Strategic Planning for Transition, Continuity, and Legacy



The Succession Journey

Understanding the Starting Point: Goals & Readiness

The journey begins with reflection. We engage the business owner in a comprehensive fact-gathering phase, designed to uncover objectives, concerns, and readiness for change. It’s essential to identify potential challenges—family dynamics, key personnel, business dependencies—and bring those into the light early. This stage sets the foundation for every decision to follow, including a target date for transitioning out of the business.

With clarity around timing and intent, we turn to exit strategies. Internal succession? External sale? Strategic partnerships? Each option carries its own implications—for control, continuity, and financial impact. This phase includes an open discussion of the owner’s preferences, desired outcomes, and the advantages and drawbacks of different types of successors. The depth of this dialogue depends on where the owner is in their contemplation—some arrive ready to decide, others need time to explore.

Succession is not just a business strategy—it’s a life strategy. We help owners articulate what they want their post-business life to look like, and what resources are needed to live it comfortably. This often involves heartfelt discussions with family and trusted advisors, as well as collaboration with a financial advisor to calculate annual income needs. The outcome? A clear picture of the assets required by the target date to sustain that lifestyle.

Here, we bridge financial reality with future vision. Owners assess their current personal assets, project their growth to the target date, and compare them to the lifestyle needs identified. The difference between projected assets and the target-date financial requirement is the Wealth Gap—the amount the business must deliver in order to close that shortfall.

Once the wealth gap is understood, the business owner determines their company’s current value. This doesn’t require a formal appraisal—just a realistic baseline using owner-led tools like BizEquity. If the business value doesn’t fully cover the wealth gap, it signals a need to improve performance, optimize operations, and elevate overall market appeal before the owner’s planned exit.

Using valuation insights, we compare the business against industry standards—leveraging KPIs and market multiples to identify improvement areas. This is not just about financial metrics; it includes operational efficiency, customer retention, and leadership depth. Owners or their CPAs can use scorecards to track how their company stacks up—and where targeted enhancements can yield the greatest impact.

Succession planning isn’t just about ideal scenarios. We guide owners and their legal counsel to develop a written continuity plan in case of incapacity or sudden death, protecting the business and its stakeholders before the planned transition. This emergency planning ensures that leadership, legal, and operational roles are clearly defined—and that the company can continue without disruption.

As the plan takes shape, we conduct a full review of the business’s legal and organizational framework. Is the current structure aligned with succession goals? Do buy-sell agreements protect all stakeholders? We examine everything from ownership arrangements to voting rights to ensure the plan is legally sound and strategically resilient.

Succession depends on people. We identify vital team members—those whose continuity and loyalty will directly impact business value and buyer confidence—and explore strategies to retain them through agreements, incentives, and leadership development.

With goals, plans, and people aligned, we work with the owner and their legal counsel to prepare formal agreements that make the succession real. This can include leases, transition contracts, key employee compensation, ownership transfer documents, and more. These must reflect not just legal precision, but the owner’s vision for how relationships evolve.

Succession is not static. We encourage the owner to annually review their process into the journey, ensuring that the plan remains on track and evolves with changing circumstances, market dynamics, and personal considerations.

No succession plan is complete without a corresponding estate strategy. We work with the owner and their legal counsel to ensure their estate plan supports business continuity, personal wishes, and family protections. This includes powers of attorney, trusts, and distribution planning tailored to the owner’s succession goals.

As the business grows, owners have an opportunity to reduce financial dependence on it. We work with the owner and their financial advisor’s strategies to grow non-business assets through profitability improvements—creating security and options that make succession less pressured and more empowering.

Finally, we return to where we began: business performance. Using annual assessments and KPI reviews, we target improvements that raise your company’s valuation. A business that performs closer to industry standards commands a higher multiple—shrinking the value gap and elevating your exit options.

For some owners, succession may involve lifetime ownership transfers to family members or partners. We explore these opportunities when aligned with tax efficiency, personal wishes, and the long-term health of the enterprise.

Your Legacy, Strategically Delivered

Succession planning through BOSS isn’t just about documents and decisions—it’s about crafting a future with clarity, resilience, and purpose.


David provides all services through Wolcott Rivers Gates
and no services are rendered through Boss

become a boss member!