About this episode

In this episode, Bob DePasquale discusses the difference between people pleasing and true generosity, emphasizing the importance of boundaries and discernment in leadership.

Too many leaders have been told they are "giving too much" and that their generosity is the reason they're exhausted. The real issue is not generosity at all, but people pleasing masquerading as giving. I break down how approval-driven "help" hurts you, your team, and the mission, and why reasoned, radical generosity actually builds healthier people and stronger organizations in this episode. You'll learn how to spot when you are saying yes just to avoid conflict, why giving people what they want is often the opposite of what they need, and how sustainable generosity requires boundaries, courage, and discernment. You'll end with a practical framework for radical generosity so you can give from strength instead of burnout and lead in a way that truly serves your team and your purpose. *Enroll in the "Feeling Generous" Email course 📧 Have a generous week of business. 📈 ======= For in depth insight on how to attract the best talent and most loyal customers, subscribe to the G2 Newsletter . I'll send you The Generous Leader's Planner at no cost to get you started. My DMs are open on LinkedIn , X , and Substack . Find the video version of the show on my YouTube channel. See full…

People in this episode

Host: Bob DePasquale

Topics covered

• people pleasing
• generosity
• leadership
• boundaries
• team dynamics
• sustainable giving

Keywords

• people pleasing
• generosity
• leadership
• boundaries
• team
• sustainable giving
• conflict avoidance
• radical generosity

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• EP #302 Clarity for Generous Teams · April 16, 2026 · 24 min
• EP #301 Interview Questions that Build Culture · April 9, 2026 · 35 min
• EP #300 Why are people leaving your company? · April 2, 2026 · 40 min
• EP #299 How to Be More Reliable (Generous) · March 26, 2026 · 24 min

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