Leading With Empathy: How to Build Trust In Times of Uncertainty

Last verified May 24, 2021

Empathy is the ability to sense other people’s emotions, coupled with the ability to imagine what someone else might be thinking or feeling. The same empathetic practices we apply in our own lives can help us communicate in selling scenarios. Particularly during times of severe uncertainty, like the one we are living through now, it’s important to apply genuine empathetic outreach. Let’s break down what empathy selling is, the three key principles to follow, and how to practice it effectively with audiences at each stage of the customer journey.

Let’s be honest, selling anything during such a complex time can feel uncomfortable, hopeless, and, at times, downright ridiculous. But if it’s your job, we’re here to help make it easier for both you and the customers and prospects that you’re reaching out to. Empathetic outreach starts by acknowledging the happenings in the world around us and giving people the space to come together over a shared experience.

Many of you have heard the quote, “Be kind, for everyone you meet is fighting a hard battle” thought to have originated from the Greek philosopher Plato. We tend to form assumptions about people and base our actions, communications, and behaviors towards others on those assumptions. This can feel like a human default-setting and it’s easy to find ourselves in this pattern of assumption-driven behavior without even recognizing it. By centering your selling practices around genuine empathy you'll set a foundation of trust and open up an effective dialogue.


Defining empathy selling

Empathy selling requires putting yourself into the mental and emotional position of a prospect or customer throughout the sales process. When you show that you understand the problem they’re faced with, that helps build trust. The concept of empathy selling is not a new one, but the ability to showcase that empathy is more important than ever.

3 key principles of empathy selling: 

  1. Ask rather than assume

  2. Humanize and contextualize

  3. Give first

Empathy selling at each stage 

We’re going to cover how to shift your approach to ensure that you are leading conversations with empathy across each stage of the customer journey: 

Engaging with unaware prospects 

This is an audience of potential buyers that don’t know you yet, so they are getting a first impression of you through whatever initial message you’re sharing. The key principle to keep in mind at this stage is: ask rather than assume. 

Communicating with built-in assumptions can lead to subtle, or not so subtle, pain-based messaging.

This typically sounds like, “Given that you’re in “X role” you must be faced with “Y problem” and here’s how we can help.”

Challenges with that message:

  • It can seem tone deaf—especially in such a turbulent landscape. Completely glossing over current events can make your audience feel like your outreach is ingenuine. 

  • It feels assumptive. Even if you do acknowledge happenings outside of work, this messaging asserts that you already know what their problems are without asking first. 

This type of outreach is overdone and can come across as lacking compassion. Changing the subtleties of your messaging can go a long way in building trust with new potential buyers. 

Examples of empathetic cold messaging: 

  • Reference and acknowledge current events. For example, jump off with, “The past few weeks have been challenging.” 

  • Relay authentic support by saying things like “How can we best support you during this time?” or “Is there an organization that you care about that we can contribute to on your behalf?”

How do we know that those subtle changes in messaging have any tangible impact on prospecting? We’ve tested it ourselves! In the wake of the COVID-19 pandemic we reached out to prospects by acknowledging and addressing current events, asking how we could best support, and offering to make a business or cause that they care about. This new approach to cold outreach email saw great results with a 10% increase in open rates and an uptick in responses. 

Even if we aren’t pushing prospects to meet with us or try our product right now, we’re building trust in this initial relationship and setting a strong foundation to build from.

Messaging to engaged prospects 

These are folks who are in a buying cycle with us but haven’t purchased yet, so they’re already familiar with your product and likely a couple team members. The principle to hone in on with messaging at this stage is: humanize and contextualize. 

Since you’ve already had some cadence with this audience, the outreach is generally in the form of a follow-up. For example:


“Wanted to follow up re: your evaluation… Here's what's new… You might be interesting in this offering."

There’s nothing inherently wrong with this messaging but, again, it can seem robotic, especially in the wake of unrest. It leaves the elephant standing in the room—unaddressed. 

Shifting messaging to engaged prospects: 

  • If there are huge stressors outside of work that we are all facing—address that elephant in the room! 

  • Add a human element to your messaging. What personal challenges are you tackling? 

  • Using humanizing language like “How are you holding up?” “I remember you mentioned X” to show that you are listening and engaged rather than on auto-pilot mode. 

  • Offer something of value (ex. a donation on their behalf, links to helpful resources, or even a small gift card for a lunch on you!).

Relating empathetically to customers 

Lastly, we’ll talk about customers (arguably the most important group). This is the relationship where there should be an existing level of trust that needs to be maintained and built upon. The reality is that a lot of companies are cutting their spending right now, and it's possible that your tool or service could be on the chopping block.

The principle we’ll focus on at this stage is: give first. 

Finding creative ways to be a value add to them during this time, beyond just what your product does for them from a business standpoint, is huge for strengthening this kind of relationship. The traditional messaging outreach with standing customers centers around ‘business as usual.’ 

Usually this sounds like, “ Hey how’s it going? How is your team? Let's talk about what’s new with our features, potential renewal or up-sell discussions.” 

Those are still points that need to be addressed, but the way that we go about addressing them can drastically change your customers impression. But when business isn’t as usual this type of messaging won’t work. It will leave customers feeling disregarded and put you at greater risk if cutbacks do come. 

Applying empathetic messaging to existing customers: 

  • Again, addresses the elephant. Starting off with vulnerable language such as “This is a tough time for all of us, how are you holding up?” 

  • If it’s a possibility for your business, provide discounts or special offers, especially for your customers that may be hurting based on their industry. 

  • Ask, “Is there anything I can do personally to support you?”

  • Provide them with templates and resources that could be helpful or relevant to their role. 

You can see throughout the customer journey how important it is to really take a look at communications and make sure that empathy is present at each stage. Customers may not remember what the subject line of your cold email was or exactly what the small gift card you gave them was for, but they will remember how those acts of empathy made them feel. The sentiment will stick. These personalized subtleties in your language will strengthen your relationships and ultimately benefit your business.