Anya Cheng | Episode #480

The Team Engagement Podcast – Season 6, Episode 480: Stop Assuming...Start Communicating

In this episode, Shawn Richards welcomes Anya Cheng, Founder and CEO of Taelor, for a conversation on communication, psychological safety, growth mindset, and the power of using people’s strengths.

Anya shares how Taelor helps busy men look their best through AI-powered styling and clothing rental. Drawing from her leadership experience at companies like Meta, eBay, Target, and McDonald’s, she explains how leaders can create psychologically safe environments by helping team members succeed rather than simply judging whether they succeed or fail.

Shawn and Anya discuss how psychological safety does not remove accountability. Instead, it creates space for people to learn, adjust, and find roles where their strengths can shine. Anya shares a powerful example of helping an underperforming employee succeed by identifying the real challenge and pairing him with the right support.

The conversation also explores growth mindset and the courage to begin before everything is perfectly figured out. Anya reflects on building Taelor without prior fashion industry experience and how persistence, creativity, and learning through action helped her create new opportunities.

Anya also emphasizes emotional wellness through communication, reminding leaders to stop assuming and start communicating. She shares how misunderstandings can grow when people create stories in their minds instead of asking questions directly.

⭐ About Anya Cheng

Anya Cheng is the Founder and CEO of Taelor, an AI-powered personal styling and clothing rental company designed to help busy men look great without spending time shopping.

Before founding Taelor, Anya held leadership roles at Meta, eBay, Target, and McDonald’s, where she led e-commerce, marketing, and product management teams. Her work combines technology, fashion, customer experience, and practical leadership.

Connect with Anya

Website: https://taelor.style
LinkedIn: https://www.linkedin.com/in/anyacheng