Difficult conversation questions.

87 difficult conversation questions from the bank, ready to practice out loud.

Learn the ideas first · free with an account

Ending a hard call with next steps SBI: feedback that names behavior, not character STAR and CARL: structuring your story Hard conversations: name it in the first 30 seconds Saying no to a hopeful client

All 87 questions

Discussing a missed promotionAn engineer who expected promotion didn't get it this cycle. They're in your office. What do you say?Opening with the hard messageSenior–leadership

Eliminating a long-tenured employee's roleWalk me through how you'd structure a conversation telling a long-tenured employee their role is being eliminated.Room for responseSenior–leadership

Contradicting previous manager feedbackWalk me through how you'd deliver critical feedback that goes against what the person has been told by previous managers.Factual groundingSenior–leadership

Delivering a rejection offerWalk me through how you'd tell a candidate they're not getting the offer after multiple interview rounds.Empathy without softening the messageMid–senior

Closing a difficult conversation clearlyWalk me through how you'd close a difficult conversation so the person has clarity on what happens next.Clear next stepsMid–senior

Delivering lower-than-expected compensationWalk me through telling a top performer their comp adjustment will be lower than they expected.Opening with the hard messageSenior–leadership

Managing anger during terminationWalk me through how you'd handle a conversation when the person being terminated reacts with intense anger.Room for responseSenior–leadership

Assessing performance with mixed dataWalk me through how you'd give performance feedback when the data is mixed and you're being asked for a clear assessment.Factual groundingSenior–leadership

Critical feedback during personal hardshipWalk me through how you'd give critical feedback to someone who's been having a personally difficult time.Empathy without softening the messageSenior–leadership

Written commitments after role changesWalk me through what you'd commit to in writing after a difficult conversation about role changes.Clear next stepsSenior–leadership

Restructuring and losing direct reportsWalk me through how you'd tell a team member their team is being restructured and they're losing direct reports.Opening with the hard messageSenior–leadership

Candidate cries during bad newsWalk me through how you'd respond when someone you're delivering bad news to breaks down crying.Room for responseMid–leadership

Handling disputed facts in feedbackWalk me through how you'd handle the conversation when the person disputes the facts you're presenting.Factual groundingSenior–leadership

Feedback to respected person underperformingWalk me through delivering feedback to a team member you respect personally but whose work has been suffering.Empathy without softening the messageSenior–leadership

Redirected difficult conversationsWalk me through how you'd handle a person who keeps redirecting a difficult conversation to other topics.Clear next stepsSenior–leadership

Announcing layoff including team memberWalk me through how you'd notify your team of a layoff that includes one of them in front of the others.Opening with the hard messageSenior–leadership

Handling silence after difficult messageWalk me through how you'd handle silence on the other side of a difficult message.Room for responseSenior–leadership

Correcting employment status misunderstandingWalk me through how you'd correct a major misunderstanding about an employee's status without escalating.Factual groundingSenior–leadership

Critical feedback before promotionWalk me through how you'd give critical feedback to someone you're about to promote.Empathy without softening the messageSenior–leadership

Repeated behavior issues not improvingWalk me through how you'd handle a conversation about repeated behavior issues when previous interventions haven't worked.Clear next stepsSenior–leadership

Announcing departure of beloved leaderWalk me through how you'd tell a team that a much-loved leader is leaving the company.Opening with the hard messageSenior–leadership

Receiving grievances during feedbackWalk me through how you'd respond when someone you're giving difficult feedback to brings up their own grievances about you.Room for responseSenior–leadership

Communicating restricted decision rationaleWalk me through how you'd communicate a decision driven by factors you're not allowed to share.Factual groundingSenior–leadership

Direct feedback in indirect cultureWalk me through how you'd give critical feedback in a culture where direct feedback isn't the norm.Empathy without softening the messageSenior–leadership

Follow-up check-in after difficult talkWalk me through how you'd structure a check-in two weeks after a difficult conversation.Clear next stepsSenior–leadership

Announcing product cancellationWalk me through how you'd notify your team that a planned product is being canceled.Opening with the hard messageSenior–leadership

Interpreting unexpectedly calm responseWalk me through how you'd handle a conversation where the person is more emotionally regulated than you expected and you're not sure what they think.Room for responseSenior–leadership

Pattern without specific exampleWalk me through how you'd respond when an employee says 'tell me one specific example' and you only have a pattern.Factual groundingSenior–leadership

Handling minimization of the issueWalk me through how you'd handle a conversation where the person reacts by minimizing the issue you're raising.Empathy without softening the messageSenior–leadership

Following up after unresolved conversationWalk me through what you'd do if a difficult conversation ended without the resolution you needed.Clear next stepsSenior–leadership

Opening about a production outageWalk me through how you'd open a conversation to tell a peer their code caused a production outage.Opening with the hard messageEntry–mid

Starting feedback on intern performanceWalk me through how you'd start a conversation telling an intern their work quality isn't meeting the bar for a return offer.Opening with the hard messageEntry–mid

Giving space after deadline accelerationWalk me through how you'd give a teammate space to respond after telling them their project deadline is being moved up by two weeks.Room for responseEntry–mid

Listening after breaking a commitmentWalk me through how you'd pause and listen after telling a colleague you can't cover their shift as promised.Room for responseEntry–mid

Using examples for disruptive communicationWalk me through how you'd use specific examples when telling a team member their communication in meetings has been disruptive.Factual groundingEntry–mid

Presenting facts about unequal effortWalk me through how you'd present the facts when telling a classmate or bootcamp peer they're not pulling their weight on a group project.Factual groundingEntry–mid

Acknowledging effort while requesting reworkWalk me through how you'd acknowledge someone's effort while telling them their first major deliverable needs significant rework.Empathy without softening the messageEntry–mid

Showing understanding about timeline limitsWalk me through how you'd show understanding while telling a new teammate you can't extend the onboarding timeline they requested.Empathy without softening the messageEntry–mid

Clarifying next steps on deadlinesWalk me through how you'd end a conversation about missed deadlines by clarifying what the person needs to do differently going forward.Clear next stepsEntry–mid

Closing with clear expectationsWalk me through how you'd close a conversation where you've told someone their work approach isn't aligning with team standards, making sure they know what to do next.Clear next stepsEntry–mid

Removing someone from leadershipWalk me through the first 30 seconds of telling a volunteer or club member you're removing them from a leadership position.Opening with the hard messageEntry–mid

Outlining steps after unprofessional behaviorWalk me through how you'd outline specific next steps after telling a peer their behavior in a client meeting was unprofessional.Clear next stepsEntry–mid

Opening about undisclosed AI-generated workA direct report just told you the analysis they presented as their own was largely AI-generated. They don't see the problem. How do you open the conversation?Opening with the hard messageMid–leadership

Feedback on suspected AI-generated sectionsHow do you give feedback on sloppy work when you suspect — but can't prove — that the weak sections came from unreviewed AI output?Factual groundingMid–senior

Telling strong performer about automationWalk me through telling a strong performer that part of their role is being automated and the job they were hired for is changing shape.Opening with the hard messageSenior–leadership

Delivering a layoff over videoYou have to deliver a layoff over video to someone you've never met in person. What do you do differently — and what do you refuse to do differently?Room for responseSenior–leadership

Addressing over-reliance on AI toolsWhat's your approach when a team member's AI-assisted output is fine, but their reliance on the tools is stalling their own growth?Empathy without softening the messageMid–senior

Structuring critical feedback in writingA difficult message has to land in writing because of time zones. How do you structure it so it's clear without being brutal, and what do you hold back for a live follow-up?Clear next stepsMid–senior

Chatbot contradicts your feedbackYou're giving critical feedback and the person pulls up a chatbot's assessment saying their work is excellent. How do you respond?Factual groundingMid–senior

Delivering decision you didn't makeYour manager asks you to tell a peer their project access is being pulled — a decision you weren't part of. How do you handle the conversation?Opening with the hard messageEntry–mid

Discovering you're being recordedMidway through a difficult conversation, you realize the other person is recording or transcribing it. What do you do?Room for responseMid–leadership

Telling executive about customer impactWalk me through telling a founder or executive peer that their behavior on customer calls is costing the company deals.Empathy without softening the messageSenior–leadership

Answering if they should leaveAfter a serious underperformance conversation, the person asks, 'Should I be looking for another job?' How do you answer honestly?Clear next stepsSenior–leadership

Addressing unedited AI outputA teammate keeps pasting unedited AI output into your shared deliverables and you're absorbing the rework. How do you raise it with them directly?Factual groundingEntry–mid

Reopening after feedback withdrawalYou gave a peer honest feedback a week ago and they've gone quiet — short replies, no calls. How do you reopen the conversation?Room for responseEntry–mid

Requiring relocation or office returnWalk me through telling a long-remote employee they're being asked to relocate or start coming into an office — under a policy you only partly agree with.Empathy without softening the messageSenior–leadership

Canceling a project mid-wayWalk me through how you'd open a conversation telling a direct report their project is being canceled after six months of their work.Opening with the hard messageMid–leadership

Confirming performance improvement planA team member asks point-blank if they're on a performance improvement plan. They are. How do you respond in that moment?Opening with the hard messageMid–leadership

Addressing production outage responsibilityWalk me through how you'd tell a senior engineer their technical decisions led to a production outage affecting customers.Factual groundingSenior–leadership

Peer promoted to manage themHow would you structure a conversation with someone whose peer was promoted to manage them?Empathy without softening the messageMid–leadership

Removing from high-visibility projectWalk me through how you'd give space for response when telling someone they're being moved off a high-visibility project.Room for responseMid–leadership

Leadership style causing attritionYou need to tell a director their leadership style is creating attrition on their team. Walk me through the conversation.Factual groundingLeadership

Delivering zero bonus decisionWalk me through how you'd close a conversation where you've told someone their bonus is zero due to performance issues.Clear next stepsMid–leadership

Competing offer with no budgetA high performer tells you they have a competing offer and asks what you can do. You have no budget to counter. What do you say?Opening with the hard messageMid–leadership

30-day performance improvement noticeWalk me through telling an entry-level employee their work quality isn't meeting the bar and they have 30 days to improve.Factual groundingEntry–senior

Blame-shifting response to feedbackHow would you respond when someone reacts to critical feedback by blaming their teammates?Room for responseMid–leadership

Denying flexible work requestWalk me through how you'd tell someone their requested flexible work arrangement can't be approved due to role requirements.Empathy without softening the messageMid–senior

Feedback during grief periodA team member's spouse just passed away. Two weeks later, you need to deliver feedback on missed deadlines. How do you approach this?Empathy without softening the messageMid–leadership

Next steps after promotion denialWalk me through what specific next steps you'd outline after telling someone they're not ready for promotion this year.Clear next stepsMid–leadership

Technical judgment misalignmentYou need to tell a staff engineer their technical judgment is increasingly out of step with the team's direction. Walk me through it.Factual groundingStaff+–leadership

Stepping back to individual contributorHow would you open a conversation telling a manager they're being asked to step back into an individual contributor role?Opening with the hard messageSenior–leadership

Handling quit threat in momentWalk me through handling the conversation when someone threatens to quit on the spot after you deliver negative feedback.Room for responseMid–leadership

Not inviting back after projectYou're telling a junior associate at a consulting firm they won't be invited back after their project ends. How do you structure this?Opening with the hard messageEntry–mid

Deal credit and league tablesWalk me through how you'd tell a banker their deal closed but they won't receive credit on the league tables due to role scope.Empathy without softening the messageMid–senior

Inappropriate client meeting behaviorHow would you give clear next steps after telling someone their behavior in a client meeting was inappropriate?Clear next stepsMid–senior

Roadmap override and pivotWalk me through telling a product manager their roadmap is being overridden by leadership and they need to pivot immediately.Factual groundingMid–senior

Layoff rumors without confirmationA direct report asks if the company is doing layoffs. You know layoffs are coming but can't confirm yet. What do you say?Opening with the hard messageMid–leadership

Delivering a denied transfer requestWalk me through how you'd structure room for response when telling someone their transfer request was denied.Room for responseEntry–senior

Addressing accent and executive presenceYou need to tell a team member their accent or communication style is affecting their executive presence. How do you approach this?Empathy without softening the messageMid–leadership

Confronting peer relationship problemsWalk me through the factual basis you'd present when telling someone their peer relationships are harming team collaboration.Factual groundingMid–senior

Director absorbed into peer's orgHow would you close a conversation where you've told a director their org is being absorbed and they'll report to a former peer?Clear next stepsLeadership

Withdrawing offer after candidate resignedThe req was cut in a budget decision and you must call a candidate who resigned their job last week to tell them the offer is withdrawn. Walk me through the call.Opening with the hard messageMid–senior

Allegations not substantiated outcomeYou're closing a workplace investigation and must tell the complainant that the allegations were not substantiated. Walk me through the conversation.Factual groundingSenior–leadership

Internal candidate rejection newsAn internal candidate didn't get the role, and their manager now knows they were looking. Walk me through how you deliver the news and address what it means for them.Empathy without softening the messageMid–senior

Senior employee policy violation warningAn investigation substantiated policy violations by a well-liked senior employee, and you're delivering a final written warning. Walk me through how you structure the conversation.Room for responseSenior–leadership

Denying protected leave extensionAn employee has exhausted their protected leave, and the extension they requested has been denied. Walk me through how you deliver the decision and what you put on the table.Clear next stepsMid–senior

Notifying contractor of ended assignmentA client ends a contractor's assignment effective Friday with no reason given. As their agency recruiter, walk me through the call where you tell the contractor.Opening with the hard messageMid–senior