Recently, Blair Search Partners CEO Trevor Blair and Managing Director Torrey Albertazzi went live with Jonathan Castillo, CEO of San Diego Youth Services, for a candid and deeply practical conversation on leadership transition.
As part of our Building a Winning Team LinkedIn Live series, the discussion explored what it truly means to step into a legacy organization following a long-tenured, widely trusted leader and how new executives can navigate that transition with intention, clarity, and respect for what came before.
Meet Jonathan Castillo
Jonathan Castillo brings more than 16 years of executive and system-level leadership in homelessness and youth services. As CEO of San Diego Youth Services, he now leads one of the region’s most critical safety nets for youth experiencing homelessness, trauma, and instability. He stepped into the role after 25 years of leadership under a predecessor who helped shape not just the organization’s programs, but its culture, relationships, and identity within the community.
Leadership of that duration creates deep continuity, which makes transition both more meaningful and more complex. What made Jonathan’s transition distinct is that the relationship did not begin on day one. Years before stepping into the role, he had already built a connection with his predecessor through shared work in the community. That connection carried into a structured transition, where both leaders were visible together across sites and staff interactions, helping create continuity during the handoff.
Designing a Transition That Builds Trust
Leadership transitions are often treated as operational. Responsibilities are transferred, access is granted, and the new leader is expected to step in and move forward.
In this case, the transition was intentionally relational and visibly structured. Jonathan and his predecessor spent three weeks working side by side and moving across the organization together. They visited multiple program sites, met with teams in person, and spent time understanding how each part of the organization functioned. Much of that time was spent traveling together, creating space not just for knowledge transfer, but for alignment in how they approached the work and the people doing it.
That visibility played an important role. Staff were not just introduced to a new leader. They were able to observe the relationship between the outgoing and incoming CEO in real time. They also saw how decisions were approached, how conversations were handled, and how continuity was being carried forward.
The transition was also timed intentionally. The final week aligned with a staff and volunteer appreciation event, where both leaders participated in a symbolic handoff, which reinforced, in a tangible way, that leadership was being passed with alignment and mutual respect.
Understanding Before Acting
One of the clearest themes from Jonathan’s experience is the importance of listening before making decisions. He explained that programs can be understood one way on paper and experienced very differently in practice.
Rather than stepping in with immediate changes, he focused on understanding how the organization actually operates. That meant going beyond reports and contracts and spending time with teams in their environments. He described rotating across multiple sites, meeting directly with staff, and learning from their day-to-day experiences of delivering services.
The Weight of Legacy
Stepping into a leadership role after a long-tenured predecessor requires understanding how the organization has been shaped over time. San Diego Youth Services has a long history, and Jonathan was clear that his role is part of a broader continuum. He pointed to the organization’s evolution as a response to community needs, not as the product of any one leader.
At the same time, he recognized the specific contributions of his predecessor. During his tenure, the organization expanded its mental health services, invested in housing solutions for youth, and strengthened its financial stability.
Understanding that context allowed Jonathan to approach leadership with clarity. The goal is not to replace what came before, but to build upon it. That includes preserving what is working, identifying where needs have shifted, and contributing a perspective that supports the organization’s continued growth.
Pacing Change, Building Trust, and Staying Grounded
Early in his tenure, Jonathan heard a consistent question from stakeholders: What is your vision? It is a familiar expectation for new leaders, especially during transition, when teams are looking for direction and clarity. Jonathan chose not to rush that answer. He recognized defining a meaningful path forward requires a clear understanding of where the organization is and what it actually needs. In a field responding directly to gaps in the community, this level of understanding has to be earned through listening and observation
This outlook helped set expectations internally and signaled a leadership style grounded in intention rather than urgency. Progress still needed to be visible, so Jonathan focused on responding directly to feedback from staff. When a concern was raised about slow response to a challenge, the team adjusted and responded more quickly the next time. Increased participation in staff meetings also became a useful indicator of engagement and alignment.
His approach is shaped by earlier experiences in his career, including receiving difficult feedback about how he was showing up as a leader. He used that moment to reflect, seek input, and develop behaviors that build trust. Today, this shows up in how he creates space for ongoing, informal feedback within his team.
Sustaining Leadership Through Connection and Continuity
Leadership at the executive level can be isolating, especially during periods of transition. Jonathan addressed this early by building a peer network of fellow CEOs stepping into new roles. What began as a small group has grown into a trusted circle that meets informally to share experiences, ask questions, and support one another, with backing from a local foundation committed to strengthening leadership across the community.
At the same time, continuity within the organization was reinforced through his ongoing relationship with his predecessor. They approached this intentionally, having direct conversations about how they would engage moving forward. This included how they would show up at events, interact with stakeholders, and maintain clarity around leadership roles.
There was no fixed cadence for communication, but the connection remained active. They stayed in contact regularly, meeting or speaking as needed based on what was happening within the organization.
This level of clarity helped prevent confusion and allowed the relationship to remain supportive without overlapping authority. It also reinforced continuity in a way that felt natural to staff and the broader community.
What’s Next?
A huge thank you to Jonathan for sharing a practical and experience-driven perspective on leadership transition.
For nonprofit executives, board members, and mission-driven leaders, the takeaway is clear. Successful transitions require intention, patience, and a strong understanding of both people and context.
As leadership changes continue across the sector, organizations that approach succession as both a strategic and relational process will be better positioned to maintain stability while continuing to evolve.
Stay tuned on LinkedIn as we continue to engage with leaders across the nonprofit and public agency sectors to explore the insights that help organizations build and sustain strong teams.
If you are navigating a leadership transition, exploring new opportunities, or looking to strengthen your team, reach out to Blair Search Partners. We would be glad to support your next chapter.