# Difficult Conversations

> Use when navigate hard talks like feedback, disagreements, and terminations using SBI, DESC, and the 3-conversations framework. Use when delivering bad news or addressing conflict.

- Skill: `oyi77/difficult-conversations` (Agent Skill)
- Install (CLI): `npx skillmds add oyi77/difficult-conversations`
- Raw SKILL.md: https://api.skillmd.com/api/skills/oyi77/difficult-conversations/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- License: Apache-2.0
- Author: oyi77 (https://skillmd.com/u/oyi77)
- Updated: 2026-09-08
- Page: https://skillmd.com/skills/oyi77/difficult-conversations

---


# Difficult Conversations

## Overview

Mindset skill for difficult conversations. Builds capability through deliberate practice and structured frameworks.


## Anti-Rationalization Table

| Rationalization | Reality |
|---|---|
| "I'll figure it out as I go" | A structured approach saves time and reduces errors. Follow the workflow in this skill rather than improvising. |
| "I already know this topic" | Familiarity breeds shortcuts. Use the checklist to verify you haven't missed critical steps. |
| "This doesn't apply to my situation" | The patterns here generalize across contexts. Adapt, don't skip — the underlying principles hold. |
| "One more tool will fix it" | Adding complexity rarely solves process gaps. Master the core workflow first. |

## When to Use

**Trigger phrases:**
- "difficult conversations"
- "Delivering critical feedback or performance reviews"
- "Addressing interpersonal conflict or disagreements"
- "Having termination, demotion, or discipline conversations"


- Delivering critical feedback or performance reviews
- Addressing interpersonal conflict or disagreements
- Having termination, demotion, or discipline conversations
- Breaking bad news to stakeholders or clients
- **When NOT to use**: Casual feedback, low-stakes disagreements, or emergencies requiring immediate action


## When NOT to Use

- When the situation requires professional counseling or therapy
- For high-stakes decisions that need expert judgment
- When the skill conflicts with cultural or personal values


## Core Principles

- **Start small** — Begin with manageable difficult conversations practices and build incrementally
- **Be consistent** — Daily practice beats occasional intense effort
- **Track progress** — Measure improvement to maintain motivation
- **Reflect regularly** — Review what's working and adjust your approach

## Daily Practice

1. **Morning intention** — Set a specific difficult conversations goal for the day
2. **Active practice** — Apply difficult conversations techniques during real situations
3. **Evening reflection** — Review the day's difficult conversations moments and lessons learned
4. **Journal entry** — Record insights, wins, and areas for improvement

## Frameworks

- **OODA Loop** — Observe, Orient, Decide, Act — for rapid difficult conversations decision cycles
- **PDCA Cycle** — Plan, Do, Check, Act — for iterative difficult conversations improvement
- **After-Action Review** — What happened? Why? What to improve?
- **Deliberate Practice** — Focused effort on specific difficult conversations weaknesses

## Common Pitfalls

- **Perfectionism** — Waiting for ideal conditions instead of starting now
- **Inconsistency** — Practicing sporadically instead of building a routine
- **Isolation** — Not seeking feedback or accountability partners
- **Overwhelm** — Trying to improve everything at once instead of focusing

## Resources

- Keep a difficult conversations journal for tracking progress
- Find an accountability partner or mentor
- Set weekly difficult conversations challenges with measurable outcomes
- Review and adjust your approach monthly

```markdown
# Daily Practice Template

## Morning (5 min)
- Set intention for the day
- Review top 3 priorities

## During the day
- Practice the skill in real situations
- Note moments of success and struggle

## Evening (5 min)
- Reflect: What worked? What did not?
- Log one lesson learned
```


## Process

1. **Prepare** — Gather requirements, verify prerequisites, set up environment
1. **Execute** — Run difficult conversations workflow with configured parameters
1. **Verify** — Validate output meets requirements, document results

## Verification

- [ ] All steps executed successfully
- [ ] Results validated against acceptance criteria
- [ ] Error handling tested with edge cases
- [ ] Documentation updated with findings