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The Sales Enablement Doctor Is In

Sales Enablement

Sales Enablement


Sales is a tough business. When you ask a sales rep to explain their job in one word, you’ll hear a range of words, from “challenging,” “stressful” and “demanding” to “exhilarating” and “exciting.” How can someone go from one extreme to another?

That’s the rollercoaster ride called sales. Some of the best sales reps have closed the largest deals in company history and been No. 1 on the leaderboard one year, and then followed up the next year without a single deal closed. They went from hero status to the rep who was under the microscope.

Sales enablement involves the process of providing the sales organization with everything it needs to be successful. That includes the information, content, tools, processes, training, or coaching that helps salespeople sell more effectively, and it provides an optimal experience for buyers and clients. The foundation of sales enablement covers a large swath, from onboarding to continual learning and the reactive skills we need to be able to address shifts in the business.

There are a lot of great materials and training programs on sales psychology that focus on why sales reps do what they do in certain situations, and how reps gain an aptitude for understanding a client’s frame of mind. The intent of these programs is twofold

  1. Help both sales reps and their managers learn from the psychological motivators that cause buyers and sellers to act and respond the way they do
  2. Better understand why certain sales techniques are more effective than others

It makes sense for sales enablement professionals to take a similar approach by playing the role of sales psychologist for our reps. After all, we’re always looking for ways to build credibility with our sales organizations. And, because we know that sales behaviors drive performance, we should design programs that help our sales team to focus on the right behaviors.

While numbers and KPIs are a critical piece of what we do, sales enablers are in a unique position of being perceived as trusted advisers and coaches. Because of this, we should make it our priority to understand what drives organizational behavior and motivates the people we work with every day.

Emotional intelligence (EQ) is essential to be a successful sales enablement professional. When you tap into the powers of EQ, you gain credibility and build trust within your sales organization while at the same time helping sales reps develop their own EQ. In turn, they can establish better sales practices and conduct more effective client conversations. There are several key elements that constitute emotional intelligence.



Self-awareness involves knowing and acknowledging how you feel along with understanding how your emotions and actions affect the people around you. Most importantly, self-awareness gives you a clear view of your strengths and weaknesses, which allows you to demonstrate humility. From an enablement point of view, we can work with reps and provide them with strategic deal coaching to better prepare them for upcoming customer conversations. One best practice I like to follow is conducting exercises that help reps identify their level of self-awareness as well as their strengths and areas for development.

In strategic coaching sessions, I acknowledge the rep’s point of view and ask them to put themselves in the customer’s shoes. I ask questions like, “how do you think the customer will perceive that?” and “how do you think the customer will feel about that?” These types of conversations and exercises prepare the rep to have more engaging, well-balanced discussions. After all, what better way to handle objectives or buyer concerns than thinking like a customer before the conversation even starts?

Now let’s look at this from a sales rep’s point of view. Buyers have access to information about companies, brands, and products, making them savvier than ever. Sales reps need to understand how they are perceived by customers so they can drive the deal to close. Their personality and attitude need to adjust based on interactions they’ve had with buyers in order to connect and be perceived as trustworthy. Their ability to recognize their own strengths provides the confidence they need to have effective and thoughtful conversations. At the same time, reps also need to recognize the behaviors that may jeopardize success and potentially threaten their credibility.



This element revolves around control and the concept of personal accountability. Statistics show that when individuals regulate themselves, they are less likely to react too strongly. These people rarely attack others and are unlikely to make rushed or emotion-based decisions. This is when the saying “it’s not personal, it’s business” is most relatable.

Sales enablement professionals can empower our sales team with the skills they need to determine their self-regulation behavior. We also can work with sales managers and leaders to define standards for the right behavior and motivate reps to take ownership of their development and success. By implementing something as simple as pre-call planning templates, we provide a framework that reps can use to better prepare for upcoming client conversations. These templates can be used to gather key pieces of information in advance, identify potential objections and a plan to address each objection and outline goals for the call. It becomes easier for the rep to self-regulate because they’re prepared.

Let’s face it, though: Sometimes what we do as sales enablement professionals is met with resistance. How many times have you heard reps say things like, “I’m too busy to attend this training,” “I need to be selling,” and “I’m only here because my manager told me to be here.” When I hear these statements, I cringe and instinctively want to go on the defensive—I’m honestly offended. My time is valuable, too, but I know what I do will help the rep in the long run.

This is when I become a true enablement master and practice self-regulation. Rather than follow my instinct, I take a step back and remember who I’m dealing with: sales reps who are pulled in every direction and are trying to close deals to put food on the table, all while working long hours and taking back-to-back calls every day. Oh, and they’re usually traveling while doing all of this, too.

Self-regulation enables me to see things from their point of view. As an enabler, I acknowledge their concerns and how they feel. I also can pivot and allow them to become stakeholders in the agenda for our session. I can offer the benefits they’ll experience if they participate and are fully engaged. In doing this, I also gain a level of trust and confidence from my reps because they understand that my No. 1 goal is their success.

For example, let’s look at two examples of self-regulation as a critical element in a sales rep’s success: dependability and credibility. Dependability is the quality of being able to be relied upon. You do what you say you will do. Buyers need to perceive sales reps as dependable. Reps should follow up when they say they will, deliver on their promises, and conduct their regular check-ins with the customer as expected.

Too often, reps schedule recurring check-in meetings, then regularly cancel those meetings because they assume there’s nothing new to discuss. This is a huge mistake—assumptions often lead to missed opportunities and miscommunication. Prospecting doesn’t just happen at the beginning of relationships; it’s ongoing. Recurring meetings keep reps relevant to the client because they are present and continually ask probing discovery questions that may uncover new information.

Additionally, reps lose credibility with each canceled meeting. Why bother scheduling a recurring meeting if you have no intention to follow through? Reps will achieve a greater level of trust and partnership with clients when they are dependable. They also decrease the chance of steps being missed that could derail a deal. We know reps are busy and pulled in multiple directions. Of course, they could use an hour back on their calendar. But, by practicing self-regulation, reps are less likely to cancel a customer meeting because they’re aware of the potential risks and perceptions.

Managing emotions is another example of self-regulation. When a rep sells, it’s literally their bread and butter. Sales cycles sometimes drag on; perhaps buyers are unwilling to commit, or maybe their business is going through a change. A sales rep can easily feel frustrated, but they can’t show this to a client. Working with buyers requires sales reps to walk a tightrope and maintain a high level of flexibility. When a rep demonstrates self-regulation, they know how to keep their cool and maintain their poker face. They also know when to challenge and nudge the buyer in the right direction.



Empathy is the ability to understand and feel another person’s emotions. Successful sales enablement professionals practice empathy and master the art of putting themselves in someone else’s situation. Empathy also can be used to develop both sales reps and managers, and it creates a healthy culture in which providing constructive feedback and coaching is encouraged and accepted.

Sales reps often ask me to provide one-on-one coaching sessions based on their performance. More specifically, I’ve been asked to provide coaching when a sales rep is at risk of being put on a performance improvement plan. These are the conversations every sales enablement manager should want to have, as it shows that you’re perceived as a trusted adviser. However, you must be skilled at having them because one incorrect statement or phrase can send the wrong message.

I never express sympathy about a sales rep being put on a performance plan; it’s a business decision, and I don’t want to undermine the sales manager or my company. I will, however, demonstrate empathy by saying things like, “how does the performance improvement plan make you feel?” and “how can enablement assist you?” I often work with reps to create an individual development and learning program that targets areas where they’re not meeting expectations. We also discuss the importance of putting emotions aside and making the necessary commitments needed to improve their impact and performance.

Making sales reps feel empowered, reminding them of their strengths, and encouraging them to voice their ideas, fears and needs is the best way to practice empathy. And empathy is directly related to productivity and loyalty. Companies that have empathy as a foundational component of their culture are likelier to see better retention and long-term success.

It’s important to note that empathy often is confused with sympathy or the act of feeling sorry for someone else’s trouble—which may be appropriate at a funeral but is inappropriate in sales. In fact, projecting sympathy in sales can be counterproductive, as it can cause the receiver to feel like you’re patronizing or condescending to them, and that undermines trust. Empathy, on the other hand, is critical in sales because it builds trust and maintains bonds.

Sales reps need to make a personal connection with customers now more than ever and having empathy throughout the process can differentiate them from the competition. Whether they’re targeting the right personas or crafting messaging that resonates with the recipient, empathy is a skill they will need right through the close of the deal. Prospects don’t want to be “sold” to. They want to know that the sales rep understands them and is invested in their success. When a sales rep is able to make this personal connection, they are able to influence their buyer.

Think of two common misses in a sales conversation: delivering a pitch and assuming it’s effective because there are no follow-up questions, and going into the standard “speeds and feeds” approach of talking about value and ROI through features and functionality. The mistake in both approaches is not asking a series of open-ended questions that help the seller better understand the buyer’s biggest challenge and the risks they face if they don’t resolve those challenges as soon as possible.

Empathy allows sales reps to ask the right questions to uncover a sense of urgency, and it enables them to pivot and articulate the positive effect their solutions provide. More importantly, sales reps can articulate value by connecting the dots of business fit vs. solution fit and what it means financially to the C-suite—who typically is the final signature on the deal.

Sales reps also often forget the risk a buyer assumes when choosing a solution as well as the stress they may feel during the approval process. By demonstrating empathy, a sales rep can ease the buyer’s stress and concerns by offering education, resources, and support. An empathetic seller places themselves in their buyers’ shoes and says, “I know that our solution can address your current challenges, but I also recognize that you might be worried about the amount of time and commitment needed to navigate this change. What can I do to alleviate some of your concerns or assist in communicating the milestones we need to hit to stay on track? Is there anyone else internally you’d like me to have a conversation with?”

Customers want to be seen and heard, and when a sales rep demonstrates empathy, prospects and customers experience a sense of security and trust in the seller.


Social Skills

Social skills—communication, conflict management, persuasion, collaboration, change management—are a must-have to handle and influence other people’s emotions effectively. Once you understand and manage yourself as a sales enablement professional, you can start understanding the emotions and feelings of others.

Often, sales enablement professionals are perceived by reps as approachable, positive, and sociable. I call myself a sales cheerleader, walking around the office giving high-fives and fist bumps. A big piece of my job is finding the uplifting and inspiring moments, then calling attention to them. There have been challenging times, though, when I’ve felt disengaged. I felt beat up and underappreciated.

In one-on-one settings, I was fine. But I also wasn’t going out of my way to walk through the office to cheer people on or bring a little fun and laughter to the room. I was head-down at my desk, focused on deliverables. It was a surprise when a rep came to my desk one day and asked what was wrong. A 30-minute conversation later, I realized my sales team had expectations of me and my energy—and when things were even slightly off, they noticed. I knew I had to turn things around because I was a source of influence when it came to other people’s emotions.

Some people have naturally strong social skills, while for others it requires a bit of work. As an enabler, I can encourage social skills through my own actions as well as work with reps to build their own social skills when needed. Communication is a great example of this: it’s a pivotal component of success.Sales Enablement doctor There are multiple ways people communicate, but this variety also lends itself to less-than-ideal communication practices and behaviors. As convenient as text and instant messages are, they’ve also created some poor and ineffective communication that, in turn, bleed into professional communications. Sales reps need to communicate often and well with clients to maintain credibility and ensure alignment. Whether it’s outreach messages for prospecting or follow-up emails to drive milestones, I work with reps to ensure their communications are on-point, on-brand, and memorable.

Conflict management is another area in which social skills and sales enablement psychology really come into play. While most of us try to avoid conflict, we know it’s inevitable. Usually, the biggest misconception about conflict assumes that conflict is negative or difficult. I’ve found that when I expect conflict and try to avoid it, I was simply delaying a much-needed conversation—and there was no actual conflict involved.

One of the best things we can do in enablement is understand how different people perceive and try to resolve conflict. This is a great time to encourage a collaborative approach to conflict resolution. Everyone is treated as equals and, although it may take a little longer to resolve the conflict, it lends itself to better and longer-lasting results. Plus, it encourages open communication.

Sales reps may face conflict internally as well as with clients. As an enabler, instill the skills they need to stay calm, actively listen and respond as professionally as possible. With client interactions, we can coach our reps on knowing whether the problem is worth discussing, and how they can best separate personal opinions from facts. Their success is in demonstrating empathy throughout the process to ensure resolution for both sides. In turn, this allows the sales rep to make a better personal connection with their buyers.


The Four Elements in Action

Imagine you’re trying to implement a new technology that would allow you to record sales calls and review them for analysis and coaching purposes. Your sales team initially perceives it as having little value to them. They’re also annoyed at the possibility of adding another step in their call process and are concerned that their calls will be viewed under a microscope. By understanding the psychology of sales reps, you can take a step back and see the situation from their point of view.

In this instance, the sales reps aren’t truly concerned about the additional step in the call process; rather, they’re afraid of change. The reps are immediately defensive because they’re assuming that this tool is being implemented to watch their calls closely. They’re also worried that their jobs are at risk if they fall short on their calls. As a sales enablement professional with a high EQ, you know exactly which elements to leverage so you can handle the situation.

You’ll practice empathy by saying things like, “I understand why you feel this way.” You’ll communicate and educate them by saying, “let me show you the benefits you’ll experience using this tool.” You’ll persuade them to be open-minded by saying, “this tool will allow you to conduct more effective calls and close more deals.”

Rather than using a top-down approach, applying EQ skills paves the way for you to make sales reps stakeholders in their own success. In turn, this leads to the final component of EQ. How do you inspire and drive change, productivity, performance, and culture? Through motivation.



Salespeople are not all created equal, so it’s important to remember that different reps are motivated by different drivers.



Comprising about 25% of the sales organization, under-performers need more guidance, coaching, and training to make numbers. We look at things like their engagement, completion of onboarding, certifications, and core competencies. These reps tend to be motivated by quarterly bonuses and pressure. We spend a lot of time prioritizing the under-performers and working with sales managers to understand their gaps. We work with these individuals on self-awareness so that they know how to identify their strengths and weaknesses, and we find ways to continuously build their confidence.


Rock Stars

These sales reps typically represent about 20% of the sales organization, and they knock down any target that stands in their way. They’re motivated by money because they have extremely rewarding commission rates. Sales enablement must be careful with this group, as we tend to ask a lot of them because they’re good at what they do, and we want to tap into that to transfer their techniques and knowledge across the sales organization. These reps are stars for a reason, and it’s usually one-part skills and natural talent, and one-part work ethic. It’s important that enablement doesn’t over-use this group—though rock stars usually are happy to help fellow colleagues, they’re not willing to do it at the expense of their own success.


Core Performers

Making up about 55% of the sales organization, core performers move the needle and perform—but get the least amount of management’s time and attention. Core performers are motivated by money, especially sales contests. They don’t get as much recognition as the rock stars, so are highly motivated by a variety of recognition and incentives.

Traditionally, core performers have served as great peer mentors. They love to be included in shout-outs during weekly sales updates, posts on LinkedIn, and in team meetings. They’re a great group to use when creating sales spotlight sessions and speaking to new hires on “day in the life of” experiences. Sales enablement professionals need to spend more time prioritizing this group—they work hard and are extremely skilled and knowledgeable. They’re also on the cusp of being rock stars, and the company’s success depends on getting them to the next level.

Leveraging the Role of Enablement

At the end of the day, sales enablement professionals must know what our sales teams consider important. And we need to find opportunities to show sales reps that enablement is aligned with the company’s vision and goals—studies show that people are more willing to work harder and longer when they share a common goal. It also helps us level-set expectations with sales managers and leaders.

Sales behaviors drive performance. Successful sales enablement teams focus on identifying, measuring, and coaching effective sales behaviors. We need to know what “good” sales rep behaviors are, emphasize learning by doing, promote change for new behaviors to stick, and measure everything to determine what worked well and what needs adjusting. Most importantly, we must actively listen to our reps and advocate for them.



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