In this episode of the Purposeful Planning Podcast, host Andy Stubblefield sits down with Jeff Savlov and Garrett Wells to explore what it really looks like to collaborate through conflict in complex family systems. Drawing from a real-world engagement involving a strained trustee-beneficiary relationship between a mother and daughter, Jeff and Garrett reflect on the challenges of stepping into a high-stakes collaboration as new partners navigating emotional tension, unclear expectations, and evolving client needs. Together, they unpack themes of ego, economics, and expectations, highlighting the importance of humility, communication, role clarity, and staying within one’s expertise while serving families in moments of transition. Through honest reflection on both the successes and disappointments of the engagement, this conversation offers practical insight for advisors seeking to collaborate more effectively across disciplines in support of families and their long-term well-being.