About this session
Difficult conversations are rarely difficult because of the words alone. They often involve tension, uncertainty, competing expectations, fear of conflict or concern about how the other person will react.
That can lead people to avoid the conversation, overprepare, become defensive or communicate so indirectly that the real issue never gets addressed.
This session helps participants prepare for and handle difficult workplace conversations more effectively.
They learn how to separate the core issue from the emotion surrounding it, clarify what they need from the conversation and choose language that is direct without becoming aggressive.
Participants then practice listening under pressure, responding to defensiveness or disagreement and keeping the conversation focused when emotions rise.
The final module helps them close the conversation clearly, follow through and decide when a situation needs escalation rather than another informal discussion.
What your people take away
- Prepare for difficult conversations by clarifying the issue, outcome and boundaries
- Communicate directly without becoming aggressive, vague or overly apologetic
- Listen and respond more effectively when the other person becomes defensive or upset
- Keep emotionally charged conversations focused on the real issue
- Close with clear next steps and recognize when escalation is more appropriate
Shared with you
See the full session
Create your free Workbliss profile to see the rest of this outline and book it. It takes a minute, with your work email.
- What each length covers, 30 minutes to full day
- Everything that’s covered, part by part
- Book online, and browse 1,500+ more sessions for your teams
Already a member? Sign in
What each length covers
30 minutes
30 Minutes — Key Points: Prepare for the ConversationA focused 30-minute session on three key points from Prepare for the Conversation: clarify the real issue, separate facts from assumptions and decide what outcome you want.
- Clarify the real issue
- Separate facts from assumptions
- Decide what outcome you want
Covers 3 of 4 points in Prepare for the Conversation.
60 minutes
60 Minutes — Module 1: Prepare for the ConversationParticipants identify the real issue, separate facts from assumptions and clarify the outcome they want before entering a difficult conversation.
- Module 1: Prepare for the Conversation
- Live Q&A
Covers 1 of 4 parts: Prepare for the Conversation.
90 minutes
90 Minutes — Modules 1 and 2: Say the Difficult Thing ClearlyEverything in the 60-minute session, plus practical work on direct language, tone, timing and communicating impact without accusation. Participants practice opening difficult conversations with greater clarity.
- Module 1: Prepare for the Conversation
- Module 2: Say the Difficult Thing Clearly
- Conversation-opening practice
- Live Q&A
Covers 2 of 4 parts: Prepare for the Conversation and Say the Difficult Thing Clearly.
3 hours
Covers 3 of 4 parts: Prepare for the Conversation, Say the Difficult Thing Clearly and Stay Constructive When Emotion Rises.
Full day
Full Day — Full Difficult Conversations WorkshopFull coverage of all four modules with preparation, communication practice, defensiveness scenarios and follow-through planning. Participants leave with a practical 30-day difficult-conversation action plan.
- Module 1: Prepare for the Conversation
- Module 2: Say the Difficult Thing Clearly
- Module 3: Stay Constructive When Emotion Rises
- Module 4: Close the Conversation and Follow Through
- Workplace conversation scenarios
- 30-day personal action plan
- Live Q&A
Covers all 4 parts.
Also available as a 4-week or 8-week program, for change that lasts. Ask us about it.
What’s covered
Prepare for the Conversation
Every length- Clarify the real issueParticipants identify what actually needs to be discussed and separate the core issue from accumulated frustration, old grievances or assumptions about motive.
- Separate facts from assumptionsParticipants distinguish what they directly observed from conclusions such as 'they do not care' or 'they are being difficult.' They identify where more information is needed before treating an interpretation as fact.
- Decide what outcome you wantParticipants clarify what they want from the conversation, such as a behavior change, clearer expectation, better understanding, decision or boundary.
- Choose the right time and settingParticipants consider timing, privacy, channel and urgency and decide whether the issue belongs in person, on video, by phone or in writing.
Say the Difficult Thing Clearly
90 minutes and longer- Open without circling the issueParticipants practice opening the conversation by stating why they want to talk and naming the issue directly.
- Describe behavior, not characterParticipants practice describing specific actions, events or patterns rather than using labels such as 'unprofessional,' 'negative' or 'difficult.' Observable language makes it easier to discuss the issue without turning the conversation into a judgment about the person.
- Explain the impactParticipants identify the practical effect of the behavior or situation on work, relationships, deadlines, trust or decision-making.
- Make the request or expectation clearParticipants practice stating what they want to happen next, whether that is a different behavior, clarification, decision, boundary or agreement.
Stay Constructive When Emotion Rises
3 hours and longer- Notice your own defensivenessParticipants identify how they react when challenged, interrupted or disagreed with, such as becoming sharper, overexplaining or shutting down.
- Listen without abandoning your pointParticipants practice hearing the other person's perspective and checking their understanding without assuming that listening means withdrawing the concern.
- Slow the conversation downParticipants practice using pauses, summaries and clarification questions when the discussion becomes fast, defensive or circular.
- Keep disagreement on the issueParticipants practice redirecting personal comments, old grievances or assumptions back toward the specific issue being discussed.
Close the Conversation and Follow Through
Full day only- Summarize what was actually agreedParticipants practice closing by confirming what both people understand, what has been agreed and what remains unresolved.
- Make next steps and ownership visibleParticipants identify who will do what and by when, particularly where the issue involves changed behavior, follow-up or a decision.
- Reset expectations when neededParticipants identify whether the conversation revealed a mismatch around roles, communication, deadlines or boundaries and make the revised expectation explicit.
- Know when to escalateParticipants distinguish ordinary difficult conversations from situations involving repeated misconduct, harassment, discrimination, threats, retaliation or issues that cannot be resolved informally.
How booking works
- Book online. Create a free Workbliss profile, then pay with session credits, by card or by invoice.
- Pick a date. Choose a date at least 14 days ahead, or book now and set the date later.
- Choose your expert. Within 3 working days, we send you profiles of the experts available for your date.
- We deliver it. Your expert is briefed on your people and goals, then runs the session live online or at your site.
Questions about Handling Difficult Conversations
How long is Handling Difficult Conversations?
Handling Difficult Conversations runs as 30 minutes, 60 minutes, 90 minutes, 3 hours or full day. You choose the length when you book. A 30-minute session covers three key points from Prepare for the Conversation: clarify the real issue, separate facts from assumptions and decide what outcome you want. A 60-minute session covers Prepare for the Conversation in full, with a live Q&A. A 90-minute session adds Say the Difficult Thing Clearly. A 3-hour session adds Stay Constructive When Emotion Rises. A full-day session adds Close the Conversation and Follow Through. It is also available as a 4-week or 8-week program.
Can Handling Difficult Conversations be delivered online or in person?
Yes, both. It runs live online, so every office can join at the same time, or in person at your site, in any country.
How do we book Handling Difficult Conversations?
Create a free Workbliss profile with your work email, then open Handling Difficult Conversations to see the price for each length and book it. You can pay with session credits, by card or by invoice, and choose a date at least 14 days ahead, or set it later.
Who leads the session?
A vetted Workbliss expert, briefed on your people, culture and goals before the session. After you book, we send you profiles of the experts available for your date within 3 working days, so you can choose who leads it.
Can it be tailored to our company?
Yes. Every session is shaped around your goals, your people and the benefits you already offer, and delivered by experts in your people’s languages.