Guest: Katherine von Jan, Founder & CEO of Tough Day
Date: June 05, 2025
Key Takeaways
- Tough Day helps employees and managers work through workplace challenges via a private, AI-powered chat assistant called Tuffy.
- Tuffy assists with performance conversations, feedback collection, roleplay, journaling, and decision-making—all within a confidential interface.
- Built on curated HR, legal, and leadership frameworks not available in public LLMs, including HBR content and partner-authored materials.
- Customizes tone and recommendations to match regional and organizational culture.
- New subscriptions available directly via Tough.Day, including individual and small team plans.
Frameworks & Concepts
- Confidential Coaching: Private, personal-device access; no data returned to employer.
- Manager Support: Use Tuffy for performance reviews, managing up, and preparing tough conversations.
- Customization Layer: Employers define HR policy stances; tone adapted for cultural fit.
Resources
