This confidential AI will save your team from meltdowns Podcast Por arte de portada

This confidential AI will save your team from meltdowns

This confidential AI will save your team from meltdowns

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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
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