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/difficult-workplace-conversations

Structured approach to workplace conflicts, performance discussions, and challenging feedback using preparation-delivery-followup framework. Use when preparing for tough conversations, addressing conflicts, giving critical feedback, or navigating sensitive workplace discussions.

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$ npx -y skills add softaworks/agent-toolkit --skill difficult-workplace-conversations --agent claude-code

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How this skill gets triggered: by you, by Claude, or both.

  • Fires itselfAuto-invocation. Claude auto-loads it when your prompt matches the work.Auto-invocation is when the right skill fires by itself at the right moment, driven by a FLOW.md router and a hook, instead of you invoking it by name. It is the difference between a skill being installed and a skill actually getting used.Read the full definition →
  • You can call itInvoke it directly when you want it.
  • Slash command/difficult-workplace-conversations

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Structured approach to workplace conflicts, performance discussions, and challenging feedback using preparation-delivery-followup framework. Use when preparing for tough conversations, addressing conflicts, giving critical feedback, or navigating sensitive workplace discussions.

SKILL.md

difficult-workplace-conversations.SKILL.md
name: difficult-workplace-conversations
description: Structured approach to workplace conflicts, performance discussions, and challenging feedback using preparation-delivery-followup framework. Use when preparing for tough conversations, addressing conflicts, giving critical feedback, or navigating sensitive workplace discussions.
allowed-tools: Read, Glob, Grep

Difficult Conversations Skill

A structured framework for approaching challenging workplace conversations including conflicts, performance issues, sensitive feedback, and emotionally charged discussions.

When to Use This Skill

  • Preparing for a challenging conversation with a colleague
  • Addressing performance issues with a team member
  • Delivering difficult feedback to a peer or manager
  • Navigating conflict between team members
  • Discussing sensitive topics (salary, promotion, termination)
  • Handling emotional or defensive reactions
  • Following up after difficult discussions

Core Framework: Preparation-Delivery-Followup

Difficult conversations succeed or fail based on three phases:

Phase 1: Preparation (Before)

**Purpose:** Set yourself up for a productive conversation

1. **Clarify the Issue**

  • What specifically happened? (Observable facts only)
  • What is the impact? (On you, team, work)
  • What do you need to change?

2. **Check Your Emotions**

  • What am I feeling? Why?
  • Am I calm enough to have this conversation?
  • What might trigger me during this conversation?

3. **Consider Their Perspective**

  • How might they see this situation?
  • What constraints or pressures might they have?
  • What do they care about that I can acknowledge?

4. **Define Your Goal**

  • What outcome do I want?
  • What is the minimum acceptable result?
  • What am I willing to compromise on?

Phase 2: Delivery (During)

**Purpose:** Have the conversation effectively

1. **Open Neutrally**

  • Start with facts, not judgments
  • Express intent to understand, not accuse
  • Create psychological safety

2. **Share Your Perspective**

  • Describe behavior, not character
  • Focus on impact, not intention
  • Use "I" statements, not "you always"

3. **Listen Actively**

  • Ask clarifying questions
  • Acknowledge their viewpoint
  • Look for shared interests

4. **Seek Resolution**

  • Propose specific actions
  • Agree on next steps
  • Set check-in timeline

Phase 3: Followup (After)

**Purpose:** Ensure lasting resolution

1. **Document Agreements**

  • What was agreed?
  • Who does what by when?
  • How will you measure success?

2. **Check Progress**

  • Follow up as promised
  • Acknowledge improvements
  • Address continued issues promptly

3. **Maintain Relationship**

  • Separate issue from person
  • Rebuild trust over time
  • Watch for regression

Key Principles

Separate Impact from Intent

**What happened:** Observable behavior **What I felt:** Your emotional response **What I assume:** Their intention (often wrong)

Focus conversation on behavior and impact, not assumed intentions.

The SBI Model

**Situation:** When and where did this happen? **Behavior:** What specifically did they do/say? **Impact:** What was the effect on you, the team, or the work?

Managing Emotions

| If You Feel | Before Acting | | ----------- | ------------- | | Angry | Wait 24 hours, write but don't send | | Hurt | Talk to neutral party first | | Anxious | Practice the conversation | | Defensive | Identify your contribution |

When to Escalate

Escalate when:

  • Safety is at risk
  • Legal issues involved
  • Repeated conversations haven't worked
  • Power dynamics prevent resolution
  • You need documentation

Conversation Types

Performance Feedback

  • Lead with specific examples
  • Connect to expectations/standards
  • Focus on future improvement
  • Offer support and resources

Conflict Resolution

  • Hear both sides separately first
  • Identify underlying interests
  • Look for win-win solutions
  • Document agreements

Sensitive Topics

  • Choose private, neutral setting
  • Allow time for processing
  • Be direct but compassionate
  • Respect confidentiality

Receiving Feedback

  • Thank them for feedback
  • Ask clarifying questions
  • Don't defend immediately
  • Reflect before responding

References (Load When Needed)

Detailed Frameworks

  • **[Conversation Framework](references/conversation-framework.md)**: Complete three-phase framework with scripts and examples
  • **[Preparation Template](references/preparation-template.md)**: Worksheet for preparing before difficult conversations
  • **[Delivery Scripts](references/delivery-scripts.md)**: Opening lines, response handling, reframing techniques
  • **[Emotional Regulation](references/emotional-regulation.md)**: Managing your own emotions before and during

See Also

  • `feedback-mastery` skill - SBI feedback model (overlaps but more feedback-focused)
  • `professional-effective-communication` skill - General communication patterns

Example Scenarios

Scenario 1: Addressing Missed Deadlines

**Issue:** Team member missed 3 deadlines in past month
**Impact:** Project delayed, others blocked
**Goal:** Understand root cause, agree on prevention plan

**Opening:** "I wanted to check in about the recent deliverables. I've noticed
the last three have come in past deadline, and I'd like to understand what's
happening and how we can address it together."

Scenario 2: Peer Conflict

**Issue:** Colleague publicly criticized your work in meeting
**Impact:** Embarrassed, trust damaged
**Goal:** Address behavior, rebuild working relationship

**Opening:** "I'd like to talk about what happened in yesterday's standup.
When you said my code 'missed obvious issues,' I felt called out in front
of the team. I'd like to understand your concerns and find a better way
to handle code quality feedback."

Scenario 3: Asking Manager for Raise

**Issue:** Feel underpaid relative to
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Opinionated skills shared by @leonardocouy for improving daily work efficiency with Claude Code. Skills are packaged instructions and scripts that extend agent capabilities across development, documentation, planning, and professional workflows.

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