I spend a lot of time talking to entrepreneurs and I've come to learn that the most insightful question I can ask is "What keeps you up at night?" I've found that it usually leads to a palpable feeling of relief and that the conversation digs a whole lot deeper from that point on.
Being responsible for a business, especially one that has the livelihood of others wrapped up in it, is stressful at times. To make matters worse, business leaders find themselves wanting or needing to put a happy face on to put employees', investors', and loved ones' minds at ease.
"What keeps you up at night?" gives the entrepreneur permission to talk about things that they otherwise feel that they have to keep to themselves. It cuts to the chase because it's clear that there's no need to keep up appearances. I've been thanked many times just for asking.
In some cases it's useful to frame the question so that we can home in on a specific topic. At MojoTech, for instance, I speak to entrepreneurs about building web and mobile applications that are critical to their businesses. The answer to "What keeps you up at night about this project?" gives me a much better idea of how to make the project a success.
That said, it not as easy as just asking the question. The hard work comes in listening carefully to the answer, asking important follow-up questions, and making good use of the information. I've found that "What keeps you up at night?" makes that hard work a whole lot easier - you may too.