The Art of a Good Question

Human beings are capable of tremendous innovations and social change when we channel our energies towards solving certain challenges. A COVID-19 vaccine was formulated in a matter of months. Seamless digital/physical shopping experiences are made real in trend-setting Amazon Fresh stores. Space X has made reusable rockets a reality and disrupted space travel economics along the way. These are just 3 of the many examples of what’s possible when deep technology intersect with a clear problem statement, inspiration and capital. 

We are very effective at solving once we get into the weeds of it, and every solution starts its life as a question. Asking questions gives us the room to explore, and along the way we get to clarify our intentions, the problems we are trying to address and the solutions that will get us there. However, asking good questions - the type that move our lives and society forward by prompting an open exchange of information and ideas - isn’t so easy.

Like with many things, I believe that if we can start by setting the right approach at a personal level, we can take that into our relationships and society for broader beneficial outcomes.

Though not exactly a PC video, Howard Stevenson’s talk called “Building a Life” is worth a listen for the insightful questions and proddings it gives about how we evaluate our lives. Howard, a professor at Harvard Business School, shared two analogies in particular that stood out for me. 

  • Life is not about balancing, it’s about juggling. The most important ball is the one that is about to drop, and not all balls are the same. Our careers are more like rubber balls, they can bounce back if they fall. But our families are like glass balls, they tend to break if dropped.

  • Plan for the ripple and not for the splash - creating long term impact and leaving a legacy is made up of the small and big things, what’s measurable and immeasurable, the significant and yet under-the-radar. Don’t leave it for too late, and count what you give away as valuable as what you have.

After watching the video, I came up with my own set of questions inspired by the points he made. Turning good external ideas into great questions enriches the type of introspection I gain, and it helps me be a better listener too. As a guiding principle, a good question is open-ended, clear, specific and thought-provoking. With questions like the below, I assess them in a personal and professional context to keep myself balanced. 

  • If I am considering a path that I can see has made others unhappy, why (realistically) do I expect my experience to be different and how will I make it so?

  • Am I successful in, and rewarded for, things that I am proud of?

  • If success is getting what I want, and happiness is being satisfied with what I have, am I happily working towards my success? #notoburnout

  • Which situations in different areas of my life represent inflection points? How should I change direction?

  • Am I in the right environment to accomplish my goals?

  • Have I objectively assessed whether the people I’m seeking help from are equipped to support me?

  • What areas of my life am I under-investing in that will cause me regret if unaddressed?

  • What am I doing today that sets me up for a better tomorrow?

  • Do the people I value feel supported by me in ways that matter to them?

Just like my meander from science to philosophy in this article, to me this all eventually links up. Whatever questions we ask of ourselves determine the values we display in our private and professional lives, and the societies we shape. Lately, the questions I’ve been asking myself have a lot less “if they would” and a lot more “how can I” and “when will I”. In doing so, improving the quality of the question has transformed the quality of the answer.

 

What are some of the questions you’ve been reflecting on recently that have impacted you? Share a comment below.

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