I was talking to a friend a few years back. We were debating the different ways of building products: highly analytical data driven approach vs insights from talking to users.

He told me that at Square they had to spend X hours every week at small businesses trying to understand how the owners actually use Square products. And a lot of ideas that ended in the roadmap came from observing users in the real environment vs looking at data and iterating. And it was something that everyone in the product team at Square practiced.

Another thing that he mentioned was how Jack Dorsey, the founder of Square, had this ability to jump from feedback on current features to a 80000 feet view and connect the present to the future.

Whenever my friend had feature review sessions with Dorsey, Dorsey would push him to think bigger. Ask him to imagine Square 5 years later. What if they became a bank. A big multi product company with X Y Z products. How does this current thing tie to that future vision. Dorsey could zoom in first, but zoom out.

And a lot of things he told me then ended up happening. I was seriously impressed. If you have worked in the Indian startup ecosystem, you know how few long term thinkers are there. Most founders don’t think beyond what is needed to secure the next round of fund raising. There are very few founders who dare to dream big. I was happy for him, but also jealous that I would probably never have the chance to work for a 0.0001% founder like Dorsey or Zuckerberg.