Difficult Workplace Conversations

A three-phase framework for handling workplace conversations you'd rather avoid. Walks you through prep (clarifying the issue, checking your emotions, considering their perspective), delivery (the SBI model: situation, behavior, impact), and followup (documenting agreements, checking progress). Includes opening scripts for common scenarios like missed deadlines, peer conflicts, and salary discussions. The anti-patterns section is honest about what doesn't work, like scripting every word or starting with "you always." Best used when you're about to have a hard conversation and need to organize your thoughts so you don't make it worse.

skills.sh installs: 4K
GitHub stars: 2.7K
last updated: Aug 21, 2026

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Install

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

Installs into .claude/skills of the current project.

Files

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

Clarify the Issue
- What specifically happened? (Observable facts only)
- What is the impact? (On you, team, work)
- What do you need to change?
Check Your Emotions
- What am I feeling? Why?
- Am I calm enough to have this conversation?
- What might trigger me during this conversation?