Key insights from “Little red book of selling”

Artem Gurnov
CX@Wrike
Published in
8 min readOct 26, 2020

Almost every customer-facing role today is involved in sales. For account managers and sales development representatives, it’s the essence of what they do. For customer success managers, the situation is different — it’s all about selling the product’s value and best practices to the customer. This is why I consider sales an important skill for any CSM and why I continuously study books and other resources to grow in this area. I always considered “How to Become a Rainmaker: The Rules for Getting and Keeping Customers and Clients” by Jeffrey J Fox as one of the best books for anyone involved in sales. But recently I stumbled upon “Little Red Book of Selling: 12.5 Principles of Sales Greatness” by Jeffrey Gitomer, and I have to say that rarely in the last couple of years have I encountered such an amazing source of practical tips on sales.

However, a majority of those tips won’t cause any aha moments. Most people are already aware of the ideas presented in the book. But, at the same time, it’s well known that knowing doesn’t equal doing. Gitomer clearly describes how simple (but not always easy) actions can help achieve amazing results and motivates readers to start taking action. I’d like to share my personal list of insights from the book.

1. People don’t like to be sold. They like to buy

The first tip sounds so obvious that it’s even hard to call it insight: “People don’t like to be sold. They like to buy.” Most salespeople choose to push their company’s products or services aggressively, often forgetting to ask the most important question: Why do their customers buy? There’s no better way to find that out but to ask the customers directly. Gitomer recommends choosing your best customers and asking them why they made the decision to purchase your product.

A big part of a customer success manager’s job is asking questions [link]. Doing so helps to better understand their business challenges and pain points and provide solutions. It also helps to identify opportunities for growth and expansion, and, yes — upsell!

2. Give first. Become known as a resource, not a salesperson

Gitomer emphasizes that the first thing you need to do when interacting with a prospect or customer is to deliver value. You need to provide solutions to the customers’ problems so they’ll be interested in continuing the conversation. And this isn’t advice only for the initial conversation. Every single time you talk to your customer you need to bring more value to the table.

I actually practiced this approach when I was working as a customer success manager and had a book of business. Prior to having a call with the customer, I reviewed my notes on previous conversations and quickly brainstormed other ways the product can potentially help the customer. I presented these ideas during the call, and also showcased our recently released features to make sure that the customers were aware of them and their value.

3. See change as opportunity

Generally speaking, people don’t like change. Most would prefer to maintain the status quo. However, those who choose to see change as opportunity often win big. Changing a key employee in the client’s organization and switching business practices open new doors and present new opportunities. The question is: Who’s going to leverage them?

This rule is very much valid for the customer success role. It’s often the case that the current conditions don’t provide any room for growth and development. But in a couple of quarters, the situation may change dramatically. A new executive can be way more open to a conversation about getting more teams involved with your product or service. A new team that was established as a result of business growth can be open to a suggestion to start using your service. One just needs to stay on top of what’s happening and not miss the window of opportunity that opens (usually) for a limited amount of time. It’s important to keep in mind that a change in the organization can also potentially lead to new risks that need to be taken into account.

4. The best teacher is failure. Willing to succeed? Be willing to take risks!

No one likes failure. People would like to be successful in every endeavor. But unfortunately (or luckily), it doesn’t work like that. To achieve results you need to make mistakes — a lot of them. Mistakes help you understand what you’re doing wrong so you can correct your course of action. At the same time, it’s critical that you learn from your mistakes and don’t make them again.

Gitomer states that many sales methods involve a certain level of risk — from edgy and unusual voicemails you leave for your customers to the methods you practice to engage them. But being edgy isn’t bad as long as you deliver results, impress the people you work with, and build long-lasting relationships.

5. Hard work makes luck

I strongly agree with Gitomer that hard work makes luck, but not everyone does. You need to become known as a person of action and work extra hours while others are sleeping. We often hear the phrase “work smarter, not harder.” While this saying is generally true, in a lot of situations it’s indeed necessary to go the extra mile.

I can easily recall multiple moments in my career when my colleagues left work on time whether or not the work was finished, and I chose to stay late. That choice allowed me to be ahead of the curve, hit quotas, and build better relationships with customers. Extra effort doesn’t always lead to immediate results, but it often leads to major positive effects in the long run.

6. Celebrate effort, not just victory

While it’s tempting to only praise results, it’s important to highlight your team’s dedication and effort. As stated in our previous point, you can’t always win — some initiatives won’t necessarily lead to any positive outcomes. But it doesn’t mean that the effort you put into working on those initiatives shouldn’t be taken into account. One of our core values here at Wrike is “fail gloriously.” We encourage our team members to try, fail, get up, and try again. Our perseverance and dedication to achieve our goals is what makes us strong.

Also, for your long-term projects, make sure you define important milestones and celebrate whenever you achieve them, not just the end goal.

7. Learning is the surest method to be ready for your success

Gitomer stresses the importance of continuous learning. One of the questions he highlights is: “How much time during the day do you spend learning something new?” Even though the idea that continuous improvement leads to growth seems obvious, it’s surprising how many people don’t actively try to learn something new. Today, you have access to an unlimited number of books on topics that can deepen your knowledge and expertise. However, for many people education ends with college or university.

Every 30 minutes you spend reading professional literature, practicing skills, and talking to an expert in your area, you grow your competitive advantage. So the question is: Why not do it? I also loved the way Gitomer talks about reading: “You don’t read a book. You study it.” To me, the difference is that when you study the book, you create a list of takeaways and practice them at work. The sooner, the better.

8. Homework doesn’t stop when you finish school

It’s hard to overestimate the importance of preparing for client meetings. The time you invest in getting ready for a meeting pays off when you can answer any question with confidence, easily present industry-based best practices, and don’t bore the customer with questions you can easily get answers to on their website. Doing your homework is an important indicator of your professionalism while a lack of preparation could be taken as a sign that you’re not taking the customer seriously.

It’s important to review all the notes from previous interactions with the customers. It’s great when a company has a shared space where all members of a customer-facing team can quickly check all the details of previous communication. Even if there’s no such thing, you can always reach out directly to the account manager, support agent, or any other person who spoke with the customer previously for more context.

9. The more value you provide the less price matters

Gitomer perfectly formulated the statement: “When there’s no value, all that’s left is the price.” Whenever a company is evaluating the possibility of getting a certain product or service, it’s all about the value. Companies want to grow, be more efficient and achieve their goals. And it’s the salesperson’s job to clearly communicate how their product or service can help do just that. Price becomes less important if your product or service can provide more benefits.

Imagine the following situation: A company needs accounting software and is evaluating the options available on the market. A lot of products offer very similar capabilities and the difference in prices isn’t too wide. There’s another solution that’s 20% more expensive, but it allows users to automatically build reports that accountants spend up to five hours every week creating manually. Do you really think that the 20% price difference would really be of importance to a decision-maker when they can save so much of their team’s time and reallocate that resource to other goals and objectives?

Gitomer states, though, that not everyone will buy value. About 30– 40% of customers will buy price, and these customers are often difficult to work with.

10. Ask smart questions — they’ll think you’re smart

It’s hard to overemphasize the importance of asking the right questions during your interactions with customers. There’s no better way to understand their challenges, the pain points, and how your product or service can help address those challenges. That said, effective questioning is one of the core competences of any customer-facing role.

Some tend to think that asking questions isn’t something that should be practiced. Well, it’s definitely not the case. Just like with any other skill, the ability to ask efficient questions can be developed and improved. It all stems from practice and preparation. Gitomer suggests having a list of 15–25 questions prepared for your call with the customer. He states that “good questions lead to the heart of the problem,” so always having some good questions definitely won’t hurt.

11. If you can make them laugh, you can make them buy

Bringing humor to the call doesn’t necessarily have the sole purpose of breaking the ice. “Making people smile is a major key in selling,” says Gitomer. I always do my best to make customers laugh during our call. The topics can be different — from showing a photo of myself in bunny ears during the product demo to cracking some jokes based on the flow of our conversation.

Here’s a thought: The meeting or call with you may be the fifth or sixth for the customer already. If it’s just another meeting in a streak, it most likely won’t be memorable. But if you share a good joke together, the client may remember you as a friendly, approachable person and be way more enthusiastic about jumping on the next call with you.

12. “You must believe that you work in the greatest company in the world, that you have the greatest product in the world, and that you are the greatest person in the world”

Honestly speaking, this tip is self-explanatory. I just want to add that although I believe that a good salesperson can sell literally anything — from home appliances and videogames to real estate — when they really believe that the product or service they’re offering is absolutely amazing, translating that to the customer becomes a much easier job!

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