Follow us on LinkedInWe talk a lot about leadership, engagement, and innovation, but self-compassion is one topic that doesn't get nearly enough attention (yet is crucial to all of the above). Not in a fluffy, feel-good, "just love yourself" way. But in a way that even the most data-driven executive, maybe even Jeff Bezos himself, could get behind.
I’m speaking from experience - not just as an executive but as a practitioner. As the Chief People Officer at the San Francisco Museum of Modern Art (SF MOMA), my day isn’t just meetings and strategy; it’s being in the trenches and making decisions that impact people’s lives.
In this blog post, I talk about why self-compassion is the most underrated leadership skill and how it directly affects workplace culture, engagement, and even business outcomes.
Why self-compassion matters in leadership
When I was practicing law, I won a huge case - getting a motion for sanctions against opposing counsel. That’s incredibly rare. But two weeks later, the managing partner threw a red pen at my head because I asked him to sign off on a motion. I froze. Then, I emailed my law professor for advice, and he wrote back with, "Ro, you know exactly what to do. Stand up, walk out, and quit. Because we all learned in first grade that you don’t treat people like that."
I left law and moved into human resources (HR), and my first role was investigating diversity-related complaints. I discovered that most of these cases weren’t about diversity at all. They were about bad management and a lack of self-awareness and self-compassion.
I saw managers projecting their own insecurities onto their teams, which created toxic environments. And it wasn’t just about bad behavior—it was about the inability to reflect, own mistakes, and move forward in a productive way.
The workplace has changed. We’re now managing four generations of employees at the same time, and they have drastically different expectations. The disconnect between executives and frontline employees is real. Executives look at their diversity stats and say, "Look at our ratios, we’re doing great!" while employees say, "This is 75% terrible."
The gap isn’t in numbers - it’s in culture. And culture starts with leadership.
Lish Barber
A case study in leadership failure
Back at Amtrak, I got a complaint from an employee who said she was being mistreated due to her race and gender. I asked for details, and she told me, “There’s a red stool at my desk.”
I followed up with her manager, who immediately responded, “Of course she has a red stool. She’s late every day, and she still doesn’t get it.”
The issue wasn’t diversity—it was management.
This manager had been trying to "teach her a lesson" in the pettiest way possible instead of addressing the real issue with a professional conversation. This is what happens when leaders don’t practice self-compassion. They project their frustrations outward, creating unnecessary workplace drama instead of constructive solutions.
The business case for self-compassion
Stephen Covey, in The 7 Habits of Highly Effective People, said:
"You can pay people for their backs and hands, but you can’t pay them for their minds and hearts."
The only way to get employees to bring their full selves to work is to create psychological safety - where they can make mistakes, admit to them, and learn without fear of punishment.
Research supports this. Amy Edmondson’s study in hospitals found that the highest-performing teams had the most reported mistakes. Not because they were making more errors but because they had a culture where people felt safe enough to report small problems before they became big ones.
That’s how you get a high-performing organization—by fostering an environment where feedback isn’t a threat but a tool.
How to train for self-compassion
At SF MOMA, we took self-compassion from an abstract idea and turned it into a practical training program.
It’s a three-day course focusing on:
1. Defensiveness training
Managers learn to respond without shutting employees down. If an employee suggests a change, the wrong response is "We’ve always done it this way." That kills innovation. Instead, we train managers to engage in dialogue, not dismiss concerns.
2. Triangulation awareness
Workplace gossip and indirect communication destroy psychological safety. We teach teams to address concerns directly instead of venting to third parties. Employees now call out triangulation when they see it.
3. Bias training that’s actually useful
We don’t do checkbox diversity training. Instead, we focus on real-world applications like understanding how unconscious bias affects decision-making and team dynamics.
The result?
A rise in complaints.
But that’s exactly what we want. More complaints mean more transparency and more transparency leads to real improvements.
Why self-compassion is non-negotiable
The next generation of employees is demanding workplaces that prioritize mental health, psychological safety, and authentic leadership. Studies show that over 25% of younger employees cite mental health as a primary factor in job satisfaction. If we don’t get ahead of this now, we risk irrelevance.
This isn’t new. Cesar Chavez talked about "disciplined freedom" in the workplace in the 1970s, giving workers the autonomy to take risks and innovate without fear. Fifty years later, we’re still struggling to implement this idea. The difference now? If we don’t, we lose talent.
85% of CEOs say they prioritize employee well-being, but 75% of employees say they don’t see it. That gap is what we need to close. And it starts with us.
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