This month, we're here with all the best questions! Questions for days.
In all seriousness, skillful questions are a consistent theme in our leadership development work.
The questions leaders ask ultimately shape what information they can access, how their teams approach challenges, whether assumptions get tested, and how much ownership individuals take for finding a way forward. For many leaders, one of the harder shifts can be from Chief Answer-Haver to Chief Empowerer (and knowing when to wear each hat).
So this month, we’ve been exploring The Power of Questions: what makes some questions more useful than others, how inquiry affects trust and judgment, and how leaders can use questions more intentionally.
In today's digest:
Coaches' Corner 🧭: Why Not “Why?” + Books on Questions
What We’re Reading 📚: Curiosity, Inquiry, and How Minds Change
The Podcast 🔊: Powerful Questions as a Leadership Skill
Where to Find Us 🗺️: UNH, Women Offshore, ICF Converge + More!
P.S. If you're getting this email, it's because you're one of the valued folks we've worked with, collaborated with, or connected with over the years. If it’s not your thing, feel free to unsubscribe at the bottom—no offense taken. But if you’re curious to stick around, we’re glad you’re here!
It's no surprise to most leaders that open-ended questions are useful. The less obvious insight is recognizing how the wording of a question can impact the quality of the thinking that follows.
In “Why Not Why?”, we take on one of our most beloved inquiry words. “Why?” is invaluable for root-cause analysis, investigation, and exploring purpose. In human conversations, though, it can sometimes sound like a request for justification, inviting people to defend a decision rather than examine it.
We share ways to use “What?” or “How?” to shift from judgment to insight.
And for anyone interested in expanding their questioning repertoire, we also pulled together six of our favorite books for asking better questions. The list spans leadership, coaching, communication, curiosity, persuasion, listening, and the science of how humans make sense of one another.
Schein explores the role of genuine inquiry in relationships, leadership, and organizational culture. His work is especially valuable when thinking about hierarchy and information flow: How do leaders create relationships in which people are willing to tell them what they actually need to hear?
Why do facts and arguments so often fail to change our minds? McRaney explores the psychology of belief and the kinds of conversations that make genuine reconsideration possible. Curiosity and thoughtful questions feature prominently, particularly when people encounter ideas that challenge how they already understand the world.
Audiobook links are affiliate links. Purchases made through them may earn Two Piers a small commission at no additional cost to you, helping support our work.
One of the most important shifts in leadership is learning how to use your expertise without becoming the bottleneck for everyone else’s thinking.
In our latest podcast conversation, Erica joins fellow coach educators Thea CharlesandBob Greene to explore one of the tools that makes that possible: powerful questions.
The conversation gets into how questions can create reflection, surface assumptions, expand thinking, and help people develop their own problem-solving capacity. It also explores some of the subtleties that make asking a genuinely good question harder than it looks. How much does wording matter? What happens when a question carries our own assumptions? And when is the most useful thing we can do simply to listen closely enough to know what to ask next?
And there’s a milestone coming up: the next episode of the Two Piers Podcast will be our 100th! Stay tuned to celebrate with us this Thursday, August 27th.
The next few months are shaping up to be full of learning, teaching, connecting, and spending time with some very interesting people.
🎓 UNH Certificate in Professional Coaching | September The Fall 2026 cohort kicks off in September. This live-online, ICF-accredited program supports aspiring professional coaches and leaders who want to strengthen their coaching skills.
⚓ Women Offshore Conference | October 1–2 | Houston area We’ll be back at the annual Women Offshore Conference, facilitating an interactive session on effective communication in high-stakes environments for professionals across offshore energy, maritime, and related industries.
💡 The Maine Women’s Conference | October 21 | Portland Closer to home, we’ll join professionals from across Maine and beyond for a day of learning, connection, and conversation at the annual Maine Women’s Conference.
🌎 ICF Converge | October 28–30 | Washington, D.C. We’ll close out October at ICF Converge, connecting with coaches, educators, organizational leaders, and practitioners from around the world while staying close to emerging research and practices in the field.
In between, we’ll be continuing our own development in mentor and team coaching, including advanced team-coaching studies beginning this fall.
Will we see you at any of these events? Reach out if you’d like to connect.
As the days get shorter and schedules get longer, we hope you find a moment to pause and reach a bit further for that powerful question before rushing on to the next thing.
And if there’s a question you’ve found particularly powerful lately, let us know! We adore a well-crafted query. (Especially if it involves cheese…)
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Erica and the Two Piers Team
PO Box 554 Woolwich, Maine 04579-9998, United States
