Unlock Transformative Change: The Art of Asking Better Questions
Welcome to the 75th episode of Harmonious Workplaces, where hosts Rich Cruz and Ben Kleinman dive deep into a topic often overlooked but fundamentally critical: the power of questions in facilitating change. In this insightful discussion, they unpack what makes a good question, how it can drive organizational transformation, and crucially, how to navigate resistance when people are hesitant to engage. If you’ve ever wondered how to ask good questions for better change, read on to discover key strategies from the experts.
Why Questions Are the Catalyst for Change
The conversation kicks off with Rich Cruz sharing his renewed interest in the topic, noting that questions have been surfacing in various professional channels, from SHRM and OD Network webinars to Dr. Jona Van Thiel’s “Quest to the Core” podcast. For Rich, questions are not just about gathering information; they are central to negotiation, persuasion, and “selling” change to stakeholders. As a consultant, Rich has been challenged by his mentor, David Bowen, to ask more questions during client engagement and throughout the change process itself. Ben Kleinman emphasizes that questions are interlinked with discussions, conversations, and sales, forming the core of building rapport and crafting shared narratives.
What Defines a “Good” Question?
Defining a “good” question isn’t always straightforward, as it’s often context-dependent. However, the hosts provide clear guidelines: a good question is generally clear, relevant, cognitively or relationally valuable, and respectful.
Ben highlights the importance of open-ended questions, which invite dialogue and allow people to think and respond in meaningful ways, without assuming a single right or wrong answer. Such questions foster exploration of a topic. Rich adds that his psychological training and works like Simon Sinek’s “Start with Why” have profoundly influenced his questioning approach, aligning with principles of Dialogic OD (organizational development) that emphasize open-ended questions and dialogue.
While open-ended questions are often championed, binary “yes” or “no” questions also serve a vital purpose. They are particularly useful in surveys for cataloging data, eliciting simple preferences, and even in high-stakes negotiations, as noted by former FBI negotiator Chris Voss. Other valuable questioning formats include:
- The Five Whys: A technique for root cause analysis, delving five layers deep to uncover the underlying issues behind a problem.
- Likert Scales: Used in surveys or dialogue, these scales (e.g., 1-5 or 1-10) offer clear, quantifiable answers for assessing feelings, preferences, or conditions like pain thresholds in medical contexts or change readiness in organizations.
The hosts also touch upon the cultural nuances of questioning, noting that directness in Western cultures differs significantly from approaches in other cultures, where questions and responses might be more indirect. Furthermore, formative experiences with questioning, whether met with encouragement or shutdown, deeply impact an individual’s willingness to engage as an adult. Simple phrases like “That’s a great question” can significantly boost autonomy and ownership.
Navigating Resistance: When Engagement Falters
Perhaps one of the most challenging aspects of asking questions is when individuals are reticent to engage or answer. As Ben humorously notes, anyone with a teenager knows that even good questions don’t always yield more than a grunt. So, what do you do when faced with resistance?
First, the hosts are clear about what not to do:
- Don’t ask the same question louder or more angrily.
- Avoid blaming language like, “What the heck is wrong with you?”.
- Do not force a response, as this erodes psychological safety and basic respect.
Instead, best practices emphasize a more thoughtful and empathetic approach:
- Respect autonomy: Acknowledge their right not to answer immediately.
- Recalibrate and show respect: Recognize that the situation is changing and adjust your approach, respecting where the other person is at.
- Build rapport: Sometimes, you need to step back, talk about unrelated topics (like the weather or a vacation), and rebuild trust gradually. This helps open the door to participation.
- Pause and reframe: If a question is met with resistance, suggest taking a break or moving on to another topic with the understanding that you’ll return to the difficult question later.
- Exercise patience and emotional intelligence: Forcing answers can trigger a “fight or flight” response, leading to shutdown or avoidance.
- Re-ground with the “why”: Reframe the question and reiterate the imperative behind it, helping people understand the importance for the organization. When there’s urgency, clearly explain the consequences of delay.
- Check-in: Ask, “How are you feeling right now?” or “Where are you in this conversation?” to gauge their state and offer a break if needed. This demonstrates awareness and emotional intelligence.
The Multifaceted Role of the Change Agent
Effectively facilitating change through questioning requires change agents to wear multiple hats. Rich suggests they act as both an “interrogator” or questioner—eliciting requirements, sentiment, and information—and a storyteller. Ben adds a third crucial role: that of a moderator. A good moderator must be present, asking questions, listening to responses, and discerning when to push harder, when to check in, or when to take a break.
For complex change efforts, a team approach can be highly beneficial, allowing different individuals to fulfill roles like questioner, moderator, and even a scribe to capture insights and data. Furthermore, employing a neutral third-party moderator can be incredibly effective. This external party can formulate and deliver questions without the emotional baggage or existing biases, leading to more objective information gathering.
Key Takeaways for Harmonious Workplaces
Asking better questions is a complex undertaking that requires significant effort, but it is undeniably worthwhile. At the end of the day, Ben Kleinman emphasizes a foundational principle: be patient and caring for the people you’re talking with, and strive to understand their perspective. By integrating clear, relevant, and respectful questions, understanding the nuances of engagement, and approaching resistance with empathy and strategic moderation, you can truly unlock transformative change within any organization.
We’d love to hear your questions and feedback! You can drop a comment or, for specific inquiries about change, organizational development, or industrial-organizational psychology, visit harmoniousworkplaces.com/askhermie. Our resident expert, Hermie the HR Hermit Crab, is very approachable and ready to answer your questions.
Until we meet again, make change your friend!

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