Asking Good Questions

Questions are more important than answers. That’s because questions seek to clarify, evaluate, and frame, while answers are temporary, conditional, and decay over time.

Questions Are Conversation Starters

The purpose of the interview in the Reflect & Engage process is to facilitate deeper insights and foster meaningful solutions by leveraging diverse perspectives. Therefore, the best interview questions are open-ended, sensitive to context, and nuanced. They are often phrased like:

I wish I knew... How to...? Would you please explain…? Under what circumstances…? Why…? How would you compare…? What are the strengths and weaknesses of…?	What are the advantages and disadvantages of…? How would you prioritize… What are the top three…? When…? What do you think about…? How do you feel about…?

The Characteristics of Good Questions

The keys to effective question formulation in the context of the Reflect & Engage process include the following:

Criterion	Importance	Explanation and Impact
Clarity & Precision	High	Static questions must be exceptionally clear and unambiguous since participants can't clarify misunderstandings in real-time. Poorly formulated questions risk generating off-topic or superficial responses.
Depth & Reflection	High	Because responses are audio-only (allowing thoughtful reflection), well-crafted open-ended questions significantly enhance cognitive depth, encouraging participants to provide insightful answers.
Tone & Delivery	High	Tone, pace, and non-verbal cues (in video) strongly influence participant comfort and engagement. A welcoming and professional delivery encourages openness.
Contextualization	High	Static questions must provide sufficient context to help respondents frame their answers effectively. Without interaction, participants depend entirely on the initial framing provided in the question.
Sequencing & Flow	Moderate	Question sequence and logical flow become essential because there's no opportunity to dynamically adjust or reorder questions based on participant responses. Poor sequencing may confuse or frustrate respondents.
Accessibility & Inclusivity	Moderate	Questions must be phrased in accessible language suitable for all participants. Pre-recording makes immediate linguistic adjustments impossible, necessitating universally understandable wording.
Length & Conciseness	Moderate	Balance between comprehensive explanation and brevity is essential. Overly lengthy questions may overwhelm or disengage participants, while overly brief questions may lack needed context.

Approaches to Questioning

Effective questioning is key to unlocking insights and fostering meaningful dialogue. Two powerful approaches are the "I wish I knew..." (IWIK) and "How to...?" (H2) methods, each addressing different aspects of inquiry.

• I wish I knew...: This approach encourages exploration and discovery by surfacing information gaps.

• How to...?: This method focuses on solving practical challenges and improving processes.

These approaches can be used together to balance exploration with application, stimulating both divergent and convergent thinking.

Here is a summary table illustrating these approaches to questioning:

Approach	Objective	Example	Value
IWIK	Surface information gaps or curiosities.	"I wish I knew how AI impacts our privacy policies."	Guides discussions toward learning and discovery.
H2	Uncover process gaps or practical challenges.	"How to integrate AI tools into our existing workflows?"	Highlights opportunities for skill-building, problem-solving, or collaboration.

Interview Question Generator

The Interview Question Generator application can aid Hosts in crafting better interview questions by leveraging structured frameworks.

Streamlit

Launch the Interview Question Generator

Here's how the Interview Question Generator application aligns with the criteria for effective question formulation:

• Clarity & Precision: The application uses structured templates and frameworks to ensure questions are clear and unambiguous, reducing the risk of misinterpretation by participants.

• Depth & Reflection: The application generates questions that encourage deep reflection and insightful responses by employing inquiry frameworks such as the Socratic Method and Design Thinking.

• Contextualization: Each framework provides specific categories and examples, helping facilitators frame questions with sufficient context.

• Sequencing & Flow: The application ensures logical sequencing of questions within each framework, which helps maintain a coherent flow.

By using structured approaches, the Interview Question Generator helps facilitators create questions that are not only clear and precise but also capable of eliciting thoughtful and reflective responses, enhancing the overall effectiveness of the interview process.

Frameworks

Here's an overview of the frameworks used by the Interview Question Generator application:

Framework	Description	Application
5R Framework for Reflection	Developed by Bain et al., this framework guides individuals through Reporting, Responding, Relating, Reasoning, and Reconstructing to critically engage with and make sense of learning .	Ideal for educational and professional development settings where systematic reflection enhances learning and growth.
Critical Reflection	Based on Mezirow's theory, critical reflection involves questioning the assumptions underlying beliefs and experiences, facilitating transformative learning by enabling individuals to change their .	Best for contexts that require challenging beliefs to foster transformative learning, such as leadership training.
Cycle of Transformation	Developed by Jeffrey Linkenbach, this framework involves four stages: Spirit, Science, Action, and Return. It is designed to create positive transformation by integrating these elements into a cohesive .	Most effective for purpose-driven change initiatives that require both meaning-making and practical action for sustainable transformation.
Design Thinking	A human-centered approach to innovation, Design Thinking involves empathizing, defining, ideating, prototyping, and testing. It is widely used for creative problem-solving and user-centered .	Perfect for user-centered innovation challenges requiring creative solutions to tangible problems.
Discussing the Undiscussable	Based on Chris Argyris's work, this framework addresses defensive routines in organizations, encouraging open dialogue about sensitive or avoided topics to improve communication and problem-.	Optimal for addressing sensitive, taboo, or conflict-laden topics that people typically avoid discussing openly.
Epidemic Leadership	Created by Larry McEvoy, this framework synthesizes science, leadership experiences, and practical techniques to address complex challenges. It focuses on creating organizations with exponential performance and .	Ideal for scaling positive change throughout networks and organizations by designing ideas that spread naturally and creating supportive conditions.
ORIDA Inquiry	The ORID framework structures conversations through Objective, Reflective, Interpretive, and Decisional questions, facilitating comprehensive exploration and decision-. The framework has been supplemented with the Appreciative category.	Best for comprehensive exploration of complex topics requiring both factual understanding and emotional perspectives, leading to concrete action.
Six Thinking Hats	Developed by Edward de Bono, this method uses six colored hats to represent different types of thinking, promoting parallel thinking and helping groups explore multiple perspectives .	Excellent for balanced group decision-making processes that need to consider multiple perspectives systematically.
Socratic Method	Rooted in the teachings of Socrates, this method uses systematic questioning to stimulate critical thinking and illuminate ideas and assumptions, often used in educational .	Ideal for educational discussions and critical examination of assumptions, beliefs, and arguments to develop deeper understanding.
Transformative Learning	Introduced by Jack Mezirow, this theory focuses on adult learning through critical reflection and questioning, enabling individuals to reassess and transform their beliefs and .	Ideal for educational settings, leadership development, and contexts where the goal is to promote significant personal or organizational change through deep reflection and questioning of existing paradigms.

Recommendations by Conversation Type

Explore how different frameworks generate different questions and build on those you feel are most appropriate for your conversation. Here are some recommended starting points:

Conversation Type	Recommended Framework	Rationale
Reflective Learning and Leadership Development	Transformative Learning	Facilitates critical reflection and transformative change by challenging assumptions and beliefs, essential for leadership development.
Innovative Strategic Re-evaluations	Design Thinking	Structured around empathizing, defining, ideating, prototyping, and testing, ideal for strategic re-evaluations requiring creative solutions.
Change Management Initiatives	Six Thinking Hats	Uses Edward de Bono's parallel thinking approach to consider multiple perspectives systematically, beneficial for managing change.
High-Stakes Organizational Assessments	ORIDA Inquiry	Comprehensive framework with Objective, Reflective, Interpretive, Decisional, and Appreciative questions, suitable for thorough organizational assessments.
Complex Culture Conversations	Discussing the Undiscussable	Designed for surfacing and addressing sensitive or avoided topics, making it perfect for complex cultural conversations.