Chapter 14 Exercises: Asking Better Questions

Instructions

These exercises are organized from foundational (conceptual) to applied (in context) to integrative (synthesis). Complete them in order if you're new to the material; experienced practitioners may jump to higher-difficulty items.

Difficulty ratings: - ★ Foundational — accessible with careful reading - ★★ Intermediate — requires reflection and some self-knowledge - ★★★ Advanced — requires applying concepts in messy, real-world conditions

Section A: Conceptual Exercises [Conceptual]

Exercise 1 — Question Type Identification ★

Instructions: Read each question below. Label it with one or more of the following types: Open, Closed, Genuine, Rhetorical, Leading, Loaded. Some questions may have more than one label. Then briefly explain your reasoning.

  1. "Did you even read the email before you responded?"
  2. "What was going through your mind when you made that decision?"
  3. "Don't you think you should have checked in with me first?"
  4. "When did you find out about the change in plans?"
  5. "Why do you always have to make things difficult?"
  6. "What would a good outcome from this conversation look like for you?"
  7. "Are you really going to defend that position?"
  8. "How did you arrive at that number?"
  9. "Do you understand why that was frustrating for me?"
  10. "What's been hardest about this situation for you?"

Exercise 2 — The Weaponized Question Audit ★

Instructions: Below are six questions Marcus might ask Diane during their conflict. For each question: - Identify whether it is weaponized or genuine - Name what the question is really saying (the implicit accusation or demand) - Rewrite it as a genuine, open question

  1. "Why do you always do things like this?"
  2. "Did you even think about how this affects me?"
  3. "How long were you planning to keep this a secret?"
  4. "Don't you think communication is supposed to work both ways?"
  5. "What am I even supposed to do with this information now?"
  6. "Were you afraid I'd say no?"

Exercise 3 — The Funnel Diagram ★

Instructions: The funnel structure moves from wide-open questions to progressively specific confirming questions. For the scenario below, design a five-question funnel sequence — from the widest opening question to the narrowest closing question.

Scenario: Your coworker submitted a project component late, and it delayed the whole team. You want to understand what happened before deciding whether to raise it with your manager.

Label each question: - Q1 (widest) - Q2 - Q3 - Q4 - Q5 (narrowest/confirming)

Exercise 4 — Why vs. What/How Swaps ★

Instructions: Rewrite each "why" question below as a "what" or "how" question that reduces the likelihood of triggering defensiveness.

  1. "Why didn't you tell me sooner?"
  2. "Why do you react that way every time I bring this up?"
  3. "Why is this so hard for you to understand?"
  4. "Why did you agree to that without consulting me first?"
  5. "Why are you being like this?"
  6. "Why can't you just be more organized?"
  7. "Why didn't you ask for help when you were struggling?"
  8. "Why would you make that promise when you knew you couldn't keep it?"

Exercise 5 — Question Stacking Analysis ★★

Instructions: Read the following turn from a conflict conversation. Identify how many questions are stacked in this turn. Then rewrite it as a single, best question.

"Did you get the memo? And if you did, why didn't you say something at the meeting? Also, were you aware that three other people had the same concern? And why didn't you come to me directly instead of going to Priya?"

Questions to answer: 1. How many questions are stacked here? 2. Which one question is most important to ask first? 3. Rewrite as a single, open, genuine question.

Exercise 6 — The Question Behind the Question ★★

Instructions: For each question below, identify: (a) What the question appears to be asking on the surface (b) What the asker is probably really asking for (the deeper need or fear) (c) How naming the real need changes what you might say or ask

  1. "Why don't you ever ask about my day?"
  2. "Were you aware that I've been handling this alone for six months?"
  3. "Do you even care about this relationship?"
  4. "Why does everyone else seem to get more resources than my team?"
  5. "Did you say that to embarrass me in front of the group?"

Section B: Scenario Exercises [Scenario]

Exercise 7 — Marcus and the Interrogation Rewrite ★★

Instructions: Recall the opening scene in this chapter — Marcus asking Diane a series of why questions that felt like interrogation. Rewrite the entire exchange (at minimum five conversational turns) so that Marcus is using genuine, open questions. Marcus can still be hurt and confused — but his questions should come from curiosity, not accusation.

Your rewritten conversation should demonstrate: - At least one "what" or "how" question replacing a "why" question - At least one use of "and what else?" - Marcus slowing down rather than escalating - A closing confirmation question at the end

Exercise 8 — Dr. Priya and the Leading Question Pattern ★★

Instructions: Dr. Priya Okafor is meeting with a resident who has missed two documentation deadlines. Priya's instinct is to ask leading, closed questions: "Don't you think documentation is a patient safety issue?" / "Isn't it your responsibility to meet these deadlines?"

Rewrite Priya's opening five minutes of this conversation using: - A genuinely open first question - The funnel structure - At least one "and what else?" - A confirming close that doesn't embed a judgment

Then write a reflection (3–5 sentences): How does Priya's rewritten approach change the likely outcome of this conversation?

Exercise 9 — Jade and the Framing Challenge ★★

Instructions: Jade wants to understand why her grandmother always prepares a particular dish for family gatherings without involving the younger women in the process. She is genuinely curious — not challenging the tradition.

Write two versions of Jade asking this question:

Version A: Jade's default, direct version — honest and curious, but likely to read as disrespect in this relational context.

Version B: A reframed version that signals Jade's curiosity and her respect for her grandmother's wisdom and authority.

After both versions, write a brief analysis (3–4 sentences): What specifically changes between Version A and Version B, and why does the change matter?

Exercise 10 — Sam's Discovery ★★

Instructions: Sam Nguyen is about to have a conversation with Tyler about the third missed deadline. In the past, Sam has told Tyler: "The standard is [X]. You need to meet [X]. This is the third time. I need you to commit to meeting [X] going forward."

Write Sam's new opening — three minutes of conversation — in which Sam asks rather than tells. Sam should: - Open with one wide, genuine question - Use at least one "what" or "how" formulation - Resist the urge to deliver the "standard" until Tyler has had genuine space to speak

After writing the conversation, answer: What does Tyler say that Sam could not have known without asking?

Exercise 11 — The Curiosity Pivot in Real Time ★★

Instructions: In each scenario below, a character is about to say a statement that is accusatory or defensive. Write the curiosity pivot — the question they could ask instead.

  1. Priya is about to say to a colleague: "You undermined my recommendation in that meeting and I'm furious about it."

  2. Marcus is about to say to his study group partner: "You never carry your weight in this group."

  3. Jade is about to say to her mother: "You treat my brother completely differently than you treat me."

  4. Sam is about to say to Tyler: "If you can't handle this workload, maybe you're not right for this role."

  5. A partner in a relationship is about to say: "You're always on your phone and it makes me feel like I don't matter."

For each, write: - The curiosity pivot question - One sentence explaining what genuine information the question could surface that the statement would not

Exercise 12 — The Pre-Confrontation Checklist in Action ★★

Instructions: Think of a real or hypothetical conflict you're currently facing or have recently faced. Work through the Pre-Confrontation Curiosity Checklist from Section 14.5:

  1. What do you think happened, and what parts are you genuinely uncertain about?
  2. What are you most afraid of discovering in this conversation?
  3. What do you actually need from this person or situation?
  4. What would you ask if you were a journalist, simply trying to understand what happened from the other person's perspective?
  5. What would you ask if you were genuinely curious and not at all defensive?

Write your answers in full. Then: based on your answers to questions 4 and 5, write the three best questions you would bring into this conversation.

Exercise 13 — The Miracle Question Applied ★★

Instructions: The miracle question from solution-focused brief therapy asks: "If this problem were solved overnight, what would be different?"

Apply a version of this question to two of the following conflict scenarios. For each, write: (a) Your adapted version of the miracle question for that scenario (b) What kind of answer you might receive (c) How that answer could redirect the conversation

Scenarios: 1. A long-running conflict between two siblings about their elderly parent's care 2. A workplace dispute about workload distribution on a project team 3. A friendship conflict about one person feeling like they always initiate plans 4. A couple disagreeing about financial priorities

Section C: Applied Exercises [Applied]

Exercise 14 — Live Question Audit ★★

Instructions: In your next significant conversation — it does not have to be a conflict — track the questions you ask. After the conversation, answer:

  1. How many questions did you ask total?
  2. How many were open vs. closed?
  3. How many were genuine vs. rhetorical/leading?
  4. Did you stack questions at any point?
  5. Did you ask "and what else?" or any equivalent follow-up?
  6. What was the most effective question you asked, and why?
  7. What was one question you wish you had asked but didn't?

Write a paragraph reflecting on what this audit revealed about your default questioning habits.

Exercise 15 — The Seven Questions Experiment ★★★

Instructions: Michael Bungay Stanier's seven essential questions are listed in Section 14.3. Over the next week, deliberately use at least five of them in real conversations — not as a script, but as genuine inquiry. Choose conversations where they fit naturally.

After each use, note: - Which question you used - What prompted you to use it - What response you received - Whether you were surprised by what you learned

At the end of the week, write a one-paragraph reflection: Which of Bungay Stanier's questions was most useful in your experience, and why?

Exercise 16 — Question Mapping a Past Conflict ★★★

Instructions: Think of a conflict you were involved in that did not go well — where the conversation escalated or shut down.

Map the questions you (and ideally the other person) asked during that conflict. For each question: - Classify it (open/closed, genuine/rhetorical/leading) - Identify what effect it appeared to have on the conversation - Write an alternative question that might have had a better effect

At the end, answer: If both parties had been operating from the Curious Confronter model, how might the conversation have unfolded differently?

Exercise 17 — Designing a Curious Opening ★★★

Instructions: You need to have a difficult conversation with someone about a pattern of behavior that has been frustrating you. Design the opening of that conversation using only questions — no statements of your position or complaint until the other person has had genuine space to respond.

Requirements: - Your opening question should be wide and open - You should plan follow-up questions for at least three different directions the conversation might go - Include at least one planned "and what else?" - Include a confirming question for the closing of your opening sequence

Exercise 18 — Rewriting a Historical Conflict ★★★

Instructions: Recall a significant conflict from your past — ideally one involving someone who matters to you. Imagine it again, but this time, design your side of the conversation using the full toolkit from this chapter:

  • Pre-confrontation checklist (what were your real questions?)
  • Opening with a genuine, open question
  • Using the funnel structure
  • Applying at least two curiosity pivots
  • Asking "and what else?" at least once

Write out the conversation as you imagine it might have gone. Then write a brief reflection: What was hardest about this rewrite? What did it require you to let go of?

Section D: Synthesis Exercises [Synthesis]

Exercise 19 — Humble Inquiry vs. Defensive Inquiry ★★★

Instructions: Based on the Edgar Schein material in Case Study 2, and the chapter material more broadly, write a 400–600 word essay on the following question:

"What makes humble inquiry fundamentally different from questioning as social pressure — and why is that difference difficult to sustain in the middle of a conflict?"

Your essay should: - Define humble inquiry in your own words - Identify the specific conditions (internal and external) that make it difficult - Name at least two concrete practices that support it - Draw on at least one of the characters from this chapter to illustrate

Exercise 20 — The Taxonomy in Conflict ★★★

Instructions: Create your own scenario — a conflict between two people you invent — and write the full conversation twice.

Version A: The conversation using weaponized questions — rhetorical, leading, loaded, stacked. Show how the conversation deteriorates.

Version B: The same conversation using the tools from this chapter — genuine, open questions, funnel structure, curiosity pivots, "and what else?"

Your conversations should each be at least 8–10 conversational turns per side.

After both versions, write a 200-word analysis comparing the two: what specifically changed, and what does that reveal about the function of questions in conflict?

Exercise 21 — Cultural Context and Curiosity ★★★

Instructions: Jade's experience illustrates that "asking better questions" is culturally mediated — the same question can read as curiosity in one context and disrespect in another.

Write a 400-word reflection on the following: How does your own cultural, family, or community background shape what kinds of questions feel safe to ask, and what kinds of questions feel inappropriate or presumptuous? How has that shaping affected conflicts you've been in?

Identify at least two specific adjustments you might make to your questioning approach in contexts where your default style might be misread.

Exercise 22 — Building Your Personal Question Bank ★★★

Instructions: Develop a personal question bank — a reference document you will actually use. Your question bank should include:

Section 1: Opening Questions (at least 5) Wide, open questions suitable for beginning a difficult conversation.

Section 2: Exploration Questions (at least 5) Follow-up questions that deepen understanding once someone has started talking.

Section 3: Curiosity Pivots (at least 5) Questions to replace specific statements you find yourself making in conflict.

Section 4: Confirming/Closing Questions (at least 3) Questions to confirm understanding before moving toward resolution.

Section 5: Pre-Confrontation Questions (the three from Section 14.5, plus at least 2 more you find useful) Questions to ask yourself before any difficult conversation.

Label each question with the type (open/closed/genuine) and a one-sentence note on when you would use it.

Exercise 23 — Connecting to Active Listening ★★

Instructions: Chapter 12 established that active listening requires holding your own perspective lightly enough to genuinely receive someone else's. This chapter argues that open, genuine questions are the spoken enactment of active listening.

Write a 300-word reflection on the relationship between these two skills: How do active listening and genuine questioning support each other? What happens when you try to practice one without the other? Can you be a good active listener but a poor questioner? Can you ask good questions without active listening?

Exercise 24 — Sam's Toolkit Retrospective ★★★

Instructions: Sam Nguyen, before this chapter's learning, approached Tyler by telling rather than asking. Think through Sam's entire change arc as depicted in this chapter and Case Study 1.

Write a 500-word analysis of Sam's transformation through three lenses: 1. What Sam believed before (about how to address performance issues) 2. What Sam discovered (through the case study conversation) 3. What Sam now needs to practice (to make this shift durable)

Your analysis should reference specific techniques from the chapter (funnel structure, "and what else?", curiosity pivot, pre-confrontation questions) and explain how each applies in Sam's management context.

Exercise 25 — Integration: Design a Questioning Workshop ★★★

Instructions: You have been asked to design a 30-minute workshop on asking better questions in conflict for a team of 12 people at your organization, community group, or campus.

Design the workshop: 1. Opening (5 minutes): An activity or question that immediately demonstrates the difference between weaponized and genuine questions 2. Content (10 minutes): The three most important concepts from this chapter to teach in a practical way 3. Practice (10 minutes): A structured pair activity that lets participants practice the skills 4. Reflection/Close (5 minutes): A question or prompt that helps participants connect the material to their real situations

For each section, explain your choices: Why did you prioritize these concepts? What are the risks in each activity, and how did you design to mitigate them?