About This Resource
This session was part of the 2025 Supervisor Success: Growing Leaders from Within CE Week series
Series Overview
Frontline supervisors are the backbone of employment social enterprises (ESEs). They keep operations running smoothly, provide technical expertise and customer service, and most importantly coach participant employees as they navigate barriers to employment. Yet many ESEs struggle to train and prepare supervisors effectively, especially when promoting participant employees into their first leadership roles. To address this challenge, REDF created a three-part Continuing Education Week series focused on practical strategies to grow and strengthen supervisor talent.
Grounded in research, trauma-informed management practices, and the lived expertise of frontline leaders, this series supports ESEs in growing their internal talent and in creating clear pathways from participant employee to supervisor and beyond.
Alongside these sessions, we’ll introduce REDF’s new Supervisor Success Toolkit, which equips ESE leaders with training content to enhance supervisor onboarding and development.
Session Description
What does this look like in practice and what are some of the challenges our supervisors may face? What does growth look like beyond the first-time supervisor role? This interactive panel brought together ESE leaders with direct experience training supervisors and growing talent from the participant level. Panelists shared lessons on supporting participant employees as they transition into leadership, navigate career crossroads, and move within or beyond the enterprise. Together, we explored how to center participant choice, encourage growth, and balance the realities of both supporting and letting go.
Panelists:
- Kirsten Ham-Marshall, Upspire (Facilitator)
- Reinaldo Cruz III, EMERGE CT
- Adewale OgunBadejo, GRID Alternatives
- James Winfrey, Chrysalis
Session Goals & Key Takeaways
By the end of this session, you will:
- Learn from real-world examples of ESEs training and supporting supervisors with lived expertise
- Gain strategies to navigate “both sides of growth”—advancing internal leadership pipelines while supporting staff who choose new paths
- Build perspective on how to keep supervisor development participant-led and mission-centered
This Session is Ideal for:
- ESE leaders, HR teams, and enterprise managers invested in long-term talent development
- Program designers shaping career pathways for participant employees