Leading with Vulnerability

16The Four Types of Questions

What makes you feel most vulnerable at work? Is it when you need to ask for help? Perhaps it's when you are receiving candid feedback from someone you trust? Or maybe it's when you have to genuinely admit to a mistake?

This is one of the questions I asked the over 100 CEOs I interviewed. My idea was to create a kind of vulnerability scale. On the lower end of the scale would be something like asking for help and on the high end of the scale would be something like admitting to a huge mistake. The idea was to show what makes leaders feel less and most vulnerable and then give some tools based on where someone falls on the scale.

This sounds like a pretty straightforward and valuable framework to create, or so I thought. Here are a few of the responses I received from CEOs when asked “What makes you feel most vulnerable at work?”

“When I have to bring to life mistakes I have made that have hurt other people, made them uncomfortable, or somehow made their lives more difficult.”

—Zig Serafin, CEO of Qualtrics (more than 5,000 employees)

“When I feel very strongly that a decision needs to be made or a pivot has to occur that the rest of the leadership team doesn't see or believe. I'm a collaborative person by nature so having to challenge my team and tell them we need to do something is really hard.”

—Sheryl Palmer, CEO of Taylor Morrison (3,000 employees)

“The absence of people I can talk to and trust. Oftentimes when making decisions you have ...