CEO Reflections | Strategic Planning and Leadership Lessons for 2026

By Francesca San Diego

, CEO

November 17, 2025

Reflecting on the transition from subject matter expert to executive leadership, this post explores the critical balance between operational execution and high-level strategy. It highlights the challenges many CEOs face when trying to "stay in their lane" and underscores the importance of trusting a specialized leadership team. By leveraging the expertise of a CFO and CPO, leaders can escape their comfort zones, empower their workforce, and focus entirely on driving the company’s long-term vision and growth for 2026 and beyond.

"Expert" Trap: It is common for CEOs to slide back into their original functional expertise, but true growth requires stepping back to focus on broader strategy.
Empowerment via Delegation: Success relies on trusting qualified professionals, such as CFOs and CPOs, to manage financial health and human capital while the CEO steers the vision.
Strategic Evaluation: Effective planning requires a hard look at the previous year's performance regarding financial goals, culture, and brand integrity.
Planning for 2026: Future success depends on answering difficult questions about your SWOT analysis, value proposition, and whether you have the right talent and capital to execute your succession plan.

As I approach my second year as CEO, I have naturally been taking stock. Of course, any person in business is likely doing the same thing at this time of year. During the strategic planning process, it is time for each of us as leaders to evaluate our performance.

Did we:

Realize our annual operational and financial goals?
Value, support, and lift our people?
Foster a culture of innovation?
Nurture our partnerships?
Remain true to our brand?
Deliver consistent shareholder value?

I wish that I could say that we succeeded 100% in every category. While we achieved some goals and missed others, the reality is: we can always do better.

Preparing for 2026-2028: The Road Ahead

To prepare for our 2026-2028 strategic planning, I consulted with leaders, advisors, and colleagues to gather insights, tools, and feedback. The goal was simple: improve, serve the company, and maximize our stakeholders’ experience and objectives.

In doing so, there were profound takeaways from my reflections and conversations that I hope to integrate into our business in 2026 and beyond. We are currently integrating our strategic goals into quarterly tactical milestones.

Upon reflection, one of my biggest challenges in 2025 was “staying in my lane.” As a leader, it is vital to empower team members to execute and to recognize where we need to integrate trusted advisors to fill skillset gaps. Many of the CEOs I spoke to faced similar challenges. Most have grown into their leadership positions, transitioning from subject matter experts to executives. I am one of those people. My career started in a financial analyst role and progressed into a CFO/COO function, with significant M&A activity along the way.

The CEO’s Gift: Relying on Experts to Focus on Vision

Finance is my first business love and my comfort zone. Often, I see myself slipping back into the strategic finance and CFO role because it is so natural for me, and I continue to serve clients in that capacity. I applaud those of us who lean on our strengths and bring subject matter experts into our companies to help us realize our vision.

One colleague advanced into a CEO position because of his incredible sales and marketing acumen. To support his growth, he relies on a Fractional CFO to drive strategic initiatives. Another colleague, who excelled in operations, relies heavily on his Fractional CPO to execute workforce planning. Thankfully, I have incredible colleagues in Nicole Devine and Jennifer Rebis, who gently remind me that they are the professionals filling those roles, requiring me to be their CEO.

The gift of having Jennifer Rebis, our talented CFO, is that it allows me to focus on strategy and vision. Jennifer provides me with the KPIs, financial information, and dashboard data necessary to understand our performance. She models our strategic ideas and identifies the capital needed while appropriately managing risk.

The gift of working with Nicole Devine, our accomplished CPO, is that she fosters a culture of innovation while cultivating change management. She supports us with succession planning, professional development, and workforce planning to recruit, retain, and develop the talent needed to execute our vision.

As I reflect on the treasures of 2025, I cannot imagine not having these skillsets on our team to drive the company’s vision forward. I am incredibly humbled to serve as a leader in an organization like PBO Advisory Group, working alongside consultants who support the finance, accounting, and human capital needs of so many organizations.

Actionable Takeaways for Leaders

For those entering their own planning phase, use these checklists to guide your discussions.

Ensure you have answered and addressed the following:

Relevance: Are our mission, vision, and values relevant to who we are today?
Anchors: What are our strategic anchors?
Analysis: What are our SWOT (Strengths, Weaknesses, Opportunities, Threats)?
Value: What is our Value Proposition?
Forecasting: Where do we want to be in 3 years and how do we measure it?
Roadmap: How do we get there?

Succession Planning Checklist

Talent: Do we have the right talent to execute our vision?
Capital: Do we have the financial resources to execute our vision?
Execution: What is our specific plan to execute our vision?

If you are identifying gaps in your C-Suite or strategic plan during this reflection period, reach out to discuss how we can support your 2026 growth initiatives.

Francesca San Diego
CEO, PBO Advisory
[email protected]
(858) 622-1681

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