“The important and difficult job is never to find the right answers, it is to find the right question.” — Peter Drucker
Individual questioning skills are powerful, but their impact multiplies exponentially when embedded in a group’s culture. Whether in a family, team, or entire organization, creating an environment where powerful questions are the norm rather than the exception can transform collective thinking and results. This chapter explores how to build and sustain cultures where the right questions consistently emerge.
Questioning—particularly when it challenges assumptions or explores uncomfortable topics—requires psychological safety. Without it, the most important questions often remain unasked.
Essential Principles:
Example in Practice:
The new CEO of a financial services firm noticed that despite claiming to value innovation, the executive team rarely questioned established strategies. In meetings, people focused on execution details rather than exploring whether they were pursuing the right opportunities.
To shift this dynamic, she instituted several changes to build psychological safety for questioning. She began each strategic meeting by asking, “What assumptions are we making that might not be true?” and consistently modeled thoughtful responses to challenges of her own thinking.
She created a “Questions We Should Be Asking” section in executive meeting agendas, giving explicit time and attention to foundational inquiries. Most importantly, when a junior executive questioned a major investment that had been the previous CEO’s pet project, she publicly thanked him and initiated a genuine exploration of the concern instead of dismissing it.
Within six months, the executive team’s discussions had transformed. Strategic questions that had been suppressed for years emerged, leading to significant shifts in the company’s market approach. A year later, the firm launched two breakthrough initiatives that emerged directly from questions that would have previously remained unasked.
Application Exercise: Assess the psychological safety for questioning in your team or organization. Where do people feel safe asking questions, and where do they self-censor? Identify three specific changes you could make to increase safety for difficult or challenging questions.
Leaders powerfully shape culture through what they pay attention to and how they communicate. Leaders who predominantly make statements and give answers create fundamentally different cultures than those who lead through thoughtful questioning.
Essential Principles:
Example in Practice:
After twenty years of successful growth, an architecture firm was struggling with the transition to new leadership. The founding partners had built their reputation on distinctive design vision, and team members expected the new managing director to provide similar clear direction.
Instead of trying to replicate the founders’ authoritative style, she deliberately adopted a question-based leadership approach. Rather than presenting a new vision, she convened a series of conversations around questions like: “What aspects of our firm’s legacy must we preserve? What must evolve? What does the changing industry require of us?”
She made her leadership visible not through definitive pronouncements but through the quality of her questions and her synthesis of the collective thinking they generated. When presenting to clients, she modeled how to explore their needs through thoughtful questions rather than rushing to showcase the firm’s designs.
Initially, some interpreted her approach as indecisive. However, as better decisions emerged through collaborative inquiry, the team began to value this new style. Within two years, the firm had developed a more adaptable culture that could respond to industry changes more effectively than competitor firms still dependent on top-down direction.
Application Exercise: Monitor your communication as a leader for one week. What percentage of your interactions involve making statements versus asking questions? Identify three opportunities where you could replace statements or directives with thoughtful questions, and experiment with this shift.
What gets rewarded gets repeated. Organizations traditionally recognize and reward people for having answers, while questioning often goes unrecognized or may even be subtly discouraged.
Essential Principles:
Example in Practice:
A global consulting firm traditionally rewarded consultants for developing repeatable methodologies and “best practice” frameworks. This incentivized consultants to present themselves as experts with definitive solutions rather than as thinking partners who could help clients explore complex challenges.
The firm’s leadership recognized that this approach was becoming less effective as clients faced increasingly novel and complex situations. They implemented a multi-faceted initiative to reward questioning excellence:
They created a “Question of the Month” program that highlighted questions from consultants that had led to unexpected insights or innovative approaches for clients. These were shared across the firm with the impact they had generated.
They revised their performance evaluation system to specifically assess consultants’ ability to ask questions that advanced client thinking. “Exceptional questioning skills” became a criterion for promotion to partner.
Most significantly, they began tracking the quality of questions in client proposals alongside the proposed solutions. Proposals with thoughtful, original questions addressing the client’s context received more resources and senior attention.
Within three years, the firm had developed a reputation for a distinctive questioning approach that set them apart from competitors still focused on pre-packaged solutions. Client satisfaction scores increased, particularly on complex engagements where the path forward wasn’t clear at the outset.
Application Exercise: Design a simple recognition system for powerful questions in your team or organization. How might you collect, evaluate, and celebrate questions that create value? Implement a pilot version for one month and evaluate its impact.
Beyond individual behavior changes, organizations can embed questioning into their formal and informal systems to create sustainable cultures of inquiry.
Essential Principles:
Example in Practice:
A hospital system was struggling with inconsistent patient care quality across its facilities. Despite multiple improvement initiatives, results varied widely, and best practices weren’t spreading effectively.
The chief medical officer implemented a structured question practice called “Vital Questions” across all departments. Each unit maintained a visible board with four questions:
These boards were updated weekly in brief stand-up meetings. Each month, department leaders would share the evolution of their questions and insights with peer departments.
The hospital also redesigned their quality review process around a sequence of questions rather than a checklist of metrics. Instead of simply reviewing data, meetings explored questions like: “What surprised us in this data? What patterns are emerging? What experiments might help us understand this better?”
Over time, this question-centered approach created a more adaptive learning culture. When a new patient safety protocol was introduced, the departments with the most developed questioning practices implemented it more successfully because they approached it with thoughtful inquiry rather than compliance-focused implementation.
Application Exercise: Select one regular process in your organization (planning, review, onboarding, etc.) and redesign it to center around a sequence of powerful questions. Test this question-centered process and compare results with the previous approach.
The Menlo Innovations Story
Menlo Innovations, a software development company based in Michigan, has built its entire organizational model around questions rather than answers. While most technology companies operate through command-and-control hierarchies and technical specifications, Menlo has operationalized a completely different approach.
Their transformation began with fundamental questions about the software development process: “Why is building software so often painful for both developers and clients? What would joyful software development look like? How might we design a company from scratch to achieve that?”
These questions led to radical reimagining of every aspect of their work:
Project Initiation: Rather than beginning with requirements documents, they start with structured question sessions called “High-Tech Anthropology,” where they ask questions about users’ actual needs and pain points.
Work Organization: Instead of assigning developers to specific tasks, they ask: “What’s the next most important thing we should work on?” Teams decide this collectively through daily question-based planning.
Quality Assurance: They don’t have dedicated QA staff. Instead, they ask: “How might we build quality in from the beginning?” This led to practices like pair programming and test-driven development.
Client Relationships: Weekly client meetings center around three questions: “What’s working well? What needs to improve? What should we focus on next?”
Hiring: Their distinctive interview process is entirely question-based, focusing on how candidates collaboratively explore problems rather than on technical knowledge.
The results have been remarkable. Menlo consistently delivers projects on time and on budget in an industry notorious for overruns. They maintain exceptional client satisfaction and employee retention. Most importantly, they’ve demonstrated that a question-centered organizational model can thrive even in a technical field traditionally dominated by answer-oriented cultures.
The Lesson:
Menlo’s success illustrates that questions can form the foundation of not just individual leadership but entire organizational systems. By institutionalizing questioning—making it the default mode of operation rather than an occasional practice—they’ve created a adaptable, learning-focused culture. Their example demonstrates that building a question-centered organization isn’t just idealistic; it can be a sustainable competitive advantage.
Creating and sustaining a question-centered culture requires attention to four interconnected elements:
This framework recognizes that sustainable culture change requires both interpersonal dynamics (safety and modeling) and institutional structures (reinforcement and systems). Neither alone is sufficient.
Five Principles for Transforming Organizational Culture:
As we reach the conclusion of this book, we’ve explored questions from multiple angles—as tools for specific contexts, as frameworks for deeper thinking, and now as foundations for organizational culture. In the final chapter, we’ll bring these threads together, exploring how to integrate the right questions not just into your work but into your entire approach to life.
Next Page: Conclusion: Integrating the Right Questions into Your Life