Recently, Blair Search Partners went live with Kristen Diggs, Chief Human Resource Officer at San Diego Youth Services, as part of our Building a Winning Team LinkedIn Live series.
Kristen joined us for an insightful conversation about one of the most emotionally complex transitions an organization can face: the departure of a long-serving, beloved CEO. Drawing on more than two decades of HR experience and firsthand insight from navigating executive transitions, she revealed what many leaders often overlook: the true success of a handover isn’t just in the plan, but in the people behind it.
Read on to explore what it takes to honor a legacy while preparing for the next chapter.
Meet Kristen
Kristen Diggs brings nearly 20 years of nonprofit HR experience to her role as Chief Human Resource Officer at San Diego Youth Services (SDYS), where she’s been leading since 2022. A cross-country transplant from Maryland, Kristen had already helped steer a previous organization through a CEO transition when she joined SDYS, making her uniquely equipped to manage what came next.
That “next” included not only the retirement of SDYS’s longtime CEO, Walter Phillips, but a broader leadership turnover across several departments. Kristen stepped into the moment with focus and foresight, and ensured the organization didn’t just brace for change, but planned for progress.
Creating a Blueprint for Continuity
The long runway of Walter’s planned retirement gave SDYS a chance to get intentional. One of the first moves was bringing in an executive coach well before the CEO search even began. This coach conducted staff interviews, ran Gallup Strengths assessments for the leadership team, and facilitated planning sessions that helped align strategy across the organization and provided data to the board and the search committee as to what they should be looking for in a new CEO.
Over the course of Walter’s transition year, the coach met with the team as a whole and 1:1 and continues to meet with Jonathan and the executive team now to ensure Jonathan’s onboarding and transition is successful.
The search itself reflected that care. The board included staff input at every stage, from listening sessions with staff, other board members, donors and community partners, to site visits. Kristen emphasized that consistent communication from the board – through email updates, internal videos, and monthly all-staff meetings – played a critical role in calming anxieties and reinforcing continuity.
Walter was very intentional with stepping out of the day to day over the year in order to give the rest of the leadership team (CFO, CHRO and CPO) visibility and the opportunity to work together on decisions and strategy. “Our message was clear: the work continues,” Kristen said. “No matter who’s at the helm, our mission remains the same.”
Honoring the Past, Welcoming the Future
As the search narrowed, the board made a small but meaningful decision: they asked Walter to announce his successor, Jonathan Castillo. That single gesture signaled trust, continuity, and grace and gave the staff immediate confidence in the incoming CEO. The board decided to also allow for a few weeks of transition and overlap between Jonathan and Walter.
Jonathan’s first week? It was strategically decided by Walter and Jonathan together to coincide with SDYS’s Staff Appreciation Week. He and Walter toured every program site together, meeting staff, showing up side-by-side, even dressing as twins for Spirit Day. On the final day of the week, they literally passed a baton—yes, a real one—at the annual staff appreciation and celebration event.
That baton now sits in Jonathan’s office, a tangible reminder of one chapter closing and another beginning.
Listening Across the Organization, Including Youth Voices
What made this transition unique wasn’t just the strategic planning; it was the cultural alignment.
With a deeply trauma-informed care lens, SDYS included input from its diverse staff and from young people receiving services through its Youth Advisory Board (YAB). From proposing campus safety upgrades to offering direct feedback to Jonathan himself, youth voices were integrated throughout the process.
As Kristen noted, “One of our youth walked right up to Jonathan at an event and told him exactly why Walter was so beloved and what that meant for him personally. And Jonathan listened.” Jonathan was able to experience at that moment the way that our youth know they have a direct line to the CEO.
Onboarding a CEO, the Right Way
Kristen and her team built a four-page transition checklist before Jonathan’s first day, covering everything from business cards to board introductions. By the time he officially stepped into the role, he’d already attended three community events with the executive team and had begun relationship-building internally and externally.
One of those events was Walter’s retirement gala with almost 300 people in attendance. At the conclusion of the gala, Walter graciously introduced Jonathan as the next CEO and let him have the floor to introduce himself to a room filled with SDYS’s board, staff, partners and supporters.
What stood out most in Jonathan’s first few weeks as the new CEO? His curiosity. Curiosity about our programs, our staff, our culture. A curiosity in asking thoughtful questions not to replicate the past, but to know how to build on the success of Walter and those CEO’s that came before him over SDYS’s 50 year history.
“He doesn’t want to change everything. He wants to raise the bar,” Kristen said. “Jonathan is looking at all of all aspects of the agency with fresh eyes and perspective, and he brings a powerful network in San Diego and a clear vision to help take us there”.
What’s Next?
Today, SDYS continues its work under new leadership, with momentum, clarity, and the same unwavering mission. Jonathan brings with him deep experience in the housing and youth services sector, plus a collaborative approach that resonates across the agency.
San Diego Youth Services is already a strong organization. We do meaningful work, we have a stellar reputation, and we’re fortunate to have an incredibly dedicated, passionate, mission driven staff. But we also have the opportunity to elevate our impact even further.“Jonathan is going to get us out there more and develop the agency and the staff to an even higher level, which we’re just super excited about,” Kristen said.
A huge thank you to Kristen Diggs for sharing her time and insights—and for demonstrating that when leadership transitions are done right, they don’t just preserve legacy. They elevate it.
Stay tuned on LinkedIn as we continue to meet with top experts in and around the nonprofit sector to discuss relevant issues, grow our understanding of the challenges and opportunities in our workplaces, and uncover the ins and outs of what it takes to Build a Winning Team.If you’re curious about Blair Search Partners, on the hunt for a new role, or looking to fill positions in your organization, reach out and let’s see what we can do together!