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Walk a mile in the buyers’ shoes. That’s empathetic selling - changing your perspective and actually relating to the prospect’s troubles or pain points instead of throwing darts in the dark that may or may not land. It helps you to take a closer look at their thoughts and feelings and understand how your solution can fit in.

In session 4 of our Outbound for Dummies series, Ashleigh Early, Co-host and Co-founder of Across the Pond and Over the Rainbow, shares everything you need to know to cultivate empathetic selling, starting today. Quoting Ashleigh, this is what empathetic selling truly means -

“Empathetic selling is approaching everything from the perspective of ‘What are they thinking?’, ‘What are they feeling?’ And ‘How can I help them in their journey?’ Versus coming at it from a ‘how do I get them to do what I want?’ angle. So the first question isn't, ‘How do I get them to take the next steps?’ It should be - ‘What are they dealing with?’ ‘What's going on in their life?’

Because you cannot get to the next steps until you understand that. So, it's really about taking a step back, taking yourself out of the equation and just focusing on what's happening for your prospects, and your clients before you move into the classic sales motions we are all overly trained on.”

Below is an excerpt from her session.

How Do You Sell with Empathy?

You start by asking questions. 

And not any questions. Start any prospect interaction by asking better prospecting questions to probe further and dig into the whys and hows before you get on with your usual product pitch.

Questions like - What's going on? What are you dealing with? Are you having this problem? - are perfect to bring out the empath in you. Based on these responses, you need to tailor your pitch.

Stay away from a ‘Would you like to buy?’ question. Instead, you can do - 

“Hey, the last time we spoke, you mentioned X. I didn't get a chance to ask you about that. Can you tell me more about what you meant? Or has that changed? I’d love to know more.”

Understand what's going on in their world. Don’t quickly jump the gun after identifying the pain. Delve deeper to understand the cost of the problem. 

Get the answer to this - ‘What is the problem leading to?’ 

As Ashleigh says, “We can't dive in and be the nosy friend who knows it all and start giving a million suggestions. When my friends start venting, I now go, okay, do you want me to listen? Or do you want me to coach?”

Be Where Your Prospects Are

Challenge your reps to not check social media until they've spent at least 10-20 minutes reading two articles that their prospects’ would be reading. 

Go to the sites you think they could be surfing through and check out the articles. Even if you don't understand a lot of it, you're getting used to the language, you're seeing what's on top of their mind, and you'll be shocked how much of it comes up during your conversations. 


How Scalable is Empathetic Selling? 

You don't have to sacrifice any activity to be selling empathetically. If anything, it should make you faster. However, where a lot of people get bogged down is the research, and they think they need a lot of research to find something to be empathetic about. 

That's a common misconception.

You don't need to do extra research. It's all about understanding those broad-set personas and combining that with individual, prospect-based research, i.e. about their specific company, online posts, etc. 

It's about utilizing the research and going, ‘How would I react in this situation?’ Your goal should be to understand and empathize with the persona in a broader sense. 

The Need for Active Selling

You need to listen to understand and not listen to respond. Interruption is the biggest mistake you can make while your prospect is sharing their pains and story. 

Here are 2 more tips by Ashleigh to become a better listener: 

1. Take all your notes on the left-hand side and put questions, comments, key dates, etc. on the right. When you’re listening, you’re not thinking about how to respond. So, with this method of note-taking, once your prospect is done with their reply, you can look at your notes and quickly pick up the question you need to ask. 

2. Anytime someone uses an unusual word, ask them to explain it further. This shows you’re not agreeing for the sake of it, but really want to understand their point of view.

Overcome these Challenges

What should you keep in mind when you’re trying to add some empathy to your sales process?

  1. Don’t close too soon. Once you identify the pain, don’t immediately start closing - you still have to go deeper understand their pain points and see the bigger picture. 
  2. Make sure you don’t revert to your older habits. Learn from each and every call and become a better version of yourself.

    Hot tip: While on a demo call, switch off your screen sharing when you’re opening the floor for questions. That way you can break the monologue. 

Level up your listening skills. Notice the cues while on a call and pay close attention to them. Don’t listen to think, but actively listen without interrupting.

An Environment of Empathetic Selling 

Do you need a good hold over emotional intelligence? Yes, and no, says Ashleigh. 

You don't have to have a really high emotional intelligence. You can just work really hard and focus on making sure you're actually listening. Of course, it does become a lot easier if you are more emotionally inclined and intuitive.

There are two things you can do to make your sales team put empathy first. 

  • The simplest thing you can do is just start doing exercises where you force your sellers to speak in the prospect’s or your customer's language. For example, something as simple as having everyone on the team rewrite persona cheat sheets and have them answer five questions about the persona as if you are that person.
  • The second step is to make sure that all of your documentation is written customer centrically.  

If you want to listen to Ashleigh's entire session recording, you can check the video below. It has all the learnings to become an empathic listener and seller in today’s world. Good luck out there!

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