As I approach my second year as CEO of PBO Advisory, I find myself engaged in what many leaders avoid: actively planning my own succession.
This isn’t about stepping away. It’s about building something that lasts beyond any single leader.
When I took on this role, I inherited an organization built on strong foundations. Our clients trust us to align their financial resources and human capital strategies. We help them navigate complexity, build capacity, and position their businesses for sustainable growth. The irony wasn’t lost on me: we advise organizations on strategic planning, yet our own succession plan needed significant work.
So we did what we counsel our clients to do. We got uncomfortable. We had the hard conversations and we started building.
Why Most CEOs Avoid This Work
Succession planning forces leaders to confront several uncomfortable truths:
First, it requires acknowledging that the organization will continue without you. For founders and long-tenured executives, this can feel like diminishing your own relevance. But the opposite is true. The organizations that outlast their founders are testaments to their leadership, not indictments of it.
Second, it surfaces gaps in your leadership team that are easier to ignore when you’re focused on quarterly results. Are your direct reports ready to step up? Do they have the strategic thinking, financial acumen, and people leadership skills to lead at the next level? If the answer is no, that’s a problem today, not a someday problem.
Third, it forces you to make decisions about ownership, equity, and financial transition that are complex and emotionally charged. How do you balance rewarding tenure with investing in future leadership? How do you create incentives that retain your best people while building bench strength?
These questions don’t get easier with time. They get more expensive.
What We’re Learning at PBO
Our succession planning process has required integration across three critical dimensions: strategic vision, financial modeling, and talent development. This is exactly the alignment we help clients create, and living it ourselves has been humbling.
Jennifer Rebis, our CFO, has built financial models that quantify transition costs, map capital requirements, and project the impact of different ownership structures. This isn’t theoretical planning. It’s data-driven decision-making that ensures we can fund leadership transitions without destabilizing operations or client service.
Nicole Devine, our CPO, has led the talent mapping work. Who has the capability to lead at the next level? Where are the skill gaps? What does the development timeline look like for internal candidates? How do we balance promoting from within with strategic external hires? These aren’t HR questions. They’re business strategy questions.
My role has been to hold the strategic thread. What does PBO need to be in three years? Five years? What kind of leadership will that future require? How do we preserve our culture while evolving our capabilities?
The integration of these three perspectives has been essential. Financial planning without talent readiness creates unfunded promises. Talent development without financial sustainability creates risk. And neither works without strategic clarity about where the organization is headed.
The ROI of Early Planning
Starting this work now, rather than waiting for a forcing event, has created several advantages:
We can develop leaders intentionally rather than reactively. Our high-potential team members are getting stretch assignments, executive coaching, and exposure to board-level strategy. They’re not waiting for someone to leave. They’re being built up now.
We can model financial scenarios without pressure. What does leadership equity look like? How do we structure incentives that reward performance while building ownership? What’s the timeline for transition, and how do we fund it? These questions require thought, modeling, and iteration. Crisis planning rarely produces optimal answers.
We can maintain business momentum. Our clients aren’t wondering about PBO’s future. They’re seeing our commitment to it. Our team isn’t destabilized by uncertainty. They’re energized by the investment we’re making in their growth.
What This Means for You
If you’re leading an organization, succession planning isn’t about your exit. It’s about your legacy.
Start the conversation now. Map your talent. Model the financials. Get clear on what success looks like. And recognize that building a sustainable organization is one of the most valuable strategic investments you can make.
At PBO Advisory, we’re living this work alongside our clients. And we’re learning that succession planning isn’t the end of leadership. It’s the beginning of building something that lasts.
Francesca San Diego
CEO, PBO Advisory
[email protected]
(858) 622-1681
If you’re ready to start planning for the future of your organization, PBO Advisory Group can help.
We work alongside business leaders to align strategy, finance, and talent into a succession plan that protects your legacy and positions your business for sustainable growth. Let’s have the conversation.
Articles & Podcast on Succession Planning
Nicole Devine, CPO | Succession Planning as Culture Continuity | Why Technical Excellence Isn’t Enough
Jennifer Rebis, CFO | The Financial Architecture of Succession Planning | Why Most Organizations Underestimate the True Cost
PBO Leadership Team | Succession Planning That Actually Works | Integrating Finance, Operations, and People Strategy
PBO Leadership Team | Beyond the C-Suite | Why Succession Planning Isn’t Just for Executives
