Leading with Empathy

An empathetic leader is able to build an inspired, committed team.

I landed an ideal job while I was still in grad school: Assistant Director of Development at the Renaissance Theatre.

I was completing a master’s degree in Arts Administration in Virginia at the time of the job posting, so to get hired in my field of study in my husband’s hometown was a dream come true. I arranged to finish my degree remotely, we quickly found a new job for my husband, and rented an apartment in Ashland, sight unseen. 

Very soon after being hired, we found out we were pregnant with our first child. I was thrilled, of course, but I was also very concerned about navigating the logistics of this new season of my life, and what messages it might send to my new employer. I didn’t want to come across as uncommitted in my job.

I was uncertain what maternity leave would look like, much less childcare. I was fearful about how my pregnancy might negatively impact my team and my job role.

So, when I met with my boss to share the news, I was unprepared for the tremendous amount of empathy and kindness with which I was met. I was aware that the news I shared with him, while exciting for my family, created complications for him. Yet, he was thrilled and empathetic with my concerns.

He shared a story about when a similar thing had happened in his own life, and together we figured out a way for me to take an adequate leave without foregoing pay, and without requiring a temporary replacement. He helped me to arrange a partially remote work schedule to ease the burden of childcare. 

The empathy my boss showed me during that time deepened my sense of belonging and commitment to the organization, and I have never forgotten the way that he met me in my fear and concern with understanding and helped guide me to a solution. 

Empathy is about meeting someone where they are, letting them know that you see them, that you’re there with them, that you understand them and that what they’re feeling is valid. Empathy is not about pity, it’s not about fixing, and it’s not about looking on the bright side. There is a time, however, for guiding someone out of the pit of despair if you know the way and lending perspective, but never until you’ve fully listened and spent the time the other person needed. 

Admittedly, I’m still learning a lot about how to best lead a team. The team I lead is filled with some of the most fantastic people I have ever known, but difficult conversations arise in any relationship or workplace. In those moments, I’m reminded of how I feel when I am shown empathy by those leading me, and I strive to do the same.

During a difficult conversation, I do my best to quiet my desire to “fix” and take a moment to fully listen, which, of course, requires that I also quiet my voice and allow the other person to speak what’s on their mind and heart first. 

In tense moments, I remember who I’m speaking with, their capabilities, their character, their value, and what makes them truly great. I think about how it feels to be where they are, and I think about what I might want to hear in that conversation. I remember moments when I’ve felt the same emotion or faced a similar obstacle.

In a difficult conversation, if you truly listen and fully see and know the person who’s vulnerable in the conversation, then they will not only feel safe with you, but they will also be open to your guidance.

I believe that leading with empathy means embodying this script in difficult moments: “I get it. I see you. I know you. I’m with you. Let’s try this path forward together.” 

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Colleen Cook works full-time as the Director of Operations at Vinyl Marketing in Ashland, where she resides with her husband Mike and three young daughters. She's an insatiable extrovert who enjoys finding reasons to gather people.