Guest: Katherine von Jan, Founder & CEO of Tough DayDate: June 05, 2025Key TakeawaysTough 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 & ConceptsConfidential 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.ResourcesTough.Day (Official Site)Katherine von Jan on LinkedInFisher Phillips Employment LawHarvard Business ReviewCharter WorksPerplexity.aiVibes.AIOpenAI

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