How to Demonstrate Empathy Even When You Don’t Know How

Demonstrating empathy is like putting on someone else’s shoes—stepping into their experience to understand their journey, struggles, and triumphs from their perspective. The challenge for many leaders is that empathy doesn’t always come naturally, especially when the situation is unfamiliar or difficult to relate to. However, empathy isn’t about having all the answers—it’s about showing up, listening, and acknowledging emotions, even when you don’t fully understand them. A simple phrase like, “I can see this is really challenging for you” can build trust and connection, reassuring others that they are seen and heard.

From Sympathy to Empathy: My Personal Lesson

During the COVID-19 lockdowns, my sister was homeschooling three children between the ages of six and nine while juggling her own responsibilities. She shared how exhausting it was—keeping them on task, preparing meals, supporting their learning, and then managing the rest of the day once school ended at noon.

At the same time, one of my direct reports was homeschooling a child while caring for a second in daycare. Initially, I struggled to understand why she seemed overwhelmed and had difficulty meeting deadlines. But after hearing my sister’s experience, I had a clearer picture of the immense pressure working parents were under. My perspective shifted from thinking, “Thank goodness that’s not me” (sympathy) to “I can see why this is so tough for her” (empathy). That change allowed me to offer better support, whether through flexibility or simply acknowledging her struggle.

“Empathy doesn’t require that we have the exact same experiences as the person sharing their story with us... Empathy is connecting with the emotion that someone is experiencing, not the event or the circumstances”.  Brene Brown.

The Leadership Gap in Empathy

Many leaders recognize the value of empathy, but there’s often a disconnect between perception and reality. Research from Harvard Business Corporate Publishing found that while 78% of senior leaders believe demonstrating empathy is important, only 47% think their companies are doing it effectively.

Bridging this gap is critical because empathy drives:

✔ Better communication by fostering openness and understanding.

✔ Stronger trust by showing employees their feelings and perspectives matter.

✔ Greater collaboration by creating an inclusive, supportive team environment.

✔ Psychological safety by allowing employees to share concerns without fear.

✔ Reduced workplace conflicts by resolving misunderstandings with compassion.

 

Without empathy, communication breaks down, trust erodes, conflicts increase, and employee morale suffers. The good news? Empathy is a skill that can be strengthened—no matter your natural leadership style.

8 Practical Steps to Build Empathy as a Direct Leader

1. Pause Before Responding

Direct leaders often jump to problem-solving. Before responding, take a moment and ask: “Am I acknowledging emotions before addressing the issue?” A simple “That sounds frustrating” can make a big difference.

2. Listen to Understand, Not Just to Respond

Instead of rushing to solutions, focus on active listening:

• Use short acknowledgments (“I hear you”).

• Repeat key points (“So what I’m hearing is…”).

• Ask clarifying questions (“Can you tell me more about what’s challenging?”).

3. Ask Instead of Assume

Instead of assuming what someone needs, ask:

• “How can I best support you?”

• “What would be most helpful for you right now?”

  This ensures your response is meaningful, not just reactive.

4. Recognize That Facts and Feelings Can Coexist

Being factual doesn’t mean dismissing emotions. You can acknowledge feelings and focus on solutions:

• Instead of “We just need to move forward,” say,

• “I know this is frustrating, and I also believe we can find a way through.”

5. Be Mindful of Your Tone and Delivery

Sometimes, how you say something matters more than what you say. A softer tone, open body language, and a slight pause before responding can make your directness feel supportive rather than dismissive.

6. Get Comfortable with Emotional Discomfort

If you’re naturally logical, strong emotions might feel uncomfortable. But you don’t have to fix them—just acknowledge them:

• “I can tell this means a lot to you.”

• “That sounds really difficult. I appreciate you sharing this with me.”

7. Practice Small Daily Acts of Empathy

Empathy isn’t just for big moments—it’s built through small actions:

✔ Checking in with a team member (“How’s your week going?”).

✔ Noticing and acknowledging effort (“I see how hard you worked on this—thank you.”).

✔ Offering flexibility (“Would it help if we adjusted the timeline?”).

8. Reflect and Adjust Over Time

After conversations, take a moment to reflect:

• Did I acknowledge emotions before responding?

• Did I ask rather than assume?

• Did I listen fully before offering solutions?

Empathy isn’t about changing who you are—it’s about deepening your awareness of others. As

Oprah Winfrey wisely said: “Leadership is about empathy. It is about having the ability to relate to and connect with people for the purpose of inspiring and empowering their lives.”

Even when you don’t fully understand someone’s emotions, showing up, listening, and acknowledging their experience is what truly makes a difference. 💙