I had a successful founder, who already had two major exits, have an interesting idea for solving a significant business issue. It was going to be their third major start-up and I asked if I could get “the pitch”. It was an ingenious idea that solved a problem in an area where few were thinking there was an issue.

I was very impressed, but there were some areas that I did not see clearly how that would work, so I asked… “Do you mind if I ask you some questions?”

Of course, there was an interested to share this new idea, and so I asked my first few questions, getting a better idea around how everything fit together in an elegant way. When questions get answered, what gets revealed does two things. First, it reveals what is clearly defined and understood. It also reveals where there are other questions.

I saw a potential gap in the pricing model, and question number four confirmed that revenue was based on customers acting in a specific (although very logical way). There were no safeguards, that I could see, to incentivize beneficial behavior or discourage harmful (to the system) behavior. I did not know that for sure, but my question number five was… “What if they don’t behave in that way?”

I have found that entrepreneurs, especially visionary founders are sharp and quick… That question was enough for them to see they had a potentially realistic and potentially serious vulnerability in their pricing strategy. They said “that would be bad… I am going to fix this and I want to talk to you again once I do.”

One month later, the founder had mapped out their processes end to end and hired me to interrogate their process. I was effectively being asked to try to break their business model… I asked questions for several hours, leading to between seven and ten good “ah ha” moments, that generated valuable information that helped the founder create a better system to better serve their customers with less risk and more securely.