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5 ChatGPT Prompts To Tell Your Boss What You Really Think

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Something isn’t going right at work and you’re not sure what to do. You know you need to have a chat, you know you need to take action, but which approach to take? What’s worth bringing up and what might blow over? If you’re feeling unsure about any element of your role, ChatGPT can help you talk it through and make a plan.

Use ChatGPT as your personal AI assertiveness coach, to figure everything out and find the confidence to speak up about what you want. Copy, paste and edit the square brackets in ChatGPT, and keep the same chat window open so the context carries through.

How to bring up problems at work: ChatGPT prompts to make your plan

Empathise first

No matter how bad it feels, it’s never you versus another person, even when that person is your boss. Even if you don’t see eye to eye, even if you don’t like them. It’s always you, plus that person, versus the problem. Get in a productive mindset by having empathy, to start your discussion on the right foot. Tell ChatGPT about your boss, explain their situation, describe the company. Talk through what’s going on and see it from their point of view.

"I'm preparing to discuss some workplace issues with my boss, and I want to ensure I understand their perspective first. Here's what I know about my boss [describe your boss’s work style, their role and responsibilities, and any current pressures they might be facing]. Can you help me analyze their situation and outline the possible challenges they are dealing with at work? This will help me approach our conversation with more empathy and understanding."

Let it all out

If you’re mad, get mad. Better to let it all out than bottle it up. Tell ChatGPT all of your frustrations with your boss. If you’re using the app, record a monologue with ChatGPT voice. If you’re on a desktop, bash away at the keyboard. Explain your frustrations, revisit conversations and allow your strong emotions to come to the surface. Just make sure you don’t do it on a work device.

"I need to vent about some ongoing frustrations I have with my boss before I can think about resolving them constructively. Please listen as I detail these problems and help me process my emotions by reflecting back the main points of concern and the emotions involved. This will help me understand my feelings better and prepare for a calm, productive discussion later. Invite me to begin by saying 'Tell me everything' and then I'll start talking."

Find the positives

Now you’ve vented out all your frustrations, flip the perspective. What are the positive outcomes of this situation? Start by feeling grateful that this has reached the point of no return, then see what positives you can draw out. A boss who goes AWOL is your chance to develop independence. A boss who has a short attention span is your chance to improve at keeping someone’s attention. There’s a flipside to every bad story and ChatGPT will help you find it.

"After expressing my frustrations, I'd like to shift my focus to the positives that can come from this situation. Having heard the challenges I'm dealing with [add more if relevant], can you help me identify the potential positive outcomes and opportunities for personal growth these challenges might offer? I'm looking to understand how I can use this situation to develop my skills and perhaps improve my work environment."

Decide what you want

There’s no point just complaining. You’re not a victim. Sort this work blip out like a hero by defining what you want. Get crystal clear on your intentions, the outcome you want to see, and your non-negotiables for the way forward. Ask ChatGPT to be your career coach, where it asks you about what’s important to help you list your requirements. Put them in priority order and know what you’re asking for and what you want to see happen.

"I want to move from just complaining about my work situation to defining clear outcomes and goals. Act as my career coach and guide me through a discussion where you ask questions, one by one, about what's truly important to me. Start by asking about specific changes I want to make and move through to asking me to list my desired outcomes, non-negotiables, and priorities. This will assist me in understanding exactly what I want to achieve and how I should approach a conversation with my boss. Our discussion should be back and forth and step by step, don't write a long list of questions."

Plan the chat

Now you’re equipped with empathy, you’ve had a rant and you can see the benefit in having this chat. You know what you want, you just need to go after it. Ask ChatGPT for help planning the discussion you’re going to hold with your boss. Set the scene, display empathy, and talk to them on a peer-to-peer level. Make the agenda to work through your points and strengthen your case with concrete examples. Go into the discussion with confidence that you can do yourself proud and achieve the result you just defined.

"Now that I have a clear understanding of my boss’s perspective, have vented my frustrations, identified the positives, and defined what I want, I need help planning the actual conversation with my boss. Guide me through setting up the agenda for this discussion, for which I will have a [duration] slot. The agenda should be based on what we have discussed so far and include empathetic opening statements, clearly outline my points, and use concrete examples to support my case where you have them. Ask me for concrete examples where required. Help me structure this talk so I can approach it with confidence and achieve the outcomes I've defined."

Turn a work problem around: ChatGPT prompts to plan a tough conversation with your boss

Don’t suffer in silence. Don’t show up every day to work for someone who’s causing you grief. Life is too short. Use these prompts to get fully prepared and solve every problem. Generate empathy for your boss’ situation then let out all frustrations without fear of repercussions. Find the positives, decide what you want, then make your agenda and lead the meeting. Your dream role could be on the other side of this conversation, so get it booked in.

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