Book: Humble Inquiry

The Gentle Art of Asking instead of Telling

I believe in supporting authors and people who do the work to help illuminate concepts like this so I won’t be sharing too much from the book, but I do think this topic is important enough to share a little bit about it and my take aways.

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This is one of those areas that I would consider myself a hypocrite. I both heavily assume, and heavily try to explain what I’m thinking when someone assumes something about me, and this book addresses both.

The main concept is simple: We don’t take the time to understand what is happening. We are so busy that instead of digging into a situation, we assume, and communicate (tell things) based on those assumptions.

The author shares this telling story:

“A vivid example came from one of my executive students in the MIT Sloan Program who was studying for his important finance exam in his basement study. He had explicitly instructed his six-year-old daughter not to interrupt him He was deep into his work when a knock on the door announced the arrival of his daughter. He said sharply, “I thought I told you not to interrupt me.” The little girl burst into tears and ran off. The next morning his wife berated him for upsetting the daughter. He defended himself vigorously until his wife interrupted and said, “I sent her down to you to say goodnight and ask you if you wanted a cup of coffee to help with your studying. Why did you yell at her instead of asking her why she was there?”

And this isn’t asking ‘Why’ to get the upper hand, to fight back or one-up — it’s asking ‘Why’ with the humble intent of understanding what’s going on.

I myself recall a presentation I gave last week where things went ok, but not great. We met to talk later and there was still a disconnection. They were telling me what was going on in their head and having read this book I thought to myself, “You know, if you would also ask me why it happened this way, I think we could get past this.”

I didn’t end up being explicitly asked, but I did manage to work my explanation into the conversation, and things got much, much clearer.

But what if we had both started with humble inquiry? And had the trust to engage the question of “What’s going on here?” during the meeting rather than afterward? I can’t say for certain, but things might have gone more smoothly.

The end goals of humble inquiry is both understanding and to be more personal which leads to better outcomes. There are several stories shared along the lines of how a team performs better when there is some level of being actual friends.


  • Ask “Why” (or my dad’s favorite, “Can you explain to me why…”)
  • Prepare space in a meeting — you don’t need to get down to business right away. Overall the process will be smoother if the team is in a place of trust.
  • You often only see a piece of a person at work — finding out what other pieces they have to themselves builds trust and a capacity for grace in situations.

One piece I wish had been addressed more was — what happens when you do achieve being actual friends? When you work in a ministry context this can be easier to achieve, it is more expected to be personable, and yet once you get there it is a very difficult space to navigate — loving and caring for your coworker, but also being in a place to make objective decisions.

All that being said — I think this is a good book to skim — it was a little drawn out and maybe is one of those “Could’ve been said in a blogpost”, but it is a worthwhile skim for you and your team to have the same framework for evaluating communications.

Ashley Crutcher is a Digital Designer at InterVarsity located in Madison, WI. She tweets at @ashleyspixels and enjoys cuddling with her cat, crocheting, working out, and thinking too much about everything.

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