Summary

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In this episode of the Recruiting Community Podcast, hosts Chris Hoyt and Gerry Crispin speak with Diana Tsai, co-founder and CEO of Upwage. Diana shares how Upwage is using AI to reshape hiring by reducing bias, accelerating emotional resilience, and transforming the recruiter’s role through AI-empowered agents. The conversation explores the three waves of AI transformation in recruiting, the emerging role of AI assistants as trusted teammates, and how thoughtful implementation can turn AI into a force for equity and innovation in the workplace. Diana also opens up about personal practices that keep her grounded—like journaling with GPTs, shadow work, stoicism, and balancing the “monk and mermaid” in leadership.

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What you'll learn

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• The three waves of AI transformation in recruiting and where we are now.
• What it means to be an “AI-empowered recruiter” and how to “hire” AI agents.
• How journaling with GPT-based tools accelerates emotional resilience.
• Why the last 20% of the hiring process will always be human.
• How AI can improve fairness in hiring, even mitigating systemic biases.
• The importance of leadership in managing hybrid human/AI teams.
• Why agentic AI isn't just hype—and how to measure its maturity.
• The vision of a “universal interviewer” that connects job seekers directly to AI-powered roles.
• How recruiting teams can build their own AI agents to scale quality and consistency.
• What successful leadership looks like in the age of AI.

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Key Takeaways

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• AI is transforming recruiting in three waves: automation of tasks (Wave 1), emergence of AI managers (Wave 2), and a universal interviewer model that redefines job applications (Wave 3).
• AI agents aren't replacing recruiters—they’re becoming trusted teammates, allowing recruiters to focus on deeper candidate engagement and strategic impact.
• Journaling with GPTs and building “soul teacher” agents can help leaders uncover blind spots and accelerate personal growth.
• True fairness in hiring comes from AI tools that create consistency, redact PII, and allow interviews to happen asynchronously and equitably.
• Agent maturity matters more than the buzzword—ask what job the AI actually does and how well it performs it.
• Leadership in the AI age involves hiring and managing both human and AI team members while enabling cultural shifts toward trust, upskilling, and innovation.
• The most successful teams are already customizing and deploying their own AI agents to create tailored, high-performance hiring systems.

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In this episode we cover:

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• Diana’s personal AI tools for emotional resilience (5:30).
• The “AI-empowered recruiter” and agent hiring mindset (12:10).
• How AI enhances fairness by avoiding schedule bias and interviewer inconsistency (19:40).
• Building agents that reflect organizational values and reduce turnover (25:50).
• What it means to be “agentic” and how to evaluate AI sophistication (31:15).
• The future of AI coordination: universal interviewers and agent networks (38:10).
• How leadership must evolve to manage hybrid teams (human + AI) (45:00).
• What traits define a great leader in the AI era (48:30).

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