Free planning tool
Prepare for a difficult workplace conversation.
Turn a tense or uncertain moment into a clear purpose, grounded facts, a direct request, and a concrete next step.
Use this checklist before a conversation about feedback, workload, boundaries, conflict, performance, or a decision that matters.
Work through the conversation in order.
Write short notes rather than a full script. The goal is to stay clear enough to listen and adapt in the moment.
- 01
Define the outcome
Decide what this conversation needs to accomplish before you choose the wording.
- What needs to change, be decided, or become clearer?
- What is the best realistic outcome for this conversation?
- 02
Ground it in facts
Separate observable events from assumptions about intent or character.
- Which two or three specific examples support the concern?
- What impact did those events have on the work or people involved?
- 03
Make the request clear
Name the action, decision, support, or boundary you are asking for.
- What exactly do you want the other person to do?
- Where can you be flexible, and what is not negotiable?
- 04
Plan the opening
Lead with purpose so the other person does not have to guess why you are there.
- Can you state the purpose in one calm sentence?
- Which detail belongs first, and which background can wait?
- 05
Prepare for the response
Anticipate questions without scripting or controlling the other person's reaction.
- What concern, objection, or missing context might you hear?
- What question will help you understand their perspective?
- 06
Close with a next step
Turn the discussion into a decision, owner, deadline, or follow-up point.
- What should each person do after the conversation?
- When and how will you confirm progress or revisit the issue?
A starting structure
Draft a clear opening
I want to discuss [topic] because [impact]. I noticed [specific facts]. I'd like us to [request]. Could we agree on [next step]?
Read it aloud once. Shorten anything that sounds defensive, vague, or unlike your natural voice.