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If you google what the characteristics of successful salespeople are, empathy is typically high on every list. It’s the E in SHERPA for a reason.

Unfortunately, few people actually experience empathy from the salespeople they deal with. Why does this dichotomy exist? If salespeople know they should be empathetic, why don’t we sense that from them during sales conversations? 

It’s because empathy is hard. Plain and simple. 

It’s hard enough in everyday life, but in sales, it’s even harder.

Even when you have it, it’s difficult to express it without skeptical prospects believing it’s a tactic. And it’s difficult for skeptical salespeople who have been burned so many times to maintain empathy with their prospects.

Do you see the empathy-free spiral this creates?

As challenging as it can be, it really is an essential part of being a successful, confident, and authentic salesperson. If you truly want to help people, you have to empathize with their point of view.

How do you develop one of the most important characteristics of successful salespeople?

If you know me or have seen my podcast, Sales Throwdown, you know I’m a C on the DISC personality spectrum. C’s often struggle to sense and express emotions because they are primarily task-focused and fact-driven versus people-focused and gut-driven. 

So for me, empathy is even harder than it is for most people. To overcome this challenge, I had to build a process.

Building Empathy Into Your Process

Most people don’t feel comfortable sharing their feelings, struggles, or fears with somebody they don’t know very well. But knowing these things helps us help them. 

That’s what makes empathy one of the most important characteristics of successful salespeople; you have to be able to make people comfortable.

That’s why I spend more time in sales conversations asking questions; it helps me better understand where people are coming from. I don’t have great intuition about how people are feeling, so I ask. Because I know I’ll have to ask, I start by setting expectations.

Questions I ask to set expectations:

  1. I’m going to ask some questions that may be uncomfortable, but they allow us to talk more about whether we can work together. Is that okay?
  2. If at any point you know this isn’t going to work for you, can you let me know?
  3. May I do the same?
  4. If we end this conversation with a yes, can we decide what the next steps are together?

I tailor these differently based on who I’m talking to, but that’s the gist of it.

The first question allows me to ask about their budget, their pains, and what expectations they have for a possible solution. I also ask about their decision-making process, who else is involved, and basically any other question I need to fill potential gaps between the discovery conversation and closing the deal. 

The second allows them to say no as soon as they’ve made their decision. And the third allows me to do the same if I believe we’re not the right fit for each other. 

Remember, you want to be able to fulfill a client’s expectations, and if you can’t, you shouldn’t take them on. That only hurts you both in the long run, no matter how badly you need to fill your quota. 

The fourth sets expectations for the future: when they’ll give their final decision, when I’ll send the contract, things like that. When we set those expectations, I’m allowed to remind the client of them. 

Why setting expectations is important

No matter how well-intentioned people are, we all get busy. We forget, or priorities change, or disasters strike. You never know. And this is where most salespeople get burned. It’s where the beginning of that jaded, negative skepticism comes from.

We’ve all had prospects that seemed super excited and ready to go, and then they disappear. We chase and chase, but we can never catch them again. It’s usually not their fault; it’s rarely malicious. But because it’s so common, we build up a wall.

Setting expectations helps prevent that. You’ll have a better chance of staying in touch, closing the deal, and maintaining empathy if something goes wrong. 

Even if that doesn’t work and they don’t do what they promised, it’s vital to put yourself in their shoes.

You’re not perfect either. I know I’m not. I have an inbox full of emails I need to deal with, tasks I’ve been putting off. It happens to all of us. 

Just because they didn’t fulfill their part of the bargain doesn’t mean they knew they wouldn’t. It requires empathy to remember that. And it takes empathy to open that line of communication to find out where they are and how it affects your relationship. 

That’s where both skepticism and helpfulness come back in. Reconnect with them. Try to get back on the same page if possible. You might have to dig a little deeper to find out what went wrong. If you do, let them know that you’re there to help, not make their lives more stressful. 

Empathy Really Begins by Listening

Setting expectations and building questions into my process allows me to listen closely and focus more intently on the conversation. 

Typically, we all listen to somebody just until something they say triggers our next question or observation. And then we lose focus on the conversation because we become stuck in our heads waiting to talk again. 

A well-built and well-used process prevents that. (Also, practice is huge here. The more you practice asking questions, the less you have to think about them.)

Your process and empathy will also help you be more flexible, believe it or not. Putting your full focus on the conversation means that you might pick up on things others would have missed. Because your process is ingrained, you can sidestep your typical next question with one that addresses whatever that thing is. 

That’s how you build mountains of trust. They’ll feel heard, and they’ll feel more comfortable having deeper conversations.

Fundamentally, empathy means putting their needs before your own, something all helpful salespeople strive to do. 

Honing the Key Characteristics of Successful Salespeople

Self-improvement is never easy, and even the most empathetic people can work on directing it more intentionally.

Easy or not, it IS that important. Empathy helps you avoid resentment. Every ‘no,’ every missed deadline or lost prospect, and every question asked of you will feel like a challenge. But selling is going to be nearly impossible if you walk around with your hackles constantly raised. 

Instead, keep in mind that everybody has their reasons for making their decisions, even if you don’t understand them. Everybody gets busy and drops the ball sometimes, plain and simple. Very few people are out to get you or purposely make your job harder. 

Empathy is a muscle that you have to develop. The more you use it, the stronger it will get. It’s a characteristic all successful salespeople have. It’s not just about selling more; it’ll help you be more confident and happy in both your job and your life. 

Want to know about more characteristics of successful salespeople?

Find out what being a Sales Sherpa means and how this sales strategy can help you improve all of your relationships.

The S in SHERPA stands for Skeptical, the (positive!) mindset you need to have effective sales conversations.

H stands for Helpful because your intent drives your ability to be the best salesperson you can be.  

Another trait that makes a sales rep successful is being Resolute.

P represents Practiced since learning how to do anything takes practice, including becoming a successful sales rep

The last letter in SHERPA stands for Accepting because it’s one of the most valuable traits a successful salesperson can have. 

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