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If you google what traits a great salesperson should have, empathy is one of the most common ones and typically high on every list. It’s the E in Sherpa for a reason.

But 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 hard as it is to have and express though, it really is a hugely important part of being a successful, confident, and authentic salesperson. If you truly want to help people, you have to be able to empathize with their point of view.

So how do we do this?

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

So for me, empathy is even harder than it is for a lot of people. I do have it though, and I’ve found ways to overcome this challenge. If you’re like me, it starts with having a process.

One of the biggest reasons I spend more time in sales conversations asking questions rather than talking is because it helps me better understand where people are coming from. Since I don’t have this inner intuition that people are feeling a certain way, I have to ask. And because I know I’ll have to ask, I have to start by setting some expectations.

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

So early in every conversation, I set some expectations. 

  1. I’m going to ask some questions that may be uncomfortable, but answering them honestly allows us to talk more about whether or not we can work together.
  2. If at any point you know this isn’t going to work for you, please let me know.
  3. I might have to do the same.
  4. If we end this conversation with a yes, then we’ll decide what the next steps are together.

It’s not quite so bluntly stated and it’s often tailored differently depending on who I’m talking to, but that’s the gist of it.

The first one allows me to ask questions about their budget, the pains they’ve been dealing with, 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 any potential gaps between the discovery conversation and closing the deal. 

The second one allows them to say no as soon as they’ve made that decision. And the third allows me to do the same if I believe there’s a reason that 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 or scope of work, things like that. When those expectations are set, I have the ability to remind the client of them. 

No matter how well-intentioned people are, we all get busy. We all 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 is so common, we build up a wall.

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

And even if that doesn’t work, that they don’t talk to their team when they’re supposed to and get back to you with an answer when they promised, it’s important 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 that they knew they wouldn’t. It requires some 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 the skepticism and helpfulness come back in. Reconnect with them. Try to get back on the same page if that’s possible. You might have to dig a little deeper to find out what went wrong, and if you do, let them know that you’re there to help, not make their lives more stressful. 

More than anything, empathy begins with listening. 

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

Typically, we, meaning practically all people, listen to somebody else just until something they say triggers our next question or observation. And then we lose focus on the conversation because we’re 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 your 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 is how you build mountains of trust. They’ll feel heard, and they’ll feel more comfortable having those deeper conversations.

At the end of the day, empathy is about putting their needs before your own, something that all helpful salespeople strive to do. 

Even then, it’s not easy. Without empathy, you can become jaded and bitter. 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. And very few people are out to get you or purposely make your job harder. 

Empathy is a muscle that you have to develop, and the more you use it, the stronger it will get. It’s an important trait to have, not just so that you can sell better, but so that you can be more confident and happy in both your job and your life. 

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