A Few of Our Favorite Books for Asking Better Questions
I’ve joked before that curated book recommendations are one of my love languages. (The others include cooking for people and sending cat videos.)
I read pretty voraciously, and one of my favorite things is coming across an idea, book, article, podcast, or talk and thinking, “Oh, I know exactly who might appreciate this.”
So, with Powerful Questions as our Two Piers theme for August, it seemed only fitting to pull together a few of the books that have most influenced how I think about questions, curiosity, listening, communication, persuasion, and the way humans make sense of one another.
Earlier this month, I joined my fellow coach educators Thea Charles and Bob Greene for a podcast conversation about powerful questions. I also wrote about why I’m sometimes cautious with one of our most beloved open-ended questions: Why? For anyone who wants to keep exploring, consider this the accompanying reading list.
Disclosure: Links to audiobooks below are Libro.fm affiliate links. If you make a purchase through them, Two Piers may earn a small commission at no additional cost to you, helping support our work.
Humble Inquiry by Edgar H. Schein
The subtitle gives it away: The Gentle Art of Asking Instead of Telling.
Schein explores inquiry as a way of building relationships, reducing hierarchy, and creating the conditions for people to tell us what we actually need to know.
I return to this one often when thinking about leadership, psychological safety, and information flow, particularly the challenge leaders face in making it genuinely safe for inconvenient information to travel upward. Curiosity is a leadership practice here, and the kinds of questions we ask can shape whether people feel invited to contribute honestly.
The Coaching Habit by Michael Bungay Stanier
You don’t have to be a professional coach to benefit from learning to ask fewer, better questions.
This is an exceptionally practical book about resisting the urge to immediately solve, advise, or take over. Its questions are simple enough to use immediately, which is probably part of why they’re so effective.
For leaders trying to create more ownership, reflection, and problem-solving capacity on their teams, it’s an especially accessible place to start. It also offers a useful reminder that one well-placed question can often do more than a long explanation.
How Minds Change by David McRaney
This one goes deeper into the psychology underneath good questions.
McRaney explores why facts and arguments so often fail to change people’s minds, and how curiosity, conversation, and thoughtful questioning can create room for people to examine and evolve their own thinking.
It has become one of my favorite books on human behavior, persuasion, belief, and what happens when two people enter a conversation with different versions of reality. It’s especially useful for anyone interested in asking questions that encourage reflection without immediately triggering a need to defend a position.
A More Beautiful Question by Warren Berger
Berger makes the case that questioning is a skill we tend to exercise freely as children and gradually constrain as adults.
He explores how better questions can fuel innovation, problem-solving, and change, including his useful progression of Why? What if? How?
For leaders, teams, and anyone working through complex problems, there’s a lot here about staying curious long enough to see possibilities that might otherwise get overlooked.
The Book of Beautiful Questions by Warren Berger
Think of this one as a broad field guide to inquiry.
Berger offers questions for decision-making, creativity, leadership, relationships, and self-reflection. It’s the sort of book you can read straight through, and it also works beautifully as a reference to keep within arm’s reach when you need a better question.
I tend to love books like this because they expand the range of questions available to us. Sometimes the most useful shift is simply having a few more ways to approach the same situation.
Supercommunicators by Charles Duhigg
Duhigg explores what highly effective communicators do differently, and questions are central to the answer.
One of the book’s most useful frameworks is the idea that conversations tend to operate in one of three modes: practical conversations about what we’re trying to accomplish, emotional conversations about how we feel, and social conversations about who we are and how we relate to one another. He offers an orienting question for each: What is this really about? How do we feel? Who are we?
That framework alone is valuable for leaders. A conversation can become surprisingly unproductive when two people are responding to different underlying questions without realizing it.
Duhigg also looks at the habits of people he calls “supercommunicators,” including their tendency to ask substantially more questions, particularly deep questions that invite people to share their values, beliefs, experiences, and identities.
He pairs that curiosity with careful listening and a practice of looping for understanding: reflecting back what you heard and checking whether you understood correctly.
For anyone interested in asking more powerful questions, this book offers a useful reminder that the quality of the question matters, and so does our ability to recognize what kind of conversation we’re actually in, listen closely to the answer, and let what we hear shape the question that comes next.
A Note on How I “Read”
I’m using read somewhat expansively here.
Many of these books first came to me as audiobooks, either borrowed through my library or purchased through Libro.fm, where my purchases support my local independent brick-and-mortar bookstore.
For me, audio is often the format that makes reading possible.
Sitting still with a physical book isn’t always the easiest way for every brain to absorb information. For many neurodivergent people, including folks with ADHD or dyslexia, audio can make books substantially more accessible. And plenty of the very busy leaders I work with tell me they simply don’t have time to sit down and read as much as they’d like.
For me, audiobooks can turn driving, traveling, walking, cooking, and household chores into opportunities to learn. I recognize that every brain is different though, and some folks prefer the written page.
My own personal pattern is often to listen first, and if I find a book especially useful, I’ll then buy the physical version so I can underline it, flag sections, revisit ideas, and keep it nearby as a reference.
Books are also only one way to engage with an idea. Depending on the person and the topic, a TED Talk, podcast episode, HBR article, LinkedIn short, or well-made illustrated summary may be far more useful than a 300-page book.
No Homework Assignments!
I do love surfacing potential book matches to folks, but I want to be clear that I’m never attached to whether someone takes me up on a resource I offer.
A big part of coaching is ensuring that the client remains in the driver’s seat. So while I’ll curate any resources I highlight based on a client’s specific circumstances and prefered medium, I recognize that people are busy, and they know their own capacity, interests, and learning preferences. I trust clients to decide which resources are useful to them, which medium works best, and what they’d rather leave on the proverbial shelf.
For me, the value is in building a broad enough library of ideas that I can occasionally say, “I have something I can put on your radar, if you’re interested.”
Consider these six books an invitation to explore further, in whatever format works for you!