question everything

A few months ago, I had the opportunity to chat with Hal Gregerson, of MIT’s Leadership Center, about his philosophy on life and business, and, more specifically, to ask what he is researching and writing about these days. I mentioned to Hal that I had been seeing him talk about ways leaders can avoid mistakes. He quickly corrected me that his ultimate point was not the avoidance of mistakes, but the ability to ask the right questions.

Ever since then, I think about questions, everywhere—“What one question…,” “These 6 questions will…,” and so on. Every other Inc article seems to be detailing the “how and what” leaders are asking. So, I’m going to get past the overwhelming advice that is out there to make way for my own.

Here is my advice—and it’s only “kinda” stolen from Rumsfeld—discover what are the “known unknowns” and explore how to find the right method to turn those known unknowns into “known knowns.” Speaking of Rumsfeld, you don’t need to ask about known knowns or unknown unknowns because those can’t ever be answered. The discovery of those answers are for the philosophers and religions to take on.

You can shine a bright light on a thing already known, which is a good thing to do, but the point of asking questions is to find new information or a different way of perceiving the world. It takes an incredible amount of skill to develop new perceptions, and to correctly identify what you don’t know and look for answers to those questions.

Relevant to the point, Hal had just been meeting with the top leadership at Amazon to find out what types of questions they asked themselves, their employees, and each other. The best story from that experience, Hal shared with me, is about current CEO, Jeff Bezos. Jeff will show up every few weeks with a poorly designed product to reverse engineer. The team would mentally think discover what questions the designers, marketers, developers, etc. asked and how they answered to make such a terrible product.

The point of the exercise is self examination of what they, as leaders of Amazon, are doing to ensure they are creating the right questions with a real chance of conjuring an answer, a known known, in their own work. The ability to understand the process beyond the end result in the work of others and reflexive question seeking has been invaluable to me.