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

• Tough.Day (Official Site)
• Katherine von Jan on LinkedIn
• Fisher Phillips Employment Law
• Harvard Business Review
• Charter Works
• Perplexity.ai
• Vibes.AI
• OpenAI