INSIDER: Ask More: The Power of Questions to Open Doors, Uncover Solutions and Spark Change
Ask More by Frank Sesno is a guide to the art, strategy, and purpose of asking better questions—questions that unlock understanding, fuel relationships, inspire action, and create meaningful change. Sesno argues that questions are not merely tools for obtaining information; they are catalysts for connection, clarity, innovation, and leadership. By breaking questions into distinct categories—diagnostic, strategic, creative, empathy-driven, scientific, confrontational, and more—Sesno shows how purposeful inquiry can transform conversations in personal, professional, and civic life.
Throughout the book, Sesno emphasizes that the quality of the question determines the quality of the outcome: better questions lead to deeper insight, better decisions, and more collaborative problem-solving. Whether interviewing world leaders, advising organizations, or helping individuals navigate conflict, he demonstrates that intentional inquiry helps people understand motivations, uncover hidden assumptions, and connect with others on a human level. The book encourages readers to slow down, listen actively, and approach conversations with curiosity rather than judgment.
Sesno illustrates these principles through stories from journalists, scientists, negotiators, CEOs, and everyday people who used strategic questioning to diffuse crises, uncover truths, build trust, and imagine new solutions. Through these examples, Ask More shows that anyone can improve their communication, strengthen leadership, and make better decisions by cultivating the habit of asking more—and asking better.
THINK POINT #1: Curiosity as a Foundation for Connection
Sesno emphasizes that genuine curiosity is the essence of effective questioning. Questions grounded in curiosity create openness, reduce defensiveness, and encourage the sharing of meaningful information. He highlights how curiosity-driven questions allow people to uncover motivations, clarify expectations, and deepen relationships, and when used intentionally, help individuals break through assumptions, understand others’ perspectives, and form stronger human connections. Curiosity shifts interactions from transactional exchanges to meaningful conversations where insight and empathy can emerge.
THINK POINT #2: Diagnostic Questions and the Search for Clarity
Diagnostic questions focus on uncovering what is happening, why it is happening, and what needs to change. Sesno shows how journalists, investigators, and problem-solvers use diagnostic inquiry to get past surface explanations and discover root causes. These pages describe the power of asking “What’s really going on?” or “Why does this matter?” as a tool for cutting through complexity and guiding effective decision-making. Whether navigating business challenges or personal dilemmas, diagnostic questions help identify patterns, clarify obstacles, and generate informed solutions.
THINK POINT #3: Strategic Questions for Leadership and Vision
Strategic questions—those that look forward, clarify goals, and help chart direction—are essential for leadership. Sesno illustrates how leaders use “where are we going?” and “how will we get there?” questions to create alignment, encourage innovation, and mobilize action. He highlights the fact that strategic inquiry fosters collaboration by giving all stakeholders the chance to contribute insight. Leaders who ask strategic questions empower others, uncover hidden risks, and build shared ownership of long-term goals. Through strategic questioning, vision becomes participatory rather than prescriptive.
THINK POINT #4: Empathy Questions and the Work of Understanding Others
Empathy questions build trust by inviting someone to share experiences, emotions, and values. Sesno emphasizes that asking, “How did that make you feel?” or “What was hardest about that situation?” strengthens connections and diffuses tension. He also underscores the importance of active listening—maintaining presence, suspending judgment, and allowing silence. When people feel genuinely heard, they are more willing to problem-solve, communicate openly, and engage in difficult conversations. Empathy questions create safe spaces where honesty and vulnerability can thrive.
THINK POINT #5: Creative and Imaginative Questions for Innovation
Imaginative questions free people from constraints and help them envision what is possible. Sesno explains how asking, “What if…?” or “How might we…?” fuels innovation by encouraging experimentation and non-linear thinking. Here, he shows that creativity often emerges from reframing problems, challenging assumptions, and exploring alternatives. By inviting people to imagine new futures, creative questioning fosters adaptability, ingenuity, and resilience. It enables individuals and organizations to break out of routine thinking and pursue bold, transformative ideas.
Asking Questions in Real Estate
For real estate agents, Ask More offers practical guidance for building trust, understanding client needs, and navigating complex negotiations. Diagnostic questions help agents assess client priorities, financial constraints, and long-term goals. Empathy questions deepen rapport, showing clients they are heard and understood during stressful transitions. Strategic questions clarify timelines, investment visions, and market strategies, enabling agents to guide clients confidently in competitive environments. Creative questions help buyers and sellers explore innovative options, from staging strategies to portfolio planning.
By mastering intentional inquiry—listening deeply, asking purposefully, and adapting questions to each situation—real estate professionals can strengthen client relationships, enhance decision-making, and deliver more personalized, effective service.
Recommended Reading
Sesno, Frank (2017), Ask More, HarperCollins Leadership: New York City, New York.
About the Author
Holly Tkach, Master of Communication Candidate
Baylor University
Holly Tkach earned her Bachelor of Arts in political science and communication from Baylor University and graduated in three years. During her undergraduate years she interned with the Network of Enlightened Women on their communications team, worked as a research and writing fellow for Texas Scorecard, and worked at the Mayborn Museum. She is now working towards earning her master's degree in communication.
