The Power of Good Questions

“That’s a really good question,” is something I’ve heard a lot — from new and old colleagues, potential patrons, clients and collaborators, and people I’m interviewing for projects — since founding Optimistic Anthropology.  This response makes me excited and I often quip in response, “Asking good questions is what I do for a living!”

I was fortunate that my upbringing and education encouraged me to ask good questions.  I grew up with family dinners where I was asked my opinion on current events at a very young age, and attending Sunday school where I was taught about one of Judaism’s holy books, the Talmud, in which Rabbis raise questions and debate interpretations of the Torah (Old Testament). 

At school, I was exposed to years of “great books” education which is steeped in the idea that everyone should read, interpret, and debate a (largely white, male, Christina, and heteronormative) set of works with contemporary significance and relevance to “a large number of the great ideas and great issues that have occupied the minds of thinking individuals for the last 25 centuries.”  And my decision to study anthropology continued to hone my curiosity about everything through questions like “how did this come to be the way it is?” and “how might we make this change happen?”

 One great resource for learning about asking great questions is the limited podcast series The Turnaround! Host Jesse Thorn interviews some of the world’s best interviewers about their approach. Check it out!

One great resource for learning about asking great questions is the limited podcast series The Turnaround! Host Jesse Thorn interviews some of the world’s best interviewers about their approach. Check it out!

Unfortunately, I’ve come to realize that good questions are asked more rarely than they should be.  And this is a real shame, because I believe that good questions are foundational to helping people, teams, and collaborations:

Understand who they are, how they came to be here, and how they plan to get to where they want to go;

  • Make new and deepen existing relationships between people;

  • Identify new possibilities and connections within and outside of their own work; and

  • Spur innovation and creativity and change, at a pace that is productive and sustainable.

Yep, questions can be pretty awesome!  But, not every question has the power to catalyze meaningful change.  So, what do I mean when I use the phrase “good questions?”

To me, a good question is:

  1. Open-ended. A good question is designed to encourage a full, meaningful answer drawing from one’s own knowledge and/or feelings. It can’t be answered with a yes or no, and it does not have the answer built into the question.  For instance, I find I ask a lot of questions that start with “How do you think about…?” or “What is it most important to understand about…?”

  2. Delivered with genuine curiosity. Sometimes questions are asked and received as thinly-veiled critiques or accusations or litmus tests (I know that I have been guilty of this in my life).  This approach is a quick way to shift a conversation from generative to defensive. Which is why word choice, tone, and timing are all important when it comes to asking a good question. For instance, I often preface an interview by acknowledging that I’m not an issue expert and ask the interviewee to describe something central in their own words.  Also, I’ve worked on an array of issues and in a range of sectors and institutions where the same word can mean really different things.  So, it’s pretty common for me to ask, “When you use the term development/equity/resident/etc. what do you mean by it?”

  3. Often can’t be answered on-the-spot (and if it can it’s telling you something important). When a good question is a powerful it spurs reflection, new thinking, previously unconsidered connections, and unexplored possibilities.  Some people embrace this opportunity and say, “I’m going to write that down and give it some thought” or “we hadn’t thought about that, but we should.”  While others – and a lot of education and workplaces teach and encourage this behavior, so it is understandable – feel it is necessary to respond immediately and will scramble to do so.  What’s amazing about good questions is not just the learning I am able to gain from the answers shared, but also the learning I gain about how the answerers think about and carry out their work.

The funny thing is that in writing this blog post, I realized that the same upbringing and education also prepared me to be a bit of a “know-it-all” (ha! understatement) for most of my life.  And it would always frustrate me when I felt like I knew the “right” answer or approach and others wouldn’t listen to me.  Most of the time, this was hubris and assumption on my part. Occasionally, I did recognize something important or useful that others were not seeing, but I wasn’t able to or patient enough to bring others along with me in my thinking.     

It was about 7 years ago that I started to change my approach.  I credit my exposure to the methodologies of adaptive leadership and facilitative leadership as well as emergent learning and the Lean Startup as instrumental in this shift.  They helped me move away from believing I needed to come up with THE answer on my own, to recognizing the power of creating the conditions for other individuals and teams to organize their thinking and generate many more questions and answers, hypotheses and possible solutions. And the amazing thing is that not only has this shift been effective in creating more positive and equitable outcomes in my work, it’s also been a far more joyful and energizing way to do the work.


What ideas and connections did this blog post spur for you?  What “good questions” have you asked or been asked?   

Share your answers in the comments below or by tweeting at @AKGold11 with #OptimisticAnthro.