Working Effectively Across Generational Differences


SIF Office, 2 Oliver St., Suite 802, Boston, MA 02109

In this session, we’ll focus on age and generational differences. We are in a moment when we have at least three generations in our organizations. This means that most of us need to figure out how to work effectively with people significantly older or younger than us. Sadly, as with many differences, they lead to conflict rather than collaboration. However, there is a tremendous opportunity for our workplaces to benefit from the age diversity we have!

We’ll explore the differences across generations and how they impact our work style and work relationships. Attendees will have the opportunity to practice managing some of the typical challenges that show up in cross-generational relationships, especially as it relates to power differentials. Participants will gain tools to help improve the quality of these relationships through personal reflection, vignettes, small group discussions, and more.

Session Facilitators

Rebecca N. Jackson, MSW, LoveSeed Coaching, Consulting, and Facilitation 

Rebecca is a clinically trained facilitator, teacher, consultant, and coach. Through LoveSeed, Rebecca applies her decades of leadership and teaching experience in supporting mission-driven organizations to strengthen their equity practices. Rebecca creates spaces where people can have difficult but necessary conversations, learn, grow, and thrive. She builds loving, sustainable, and brave leaders, teams, and organizations that bring their equity values to life. 

After serving as pastor of a small Mattapan church from 1999-2005, she attended Simmons College Graduate School of Social Work, where she focused on trauma-informed care for young people and families. She joined Trinity Boston Connects in 2012 and founded Trinity Organizational Equity in 2017, where she facilitated the organizations’ pursuit of racial equity, restorative justice, and trauma inclusion in the internal functioning, programs, and HR. She also teaches at Bridgewater State University Graduate School of Social Work, Boston College Graduate School of Social Work, and Harvard University Graduate School of Education.

Brianna Boggs, Coach and Consultant 

Brianna Boggs is a leadership coach and consultant focused on supporting executives and boards of directors through leadership challenges. Her practice focuses on executive coaching for mission-driven leaders, racial justice education, and fundraising for social justice work. Through her work, she helps white leaders develop skills to push their organizations to deeper engagement in issues of race and equity, internally and externally. As co-founder and co-facilitator of the Racial Equity Leaders Learning Circle, Brianna facilitates a 10-month cohort for nonprofit senior leaders seeking to dig deeply into the personal side of leadership on racial equity and implement new practices to improve their organizations. Prior to coaching and consulting, Brianna’s career focused on fundraising and communications in social justice organizations including GLAD (GLBTQ Legal Advocates & Defenders), Trinity Boston Connects, and StreetSafe Boston.


Please contact Zane Diamond at with any questions.