Beautiful Questions

Updated: Feb 12, 2020

I was recently out on a run with a close friend.  We were talking about life, work, and jobs when she asked me a question that knocked me over.  She asked, “What would happen if you just didn’t make any career decisions this year?” I hadn’t thought about that question, nor had I thought about my career as something that may be more emergent this year as opposed to mapped, dictated and decided.  I didn’t have an immediate response to her question, but over the next few weeks her question stuck with me as I grappled with an answer.


When was the last time you were with a friend or a colleague and she asked you a question that just “hit” you? You know, the question that made you see yourself or the world in a different light, or that made you explore an area of your thinking that you hadn’t thought to explore, or that completely changed your perspective on something?


The philosopher David Whyte calls this a “beautiful question.” He remarks that a beautiful question shapes a beautiful mind, and that: “...a beautiful question starts to shape your identity as much by asking it, as it does by having it answered.”   We can ask others beautiful questions, and we can also ask ourselves these beautiful questions.


A beautiful question shapes a beautiful mind.

As managers, we are in a unique position to help our team members develop and grow.  Last week we spoke about development plans - and helping your team members own their own development by articulating the skills they want to build over the year.  We ask our team members where they want to go and what capabilities they need to get there. We’ve also talked about the power of coaching your team members.  During coaching, we ask questions that help your team build the muscle to work through difficult decisions.  Coaching can push our teams to challenge their thinking, explore options they might not have otherwise, and see others’ points-of-view.  And, we’ve talked about making sure that as a manager you are asking the simple questions:  How are you doing? And being open and receptive to the answers that come up.


But, what about the power of every so often asking your team member a beautiful question?  Asking them a question that might not have an immediate answer, but that gets their mind turning and expanding in a way that it might not have otherwise? A question that shifts their perspective or identity in a new way?


Before you think I’ve gone all woo-woo on my evidence-driven, research-backed management blog, let’s explore what else beautiful questions help us to do:


Why Beautiful Questions?


  • As humans, we hate ambiguity.  We strive for certainty and structure.  This constant desire for clarity is called the “Ambiguity Effect”, first coined by economist Daniel Ellsberg.*  It’s the tendency for humans to avoid options where the outcome is uncertain or unknown.  Well, beautiful questions help us to override this effect. They force us to get more comfortable with responding “I don’t know” and sitting in the uncertainty of future options.


  • Beautiful questions encourage vulnerability and therefore trust between you and your team members.  They show your team that you care about getting to know them in a deeper way, and in a way that might not directly relate to their current role.  [Beautiful questions pop up all the time when we talk about falling in love. Why? Because these questions naturally build vulnerability and closeness.]


  • We love goals! We set long-term goals (New Year’s resolutions) and short-term goals (to do lists) all the time.  One of the challenges with goal-setting, though, is that it can prevent you from seeing things outside the path to reach those goals. We don’t like to look outside our prescribed path because we all suffer from the “status quo bias” - we have a strong bias for things to stay the same.  Beautiful questions challenge us to confront a potential change in goals and give us permission to think outside our paths.


I’ve been soliciting beautiful questions from friends, colleagues and acquaintances over the past few weeks.  So thank you (you know who you are!) for your input.** Here are five questions to get you started - but the list of beautiful questions is endless!  So, go grab a coffee with your team member and ask him a beautiful question!


  • What 3-5 adjectives or phrases do you want people to use to describe you in 2020?

  • What are the things (people, places, activities) that make you feel truly happy? What do you not like doing?

  • Where in your life is there something that you want and you are stuck?

  • What did you learn about yourself this past year that you didn’t know before?

  • Who do you want to spend more time with this year?


*Fun Fact! Daniel Ellsberg also released the Pentagon Papers!


** The sources for some of these beautiful questions:

My favorite coach.

Baptiste Institute.

Jen Coken’s Blog.

Byron Katie’s “The Work.”



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