Aaron Levie advises aspiring enterprise software founders to conduct many interviews (e.g., "walk me through your day") with people who work in large companies to identify where they waste time on repetitive, inefficient processes. By listening for tasks that are repeated—meeting scheduling, payroll, expense reporting, document sharing—founders can spot gaps where technology could deliver markedly better solutions and build a company to address them.
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The question was, how do you discover issues that enterprises are having without necessarily working inside the enterprise? I would just go interview like 100 people. Just like, walk me through your day. What are all the places where you are less effective, less efficient, having to do repetitive or redundant work? And don't ask for technology problems. Just listen to where they're spending their time, what processes do they keep repeating over and over again? And then you can kind of start to imagine, well, how could software go and attack that problem? How could software attack the problem of meeting scheduling? Not a big market, but one space? How could software attack the problem of payroll? How could software attack the problem of expense reporting? All these kind of things are the drudgery of working inside of a big company. But if you haven't worked in one of those big companies, you at least have to get as much information as you can from people that do work in those big companies. And then you can kind of start to see patterns of like, okay, this seems like a really big problem. And in our case, if you had interviewed clients or people that worked in big enterprises 15 years ago and you said, walk me through your day, I think you would have eventually spotted how much time is wasted when people are working with their documents and they're trying to share their documents and they're trying to access their documents from different devices. If you really peeled it apart and you asked all the right questions, you would have actually discovered this problem. We discovered it because of what we were doing in our personal lives in college. But you would have also discovered it by just understanding where people are spending time in the workplace and then saying, hey, wait a second, that doesn't make sense. Because technology today could solve that problem way better than what they're getting as solutions. As soon as you find that gap, that's where you can build a company.