The Difficult Conversations Prompt Library | Human Skills Edition

Human Skills Edition

The Difficult Conversations
Prompt Library

100 AI-engineered prompts to help you roleplay, script, and navigate high-stakes professional scenarios with confidence and empathy.

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Browse the 10 categories below to find the exact difficult situation you are facing right now.

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1. Performance Management

1. The "Nice Person, Poor Results" Talk

Objective: Accountability

Act as a communications coach. I need to deliver a performance review to an employee who is culturally a great fit and very well-liked, but consistently misses deadlines. Write a script for the opening 5 minutes. The tone should be warm but firm. Use the "Situation-Behavior-Impact" framework.

2. Sudden Performance Drop

Objective: Inquiry

I need to speak to a high-performer whose work has suddenly slipped. I suspect burnout. Provide 5 open-ended questions I can ask that allow them to share safely without me making assumptions about their personal life.

3. The PIP Notification

Objective: Clarity

I am placing an employee on a Performance Improvement Plan (PIP). Review these 3 bullet points [insert points] to ensure they are specific, measurable, and objective, avoiding subjective adjectives like "lazy."

4. Denying a Promotion

Objective: Retention

My report expects a promotion but lacks strategic skills. Roleplay this. You play the defensive employee. I will practice holding my ground while offering a development plan. Start by saying: "I really thought this was my year."

5. Feedback for a Defensive Peer

Objective: Disarming

I need to give feedback to a peer who usually argues. Write 3 opening sentences using "I" statements (e.g., "I've noticed," "I feel") to lower their guard. Avoid "You" statements.

6. Addressing "Quiet Quitting"

Objective: Re-engagement

An employee is doing the bare minimum. Suggest a script for a "Stay Interview" to uncover their motivators without sounding accusatory.

7. The Brilliant Jerk

Objective: Culture

I have a top engineer who is rude to junior staff. Write a "Sandwich Method" critique ensuring the negative feedback is substantial and not watered down by the praise.

8. Upward Feedback (Micromanagement)

Objective: Autonomy

My boss is micromanaging me. Rewrite this draft to sound professional: "Stop checking my work every hour, I know what I'm doing." Focus on how autonomy improves my output.

9. The Project Reset

Objective: Scope Control

The team is missing milestones. Outline an agenda for a 30-minute "Reset Meeting" that acknowledges past failures without blame but establishes strict new accountability.

10. Hygiene/Attire Conversations

Objective: Dignity

I have to talk to an employee about [body odor/inappropriate dress]. Give me a script that is direct, private, and compassionate, ensuring they maintain their dignity.

2. Salary & Negotiation

11. Asking for a Raise (Data-Led)

Objective: Leverage

I am asking for a 15% raise. Structure a 1-page memo connecting my recent accomplishments [Project A, B] directly to company revenue. Tone: Confident, not pleading.

12. Denying a Raise Request

Objective: Morale

I have to deny a raise due to budget cuts. Write a script that is transparent about financials but pivots immediately to non-monetary perks or a specific review timeline.

13. Countering a Job Offer

Objective: Value

I received an offer for $90k, but I want $105k. Write a polite email response stating that based on market research and my experience, I am looking for $105k.

14. Understanding Equity

Objective: Clarity

Provide 5 smart, probing questions to ask a Founder about my stock options package to understand their true potential value without sounding greedy.

15. Responding to Lowballs

Objective: Boundaries

A recruiter quoted a salary 20% below market. Write a phone script expressing surprise at the low number and asking if there is flexibility, indicating I cannot proceed at that level.

16. Budget for Training

Objective: Upskilling

I need approval for a $2,000 course. Write a brief pitch to a frugal boss framing this cost as an investment with clear ROI for the company.

17. Pay Disparity Discovery

Objective: Fairness

I found out a new hire makes more than me. Roleplay the conversation with my manager. I want to sound curious about market value, not angry.

18. Negotiating Severance

Objective: Exit Strategy

I am being laid off. Write a polite but firm email justifying a request for 8 weeks severance (vs 4 offered) based on my 5-year tenure and smooth handover plan.

19. Explaining Pay Grades

Objective: Transparency

I am a manager. I need to explain to an employee why they are at the "top of their band" and cannot get a raise without a promotion. Explain the compensation structure clearly.

20. Rate Negotiation (Freelance)

Objective: Profitability

I am a contractor. I need to tell a long-term client that my rates are increasing by 20% next year. Write an email that focuses on the value I've delivered and the increased market rates.

3. Interpersonal Conflict

21. Passive-Aggression

Objective: Directness

A colleague makes sarcastic jokes about my work. Give me a script that assumes positive intent ("You might not realize...") but clearly asks them to stop.

22. Mediation Script

Objective: Peace

Two of my reports hate each other. Provide an opening statement for a mediation meeting that sets ground rules and focuses on shared business goals.

23. The "Mea Culpa"

Objective: Trust Repair

I dropped the ball on a major deliverable. Write an apology script to my boss that owns the mistake 100%, explains (briefly) why, and details the fix.

24. Stolen Credit (In Moment)

Objective: Correction

A colleague just presented my idea as their own. Give me a phrase to say *in the meeting* that gently corrects the record (e.g., "Glad you brought up my point...").

25. The Credit Hog Boss

Objective: Visibility

My boss presents my work without mentioning me. Script a 1:1 asking to present my own findings next time as a "development opportunity."

26. Handling Gossip

Objective: Professionalism

My team is gossiping about another department. Write a script for me to shut it down immediately during a team meeting without sounding like a parent.

27. Political Discussions

Objective: Neutrality

Coworkers are having a heated political debate in the open office. Give me a polite but firm phrase to redirect them back to work or move them to a private room.

28. The "Oversharer"

Objective: Boundaries

A colleague constantly unloads personal drama on me. I want to be supportive but I need to work. Give me a script to limit these interactions.

29. Project Sabotage

Objective: Alignment

A peer is delaying their part of a project, causing me to miss deadlines. Write an email copying our managers that factually states the delay and asks for an updated timeline.

30. Bypassing Hierarchy

Objective: Protocol

A skip-level manager gave me work without telling my boss. I need to inform my boss without getting the senior manager in trouble. Draft the email.

4. Saying "No" & Boundaries

31. The Capacity Check

Objective: Prioritization

My boss assigned a new project but I'm at 110% capacity. Write a response asking to prioritize: "If I take this on, which of [Project A, B, or C] should be paused?"

32. Impossible Deadlines

Objective: Reality Check

A client wants this by Friday. Impossible. Write an email proposing a new timeline (next Wednesday) explaining the benefit to them (quality assurance).

33. After-Hours Boundary

Objective: Wellness

My manager texts me at 9 PM. Script a 1:1 conversation explaining that I unplug after 6 PM to recharge, but will be fully online at 8 AM.

34. Declining "Pick Your Brain"

Objective: Time Management

I get too many coffee chat requests. Write a polite template declining a meeting with a stranger, but pointing them to my existing articles/content.

35. Saying No to Volunteering

Objective: Focus

I've been asked to join the "Party Planning Committee." I need to focus on my KPIs. Write a polite refusal that emphasizes my current project load.

36. Vacation Protection

Objective: Disconnect

Write an Out of Office auto-responder that clearly states I have no access to email and provides a specific contact for emergencies only.

37. Pushing Back on Scope Creep

Objective: Scope

A stakeholder wants to add "just one small feature." Explain that this requires a Change Order or will delay the launch by 2 weeks.

38. Declining a Meeting

Objective: Efficiency

I am invited to a meeting with no agenda. Write a polite email declining to attend until an agenda and goal are shared.

39. Refusing to Relocate

Objective: Lifestyle

My company wants me to move to HQ. I want to stay remote. Write a script making the business case for why my location doesn't impact my high performance.

40. Ending a Client Relationship

Objective: Closure

A client is too demanding and low-paying. Write a professional "break up" email stating we are moving in a different strategic direction.

5. Managing Up & Leadership

41. Bad News to CEO

Objective: Transparency

We missed Q3 targets. Write an email: Headline (we missed), Context (Why), Solution (Fixes), and Ask (What we need).

42. Disagreeing with Strategy

Objective: Dissent

My boss wants Strategy A. Data supports Strategy B. Script an opener that doesn't make them look bad but invites them to view new data: "I want to ensure the best outcome..."

43. The Waffling Leader

Objective: Action

My boss delays decisions. Write an email outlining the "Cost of Inaction." If we don't decide by Friday, we lose X.

44. Asking for Resources

Objective: Scaling

My team is drowning. Pitch a request for 2 new headcount by showing the revenue potential we are currently missing due to lack of staff.

45. Admitting "I Don't Know"

Objective: Integrity

An executive asks a question I don't have the answer to. Give me a script that sounds competent, not clueless. "I want to be precise, so let me verify..."

46. Managing a "Visionary"

Objective: Grounding

My boss has 10 new ideas a week. I need to tell them we can only execute 2. Script a conversation about prioritization.

47. Pre-Paternity/Maternity Leave

Objective: Handover

I am going on leave. Write a handover plan email to leadership that instills total confidence that the ship will sail smoothly without me.

48. Resigning Gracefully

Objective: Bridges

I am leaving for a competitor. Write a resignation script that focuses on gratitude for my time here and doesn't get drawn into where I am going.

49. Clarifying Ambiguous Goals

Objective: Definition

Leadership sent a vague goal: "Be more innovative." Write an email asking for specific success metrics so I know what to aim for.

50. Saying No to a Promotion

Objective: Fit

They want to make me a manager. I want to stay an Individual Contributor. Script a conversation declining the "promotion" without looking unmotivated.

6. Crisis & Public Relations

51. The Layoff Announcement

Objective: Empathy

I have to announce a 10% reduction in force to my team. Write a speech that is direct, avoids corporate jargon ("right-sizing"), and focuses on support for those leaving.

52. Client Data Breach

Objective: Trust

We lost client data. Write an email to customers. Structure: What happened, what we are doing to fix it, and how we are protecting them now. No hiding.

53. Executive Exit

Objective: Stability

Our beloved VP is leaving abruptly. Write a note to the team that quells panic and focuses on the continuity of our strategy.

54. The "Failed Launch" Post-Mortem

Objective: Learning

Our product launch failed. Lead a meeting script that encourages team members to admit faults without fear of punishment. "Blameless Post-Mortem."

55. Rumor Control

Objective: Clarity

There is a false rumor that the company is being sold. Write a Slack message to the company addressing it head-on to stop the distraction.

56. Addressing a PR Scandal

Objective: Integrity

A senior leader made an offensive comment publicly. Write an internal memo to employees reaffirming our company values and distancing the brand from the behavior.

57. Canceling a Project Mid-Stream

Objective: Morale

We are killing a project the team has worked on for 6 months. Write a speech acknowledging their hard work but explaining the strategic pivot.

58. System Outage Comms

Objective: Patience

Our service is down. Write a tweet and status page update that is apologetic, human, and provides a realistic ET (or admits we don't know yet).

59. The "No Bonus" Year

Objective: Retention

Profitability is down. No bonuses this year. Script a town hall segment explaining this without blaming the employees.

60. Safety Incident

Objective: Safety

There was an accident in the warehouse. Write a memo to all staff prioritizing health and safety over speed/quotas for the next week.

7. DEI & Belonging

61. Addressing Microaggressions

Objective: Education

A team member made a comment about a colleague's hair. Script a private coaching moment explaining why it was a microaggression and how to do better.

62. Gender Pronoun Correction

Objective: Respect

A client keeps misgendering my employee. Write a polite but firm email correcting them and asking them to update their records.

63. Inclusive Meeting Facilitation

Objective: Inclusion

I notice men interrupt women on my team. Give me 3 phrases to use as a moderator to intervene in real-time and pass the mic back.

64. Accommodations Request

Objective: Accessibility

I have a disability and need specific software. Write a request to HR that is professional, cites my rights, but is collaborative in finding a solution.

65. "Culture Fit" vs "Culture Add"

Objective: Bias

A hiring manager rejected a candidate for "bad culture fit" (meaning they are different). Script a challenge to this bias, asking them to define "fit."

66. Religious Holiday Off

Objective: Balance

I need time off for a religious holiday not observed by the company. Write a request to my manager.

67. Neurodivergent Communication

Objective: Clarity

I have ADHD and struggle with vague verbal instructions. Write a script asking my boss to send all tasks in writing with bullet points.

68. The "Manterrupter"

Objective: Space

A male colleague constantly interrupts me. Give me a script for a 1:1 feedback session where I ask him to be an ally and hold space.

69. Responding to a Joke

Objective: Standards

A client made a racist/sexist joke. Write a polite but firm immediate response: "We don't do that here."

70. Name Pronunciation

Objective: Identity

My boss keeps mispronouncing my name even after I corrected them. Write a script to address this again, emphasizing why it matters.

8. Remote & Hybrid Work

71. "Camera On" Exhaustion

Objective: Wellness

I want to propose a "Camera Optional" day for my team. Write a pitch focusing on how audio-only reduces fatigue and increases focus.

72. Time Zone Boundaries

Objective: Respect

I work in London, my team is in LA. They keep booking 9 PM meetings. Write a message establishing my "Overlap Hours" and declining meetings outside them.

73. The "Digital Nomad" Correction

Objective: Compliance

An employee moved to Bali without asking. I need to explain tax/compliance implications and tell them they must return or switch to a contractor role.

74. Async First

Objective: Efficiency

We have too many status meetings. Write a memo moving us to "Async Updates" via Slack/Notion. Explain the format and expected cadence.

75. Return to Office Resistance

Objective: Policy

An employee refuses to come in on mandatory hybrid days. Script a conversation explaining that this is a job requirement, not a suggestion.

76. "Ghosting" During Work Hours

Objective: Accountability

An employee is unreachable for 4 hours at a time. Address this performance issue without sounding like I'm tracking their keystrokes.

77. Isolation Check-In

Objective: Connection

A remote employee seems lonely and disconnected. Script a check-in that offers support and connection opportunities without being intrusive.

78. Written Tone Correction

Objective: Soft Skills

My report sounds rude in Slack messages (too blunt). Coach them on "digital body language" and the use of softeners in text.

79. No Meeting Fridays

Objective: Culture

Propose "No Meeting Fridays" to leadership. Focus on deep work, developer velocity, and reducing burnout.

80. Distracted on Calls

Objective: Presence

An employee is clearly multitasking (typing/looking away) during video calls. Give feedback on the importance of active listening and presence.

9. Career Pivots & Exits

81. Asking for a Reference

Objective: Networking

I need a reference from a boss I haven't spoken to in 3 years. Write a warm reconnection email that asks for the favor without being transactional.

82. The Resume Gap

Objective: Narrative

I have a 2-year gap on my resume due to caregiving. Script a 30-second elevator pitch for an interview that owns this gap confidently and pivots to my excitement to return.

83. Internal Transfer Request

Objective: Mobility

I want to move from Sales to Product. Write a pitch to the Product VP explaining how my customer-facing experience makes me a better Product Manager.

84. Declining a Recruiter

Objective: Relationships

I'm not interested in this job, but I want to stay on the recruiter's radar for future leadership roles. Write a "Not now, but keep in touch" email.

85. Answering "Why are you leaving?"

Objective: Professionalism

I am leaving because my boss is toxic. I need an answer for interviews that doesn't badmouth my current employer but explains my desire for new management.

86. Retracting an Acceptance

Objective: Integrity

I accepted a job offer but just got a better one. Write an apologetic but firm email withdrawing my acceptance.

87. The Demotion Conversation

Objective: Fit

I am managing a team but I hate it. I want to go back to being an IC. Script a conversation with my boss asking to step down without getting fired.

88. Asking for Mentorship

Objective: Growth

I want a senior leader to mentor me. Write a request that respects their time, has a specific goal, and asks for a 30-minute introductory chat.

89. Firing a Vendor

Objective: Clarity

We are terminating our contract with an agency. Write a formal notice email that is professional, cites the contract clause, and outlines the offboarding steps.

90. Reaching Out to Alumni

Objective: Networking

I want to work at Company X. I see an alumni from my university works there. Write a LinkedIn message asking for 15 mins of advice on breaking in.

10. Client & Stakeholder Management

91. Telling a Client "You're Wrong"

Objective: Advisory

A client wants a feature that will hurt their conversion rate. Script a conversation where I challenge them gently: "I can build this, but I'm concerned it will negatively impact X..."

92. Raising Prices

Objective: Revenue

I need to raise prices on legacy clients. Write an email explaining the increase is due to improved service/infrastructure, not just inflation.

93. Handling an Angry Client

Objective: De-escalation

A client is screaming on the phone. Script a de-escalation technique: "I can hear how frustrated you are, and I want to fix this. Let's slow down so I can..."

94. Delivering Late Work

Objective: Transparency

We are going to be 3 days late. Write an email telling the client *before* the deadline passes, offering a concession or explanation.

95. Resetting Boundaries

Objective: Respect

A client calls my personal cell on weekends. Write an email redirecting them to the support portal and office hours.

96. Upselling a Client

Objective: Sales

I see an opportunity to help a client with X. Write an email "checking in" that pivots to a suggestion for a new paid project.

97. Clarifying Feedback

Objective: Precision

A client said "I don't like the design." Write a response asking specific questions (color? layout? vibe?) to get actionable feedback.

98. Refusing a Discount

Objective: Value

A prospect asks for a discount. Write a response that stands firm on price but offers to reduce scope to meet their budget.

99. Collecting Overdue Payment

Objective: Cash Flow

A client is 30 days late. Write a firm email attaching the invoice again and pausing work until payment is received.

100. The "Scope Gap"

Objective: Agreement

We are misaligned on what "done" looks like. Write an email summarizing what was agreed in the SOW vs what they are asking for now.