Dr. Andrea Hollingsworth
Hollingsworth Consulting

“How often should I cry-hug my direct reports?”

Hakeem posed that question to me a few minutes before I began my flagship workshop on Compassionate Leadership with him and other top leaders in his organization.

Chief Data Officer at his company, Hakeem was already a highly respected and well-loved leader. And he was fully on board the compassionate leadership boat. He just needed to know one thing: Precisely how touchy-feely-weepy should he get with his people, and how often should that happen? What kind of cry-hug schedule should he set, here?

It’s pretty common for people to hear “compassionate leadership” and assume it boils down to becoming a misty-eyed wannabe therapist at work. This characterization feels weak, soft, squishy, ineffectual, and inappropriate.

The good news is that it’s also wrong!

Let’s clear things up and explore four things compassion is not.


1. Compassion Isn’t Empathy 

While empathy involves resonating with someone’s experience and emotions, compassion goes a step further. It not only “gets” the other person’s experience, it takes action to alleviate suffering. Compassion says, “I see your distress” and“I’m going to support/help you in X, Y, and Z ways.” 

Compassion doesn’t stop at emotional resonance; it is intelligent and strategic about helping ease pain and bring about betterment.

2. Compassion Isn’t a Fixed Personality Trait 

Compassion isn’t something you either have or don’t have. It’s a core leadership competency that can be developed and honed. Just like any skill, with practice, conscious effort, and commitment, anyone can become more compassionate and make a positive impact. 

Growing up, my dad wasn’t exactly known for his compassion. Though he had a huge heart of gold, he could often be tough and dismissive. However, as he got older, he started to change. He began to prioritize listening over speaking, concern over curtness. He found creative ways to support and encourage me when I felt overwhelmed. My dad consciously worked on becoming more compassionate, and it made a positive impact on him, me, and many others.

This personal transformation aligns with the findings of cognitive neuroscientists. Neuroimaging studies suggest that engaging in compassion practices can reshape the structure and function of the brain.

While compassion may come more naturally to some, it is a skill that can be developed by anyone who is willing, committed, and properly guided.

3. Compassion Isn’t Pity

This is for two reasons.

First, pity looks at pain from a distance, whereas compassion risks getting in there. There’s a wise and boundary-conscious involvedness that comes with compassion. It’s the difference between saying, “Oh, you poor thing, how dreadful! I’ll be over here feeling sorry for you” (pity), versus, “Hey, we’re all human, we all have to ride the struggle bus sometimes. I feel you, and I’m going to do what I can to support you in this” (compassion).

Second, pity reduces the sufferer to just their pain, whereas compassion sees the whole person. When people are struggling at work, there are always a great many variables at play. A compassionate leader will take the time to understand and strategize around those variables, but also to view the person in light of their strengths, potentials, and capacities for resilience.

Compassion makes someone feel humanized, validated, and empowered. Pity makes someone feel like hurt is all they’ve got.

4. Compassion Isn’t Weak

According to clinical psychologist Paul Gilbert, the essence of compassion isn’t kindness, it’s courage. He’s right.

It takes strength to confront pain, express support, and make difficult decisions in a humane, connected, and effective manner.

Compassionate leaders do hard things with heart. 

When they deliver tough news, they lean in instead of shutting down. 

When they make unpopular decisions, they choose connected dialogue over mechanistic indifference.

They balance an exacting mind with an open heart.

And they create spaces where people can be fully human, even in the most challenging of circumstances. 


There may be a time and place for cry-hugs in the workplace. But Hakeem, for one, was relieved to hear that compassionate leadership doesn’t boil down to them. And I hope you are too!

About Andrea

Dr. Andrea Hollingsworth is Founder and CEO of Hollingsworth Consulting, author of the bestselling book The Compassion Advantage (2024), and one of today’s leading global experts on compassionate leadership. Since 2008, she has been studying, speaking, and writing about the science and spirituality of human emotions and relationships. Her articles have been published more than a dozen times in peer-reviewed journals, and she has taught at prestigious institutions like Princeton, Boston University, and Loyola University Chicago. In addition, Dr. Andrea has delivered talks to audiences at some of the top-ranked universities in the world—including Cambridge University in England and Heidelberg University in Germany.

Dr. Andrea spends most of her time inspiring leaders and teams to use The Compassion Advantage to build supercharged organizations through cultures of care— especially in times of challenge and change. Andrea lives with her family in Minnesota where she cheers hard at her son’s soccer games and relishes every opportunity to visit the north shore of Lake Superior.