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Improving sales conversations through empathy and active listening



To start off with what has already become a cliche, 2020 has been a rough year. As we enter these last couple of months, with many of us still in at least partial lock-down, it can be very easy to feel completely run down and out of breath. Those of us in sales world are having a uniquely difficult time due to an uncertain and equally worn out market. Between an election year, the novel and disruptive COVID-19 virus, and the upcoming holiday season, many people and companies are doing exactly what one would expect: Hunkering down for winter. Something we cannot lose, however, even with all the Zoom fatigue and evaporating budgets and constantly retreating goal posts, is our ability to truly listen to what people are saying to us. 

In the sales environment, it’s not uncommon to feel that every conversation with a prospect is the same one over and over again. You’ll hear a lot of the same objections, a lot of the same excuses for missed appointments, and a lot of other salespeople talking about experiencing the exact same thing. This is a trap. Every single conversation can’t possibly be the same thing over and over again because we talk to so many different people. So many different walks of life, personal experiences, and ideas are encapsulated in the people we have the opportunity to speak with every day. The only way to not only survive but thrive is to bring a genuine sense of curiosity and empathy to each interaction. The only way to do that is to practice active listening.


Let’s look at an example. 

It’s late October and your monthly quota is looming. There’s one deal, however, that can push you over the edge and get you to your goal. You’ve been talking to Bethany, your point of contact at this company, for weeks. The initial discovery call went great and there’s a clear use case for the product you’re representing. The timeline you discussed with her is perfect for getting you to your goal. However, she’s recently had to reschedule the last couple of meetings and you’re starting to get worried. Just now you’re able to reconnect. You jump on what has to be the fifth video call you’ve had with her and she says, “I really appreciate your time, but we’re not going to be moving forward with this right now.” You try to understand the reasoning, but the decision has been made. Your heart sinks as you realize that the window for hitting goal this month has closed. You experience all five stages of grief within a couple of minutes of the call ending before sinking into the tired old excuse of, “I guess some people just don’t appreciate what I’m trying to do here.” 

If we take a step back for a moment, something really important for us to remember is that Bethany is her own person with her own goals. It’s entirely possible she was excited about what you were offering, but it’s not a good fit for them right now. Yes, it’s unfortunate you’re not going to hit goal this month, but what is she currently going through? Did you ask? If we go back to earlier in your conversations with her, you remember she did say something about a very important deadline she was working on but it’s not even in your notes because it didn’t seem notable to you at the time. Was this what caused them to put things on hold? 

It shouldn’t be difficult to diagnose exactly where things went wrong in this hypothetical scenario, but I think it’s safe to say that anyone who’s been in a sales role has experienced this type of call. Even the best of us deal with rejection - it’s part of the deal. But if we practice active listening, it’s very likely we wouldn’t be counting on a deal like this one to get us over the finish line. The problem in the above situation is that we completely failed to recognize the other things on Bethany’s plate. If a prospect you’re speaking with specifically mentions other priorities or roadblocks, it’s imperative to ask more questions. Listen for the way they talk about their business and what’s on their calendar. Take those into consideration when discussing timelines or next steps. If somebody was to come out and tell you they were having a rough morning, would you respond by saying, “my morning’s been good, thanks for asking!” or would you take a moment to try and understand why their day has been rough so far?  

The example we’ve explored is pretty obvious, but even if the real-world cues aren’t quite as on-the-nose, what’s really important here is that active listening is nothing more than actually listening. That said, there are a couple things you can practice to hone your skill and engage in much more rewarding conversations both in and out of work:

Ask better questions

When someone says something that you don’t fully understand, it’s completely unhelpful to simply nod your head and act like you know what they’re talking about. Especially when it comes to people who, often rightfully, feel they know more about a certain topic than you do. Acting like you know what you’re talking about rather than encouraging them to explain is a sure tell that you’re not particularly interested in what they have to say and are most likely just waiting for your turn to speak. Additionally, don’t be afraid to dig deeper into things that are clearly of interest to the person you’re speaking to. It’s usually easy to spot when a certain topic is important to them so it’s good to ask specific questions to learn more and encourage them to elaborate. You can learn some really interesting stuff this way. 

Reiterate what they said

No, this doesn’t mean repeat things word for word. What this means is that when someone mentions a concern they have, for example, make sure they know you heard them. For example:

Statement: “I’ve found that implementing these best practices is a good way to get everyone on the same page.”

Response: “You mentioned wanting to make sure everyone is on the same page, right? Has this been a problem in the past?”

Reiteration will confirm the other person is being entirely understood and ensures their trust in the sales recommendation because you confirmed you heard their concerns and are making a decision based on their unique situation.

Get out of your own head and be present in the conversation

If we remember the earlier example, hitting quota was very much on the front of our mind. That concern dominated the conversation to the point where we missed crucial information in the sales conversation. If we spend our time with someone constantly thinking of the next thing to say or our mind is elsewhere, it becomes extremely difficult to pay attention to not only what is being said but how things are being communicated. This is difficult for those who are new to sales, especially when it comes to technical sales positions, as they’ve likely crammed their brain with so much knowledge or good responses they heard from someone else. They end up spending more time flipping through their mental reference sheet looking for the right thing to bring up next instead of finding something that truly works for the customer. The ability to relax and focus on what the other person is saying will take you much further in sales than simply being able to recite a feature for any given scenario.

There’s a lot more to talk about when it comes to active listening, but those three steps will go a long way to helping you stay more present and have better conversations.