The Empathy Edge Kasey D'Amato: Making High-Stakes Decisions Requires Empathy and Self-Compassion
What happens when you’re standing at a pivot point — the kind where your next move could shift everything for your business, your team, or your career? In those high-stakes moments, success doesn’t come from spreadsheets alone. It requires empathy, emotional intelligence, and even self-compassion.
Kasey D’Amato knows this firsthand. A keynote speaker, executive coach, and strategic advisor, Kasey has guided founders and corporate leaders through major transitions with clarity and resilience. In our conversation, we dug into her four pillars of holistic leadership and how self-regulation shapes better decisions. We explored the “decision threshold,” why every choice has three outcomes, and how to balance head, heart, and gut when the numbers don’t tell the full story. Kasey also shared why grounding yourself is key to hearing other perspectives without defensiveness — and how empathy and self-compassion aren’t soft skills, but strategic advantages when the stakes are high.
To access the episode transcript, go to www.TheEmpathyEdge.com, search by episode title.
Listen in for…
- Finding the balance of the decision threshold - that point between gathering information and making the decision.
- Why does every choice have three outcomes?
- The Four Pillars of holistic leadership and how self-regulation shapes better decisions.
- How to balance head, heart, and gut when the numbers don’t tell the full story.
- Utilizing the Two-Minute rule to move out of indecision.
"I believe it is the critical moments of decision and how you handle your emotional intelligence in those critical moments and pivots that set you up for success, no matter how big your failures are along the way." — Kasey D'Amato
Episode References:
- The Empathy Edge Podcast Episode: Ilana Ben-Ari: How the Empathy Toy is Changing the World
About Kasey D'Amato, Business Leader and Holistic Coach:
Kasey D’Amato is a keynote speaker, executive coach, and strategic business advisor who helps business founders and corporate leaders navigate high-stakes decisions and transitions with clarity, confidence, and resilience — without burning out in the process.
With over 20 years of experience across healthcare, entrepreneurship, and business consulting, Kasey brings a unique blend of business acumen, human behavior expertise, and emotional intelligence to her work. She is a former Dermatology PA who went on to launch multiple ventures — including a global skincare brand, a healthcare consulting agency, and an executive leadership advisory.
She’s consulted with Fortune-level companies, led workshops across the healthcare and financial industries, and spoken at major institutions like UCLA, USC, and the University of Miami.
Kasey is known for her dynamic, actionable, and emotionally intelligent approach to leadership — guiding ambitious entrepreneurs and executives to think bigger, lead better, and align their next move with both performance and personal fulfillment.
Connect with Kasey:
Website: https://www.kaseydamato.com/
LinkedIn: https://www.linkedin.com/in/kaseydamato/
Facebook: https://www.facebook.com/kasey.damato/
Instagram: https://www.instagram.com/kaseydamato/?hl=en
Connect with Maria:
Get Maria's books: Red-Slice.com/books
Hire Maria to speak: Red-Slice.com/Speaker-Maria-Ross
Take the LinkedIn Learning Courses! Leading with Empathy and Balancing Empathy, Accountability, and Results as a Leader
LinkedIn: Maria Ross
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Get your copy of The Empathy Dilemma here- www.theempathydilemma.com