Difficult Conversation Prep
Describe a challenging conversation you need to have and get scripts for different approaches
We've all been there: staring at our phone, drafting and re-drafting a text message. Rehearsing what we'll say in the mirror. Procrastinating on that conversation we know we need to have but can't figure out how to start.
Whether it's asking for a raise, addressing a performance issue with a team member, setting boundaries with a family member, or breaking up with someone, difficult conversations are an inevitable part of life. The good news? AI can be your conversation coach, helping you think through different approaches, anticipate responses, and find the right words for sensitive situations.
Today's prompt turns your AI assistant into a skilled mediator who can help you prepare for challenging discussions with empathy, clarity, and confidence.
Task
Use this framework to prepare for your difficult conversation:
"I need to have a challenging conversation about [TOPIC] with [PERSON/RELATIONSHIP]. The situation is [BRIEF CONTEXT]. I'm feeling [YOUR EMOTIONS] and I'm concerned about [SPECIFIC WORRIES]. Can you help me craft different approaches for this conversation, including: 1) A direct approach, 2) A gradual/gentle approach, and 3) A solution-focused approach? For each, please provide opening lines, key points to cover, and ways to respond if they react defensively."
The key is being specific about the relationship dynamics, your emotional state, and what you're hoping to achieve.
Sample Problem
Let's work through a common workplace scenario:
"I need to have a challenging conversation about my workload with my manager, Sarah. The situation is that I've been consistently working 60+ hour weeks for the past three months, taking on extra projects while my salary hasn't changed, and it's affecting my personal life and mental health. I'm feeling overwhelmed and undervalued, but also worried about seeming ungrateful or lazy. I'm concerned about Sarah thinking I can't handle the responsibility or that I'm not committed to the team. Can you help me craft different approaches for this conversation, including: 1) A direct approach, 2) A gradual/gentle approach, and 3) A solution-focused approach? For each, please provide opening lines, key points to cover, and ways to respond if they react defensively."
Solution
OpenAI Response (ChatGPT 4o)
Here are three tailored approaches you can use to have a constructive conversation with your manager, Sarah, about your workload. Each is designed to match a different tone and strategy, depending on your comfort level and the relationship dynamics.
1. Direct Approach
This is clear, respectful, and assertive—best when you need to express urgency and establish boundaries quickly.
Opening Lines
“Sarah, I want to be candid with you about something that’s been weighing on me. I’ve been consistently working over 60 hours a week for the past few months, and it’s starting to take a toll on both my mental health and personal life.”
Key Points to Cover
You've taken on additional responsibilities and projects without a change in compensation or role.
It’s unsustainable and affecting your well-being.
You’re committed to the team and delivering value, but the current pace isn’t viable long-term.
You want to work together on a sustainable plan moving forward.
If She Reacts Defensively
“I hear you—and I want to be clear that this isn’t about not wanting to work hard or contribute. It’s about being able to keep contributing at a high level without burning out. I’m asking for support so I can keep doing great work in a sustainable way.”
2. Gradual/Gentle Approach
This softens the message, focusing on mutual goals and a tone of concern rather than frustration.
Opening Lines
“Hey Sarah, I really value the opportunities I’ve had recently—there’s been a lot of exciting work. That said, I’ve noticed that my workload has grown quite a bit, and I’m starting to feel the impact.”
Key Points to Cover
Acknowledge and appreciate the trust being placed in you.
Share how the workload has been creeping up and now feels overwhelming.
Emphasize your desire to maintain high performance—but need support or balance.
Ask if you can revisit workload distribution or priorities together.
If She Reacts Defensively
“I totally get that we’re in a busy season—and I want to help us through it. I’m just trying to flag this early so we can prevent burnout before it becomes a bigger issue.”
3. Solution-Focused Approach
This frames the issue as a shared problem and presents ideas for solving it—ideal for managers who value proactivity.
Opening Lines
“Sarah, I’ve been thinking a lot about how to manage the volume of work I’ve been handling lately. I’ve got a few ideas I’d love to run by you for how we can keep things moving smoothly without burning out.”
Key Points to Cover
Highlight the current hours and impact (briefly).
Present options, such as:
Prioritizing or dropping lower-impact projects.
Bringing in temporary help or delegating.
Revisiting compensation/responsibilities if the workload is long-term.
Ask for her input and alignment on what to focus on.
If She Reacts Defensively
“I understand this might be tough to solve right away, and I really appreciate how much you’re juggling too. I’m just trying to be proactive so we don’t run into deeper problems later.”
Final Tip
Regardless of the approach you choose, end with:
“I want to continue contributing meaningfully, and I’m committed to the team. I’m just asking for us to find a way to do it that’s sustainable.”
Let me know if you’d like a written script or practice mock dialogue.
Extra Credit
Once you have your conversation scripts, try these advanced techniques:
Role Reversal Prep: Ask your AI to play the other person's role and practice the conversation. Use: "Now pretend you're [PERSON] and respond to my opening approach. Based on what you know about them, how might they actually react?"
Emotional Regulation: Get help managing your own emotions during the conversation. Try: "What are some techniques I can use to stay calm if this conversation gets heated? How can I take breaks or reset if I feel myself getting defensive?"
Follow-up Planning: Prepare for what comes after. Use: "Assuming this conversation goes well, what should be my next steps? What if it doesn't go as planned - how do I follow up professionally?"
General Takeaways
Difficult conversations become more manageable when you've thought through multiple approaches and prepared for various reactions. AI excels at helping you see situations from different perspectives and crafting language that's both honest and diplomatic.
The magic happens when you're specific about the relationship context, your emotional state, and your desired outcomes. Generic advice rarely works for sensitive interpersonal situations, but tailored scripts that account for personalities and dynamics can transform dreaded conversations into productive dialogues.
Remember: the goal isn't to manipulate or "win" the conversation, but to communicate effectively and preserve relationships while addressing important issues. AI can help you find that balance between authenticity and tact that makes difficult conversations not just bearable, but genuinely helpful for everyone involved.
What challenging conversation have you been putting off? Try today's prompt and see how AI can help you approach it with more confidence.