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Mike Lieberman, CEO and Chief Revenue ScientistThu, Apr 1, 2021 13 min read

What Is Sales Enablement In The Year 2021?

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Sales Enablement Produces Some Of The Fastest Revenue Improvements

Square 2 has been helping clients with sales execution for over 10 years. Our second book, "Fire Your Sales Team Today," was all about creating a sales experience that guides prospects instead of trying to sell them.

In 2017, we wrote our first article on What Is Sales Enablement? While a lot has changed over the past four years, much of the strategy and thinking we outlined in "Fire Your Sales Team Today" remains the same in 2021.

However, the execution upgrades required to activate sales enablement tactics have changed. The tools have progressed at an accelerated pace, while some of the tactics have also changed. Most of all, your prospects have continued to get smarter, become more aware of poor sales execution and, unfortunately, become much more distracted than in the past.

This means today’s sales enablement playbooks are different than in 2017. Here’s what sales enablement looks like today.

If you want to start the conversation with a definition, sales enablement has its share of different ones. Ours is pretty simple:

Sales enablement is the systems, processes and methodology that help salespeople turn more leads into new customers faster. But to be more direct, effective sales enablement helps you create a sales process that matches almost perfectly to your prospects buyer journeys.

This makes your prospects feel safer and more emotionally connected to your company, team and products/services. The result of those feelings is increased close rates and shorter sales cycles.

To be even more helpful, let’s break that definition down into smaller, bite-sized chunks.

Your Sales Process Is Still King

At Square 2, all of our sales enablement engagements start with the sales process. You can’t do much else without a defined sales process. If you don’t have a defined, visual and detailed sales process that every sales rep follows religiously, then you don’t have a sales process.

The way we start either documenting an existing sales process or designing a new sales process with clients is to use a technique we learned from Disney called experience mapping.

Experience mapping identifies every touch point from click to close, and it allows us to create a positive, differentiated and creatively architected experience. Research has validated that the more remarkable the experience, the shorter the sales cycle and the higher your close rate.

It’s really that simple. Each touch point has to be aligned with your prospects’ buyer journeys and satisfy their questions, issues or challenges.

But simply satisfying them isn’t good enough. To use Disney’s vernacular, you have to create little wows along the way. In the book "The Power of Moments" by Chip Heath and Dan Heath, they call these interactions peaks.

You want to design a sales process that is filled with these little wows and peaks. You want your sales process perfectly aligned with each prospect’s buyer journey, and you want it to be designed to help move your prospects along that journey in a more proactive way.

Get Your Sales Team To Think Like Sherpas (Guides)

One of the best ways to think about your new or your redesigned process is to look at the role of your sales reps. Historically, the rep role has been to convince, to pitch and to persuade. Those days are over for a number of reasons.

First, most people have created defenses to protect themselves.

Next, these types of conversations don’t feel great. When you’re trying to get a prospect to feel safe and to emotionally connect with you, convincing or persuading someone isn’t going to deliver the desired results.

Finally, your prospects are no longer a captive audience. In the old days, sales controlled the process. If someone needed anything, they HAD to talk to sales. That’s not the case today. I can learn almost everything I need about a company or product without ever talking to anyone in sales.

Most people go out of their way to NOT talk to salespeople. But people do want and need help, which is why we recommend refocusing your sales team away from selling and toward guiding.

This idea of being a guide is life-changing for many salespeople. Let’s compare salespeople to guides, like a Sherpa who guides you up Mount Everest.


  • Most have been working in an industry or at a company for some time
  • Most want to share their expertise with their prospects
  • Most have access to information or resources that prospects couldn’t get or might want
  • Most salespeople do want to be helpful if they can
  • Most really seem to like sales and the sales role

 Sherpas (Guides)

  • Most have climbed the mountain so many times they now help others
  • They have knowledge that most people don’t and they know the best routes to take
  • They know about the equipment and gear needed to get to the top
  • They like helping people get to the top of the mountain and sharing their passion for the mountain

There are a lot of parallels. One of the biggest is that Sherpas understand the goal get to the top and back safely. Sales reps need to understand each prospect’s goals in the same way simple, articulated and clear.

Once they have a shared understanding of the goal, they should guide the prospect along their buyer journey until the goal is achieved.

This is what we call the guided sales process. Sales reps act like guides and the sales process is designed to guide someone to their goals.

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Arm Them With Content

One of the best ways to create a guided sales process that helps prospects feel safe and emotionally connect with your company, reps and products/services is through the use of content.

Today, most companies have a lot of content like research, educational whitepapers, e-books, videos, podcasts, tip guides, playbooks, webinars, case studies and more.

Unfortunately, most of this copy is not designed to fit into a guided sales process because it’s about the company or its products/services. The content is not about the prospect nor does it answer their questions or address their concerns.

The best way to design a sales process that strategically leverages content for reps is to know in detail all of the questions prospects ask along the way.

You know people ask different questions depending on where they’re at in the sales process. These questions can inform your content strategy.

Here is an example: Some of our prospects aren’t sure they even need an agency, so an early buyer journey stage question might be, “What does a digital agency do?” Or they might want to know if they’re missing something with their in-house team’s marketing execution. They might want to know, “What are the best digital marketing tactics to generate leads in the software industry?”

At the end of the sales process, or late in their buyer journey, their questions look more like this: “What results should I expect an agency like yours and a program like this to generate, and in what time frame?” “Who will we be working with on your team when we get started?”

When they do ask the questions, you’re prepared with content that is directly related to their concerns. Quickly assuaging those concerns helps people feel safe.

Make sure you ask a lot of questions, too. The more questions you ask, the safer people feel and the more emotionally connected they get. Just think about the last new person you met at a party. If they talked about themselves the entire time, you’d be turned off. But if they asked you a lot of questions about yourself, you’d be happy they were trying to get to know you.

It’s the same with sales. Design a process that allows you to ask a ton of questions. Get them talking about themselves (their favorite topic) and they’ll feel very good about you, your company and your offerings.

Activate Chat

This is a bit tactical, but it is relevant and important. You want to accelerate sales. You want to shorten the sales cycle. You want to get the best prospects to the front of the line. Chat does all of this.

People are very impatient today. They want to talk now and they don’t want to wait. This is especially true of people motivated to buy, ready to move fast and with the authority to buy.

Chat, by its nature, pushes these people quickly into conversations with sales reps. Why call you, fill out a form or send an email when they can click a button and chat right now?

Chat should be a part of everyone’s websites. Sales teams should be monitoring chat. Targeted accounts should be aligned to reps via chat. Even at night, chat bots can take over collecting email addresses or phone numbers, and then reps can return those inquires in the morning.

Using chat enables your sales process and shortens the sales cycle in almost every situation.

Track Performance Data, Uncover Insights And Drive Action Planning

Finally, sales enablement means applying data and science to sales. Sales has historically been managed on a lot of gut, intuition and past experiences for decisions. Now it has to be managed based on data.

Are you going to make your sales goals this quarter? Of course, because you know you have enough leads, sales-qualified leads (SQLs) and sales opportunities working for enough revenue to ensure you hit your numbers. There should be no doubt. If you don’t have enough in the pipeline, you should be actively working to fix that.

Here’s an example: If you know that 3% of website visitors turn into sales opportunities, then you know how many sales opportunities you should expect each month. If website visitors drop for a few months in a row, you might be in jeopardy of missing your sales targets.

If you know your close rate on submitted proposals or contacts, then forecasting becomes much easier. You can also work to actively improve that close rate. Going from a 20% close rate to a 40% close rate will double revenue. It’s one of the most overlooked areas of sales enablement work that almost always delivers big returns to clients.

Over the past two years, our sales enablement practice has exploded. Yes, the pandemic caused some companies to finally address their antiquated sales process. Today, most companies are now actively working on sales enablement, and it will have a major impact on revenue and overall company growth.

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Mike Lieberman, CEO and Chief Revenue Scientist

Mike is the CEO and Chief Revenue Scientist at Square 2. He is passionate about helping people turn their ordinary businesses into businesses people talk about. For more than 25 years, Mike has been working hand-in-hand with CEOs and marketing and sales executives to help them create strategic revenue growth plans, compelling marketing strategies and remarkable sales processes that shorten the sales cycle and increase close rates.