I am curious about other people. I also spent a stint as a career coach where my role was to help people gain a better understanding of how they are driven and where they are going.

The easiest way to help people open up is to ask the right questions. Human of New York is a social media profile of random strangers around New York City. The creator often gets asked how he gets people to open up. He’s said his favorite questions is:

“What is your greatest struggle right now?”

I love this question — its almost as scary to ask as it is to answer. What I’ve found is that many people want to answer questions like this — they just are never asked. Conversations stay at the surface level and people are afraid to go deep.

Some of my favorite questions for helping people in their career are:

– What are you trying to cause?

– What brings you alive?

– What’s the best day of work you have ever had?

– Do you want your boss’ job?

– Who inspires you?

– What matters to you most?

These are just some of the questions I’ve used and also asked myself — what are your favorite questions?

33k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

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