Your workshop companion
Managing Difficult
Conversations
Structure for the conversations that matter.
Revisit the framework, prepare your notes, and leave with a clear plan for what comes next.
Address it early.
Timely feedback keeps conversations smaller, clearer, and easier to manage.
Stick to facts.
Describe what happened. Focus on behavior, rather than labels or assumptions.
Leave with clarity.
Confirm what is changing, who is doing what, and when you will check back in.
Set the Tone
Start with intention.
Help the other person understand the kind of conversation you are about to have, how long it may take, and what is at stake.
Establish intensity.
Casual, potentially uncomfortable, difficult, or very difficult: match the tone to the conversation.
Estimate duration.
A few minutes, less than an hour, or an ongoing conversation: give a realistic sense of the time involved.
Address the elephant.
When it is relevant and true, reassurance such as “Nobody is losing their job today” can clarify the stakes. Otherwise, skip it.
Try it · 01
Practice your opening.
Use the workshop scenario to write the first two sentences you would use to begin the conversation.
A normally reliable employee has submitted several pieces of work over the past month with errors that you would typically expect them to catch. You have had to correct some of the work before it went to others.
Review the tone-setting reminders
Intensity: Establish whether this is casual, potentially uncomfortable, difficult, or very difficult.
Duration: Indicate whether it will take a few minutes, less than an hour, or involve an ongoing conversation.
The elephant: Address the fear of losing a job when that reassurance is relevant and true, or skip it.
Your writing stays on this page and is not submitted or saved. Copy anything you want to keep before refreshing or closing.
Assess Honestly
Make the feedback specific.
Use the SBI model to describe what happened and why it matters. Keep the focus on observable behavior.
Situation
Describe when and where it happened.
Behavior
Focus on what the person did, not who they are.
Impact
Explain the outcome of that behavior.
Try it · 02
Build your feedback.
Prepare a few notes for each part. Your notes come together alongside the fields as you type.
Your writing stays on this page and is not submitted or saved. Copy anything you want to keep before refreshing or closing.
Plan for the Future
Create radical clarity.
“Let’s just keep working on it” leaves too much open to interpretation. Make a collaborative, specific plan for what happens after the conversation.
Try it · 03
Leave with a shared plan.
Use these five questions during or after your conversation to make the next steps clear.
Your writing stays on this page and is not submitted or saved. Copy anything you want to keep before refreshing or closing.
Keep these close
Good conversations
take practice.
The framework provides structure. These habits help you use it well.
Regulate yourself first.
Before and during the conversation, slow down. Take a breath and be honest about your attitude before sitting down to talk.
Environment matters.
Find a reasonably private setting with limited distractions, where the other person can be honest and vulnerable.
Notes, not scripts.
Know your essential facts, the outcome you need, and the questions you want to ask. Prepare your thoughts without memorizing paragraphs.
Keep following up.
Set short, intermediate milestones, such as one week or one month. Use the time between discussions to recognize meaningful progress.
Don’t stop at “I don’t know.”
Allow time to think, then keep exploring the decisions and behaviors together. Use the workshop’s follow-up questions:
- “Take a second. What do you think was happening?”
- “If you had to make your best guess, what contributed to it?”
- “What would help us understand it better?”
Common mistakes to avoid
Keep the purpose in view.
Letting feedback sit.When the issue is clear and emotions are steady, address it promptly. The workshop’s target is within 24 to 48 hours. If emotions are high, allow a sleep cycle to settle.
Turning it into an interrogation.A difficult conversation is not a chance to list every correction item and interrogate someone about each one.
Prioritizing harmony over substance.“Nobody got mad” is not the only measure of success. Helping someone develop can involve meaningful challenge and tension.
Confusing rules and standards.Rules set boundaries with consequences. Standards describe criteria with some ambiguity. Be clear about which expectation you are setting.
Overlooking what is going well.Find opportunities outside difficult conversations to specifically recognize and appreciate good performance.
Everyone leaves
with radical clarity.
Before you finish, confirm what each person heard, what is changing, and when you will check back in.