Your next manager could be powered by AI, with Katherine von Jan
Mar 26, 2025
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Katherine von Jan, CEO and co-founder of Tough Day, discusses her mission to revolutionize workplace management with AI tools. She shares insights on the transformative role of AI for Gen Z, including the concept of 'unbossing' that promotes self-management. Von Jan explains how AI like Tuffy can address workplace conflicts and improve communication, while highlighting the importance of cultural sensitivity and human feedback in AI development. The conversation emphasizes adapting to technology to foster inclusion and enhance employee experiences.
AI tools like Tough Day enable more effective management by handling routine tasks, allowing leaders to focus on coaching and employee engagement.
The un-bossing concept, supported by AI, empowers employees to address workplace issues proactively, fostering a healthier and more inclusive workplace culture.
Deep dives
The Role of AI in Modern Management
The podcast discusses how artificial intelligence (AI) is redefining management roles within organizations. Traditional management often contributes to burnout and stress, making many Gen Z professionals hesitant to engage in structured hierarchies or to take on managerial roles. Studies indicate that a significant portion of younger professionals show a preference for 'unbossing,' seeking ways to manage themselves without the direct oversight of traditional managers. By integrating AI like Tough Day's platform, organizations can offer employees a support system that addresses their challenges while allowing managers to focus on high-impact coaching and mentoring.
Creating a Safe Space with AI
Tough Day introduces a 'warm line' concept, aimed at providing employees a safe, anonymous space to discuss workplace issues before they escalate. The platform uses AI to facilitate these conversations while ensuring confidentiality so employees can communicate openly without fear of being judged or facing repercussions. This proactive approach allows individuals to express concerns about diverse topics, from policy-related questions to more sensitive issues, without the fear of triggering formal reporting procedures. Consequently, this system not only helps employees navigate challenges but also promotes a healthier workplace culture.
Efficiency and Employee Retention
The podcast emphasizes that implementing AI in workplaces can lead to significant cost savings and improved employee retention rates. By reducing the administrative burden on managers, AI tools like Tough Day can handle routine questions and operational inquiries, freeing up management resources for deeper engagements with their teams. This efficiency is crucial in preventing employee disengagement, often leading to 'quiet quitting,' where employees become less productive. Retaining employees is especially important, as replacing them can be financially costly, making AI an attractive solution for businesses looking to optimize both performance and retention.
Navigating DEI Challenges through Technology
As organizations face increasing scrutiny regarding Diversity, Equity, and Inclusion (DEI) initiatives, Tough Day acts as a critical resource. The platform empowers companies to customize their approach to DEI by using AI to provide tailored support based on their specific values and policies. This is particularly relevant in a climate where some organizations are even rolling back their DEI efforts amid political challenges. By tracking trends and offering tailored recommendations, the AI helps organizations navigate these complex waters and fosters a workplace environment that prioritizes inclusivity.
A great manager can make a person feel more satisfied and included at work, and set them on a great career trajectory. But a bad manager can cost a company lots of time and money, or even drive away valuable talent. Katherine von Jan is building a better manager, powered by AI. As CEO and co-founder of Tough Day, von Jan is building AI management tools based on the best leaders and latest research, tailored for a company's values and norms. Tough Day might handle basic questions about PTO, but it might also help with sensitive stuff like addressing workplace conflict before it escalates. In this episode of Pioneers of AI, we explore why AI could be great for the future of management, the concept of un-bossing, and von Jan’s inspiration for Tough Day.
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