Jason Fried at the 37signals blog Signal v. Noise spent some time speaking with Clayton Christensen and kindly shared some of what he learned. 

Christensen described an orientation to learning as follows:

Questions are places in your mind where answers fit. If you haven’t asked the question, the answer has nowhere to go. It hits your mind and bounces right off. You have to ask the question—you have to want to know—in order to open up the space for the answer to fit.

I wrote in my last post about how we can miss things if we’re not looking for them. There’s a popular test that demonstrates this shortcoming of our brains in a fairly dramatic manner.

If we accept this shortcoming, then we also have to accept the fact that those who have an entirely different mindset than us will see things we completely miss. Specifically, entrepreneurs approaching investors are often rightly frustrated that the investor “just doesn’t get it.” A feature can seem insignificant to someone that is seeing it for the first time.

Yet, the entrepreneur that has been immersed in the end user’s world is thinking: You don’t get it! It seems minor, but once you peel the onion back and get to the heart of the customer’s problem, this solves it! It’s an elegant, perfect solution, and we’re sitting on a gold mine here. 

And there you have an impasse.

Part of the solution is having folks come to the table with a common knowledge base. In fact, “knowledge” is not even the right word—perhaps “empathy” base: a common sensitivity to the customer problem being addressed.

While great, I don’t think that’s necessary. Acknowledging this dynamic can help solve it. In short, what is significant to those presenting a solution will likely seem insignificant to an outsider—at first. 

Perhaps the right way to proceed is to spend time on the product and features to get a sense of the solution and then start from the beginning, asking the entrepreneur to explain what problem they were trying to solve and the process by which they went about it doing.

Of particular importance are the questions they asked. What were the questions at the outset? What did they learn? How did those questions change? What are the outstanding questions now? In hindsight, what were the most significant questions and subsequent learnings? What do they feel are the most important questions now and what are their hypotheses around those questions?

Throughout, the investor should compare those questions to the questions in his own head. Wherever the entrepreneur presents a question or answer that doesn’t fit with the investor’s own set of questions or prioritized order—that’s the time to stop and discuss. 

Do this in enough detail, and you’ll get a sense of whether you’re moving toward a common base of understanding. To be clear, the investor likely won’t get the same level of conviction in that meeting, but both sides should get a sense of whether he has the potential to get to that level of commitment. 

The key is to focus on the questions and figure out what key questions are different.