In Praise of Vulnerability

Or Why You Want a CEO that Cries

I’m a crier. To know me is to know that it doesn’t take much to open the floodgates. A classic for me is the opening scene of The Lion King, when Rafiki takes the baby Simba and holds him upwards to the exultation of his adoring animal kingdom. It doesn’t matter how many times I’ve seen it. I cry. Every time.

Earlier in my career, a friend of mine commented that she found “vulnerability’ to be irritating, if not downright off-putting. Her thoughts didn’t particularly strike me at the time, but a few weeks ago while recording a new episode of Kickstart’s podcast, Perfect Pitch, with Mike Peregrina, co-founder of Homie, I was reminded of them again. Mike told the story of a family that used the money saved by selling their home with Homie to pay the cost of in vitro fertilization, something that they otherwise could not afford. In telling this story Mike teared-up. He concluded, “I can’t ever tell that story without crying.” This naturally segued into a discussion on vulnerability being among the characteristics of successful entrepreneurs. Mike’s thoughts on the subject reminded me of my conversation with my friend. I now think her point of view was misinformed at best, and dead wrong at worst. Let me tell you why.

Vulnerability, in my view, is a fundamental characteristic of a caring, mature adult. In a leader, it conveys authenticity, honesty, and integrity. A leader that is willing to be vulnerable can exercise positive influence that cannot otherwise be replicated. In my own experience, this is manifest in three specific ways.


I’ll never forget one particular week when I was working in healthcare. Taken in sum, it was a doozy. Early in the week a critical merger I had been working on for months fell apart. It was a spectacular and very public failure. Two days later my CFO informed me that a large decline in elective surgeries had us operating at a deficit for the first time in my tenure as CEO.

Then Friday came.

It was an absolute highlight of my career. In a conference room I listened to a team of nurses, technicians, and other staff present the results of a Kaizen project they had just completed. I had bet the future of the organization on Lean (the Toyota Production System) and this was the very first completed project in what would be a long journey. Over three days the team had exceeded very high targets for time and accuracy improvement in sterile processing, a major determinant of safety, quality and productivity in surgery. As the team proudly presented their results, I broke into tears. Needless to say, this wasn’t exactly expected. After congratulating them, I confessed that it had been a very hard week and that this report brought some deep and powerful emotions to the surface. I expressed my sincere gratitude for their dedication to the task and for what they had accomplished. We had a large organization and many of the people on this team had never met me. This was one of those classic moments of truth, and with no forethought my vulnerable self just came out. Perhaps not surprisingly, some of the team members and others sitting in on the meeting also cried. We formed a bond that day. It was intangible but based on feedback I heard afterwards it was very, very real. A sincere expression of gratitude to my team led to a bond we otherwise would not have formed. And every single time in my life that someone has expressed sincere gratitude to me for something — anything — it affects how I see that person, how I perceive their character and maturity, and my desire to give even more in the future.


Venture capital is a profession with the highest highs and the lowest lows. The highs are the best — amazing teams succeeding against all odds to create companies that are changing the world. The lows are really, really hard. I’ve sat with CEOs that have simply run out of energy and are nearly breaking down. I’ve seen close friends that founded a company together break up, accompanied by devastating accusations and hostility. I’ve counseled with A CEO suffering from the deepest and most persistent clinical depression I’ve ever witnessed. All of these occasions were fraught with emotion. In their most vulnerable moments, and in private with me, these CEOs cried. And I cried with them.

Develop a practice of listening and watching very, very carefully for the verbal and nonverbal cues that indicate a hunger for empathy and compassion. Once you start to see them, they will blare at you with the volume of a foghorn. Most people will not ask for your empathy because it can feel embarrassing or because of concerns they will come across as needy or weak. Or simply because in their pain they cannot find the words to ask for it. You will have to give it without request.

And never forget that there is a hierarchy here. When compassion is needed, apathy is devastating. Sympathy at least shows you notice, but it can feel trite. Empathy shows an effort to really understand. Compassion is empathy in action. It doesn’t have to be a heavy lift, but some bit of action, no matter how small, is what we all need. The aforementioned CEOs didn’t need me to fix all of their problems. But they did need me to sit with them. To listen to them. To remind them that their problems were neither permanent nor pervasive. And in doing so, we each emerged stronger.

A few weeks ago, my mother died. This was one of those moments of truth where those that understand compassion come forth, immediately, and show it. I will be eternally grateful for those that did.

The human soul doesn’t want to be advised or fixed or saved. It simply wants to be witnessed — to be seen, heard and companioned exactly as it is. When we make that kind of deep bow to the soul of a suffering person, our respect reinforces the soul’s healing resources, the only resources that can help the sufferer make it through.” — Parker Palmer


On the morning of May 21, 1998, I was sitting in a board committee meeting. Thirty minutes into the meeting one of my staff poked her head in the door and with some apparent urgency motioned me out of the room. She told me that there had been a mass shooting at Thurston High School, only a few miles from our largest hospital. I was immediately struck by the gravity of what she was telling me but wasn’t sure what, if anything, I could do. I had confidence in our team, so I thanked her and returned to the meeting. Fifteen minutes later she was back. I knew it had to be bad. I ended the meeting early and accompanied her to our emergency room. Over the next 45 minutes 21 students were delivered by ambulance to our hospital. For some their injuries were serious but not life threatening. Others were near death. One had to be resuscitated twice on the way to surgery. Another had a bullet pass through her head on a path that would almost certainly mean permanent, severe disability if she were to survive at all.

When the course of care was established and underway for all of these students, I called our entire management team into our auditorium. Once together we provided a general update on what we knew, and what we were doing. Then we prayed together. We grieved. We cried. We hugged. We created space for people to feel what they were feeling — pain, sadness, anger, fear — and express it. Then we went back to doing what we needed to do to help save those kids.

Once again, this was a moment of truth. We all had jobs and were well compensated for performing them. This wasn’t about doing a job. This was about acknowledging a time of deep sadness and, after sharing that together, a time to show what we were made of.

2020 is a year that has inflicted us all with plenty of reasons for sadness. Most of us have never seen in our entire lives such a steady stream of adversity. People everywhere and from every walk of life are in pain. Let us please not ignore that. It’s real. This — right now — is a time to show what we are made of.

Ancient religious texts from almost every tradition exhort us (using different words) to “mourn with those that mourn.” Doing so is not to show, nor enable, debility. It’s to show you actually care.

Vulnerability in leaders is not a warning of weakness. It is a sign of supreme strength. It is an attribute to be embraced, cultivated, and openly demonstrated. Great leaders are grateful. They are empathetic and compassionate. And they can accept sadness as fundamental to the human condition, even in the workplace. And sometimes, great leaders cry.



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