Difficult conversations, ready to practice
88 situations that are hard to get right. Open one to see what makes it difficult and what tends to work, then say it out loud to an AI counterpart and get a scorecard on your own words.
Workplace
📋 Performance Management
- The Chronic Deadline MisserYour direct report keeps missing deadlines but always has a reasonable excuse.
- Declining Work QualityA previously strong performer is producing sloppy work and seems disengaged.
- The Promotion ConversationYou need to explain why someone wasn't promoted and keep them motivated.
- Remote Work AccountabilityA remote employee is consistently unreachable during core hours.
⚡ Peer Conflict
- Taking Credit for Your WorkA colleague presented your team's work as their own in a leadership meeting.
- The Public UnderminerA peer regularly questions your decisions in front of others.
- Competing for ResourcesAnother team lead wants the same headcount allocation you need.
- The Process StandoffYou and a peer disagree on how a cross-team workflow should run.
🤝 Negotiation
- Scope Creep After AgreementA stakeholder keeps adding requirements after you've agreed on scope.
- The Vendor RenegotiationA vendor wants to increase rates mid-contract with vague justifications.
- The Impossible TimelineLeadership wants a project delivered in half the realistic timeline.
- The Salary NegotiationYou're negotiating a raise with a manager who deflects with vague promises.
🛡 Boundaries
- The Weekend TexterA colleague constantly messages you outside work hours expecting responses.
- The Workload DumperSomeone keeps volunteering you for work that isn't yours.
- The "Just Joking" ColleagueSomeone makes comments that cross the line and hides behind humor.
- The Oversharing InterrogatorA colleague pushes for personal information you don't want to share.
🎢 Frontline Teams
- The No-Call/No-ShowA seasonal crew member skipped a Saturday shift without calling and thinks it's no big deal.
- After the Guest Blew UpDebrief a crew member who snapped back at an angry guest in front of the queue.
- The Once-Reliable LeadA returning seasonal team lead's standards have slipped since being passed over.
- The Refund DemandA furious guest at guest services wants a full refund after two ride closures.
Healthcare
💔 Breaking Bad News
- Delivering a Cancer DiagnosisTell a patient their biopsy results came back positive for cancer.
- Receiving a Cancer DiagnosisYour doctor is about to deliver serious biopsy results. Practice advocating for yourself.
- Notifying a Family of a Sudden DeathDeliver the news that a loved one has died unexpectedly in the hospital.
- Hearing That a Loved One Has DiedA physician is about to tell you devastating news. Stay present and ask what you need.
- Poor Prognosis for a Young ParentExplain that treatment is unlikely to cure a young parent with advanced disease.
- Learning Your Prognosis as a ParentYour oncologist needs to discuss serious news about your illness and your children.
- Treatment Is No Longer WorkingTell a patient their current therapy is not controlling the disease.
- Learning Your Treatment Is Not WorkingYour doctor has difficult scan results. Practice processing the news and asking what is next.
📋 Informed Consent
- High-Risk Surgery ConsentObtain informed consent for a major operation with meaningful complication risks.
- Deciding on High-Risk SurgeryYour surgeon recommends an operation with real risks. Ask what you need to decide.
- Chemotherapy Side EffectsA reluctant patient must understand chemotherapy risks and benefits.
- Pushing Back on ChemotherapyYou are unsure about chemo. Practice voicing concerns and asking for alternatives.
- Patient Questions the Recommended ProcedureAddress skepticism while meeting standards for informed consent.
- Questioning a Recommended ProcedureYou are not convinced you need the procedure. Advocate for clarity and options.
- Patient Pushes a Researched TreatmentRespond to a patient requesting a specific therapy they found online.
- Advocating for a Treatment You ResearchedAsk your care team to consider a therapy you believe could help.
👨👩👧 Family Conflict
- Mediating Siblings on a Parent's CareFacilitate a meeting where adult children disagree on goals for an ill parent.
- Disagreeing With Siblings About Mom's CareYou and your siblings clash over what Mom would want. Practice staying grounded.
- Family Insists on "Everything"Discuss limits of intensive care when a family demands maximal intervention.
- When You Want "Everything" for Your Loved OneYou fear the team is giving up. Express your fears and ask for a clear plan.
- Advocating for a Parent's Stated WishesSupport a family member who says they know what the patient wanted.
- Honoring What Dad Said He WantedYour sibling resists limiting treatment. You hold the proxy — navigate the conflict.
- Family Challenges the Care PlanA family openly disputes the team's recommendations in a meeting.
- Challenging a Care Plan You DistrustYou believe discharge is unsafe. Practice pushing for answers and advocacy.
💊 Non-Compliance
- Patient Not Taking MedicationsExplore barriers to adherence without lecturing.
- Feeling Judged for Missing MedsYour doctor brings up adherence. Explain your reality without shutting down.
- Patient Missing Follow-UpsAddress repeated no-shows while staying collaborative.
- Explaining Missed AppointmentsYou have skipped visits. Practice asking for flexibility without making excuses.
- Lifestyle Changes After a Cardiac EventDiscuss diet, activity, and risk reduction after MI — meet resistance with empathy.
- Pushed to Change Everything After a Heart AttackThe list of changes feels impossible. Negotiate priorities with your cardiologist.
- Pressured About Medication ComplianceA patient feels hounded about pills; rebuild trust and shared goals.
- Pushed on Meds — Advocate for DignityYou feel treated like a non-compliant label. Set boundaries and ask for partnership.
🕊️ End-of-Life
- Introducing Palliative CareSuggest palliative involvement without implying abandonment.
- Hearing "Palliative Care" SuggestedYou fear it means the end. Ask what it really means for you.
- Discussing DNR With FamilyFacilitate a code status conversation when opinions diverge.
- DNR Discussion With Your FamilyYou disagree with relatives about Mom's code status. Speak clearly and calmly.
- From Curative to Comfort CarePivot the conversation when disease-directed therapy is no longer beneficial.
- When Curative Treatment Is StoppingYour team suggests shifting goals. Process grief and ask practical questions.
- Discussing Hospice OptionsExplain hospice eligibility and what services include.
- Asking About HospiceYou want to understand hospice without committing on the spot.
🩺 Provider-to-Provider
- Nurse Challenges a Physician OrderQuestion an unsafe or unclear order while maintaining professionalism.
- Disagreeing on Discharge ReadinessPush back when you believe discharge is premature.
- Handoff Communication BreakdownAddress a dangerous gap between shifts or services.
- Interdisciplinary Care DisagreementResolve conflicting recommendations across specialties.
Mental health
🆘 Risk Disclosure
- Doorknob Disclosure at Minute Fifty-TwoAssess suicide risk when a client discloses as the session is ending.
- The Passing RemarkFollow up a minimised hint about not wanting to be alive.
- "Promise You Won't Tell Anyone"Assess a client's plan without agreeing to keep it secret.
- "It's Nothing New"Take long-standing suicidal thoughts seriously without overreacting.
🧩 Rupture & Repair
- "You Don't Actually Care"Repair the alliance after a client says you're only in it for the money.
- Ten Minutes LateOwn your lateness and explore what it stirred up for the client.
- The Detail You ForgotRepair after forgetting something important the client told you.
- Silent After I Pushed Too HardRebuild safety after an interpretation lands badly.
🪟 Frame & Boundaries
- "Can I Text You When It's Bad?"Hold the frame warmly when a client asks for between-session texting.
- "I Can't Pay This Month"Discuss a fee shortfall directly without shame or a fixed workaround.
- The Expensive GiftRespond to an expensive gift without rejecting the client.
- "Let's Get Coffee Sometime"Decline a dual relationship while keeping the alliance intact.
🤐 Silence & Withdrawal
- Three Sessions of One-Word AnswersTolerate silence and wonder aloud with a client who has gone quiet.
- Something They Haven't SaidMake it safe for a client to say something shameful.
- "I'm Fine"Reflect rather than interrogate a client who insists everything is fine.
- Silent Since I Asked About DrinkingRepair after a question about alcohol lands as judgment.
📞 Mandated Reporting
- A Child Is Being HurtReport harm to a child while staying transparent and on the client's side.
- "You're Going to Ruin My Family"Hold the limits of confidentiality without becoming defensive.
- Silent After the Limits TalkKeep a client engaged after explaining your reporting duty.
- "If You Report This I Can't Go On"Address a reporting duty and a client's own risk in the right order.
🚪 Termination
- "So You're Dumping Me"Hold a planned ending while making room for the client's anger.
- Checked Out Before the EndingName what you notice as a client withdraws from a planned ending.
- "Can We Stay in Touch?"Hold the frame and leave the door open at the end of therapy.
- Risk Returns as the Ending NearsAssess returning suicidal thoughts and adjust the ending plan.