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Preparing for a Hard Conversation

How to best use your AI to support you at work

Toolbox / AI Prompt Supports / For Employees

When this is useful

This reflection is for moments when you know you need to raise something at work, but feel uncertain about how to begin.

You may be anticipating a conversation with your manager or a colleague about workload, boundaries, expectations, burnout, or misalignment. This page is designed to help you clarify what you want to say and why before entering the conversation itself.

What this conversation helps clarify

This guided reflection can help you:

  • Clarify what outcome you actually want from the conversation

  • Separate facts from interpretations or assumptions

  • Identify what you’re worried might happen if you speak up

  • Choose language that is clear without being reactive

  • Prepare to preserve the relationship, not “win” the exchange

You don’t need a perfect script.
Clarity usually comes before confidence.

Guided AI reflection

(copy and paste into your AI tool)

I want you to act as a thoughtful, non-judgmental facilitator, not a coach, therapist, or problem-solver.

Help me prepare for a difficult conversation at work.

Before suggesting language or tactics, please help me reflect by asking questions that clarify:

  • What prompted me to consider having this conversation now

  • What outcome I hope for, realistically

  • What I’m afraid might happen if I speak honestly

  • What facts I can point to, versus interpretations I may be making

  • What constraints the other person may be operating under

Please:

  • Ask one question at a time

  • Avoid giving advice unless I explicitly ask for it

  • Periodically summarize what you’re hearing and check if it feels accurate

  • Help me notice where emotion might interfere with clarity

  • 'Avoid metaphors or strong labels unless I’ve already used similar language or you ask permission first.

  • Help me clarify what I’m noticing, not what I should fix or decide.

When I’m ready, help me draft language that is clear, grounded, and focused on preserving the working relationship.

Start by asking me what feels hardest to name right now.

How to use this reflection

  • You don’t need to answer every question.

  • You can pause and return later.

  • You can stop if something feels emotionally heavy.

    This is a private thinking exercise, not a rehearsal or a performance. Its value is in preparing your thinking, not perfecting your delivery.

A closing note

Hard conversations often feel risky because they carry both practical and relational weight.

If this reflection helps you enter the conversation with a little more steadiness, clarity, or care, that alone can change how it unfolds.