23: Empathy Is NOT Being Nice What Great Leaders Actually Do ft. Dr. Melissa Robinson-Winemiller episode artwork

EPISODE · Mar 30, 2026 · 41 MIN

23: Empathy Is NOT Being Nice What Great Leaders Actually Do ft. Dr. Melissa Robinson-Winemiller

from The Midgame Mindset · host Rich Bishop

What most leaders call "empathy" is actually just being a doormat — and there's a big difference.Dr. Melissa Robinson-Winemiller is a TEDx speaker, executive coach, author of The Empathic Leader, and has brought her frameworks to the stages of Oxford and Cambridge. With a TEDx talk approaching 150K views in just four months, she's at the forefront of one of the most urgent conversations in leadership today: what empathy actually is, why it's not what you think, and why it may be the most valuable business skill of the next 20 years.In this episode of The Midgame Mindset, Rich and Dr. Melissa go deep on why empathy is being both weaponized and misunderstood — from performative CEOs crying on LinkedIn to leaders using "too much empathy" as an excuse to avoid hard decisions. They also explore the fascinating intersection of AI, human connection, and what the supply-and-demand curve looks like for leaders who can truly connect.#leadership #ai #trust Key Takeaways:- The biological and developmental basis of empathy- Empathy in leadership and organizational culture- The impact of social media and AI on empathy and social skills- Distinguishing genuine empathy from performative acts- Strategies for developing empathy in leaders and teams- The role of empathy in trust-building and decision-making- Generational differences in empathy and technology use- The importance of boundaries and kindness in empathetic leadership- The challenges and opportunities of AI in sales and marketing- Future trends in empathy and leadership developmentEpisode Chapters:00:00 The Rise of AI and Empathy in Leadership02:59 Dr. Melissa's Journey to Empathy05:50 Understanding Empathy: Nature vs. Nurture09:02 The Dual Faces of Empathy in Society11:51 Empathy in Leadership: Balancing Kindness and Tough Decisions15:09 Hiring with Empathy: Building a Strong Culture18:02 Generational Perspectives on Empathy20:50 Empathy in the Age of AI24:10 Future Challenges in Leadership and EmpathyMore about Dr. Melissa Robinson-Winemiller- EQ via Empathy: https://www.eqviaempathy.com- The Empathic Leader: https://a.co/d/08jLDugw- TedX-5 steps to start being kinder to yourself : https://www.youtube.com/watch?v=IaoXSEWeILo- Time2Change Podcast: https://www.youtube.com/playlist?list=PLign4alKxXOG31-FsQSS3MIJOB1IHq-6wMore from Rich Bishop:- Sign Up for Midgame Consulting’s Newsletter: http://eepurl.com/i2340o- Connect with Rich Bishop on LinkedIn - / richbishop2 - Midgame Consulting – https://www.midgameconsulting.com

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23: Empathy Is NOT Being Nice What Great Leaders Actually Do ft. Dr. Melissa Robinson-Winemiller

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