Chapter 9: Questions in Specific Contexts

“Judge a man by his questions rather than by his answers.” — Voltaire

While previous chapters have explored general principles and frameworks for asking powerful questions, this chapter focuses on applying these skills in specific, high-stakes situations. Whether you’re interviewing for a job, negotiating an important deal, or teaching others, having the right questions ready can dramatically improve outcomes.

Questions for Job Interviews (Both Sides)

The job interview is a mutual exploration where both parties are trying to determine fit. Powerful questions from either side can reveal what’s truly important.

Essential Questions for Candidates to Ask:

“What does success look like in this role after 90 days? After one year?”
“What are the biggest challenges the person in this position will face?”
“How would you describe the team culture, and what type of person thrives here?”
“What’s something you’re proud of about working here that isn’t obvious from the outside?”
“What concerns might you have about my fit for this role?”

Essential Questions for Interviewers to Ask:

“Tell me about a challenge you faced where the path forward wasn’t clear. How did you approach it?”
“What’s something you’ve learned recently and how did you go about learning it?”
“What type of work environment brings out your best performance?”
“What questions do you have about our organization that haven’t been answered yet?”
“What’s something you believe that most people would disagree with?”

Example in Practice:

Sarah was interviewing for a product manager role at a fast-growing startup. Rather than asking generic questions about company culture, she asked, “What’s been the most difficult product decision the team has made in the past year, and how was that decision reached?” This question revealed the company’s actual decision-making process and highlighted potential challenges in the role. The interviewer was impressed by the depth of the question, and Sarah gained crucial insights that helped her determine this wasn’t the right environment for her work style.

Application Exercise: Before your next interview (on either side), prepare questions that go beyond surface information to reveal values, decision-making processes, and potential areas of misalignment. Prioritize questions that help determine genuine fit rather than questions designed to impress.

Questions for Crucial Conversations

Difficult conversations—whether about performance, relationships, or sensitive topics—often go poorly because people enter them with statements rather than questions. The right questions can transform potential conflicts into productive dialogues.

Essential Questions for Crucial Conversations:

“I’m curious about your perspective on what happened. How do you see the situation?”
“What’s important to you in resolving this issue?”
“What am I missing or not understanding from your point of view?”
“How has my behavior contributed to this situation?”
“What would a good outcome look like for both of us?”

Example in Practice:

A department head needed to address performance issues with a long-tenured employee. Instead of beginning with criticism, she opened with, “I’ve noticed some challenges with recent project deliverables, and I’d like to understand your perspective on what’s happening.” This approach created space for the employee to share significant personal challenges that were affecting their work. The conversation shifted from a potential termination to a collaborative problem-solving discussion about temporary accommodations and support.

Application Exercise: Identify a challenging conversation you’ve been avoiding. Write down the statements or accusations you’re tempted to make, then transform each into a genuine question that invites dialogue rather than defensiveness.

Questions for Negotiations

Effective negotiation depends less on asserting positions and more on understanding underlying interests. Questions are the primary tool for uncovering these interests and finding creative solutions.

Essential Questions for Negotiations:

“What are your most important priorities in this agreement?”
“What constraints are you working with that I might not be aware of?”
“How will you evaluate whether this deal was successful a year from now?”
“What aspects of my proposal present the biggest challenges for you?”
“What alternatives do you have if we don’t reach an agreement?”

Example in Practice:

During a contract negotiation between a software vendor and a large enterprise customer, the vendor was pushing back on customization requests. Rather than simply refusing, their representative asked, “Can you help me understand what business problem those customizations would solve for you?” This question revealed that the customer’s actual need could be addressed through configuration of existing features rather than costly custom development. This solution saved money for the customer while maintaining the vendor’s profit margins.

Application Exercise: Before your next negotiation, prepare questions aimed at understanding the other party’s interests, constraints, and alternatives. During the negotiation, commit to asking at least three questions before making any counter-offer.

Questions for Teaching and Learning

Whether in formal education, workplace training, or mentorship, questions are more powerful than declarations for promoting deep learning and critical thinking.

Essential Questions for Educators and Mentors:

“What do you already know about this topic?”
“How might this connect to something you’ve encountered before?”
“What’s a different way to look at this problem?”
“What’s the most important question we haven’t answered yet?”
“How would you explain this to someone else?”

Essential Questions for Learners:

“How does this concept apply in different contexts?”
“What are the limitations or exceptions to what we’re learning?”
“What’s the evidence supporting this conclusion?”
“How has our understanding of this topic evolved over time?”
“How might I use this information in my own work/life?”

Example in Practice:

A software engineering manager was helping a junior developer debug a complex issue. Rather than pointing out the error, she asked, “What assumptions are we making about how this data is being processed?” This question led the junior developer to realize they had misunderstood a key aspect of the system architecture. By discovering this through questioning rather than being told, the developer gained deeper understanding and was more likely to avoid similar errors in the future.

Application Exercise: If you’re in a teaching role, prepare a lesson that relies primarily on questions rather than statements. If you’re a learner, commit to asking at least two questions in your next learning opportunity, even if you feel you understand the material.

Questions for Innovation and Creativity

Innovation rarely emerges from routine thinking. Questions that challenge assumptions and explore new possibilities are the genesis of creative breakthroughs.

Essential Questions for Innovation:

“What if the opposite were true?”
“How would we approach this if we started from scratch today?”
“What would [someone from a completely different field] do?”
“What if the constraints we’re accepting aren’t actually real?”
“What would this look like if it were ridiculously easy?”

Example in Practice:

A struggling retail chain was trying to compete with e-commerce giants by improving their in-store technology. During an innovation workshop, someone asked, “What if physical retail isn’t actually competing with online shopping but serving a completely different need?” This question shifted the conversation from technology features to the experiential aspects of shopping that can’t be replicated online. The company pivoted to creating community-centered stores with events, personalized service, and social spaces—areas where they could offer unique value compared to online alternatives.

Application Exercise: Select a challenge or opportunity you’re facing. Generate at least 10 “what if” questions that challenge your fundamental assumptions about the situation. Choose the most provocative question and explore where it leads.

Case Study: How Questions Transformed a Struggling School

The Momentous School Turnaround

Momentous School in Dallas, Texas, was struggling with poor academic performance, behavioral issues, and low parent engagement—challenges common to many schools serving low-income communities. Rather than implementing the usual remedies (stricter discipline, test prep focus), the new principal initiated a radical approach centered on questions.

First, she questioned the fundamental assumption about what was needed: “What if our students’ academic struggles aren’t primarily academic issues but are related to other factors?” This led to research about childhood trauma and brain development.

Then, she engaged teachers with questions like: “What if we prioritized emotional regulation before academic content?” and “How might we create a classroom where students feel safe enough for their brains to learn effectively?”

For parents, she asked: “What would make you feel like a valued partner in your child’s education?” rather than telling them how they should be involved.

With students, teachers began asking: “How are you feeling today?” and “What do you need to be successful today?” before jumping into lessons.

The question-centered approach transformed the school culture. Teachers became curious problem-solvers rather than frustrated disciplinarians. Parents became engaged partners rather than distant observers. Most importantly, students began to use questions themselves, developing metacognition and self-regulation skills.

Within three years, the school saw dramatic improvements in both academic metrics and behavioral incidents. Test scores rose, attendance improved, and disciplinary actions declined significantly.

The Lesson:

By using questions to challenge assumptions and engage all stakeholders as contributors rather than problems to be fixed, the school created sustainable change that fixed-answer approaches had failed to achieve. The questions created agency and ownership that would never have emerged from imposed solutions.

Chapter Summary: Context-Specific Question Framework

While each context requires specific types of questions, a common pattern emerges across all high-stakes situations:

Understanding Questions: Begin by seeking genuine comprehension of the other party’s perspective, needs, and constraints
Interest-Revealing Questions: Move beyond stated positions to uncover deeper motivations and priorities
Possibility-Opening Questions: Explore creative options and alternatives that may not be immediately obvious
Concern-Surfacing Questions: Proactively identify potential obstacles or objections
Commitment-Building Questions: Establish next steps and shared understanding

By adapting this general progression to specific contexts, you can transform typical transactional interactions into opportunities for deeper connection, learning, and mutual value creation.

Five Meta-Questions for Any High-Stakes Situation:

“What am I assuming about this situation that might not be true?”
“What does success look like for all parties involved?”
“What information am I missing that would change my approach?”
“How can I frame questions to create psychological safety?”
“What’s the most important question I should ask but am avoiding?”

In the next chapter, we’ll explore how to build questioning into organizational culture, moving beyond individual skill to create environments where powerful questions become the norm.

Next Page: Chapter 10: Building a Question-Centered Culture