Compassion in Leadership is not a weakness. It is a strength. Here’s why and how.

Jamie Cabaccang
Jul 3 · 7 min read

For the longest time, I thought being “caring” and “compassionate” was a weakness for me

and that I could never become a manager. I turned down 3 opportunities to become a manager because I had limiting beliefs. From the experiences I’ve had in my career, I had the belief that I had to be tough, assertive and confrontational. I received feedback during an annual review that I had to “be more aggressive” if I wanted to be promoted.

“I thought I had to become an asshole if I was ever going to take on a manager position.”

One of my aha moments was when Nikki Kloeppel gave me the gift of realizing that my caring and compassion was a strength. Not a weakness. She was my coach for the Dale Carnegie Leadership training at Microsoft. The class witnessed this moment, as they all raised their hand when she asked “who would want a more caring and compassionate manager in their life?”

I got it. I finally got it.

As I reflect, some of the greatest teachers in my life were the managers who genuinely cared. And even the managers who didn’t care were also some of my greatest teachers.

I finally accepted a manager role leading a team of Designers for a Microsoft Incubation team — under one condition: I will lead authentically and with compassion. My manager at that time, Riccardo Giraldi, supported that and believed in me. We were a high performing team inventing new hardware and software technologies that even created new teams within Microsoft. We had group meditations and “Feelings Meetings” which cultivated psychological safety, trust and creativity (I’ll save that for another Medium post). It validated that genuinely caring for your team can go a long way and even create impactful results. Being compassionate is the core foundation of successful leadership. The best part is I didn’t have to change who I was.

I’m now the Design Lead for the Pinterest Seattle office. Our company mission is to “Bring everyone the inspiration to create a life they love”. Compassion is seen and felt across the company from individual contributors to our leadership. They truly value, nurture and celebrate our employee culture and the individual humans that make up our company. It’s in alignment with my own personal values and I am supported to do great work with compassion.


I recently had the opportunity to attend the very first Wisdom 2.0 Compassion in Leadership Summit.

Here are some learnings that every leader should be mindful of:

  1. Empathy is not the same as Compassion. Compassion = Empathy + Action. “Empathy is experiencing another’s feeling but compassion is seeing from their lens in a way to help suffering.” — Jeff Weiner, CEO of LinkedIn
  2. “Me” to “We”. As an individual, you aren’t meant to know everything or feel like you have to carry it all on your own. In fact, you shouldn’t have all the answers. With a variety of experiences, expertise and perspectives, WE can move something forward and create huge shifts (what I like to call “create magic”). And when you are a leader, give credit to the individuals. As a leader, be the support that lifts them up from the bottom and grows them. We all rise together.
  3. Compassion doesn’t mean you need to be “soft and squishy”. It’s a force. Hold the space to be emotionally available to others. Be a listener. It takes a lot of courage for an individual to open up to their manager as we sometimes feel like we need to show up as “having our sh*t together”. Be an observer of the unspoken. Especially before you start prescribing things. Have courage to be honest with your team. This doesn’t mean you have to spill your guts and share all the details. Just create an awareness around your feelings. Ebony Beckwith, Chief Philanthropy Officer of Salesforce, spoke about this so eloquently.
  4. The people you work with are humans. See and treat them as such. Coming to work does not stop life. Bringing your whole self to work comes with caring for others. “When you understand others from their perspective, it enables you to ask the difficult questions and approach difficult situations differently. You will ask a different set of questions and it enables you to avoid unintended consequences. Carry humility. We are all individuals. And when you treat people with that kind of respect, it’s incredibly powerful.” — Jeff Weiner, CEO of LinkedIn. I learned this from the “Feelings Meetings” I facilitated at Microsoft and now Pinterest. These meetings allow you to be an observer and really see your co-workers as humans.
  5. And my “WAKE-THE-F*CK-UP” moment was when I was reminded… it all starts with having compassion for YOURSELF. I was all gung-ho about attending this summit to learn new ways of being an effective and successful compassionate leader but damn. THIS was the “aha moment” for me. This past year has been one of the most challenging years for me. This was the reminder I needed to hear. It is so easy for me to be compassionate and caring for people at work, home and within the Techies + Wellness community that I’m cultivating but I somehow forgot about including myself. It all begins with me. I knew this. I mean, it’s so basic. But yes, I somehow forgot (I’m human). It’s time to revisit my commitments to myself, my values and move from a place of suffering and into resilience. It’s time for me to accept myself as I presently am, with gratitude, and give myself the permission to be compassionate to myself. When I can accept and receive myself fully, I can give fully with a joyful heart. Thank you Rhonda Magee, Author & Law Professor, University of San Francisco for this aha-moment.

Why should companies care?

  • People want to work for companies that have a giving mindset and a values-oriented mission.
  • Happiness is the vehicle to productivity. Retention goes up and it’s easier to hire.
  • “Compassion is the lifeblood of the community” — David Simas, CEO, The Obama Foundation
  • It brings long term value to any company. Building teams with compassion creates trust, empathy and demonstrates you are there for one another.
  • Compassion is free. It doesn’t take away from the bottom line to do good.
  • “The business of businesses improve the state of the world” — Ebony Beckwith, Chief Philanthropy Officer of Salesforce
  • Investing in employee success is investing in your success and your organization’s success. It’s a win-win-win.

Let’s be mindful that mental illness is real life.

I connect with Techies on a very deep level with the work I do outside of tech and deep 1:1 work. Depression and anxiety are two of the most common things I hear. It affects our ability to show up as our higher selves and it affects more people than you are even aware of. Trauma, self-worth, stories and labels we’ve attached ourselves to can often be triggered at work, our productivity is greatly affected and we begin to either:

  1. Put our mask on and smile through the pain.
  2. Put our armor on and shut down.

According to the World Health Organization (WHO), mental health is defined as a state of well-being in which every individual realizes their own potential, can cope with the normal stresses of life, can work productively and fruitfully, and is able to make a contribution to her or his community.

Many just want to be heard, understood and appreciated. Now that you have an awareness of compassion for yourself, for others and that successful leaders are already practicing compassion in their roles you can start being intentional and taking action!

Be comp”ACTION”ate.

(Yes, I made it up and I’m keeping it in this post). Who knows? You might just win a Compassion Award (yes, that is also a thing). And you don’t need to have a leadership or manager title to take action. Be the example. Be the change. If you helped one human, that is powerful in itself and you will see just how fulfilling that human connection could be and how far your influence goes.



Jamie Cabaccang

Written by

Transforming lives through technology and Reiki. Pinterest Design Lead. Inventor. Artist. Reiki Practitioner. Gypsy Soul. Founder of Techies + Wellness.

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