My favorite interview question for early stage startup candidates

When I was 8 years old, my mother passed away. My parents told me by the time I was 2 years old that she had terminal breast cancer which she had since I was born and that it’s likely that she will no longer be with us at some point in the future.

Needless to say, this shaped me from a very young age. When I think about startups I immediately think about the trauma that the team will go through on a day to day basis and the stamina they will require to endure the ups and downs of trying to create new things for the world.

If I am interviewing an early stage startup team member, let’s say first 7 team members, I like to think of these people as the type of people that can deal with uncertainty and figure out things on the fly, sometimes minute by minute.

The most insightful thing I can ask candidates is:

What’s your earliest, most traumatic memory?

It helps me understand how this person will deal with the reality of early stage startups. I’m trying to figure out if they’ve dealt with trauma and uncertainty. More importantly how they handle themselves when the ground under them is cracked and moving at the same time. I believe these moments shape you forever, so I want to hear what someone has to say.