About This Resource
This toolkit was developed as part of our 2025 CA RISE and WIOA programs.
Toolkit Description
The Supervisor Success Series Toolkit is a practical, adaptable training resource developed by REDF to help employment social enterprises (ESEs) onboard and develop new frontline supervisors.
Frontline supervisors play a critical and nuanced role—overseeing day-to-day operations, supporting participant-employees, and translating mission and values into action. For new supervisors—especially those promoted from participant-employee roles—the transition can be complex. This toolkit offers clear, trauma-informed approaches to prepare them for success.
Development Process
REDF worked with Kirsten Ham (a former ESE co-founder and now consultant) and Elizabeth Strand (a REDF Farber Fellow) to develop this toolkit. They collaborated with ESE leaders, and partner organizations in the ESE community, including many CA RISE portfolio organizations to gain valuable insights. The toolkit builds on lessons from Chrysalis’ Supervisor Training that was developed alongside REDF in 2022. The Supervisor Success Series is a structured but flexible toolkit that helps social enterprises engage supervisors in discussion on how to lead with confidence, clarity, and compassion.
Toolkit Overview
The Supervisor Success Series Toolkit contains six core 30- to 45-minute modules that can be delivered together or individually. There is also an introductory train-the-trainer module to help orient ESE leaders and ask critical questions before launching this training module.
- Mission & Values for Leaders – What is our purpose? How will you build this into your leadership style and represent our organization?
- Role of the Supervisor & Performance Management – What do we as an organization expect of you as a new team leader from your first day? What are your goals?
- Managing for Success – Build executive-functioning skills and burnout-prevention habits for day-to-day leadership.
- Lived Expertise & Trauma-Informed Leadership – Lead authentically while maintaining healthy boundaries and trust. Structure your day-to-day with ease. Well-being for leaders.
- Giving Feedback & Empowering Your Team – Practice encouragement-focused corrections and escalation awareness.
- De-Escalation & Conflict Management – Apply grounding tools to maintain calm, safety, and team stability.
Recommended Use
Social enterprises can adapt and sequence the modules based on their size, target population, business model (permanent vs. transitional), and onboarding process (we strongly encourage two weeks of shadowing a current supervisor – this could be alongside training). Modules include:
- A detailed facilitator guide
- A PowerPoint slide deck with warm-ups, optional activities, and discussion questions
- An introductory train-the-trainer video by ESE leader Kirsten Ham-Marshall
The toolkit represents the first step in supervisor development— these modules are very simple and intended to be heavily edited and paired with on-the-job shadowing, mentorship, and continuing education. The modules are currently focused on a broad spectrum of the soft-skills needed for supervisors at ESEs to be successful and will eventually build on more technical skills by industry and target population specific needs.
About ESE Consulting
Kirsten Ham helps mission-driven businesses strengthen their operations and build sustainable earned revenue streams. As co-founder of UpSpire, she grew a social enterprise from one employee to more than 200, creating pathways out of homelessness and the justice system through full-time, benefited employment. Now serving as COO at Hawai‘i Farmers Union, she leads initiatives that strengthen Hawai‘i’s agricultural resilience and expand local economic self-reliance.
Drawing on more than a decade of hands-on experience scaling mission-driven ventures, Kirsten consults with employment-based social enterprises across the country—coaching leaders, shaping strategy, and helping them build stronger systems faster and better than she did. Her focus is always on practical growth that lasts.
She and her family farm and ranch in Waimea, Hawai‘i Island. She is best reached at Kirsten@eseconsulting.org.