Chapter 17 Exercises: Choosing the Right Time, Place, and Medium

Section 17.1 — Timing Is Not Trivial

Exercise 17.1 [Conceptual] ★ Define the "timing window" concept in your own words. What are the two poles that bound it, and why is each extreme problematic? Give one example of a confrontation you have encountered or observed that went wrong because it was timed too soon, and one that went wrong because it was delayed too long.

Exercise 17.2 [Conceptual] ★★ The chapter distinguishes between an "ambush confrontation" and a "request to meet." List three situations in which the ambush confrontation might be unavoidable, and for each situation, identify what you would do to mitigate its negative effects if you found yourself in it. Then list three situations in which the request-to-meet approach would be clearly superior and explain why.

Exercise 17.3 [Scenario] ★★ Read the following scenario and answer the questions below.

Tariq has been bothered for several weeks by Marcus's habit of leaving dishes in the sink. He has said nothing. One evening, after a particularly stressful day, he comes home to find a full sink of dishes and finally says something — in a sharp tone, while Marcus is eating dinner and watching TV.

a) Identify at least three timing problems with Tariq's confrontation. b) Describe what a better-timed version of the same conversation would look like. c) Write the exact request-to-meet message Tariq could have sent Marcus earlier in the week.

Exercise 17.4 [Applied] ★★ Think of a difficult conversation you need to have or have recently avoided having. Using the Timing Assessment Checklist from section 17.4, evaluate whether now is the right time for that conversation. Write a brief (one paragraph) honest assessment of your timing readiness, noting any checklist items that concern you and what you would need to address them.

Exercise 17.5 [Conceptual] ★ In your own words, explain the concept of "decision fatigue" and describe two specific ways it affects the quality of difficult conversations when one or both parties are experiencing it.

Section 17.2 — The Environment Shapes the Conversation

Exercise 17.6 [Conceptual] ★ Explain the psychological distinction between "home territory," "opponent's territory," and "neutral ground" in a confrontation context. For each, describe one confrontation context (personal or professional) in which each setting would be most appropriate.

Exercise 17.7 [Scenario] ★★ Sam needs to address a persistent performance issue with Tyler, one of his direct reports. Tyler is defensive and tends to escalate when confronted.

Design the ideal environmental setup for this conversation. Consider: Which room? What physical arrangement? What time of day? Who else might be present (if anyone)? What should Sam avoid? Write a one-page environmental design rationale.

Exercise 17.8 [Applied] ★★ Identify a difficult conversation you have been avoiding or delaying. Identify the real reason you haven't had it yet. Then identify two specific environmental factors that could make the conversation more likely to succeed, and describe how you would create those conditions.

Exercise 17.9 [Conceptual] ★★ The chapter discusses "walking conversations" as a specific tool for certain kinds of difficult conversations. Describe three types of confrontation situations in which a walking conversation would be particularly useful and three in which it would be inappropriate or counterproductive. What is the underlying principle that determines when walking works?

Exercise 17.10 [Synthesis] ★★★ Jade needs to have a conversation with her mother Rosa about the pressure she feels to pursue a career path Rosa has chosen for her. Rosa is emotionally volatile and tends to escalate quickly. Jade lives in a small apartment with Rosa when she's not at school.

Design a complete "environmental strategy" for this conversation. Address: timing within the week, time of day, location (given their shared living space), physical setup, what Jade should do if Rosa attempts to move the conversation to a different location mid-conversation, and what Jade should do if Rosa leaves the room.

Section 17.3 — Choosing Your Medium

Exercise 17.11 [Conceptual] ★ In your own words, explain media richness theory and its application to confrontation. Why is in-person the default for significant confrontations? What is lost at each step down the richness ladder?

Exercise 17.12 [Scenario] ★★ For each of the following confrontation scenarios, identify the most appropriate medium and briefly explain your reasoning:

a) Marcus needs to raise concerns about his workload with Diane. They work in the same office. b) Dr. Priya needs to address a documentation failure with Dr. Vasquez, who reports to her. c) Sam needs to address a concern with his boss Marcus Webb, who is based in another city. d) Jade wants to apologize to Destiny for something she said during an argument. e) Marcus wants to ask Tariq not to play music late at night. f) Dr. Priya suspects a colleague is taking credit for her research in public presentations. She wants to address it. g) Sam needs to tell Tyler that a project deadline was moved up by two weeks.

Exercise 17.13 [Applied] ★★ Think of a difficult conversation that was attempted or conducted via email or text message that went poorly. (You may use a personal experience or a hypothetical example.) Analyze the failure using the media richness framework. What information was lost because of the lean medium? How might the conversation have gone differently in a richer medium?

Exercise 17.14 [Scenario] ★★★ You propose an in-person meeting to address a significant workplace concern with a peer colleague. They respond: "I'd prefer if you just put your concerns in an email. I process things better in writing."

Write a three-paragraph response (as you would send it, in an actual email or message) that: (a) acknowledges their preference genuinely, (b) explains specifically why you believe the conversation needs to happen in a richer medium, and (c) proposes a workable middle-ground solution. Do not be dismissive or condescending.

Exercise 17.15 [Synthesis] ★★★ You are a manager who has just discovered that two members of your team have been conducting a significant interpersonal conflict entirely over email for the past three weeks. Both have copied you on a lengthy email thread. The thread has become increasingly hostile, and one party has now cc'd HR.

Write a plan — not the emails themselves, but the plan — for how you will intervene in this situation, including: what medium you will use to contact each party, what you will say initially, how you will structure the next steps, and how you will address the existing email record.

Section 17.4 — Timing for Emotional Readiness

Exercise 17.16 [Conceptual] ★ What is the difference between "I am not ready" (legitimate emotional unreadiness) and "I am not ready" (avoidance rationalization)? Identify at least three diagnostic questions you could ask yourself to distinguish between the two.

Exercise 17.17 [Scenario] ★★ Sam has been avoiding a conversation with Marcus Webb, his boss, about an unrealistic workload. He tells himself he's waiting for the right moment. It has now been six weeks.

Using the emotional readiness indicators from section 17.4, evaluate whether Sam's delay is more likely genuine readiness-building or avoidance. What would Sam need to do to move from avoidance into legitimate readiness? Write a specific, actionable plan for Sam.

Exercise 17.18 [Applied] ★★ Complete the Timing Assessment Checklist for a real or realistic confrontation situation in your life. Be honest about each item. Write a paragraph-length reflection on what the checklist reveals about your readiness and what you would need to change before proceeding.

Section 17.5 — When the Other Person Controls the Conditions

Exercise 17.19 [Scenario] ★★ You are Jade. Your mother Rosa has cornered you in the kitchen during a family dinner and is demanding to discuss your career plans right now, in front of other family members. You are not prepared, the conditions are terrible, and she is clearly already emotionally activated.

Write out what you would say — word for word — to acknowledge her urgency, decline to have the full conversation right now, and propose a better alternative. Then write a brief analysis: What are you trying to accomplish in each sentence? What risks does each approach carry?

Exercise 17.20 [Synthesis] ★★★ Consider a confrontation situation you are currently facing or have recently faced in which you felt (or feel) that the other party was controlling the conditions in ways that disadvantaged you — bad timing, wrong medium, poor environment.

Write a comprehensive "condition-recovery plan" that addresses: a) Exactly what conditions the other party is imposing b) What the ideal conditions would look like c) What you can realistically negotiate d) What you cannot change and must accept e) How you will acknowledge the constraint while still having the most effective conversation possible f) Your opening statement to request better conditions

Synthesis and Application

Exercise 17.21 [Synthesis] ★★★ Return to Marcus's 4:55 Friday hallway moment from the chapter opening. Write a completely revised version of Marcus's approach to the same conversation. Your version should include: - The exact timing of when Marcus makes his request-to-meet - The exact wording of the request-to-meet (email or spoken) - The location and environmental setup of the actual conversation - The medium (and justification) - The day and time of the actual conversation - What Marcus does in the intervening time to prepare emotionally

Do not write the conversation itself — only everything that happens before the first substantive word is spoken.

Exercise 17.22 [Applied] ★★★ Dr. Priya needs to address a pattern of Dr. Vasquez's behavior in interdepartmental meetings — he regularly minimizes her contributions and redirects credit toward himself. She has tried to address this informally once before but it was not effective. She needs a more formal confrontation.

Design a complete "contextual strategy" for Priya's confrontation, using all the frameworks from this chapter: timing window, request-to-meet wording, environmental choice, medium selection, and emotional readiness assessment. Write each component explicitly.

Exercise 17.23 [Conceptual] ★★ The chapter argues that choosing the right conditions is "a form of respect" for the difficulty of the task at hand. Do you agree? In what sense is attending to timing, environment, and medium a form of respect — for the other party, for yourself, or for the relationship? What does it suggest about someone who consistently ignores these conditions?

Exercise 17.24 [Applied] ★★★ Design your own personal "confrontation preparation protocol" — a personalized checklist or system that you would actually use before initiating a difficult conversation. It should incorporate: timing assessment, environmental planning, medium selection, emotional readiness check, and request-to-meet drafting. Make it specific enough to be genuinely useful, and brief enough that you would actually use it.

Exercise 17.25 [Synthesis] ★★★ The chapter makes the claim that the conditions of a difficult conversation are "active participants in the outcome." Write a two-page analytical essay defending or challenging this claim, using at least three specific scenarios (real or hypothetical) as evidence. If you challenge the claim, identify what conditions you believe actually do or do not matter, and why.