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Writer's pictureRiley Bauling

How to ask better questions and why we all need to

Updated: Jan 3

One of the first assignments I got as a college journalist was to write a profile for my college newspaper on the winningest basketball coach in University of New Mexico history.


Don Flanagan, the coach of the University of New Mexico women’s basketball team, was hard to get an interview with. His team was one of the most successful in the state, and as a 19-year-old with little to no training, I was scared out of my mind to interview him.

I brought two recorders, three notebooks, and probably like six pens to be 100 percent sure I wasn’t going to miss something he said, misquote him, or otherwise mess up an opportunity I felt I had no business getting in the first place.


I showed up 30 minutes early, had read seven profiles on him, and knew deep down just about everything there was to know about him.


I hemmed and hawed over the first question I was going to ask, eventually going with, “So tell me how you got into basketball to start.” I figured this was an easy entry point. I’d take it, run with it, and then we’d be off.


His answer, “That’s not the question you want to ask.”


“Um, what?” I said. I’m full-blown sweating at this point, fiddling with my recorder, which was precariously resting on my knee.


“You want to know why I care so much about basketball. That’s a lot more interesting,” he said.


We went with that question. Which, as he predicted, was a lot more interesting. He talked of his family, the importance that he thought basketball and teams played in the womens’ lives he coached, and what it meant to do it in New Mexico..


I remember that even 20 years later because I learned a valuable lesson that day: Questions matter. They matter a lot more, I think, than answers do.


Problem is, we’re pretty bad at asking the right ones or even asking them at all.

That interview with Flanagan went well because he was kind, caring, and open. Without his guidance, I would have bombed beacuse I ran head on into several of the obstacles we put in our own ways when it comes to asking good questions.


Warren Berger, a self-proclaimed questionologist who wrote a wonderful book on questions called, surprise, “The Book of Beautiful Questions,” outlines five enemies we need to actively combat when it comes to asking good questions.


  1. Fear – we’re scared of being seen as not knowing the answer, so we avoid asking questions that will tell others we don’t.

  2. Knowledge – we fall into a trap of expertise, feeling like we know enough about a topic to not need to ask any questions about it.

  3. Bias – we are predisposed to certain ways of thinking and ideas and therefore less open to learning about them.

  4. Hubris – relatedly, we think that our biases are the right ones and others’ biases aren’t (e.g., Everyone else is biased). We do things like say, “I went with my gut instinct,” to make decisions because we trust our guts too much.

  5. Time – quite simply, we just don’t make time for questions in our constant pursuit of trying to get things done.


Three of those enemies got in my way as a 19-year-old who desperately wanted to not be seen as incompetent: fear, knowledge, and time. I was scared of looking ignorant, I wanted Flanagan to know how much I knew and that I’d done my homework, and I was worried that I wasn’t going to get through all my questions with the time we had.


How can we take this and improve our own ability to find the time for and ask better questions for ourselves and the teams we lead?


For each series of questions, I’d suggest first starting with yourself and then broadening it to your team as a whole:


  1. Diagnose root cause: Review the five enemies (fear, knowledge, bias, hubris, time). Which do you think is likely the biggest enemy for you/your team now? Why do you think that is? What conditions have you/your team created that have led to this?

  2. Plan for success: Pick the enemy you most want to focus on and the situation or context where it is most likely an issue for you. What would it look like for you/your team to successfully overcome this enemy in that context? What impact do you think that would have?

  3. Plan for obstacles: What obstacles or challenges do you think might get in the way of that success? What could you/the team do to overcome those obstacles?

  4. Make a plan: What’s the most immediate next step you/your team can take to combat this enemy? How will you know you're successful?

George Carlin has a great quote about the power of questions, “Some people see things that are and ask, ‘Why?’ Some people dream of things that never were and ask, ‘Why not?’ Some people have to go to work and don’t have time for all that shit.”


I think our work, like our personal lives, would drastically improve if we heeded the advice inherent in Carlin’s quote. Make time for questions, overcome the fear of looking stupid, and see where it leads you and your team.



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