My favorite interview question

"What does success in life mean for you?"

Candidates are usually taken aback by this question. Especially when I ask it right after going deep into why they chose Temporal over Airflow when designing the data pipeline architecture at their last job. Jokes aside, here's why I like this question:

Building a startup is hard. It's a mental and emotional roller coaster, and I've come to realize that it certainly isn't for everyone. But for the right person, it can be the most fulfilling work there is.

You pour so much of your soul and energy into something that, sooner or later, you'll find yourself asking, "Why am I doing this?" To clarify, the question isn't meant to suggest you shouldn't be, but rather that you'll only find success if you have a clear and confident answer.

Moreover, the equation only works out if you truly derive fulfillment from the work you do. And that fulfillment could look very different for different people. Some people deeply enjoy working with other highly capable people. Others want to win at all costs. The only requirement is that working here is meaningfully getting you closer to whatever fulfillment means for you. Otherwise, I'll be the first to tell you that it isn't worth it.

So what does it look like when people do find the fulfillment they're seeking? I see people who can't wait to come to the office each day because they're surrounded by the most talented people they've ever known. I see people who enjoy difficult problems tackle a new, exciting challenge each and every day. And I see people who truly believe they're building towards a generational company.

Fundamentally, I believe everyone should optimize for fulfillment in life. But far too few people ask themselves what it means for them. So even if my question makes the candidate sitting across from me realize it's something else that they'd rather be doing, I'll rest easy knowing it was for the better.