Leading with Empathy

Empathy is one of the greatest gifts in connecting humanity to one another.

Scout, the young female narrator, shows interest in a reclusive, phantom-like neighbor, and following a few attempts to get the neighbor, otherwise remembered as Boo Radley, to come out of his house, her father, Atticus, tells Scout it’s not kind to bother someone you haven’t taken the time to get to know. He attempts to enlighten her childlike perspective and explains, “You never really understand a person until you consider things from his point of view… until you climb in his skin and walk around in it.” 

Beyond the odd metaphor of stepping into someone else’s skin (I always get a weird image of snake skin here), I try to reflect on how important it is to consider the point of view of others. Sometimes we forget everyone we encounter has a story. The assumptions and narratives we create about other people without getting to know their stories, from their point of view, are what often keep us from connection and understanding.

As a leader, it is so important to connect with and understand the people you are leading. We lead better when we know who we are leading, and people follow better when they feel known and understood. Empathy is the ability to not only share the feelings of others but attempt to understand those feelings. Sharing and understanding what others on your team are going through or have gone through can bring your leadership to another level. 

When a leader leads with empathy, the team that works for you, serves with you, or learns from you shifts from not just seeing their leader as someone they respect, but as someone who respects them, cares for them, and understands them. At our deepest level, we all want to be loved and understood. Here are a few tips to try as you attempt to empathize and build relationship with those you lead:

Make time

Opportunities to show empathy will present themselves all the time, however, finding the time to step into those opportunities are few and far between. When turning in an assignment, I might have a student write a comment on their paper that they had a hard weekend, providing an excuse for why it’s not complete. It’s easy to brush off moments like this, grade the paper as-is, and move on with my day. It’s harder to see this as an entry-point, a chance to find a moment during the class period and check in. At my best and most aware, I try to take advantage of these moments and find a spare minute or two during class to go to their desk and address the comment.

Making time for these interactions can be so hard because it doesn’t seem “productive” in the moment. There are so many other things I could or should be doing to help students, but I’ve come to find moments like these actually help my students more because they recognize I truly care about them. Feeling cared for often reciprocates feelings of care back. Students who feel seen and known are so much more likely to complete assignments on time, ask questions, or work harder because they know they will receive support from me despite the outcome of their assignments. 

Ask questions

Along with being a high school English teacher, my husband and I also pastor a church in Washington state and have been the lead pastors there for eight years. We spent a few years as youth pastors prior to becoming lead pastors. Being a youth pastor can be so intimidating because of how disconnected (and old) you can feel trying to connect with young people. Even a few years out from high school and college, you can feel so irrelevant when it comes to connecting with young people about what is in-style or popular. However, what I learned early on in youth ministry and teaching is that I didn’t need to know all the new music artists, social media platforms, and Netflix shows; instead, I needed to know the right questions to ask so the students would be the ones talking, and not me. No one needs a millennial attempting TikTok dances to try to be relevant (although many of us have tried…). 

The funny thing is, people often feel close to you when they reveal things about themselves. You can ask someone ten questions, they can talk for the next hour, and if you’re engaged in those questions, then they can feel a closeness with you without even engaging in your side of the questions. Questions allow entry points to information about people, and when we learn about others, we develop an understanding of how someone else feels that we wouldn’t otherwise know if we hadn’t asked.

Be a learner

Asking questions is great, but it can become insignificant if we don’t attempt to learn. There have been a few times as a teacher and pastor where I’ve asked questions without the intention of learning. I’ve created a bridge to see someone’s world, but I didn’t actually cross over to see the other side. 

It’s important to not only ask good questions, but also attempt to understand the answers. Understanding involves follow-up questions! Be a learner. What confuses you? What do you find interesting? How did they get there? Don’t just jump on the first opportunity to share your own story (although this can be a great technique to connect with someone), but instead ask more questions that lead towards clarity or how that person feels about what they’re sharing.

My husband is one of the best leaders I know because of how he cares for the people he leads. In his one-on-one meetings with our church staff, he asks them the same three questions every week:

1. What’s the best thing you’re doing in your job? 
2. What’s the worst thing you’re doing in your job? 
3. How can I help you do your job better? 

Asking someone what is the best thing they’re doing in their job allows the opportunity to celebrate with people you’re leading. We can be so critical as leaders on those we lead that we often miss the little wins! When you celebrate the little wins, you experience big wins together.

Asking what is not going well in their job can be a hard question, but it allows for space to recognize short-comings and expose weaknesses. Stepping into someone else’s shoes and asking them how they see how they’re doing (instead of you just pointing these things out) helps you as a leader recognize what they see (and what they don’t). 

Finally, asking how you can support someone makes them feel like you care about them. Those you lead should feel like jewels, not tools. When you care, they’ll care. 

Once you provide time to ask questions and learn, the last tip for leading with empathy is to follow up.

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