I ask every single founder I get to spend time with one on one, a very simple, yet important question:

“What will your product and as a result, the world, look like in 5-10 years if your company is wildly successful?”

It seems like an open-ended question, right? Well it’s meant to be, but you can clearly tell which founders are going to build something big by the answer or those that are building something much more short term. It also surfaces those that are obsessed with the product. It’s very related to a question Hunter Walk asks many founders. http://hunterwalk.com/2014/11/18/the-most-difficult-question-i-ask-founders/

Here are the things I look for in the answer:

An overarching ambitious vision that is way bigger than what you’d see today

If you saw AirBnB in 2009 without talking to the founders, you’d think of it like Couchsurfing in terms of vision – impressive yet limited. I bet Brian Chesky’s vision and story was something much larger back then, something that matches up with where they are today and where they certainly will be in five years. It’s obvious now, but wasn’t so obvious back then. Great founders have put a lot of thought into what the world and their companies look like many many years from now. The answer should scare you and excite you at the same time.

A true long term roadmap that has thought into it

Dennis Crowley is famous for having a very long roadmap for Foursquare. It’s a problem he’s been working on for almost a decade. Great founders are going to have a long term roadmap with thought into it. They won’t just have thought a year ahead, but many many years ahead. It’s also why it’s tough to compete with great founders by “copying their idea”. You’re already behind the 8 ball as you’re copying their latest release, while they are already working on the next thing you’ll copy and they know what comes next. This roadmap is what makes the ambitious vision not crazy, but very possible. It makes you know that the founder and this product are one.

An intoxicating sense of conviction

Working on a problem for 10 years with a crazy big vision – the AirBnBs, Ubers, Teslas, etc. of the world have an intoxicating sense of conviction. They start to supersede the possibility of failure and have a conviction in their gut that this is going to happen no matter what. They have such a sense of conviction that you believe it in your gut as well. If they can get you to believe, then odds are they can get investors, founders, and customers to believe. You also know that they are a machine that will run through walls to make it happen.

An understanding of what the big hurdles are

It’s easy to get drunk on your own kook-aid and just think things will be perfect. Great founders have a long term vision and roadmap, but balance their conviction by knowing the hurdles ahead. Instead of ignoring them or thinking they’ll disappear, they tackle them straight on. Take Uber for example. They did not skirt around taxi regulation as an issue or just think it would go away. They realized early on it would be an issue and they hit it head on. It also shows a sense of crazy in a good way. Founders that recognize the big hurdles or as Paul Graham likes to say it, the schlep, and still continue on are likely the crazy type that you want in your corner. http://paulgraham.com/schlep.html

There are a ton of other questions to ask entrepreneurs, but this is the one I like the most. It provides the best stories and when you’re with a great entrepreneur, it really resonates.