AI Ethics, Empathy & The Future of Work | Yuying Chen-Wynn

What if technology isn’t replacing humans but revealing what makes us more human? In this episode of Executive Connect, Yuying Chen-Wynn, founder and managing director of Wittingly Ventures, former Microsoft executive, and MIT alum, shares how empathy, adaptability, and experimentation are redefining what great leadership looks like in the age of AI.

With over 20 years of experience leading digital transformation across four continents, Yuying reveals how leaders can balance innovation with ethics, create cultures that embrace change, and implement AI responsibly without losing trust or creativity. She breaks down the mindset shifts every executive needs to thrive in a world where change is constant and curiosity is currency.

In this episode, you’ll discover:

• Why empathy is the most underrated skill in AI transformation

• How to build guardrails for ethical and responsible AI use

• The three traits every leader needs to thrive with technology

• Why fear, not failure, slows innovation

• What the future of work will really look like in the next five years

If you want to lead through disruption, drive transformation, and stay human in a world of machines, this conversation will change how you think about the future of leadership.

⏱️ Chapters

00:00 Why You Can’t Start with Regulation
00:40 From Microsoft to Global AI Leadership
02:00 Lessons from 20 Years Across Four Continents
04:00 What Global Transformation Teaches About Culture
05:20 AI as a Strategic Business Enabler
07:00 How Natural Language Changed Everything
09:00 The Role of Empathy in Leading Transformation
11:00 Why Leaders Must Spend 80% Listening
13:00 The Hidden Fears Behind AI Resistance
14:00 Building Guardrails for Ethical AI
16:00 What Every Company Needs Before AI Adoption
18:00 Skills That Define Future-Ready Leaders
19:00 Adaptability, Learning, and the Power of Tinkering
21:00 Why Curiosity Beats Credentials
23:00 Human Connection in a Digital World
25:00 How Employers Are Redefining Talent and Hiring
27:00 The Next Five Years of AI and Work
29:00 What Automation Will Really Look Like
31:00 Redefining Productivity and the Workweek
33:00 Embracing AI Without Losing Humanity
35:00 Technology as an Amplifier for Creativity
36:00 Where to Learn More About Wittingly Ventures

🔗 Connect With Yuying Chen-Wynn

Website → https://www.wittinglyventures.com
LinkedIn → https://www.linkedin.com/in/yuyingchenwynn

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