📱 Best Platforms
LinkedIn for targeting managers and HR professionals. Zoom for role-play coaching sessions. Superpeer for selling packages. Calendly for booking. Notion for conversation planning frameworks.
📖 The Hustle
Most professionals dread difficult conversations — giving critical feedback, negotiating conflict, firing someone, saying no to a boss, or addressing workplace tension. If you have experience in management, HR, conflict resolution, or counseling, you can coach people through these high-stakes interactions. Offer structured coaching where you help clients prepare for a specific difficult conversation: clarify their objective, script their opening, anticipate reactions, practice delivery through role-play, and develop de-escalation techniques. Charge $125-250 per session. The most effective format is role-play — you play the other person with realistic pushback while the client practices navigating the conversation in real time, then debrief. Create frameworks clients can reuse: the SBI model (Situation-Behavior-Impact) for feedback or the DESC script for conflict resolution. This is emotionally demanding but high-impact work — helping a client successfully navigate a conversation they've been dreading for months creates deep gratitude and strong referrals.
🚀 First Step
Create a free 'Difficult Conversation Planner' template with a step-by-step framework, share it on LinkedIn, and offer a free 20-minute conversation strategy call.
🔑 Keys to Success
- Use intensive role-play in coaching sessions — practicing the actual conversation with realistic pushback is far more effective than discussing it abstractly
- Teach specific named frameworks (SBI, DESC, NVC) — reusable mental models give clients confidence they can handle future difficult conversations independently
- Focus on workplace conversations specifically — manager-direct report, peer conflict, and upward feedback situations have distinct dynamics that general conflict advice misses
🛠 Tools & Resources: LinkedIn, Zoom, Superpeer, Calendly, Notion, Loom, Google Docs