over again: I think I can, I think I can, I think I can...Software sales (or any sales) is not for the faint of heart. You will need to be able to handle rejection—whether you’re an inside sales rep getting hung up on several times a day, or a territory manager who flew out for a meeting with a client, only to have that client go with a different solution. But the most successful sales reps look at the long game, not the short game, and they constantly bring their persistence and optimism to the table. As much as 35-50% of sales go to the vendor who calls first, and the sooner you do so, the better—following up with a prospect within five minutes of a signup makes a conversion nine times more likely. Don’t let the setbacks keep you down. Keep going and always put in your best effort. When little things like being the early bird caller add up to your name at the top of the quarterly metrics, you’ll feel like the engine coasting down the hill saying: I thought I could, I thought I could, I thought I could…

The Giving Tree and Lifetime Client Relationships

The Giving Tree is the story of a tree that always has something to give its favorite little boy, even when he turns into an old man. When it comes to sales, this book reminds us of the power of lifetime relationship building. Selling vacuum cleaners door to door across America probably does not involve lifetime relationship building (although it’s probably great if you love taking road trips). But connecting clients with a software solution often means building a lifetime relationship. They will need support and maintenance on the product. As their business changes they will need new solutions. As they grow, you may have better solutions for them. In many cases, increasing customer lifetime value is often more cost effective than acquiring new customers. For sales reps, the benefit of a lifetime relationship is that it's easier to close a sale or upgrade with a current client than it is to convince a new prospect of something from scratch. Be the tree that’s always there, whether your client needs leaves, apples, or a trunk to make a boat.

A final word about sales lessons...

I hope you had fun getting some lessons in software sales from these surprisingly motivational books—and the pictures are pretty cool too. From the importance of a sales process to the power of upselling, it’s amazing how lessons about how to improve your sales game are all around you. If you happen to be looking for the next place to grow your software sales career, or you’re looking for pre-vetted talent, get in touch with me at I’m a software sales recruiter with 40 years in the industry. Let’s connect and talk about your next role or your next hire!

18 views0 comments


bottom of page