The Future of Feedback: Building Trust and Better Leaders with AI with Milli Feldman

Building a startup takes a different kind of talent, leadership, and mindset. In this episode of Trust Stories, Tom Keenan sits down with people operations leader Natalie Ledbetter to explore why even experienced professionals can struggle in early-stage companies. Drawing on her experience building people functions at startups and advising venture-backed founders, Natalie shares what she's learned about hiring the right people at the right time, avoiding processes that slow growth, preparing employees for leadership, and setting realistic expectations around equity and ownership. They also discuss why diverse perspectives matter from day one and the people mistakes that become much harder to fix as a company grows.

Daniel Space joins Tom Keenan to talk about why HR business partners need more than HR expertise to become true strategic partners. They discuss why understanding the business changes how HR operates, what Daniel learned working across companies like EA and Spotify, and how better coaching, more consistent feedback, and AI could reshape the way managers support their teams.

In this episode of Trust Stories, Tom Keenan sits down with Fred Leong, Head of People and Culture at dv01, to unpack why traditional performance management so often breaks trust. They discuss the difference between transparency and honesty, why delayed feedback and difficult conversations can derail performance, and how AI could help create a more continuous, useful, and human approach to coaching and development. This conversation is both philosophical and deeply practical. It is a reminder that trust is not built through messaging or performance. It is built through small risks, honest moments, and the courage to genuinely listen.