Succession Planning vs. Selling: Deciding the Right Path for Your Middle Market Business


When it comes to deciding whether to dive into succession planning or sell your business outright, it’s no small matter. It’s a momentous crossroads that could shape your financial future, define your company’s legacy, and impact the lives of your employees. This guide is here to lend a hand by offering a thorough breakdown of both options: succession planning and selling. Our goal is to equip you with the insights you need to navigate this decision-making process wisely. We’ll explore the upsides and downsides of each approach, along with the key factors — financial, legal, and emotional — that you’ll want to consider along the way.

Pros & Cons of Succession Planning

Succession planning involves a strategic approach to secure ongoing leadership within a business. This process revolves around getting ready for the future, ensuring the sustained success of the company, and safeguarding its values and culture.

Some of the benefits of Succession Planning include:

  1. Long-Term Vision: Succession planning facilitates a forward-looking strategy to sustain the business over the long term. It additionally supports a gradual transition of leadership, fostering stability and continuity.
  2. Cultivates Talent: Supporting the development of internal talent establishes a foundation for potential leaders who grasp the fundamental aspects of the business, aligning seamlessly with its culture.
  3. Maintain Control: Maintaining a certain level of control empowers business owners to shape the trajectory of the company, even after transitioning away from a primary leadership position.

However, there are drawbacks to succession planning. It can be a time-consuming and intricate process, demanding meticulous talent evaluation and possibly incurring substantial training expenses.

Furthermore, the emotional challenge of releasing control and trusting a successor can be daunting for numerous business owners, potentially resulting in internal conflicts if not handled effectively.

Pros & Cons of Selling

Some of the benefits of selling your middle market business include:

  1. Liquidity: Selling offers prompt liquidity to the business owner, providing the opportunity to invest, save, or explore other ventures or retire comfortably.
  2. Clean Break: For individuals seeking a total departure from the business, selling provides a distinct and conclusive separation, paving the way for new endeavors or retirement.
  3. Market Value: Selling has the potential to optimize the financial returns on the business, particularly if sold at the market’s peak or to a strategic buyer.

Yet, selling a business comes with its share of risks, including the potential loss of legacy and the disruption of the company culture post-acquisition.

Moreover, the sales process can be unpredictable and might necessitate revealing sensitive company information to potential buyers, introducing confidentiality risks.

Considerations in Deciding Between Succession Planning and Selling

  1. Business Goals: Evaluate the extended goals of your business. Is your vision more aligned with fostering future leaders or with cashing out and moving forward?
  2. Company’s Current State: Evaluate the well-being and stability of your business. A resilient and secure business is appealing to both potential successors and buyers.
  3. Personal Aspirations: Reflect on your personal goals and life stage. Consider whether you prefer to maintain a legacy or embrace new opportunities.
  4. Market Conditions: Factor in market trends and industry forecasts. Timing the market can influence the success of both a succession plan and a sale.

Financial Considerations of Succession Planning and Selling

Understanding the financial impact of succession planning versus selling is crucial for making an informed decision. You will need to consider the following:

Business Valuation

Obtain a comprehensive business valuation to understand your company’s worth in the marketplace.

Tax Implications

Consider the various tax implications of each option, which can significantly affect your net proceeds.


Succession planning may lead to gradual financial benefits over time, whereas a sale offers a lump sum.

Include in this calculation the expenses linked to engaging advisors, legal professionals, and any required restructuring. Ensure every financial decision is made with a keen awareness of the return on investment and its influence on your financial plans.

Legal Considerations of Succession Planning and Selling

Ensuring that all legal bases are covered is a top priority when deciding to embark on succession or pursue a sale.

  1. Review existing contracts, such as shareholder agreements, to check for any buy-sell provisions or transfer restrictions.
  2. Ensure compliance with all regulatory requirements that could affect the transfer of ownership or sale of the business.
  3. Consult with legal experts to manage succession or sale in a way that minimizes legal risk and maximizes protection of assets.

Smooth transitions, whether passing the torch to a successor or handing over the keys to a new owner, hinge on careful attention to these legal considerations.

Emotional Considerations of Succession Planning and Selling

Determining the future of your business requires consideration not only of practical aspects but also emotional factors. Navigating the emotions tied to succession or selling is crucial.


Succession planning has the ability to preserve the company’s legacy and uphold its culture, which is a point of pride for numerous business owners.


For some, the business is an extension of their identity. Selling may represent a significant personal change requiring emotional adjustment.

Employee Welfare

The emotional impact of the decision can be profound, considering employee loyalty and their future. A successful succession may keep the workforce intact, while selling could potentially disrupt it.

It is important to acknowledge these feelings, engage in honest self-reflection, and perhaps even seek professional guidance to work through the emotions tied to the future of your business.

Recommendations for Middle Market Business Owners

Middle market business owners face a complex decision when choosing between succession planning and selling. We’ve highlighted key points to consider, including the strategic, financial, legal, and emotional aspects of each option.

It is recommended that business owners engage with both financial and legal advisors to make the most informed choice. Ultimately, the right decision depends on your unique circumstances, goals, and the legacy you envision for your business.

If you would like assistance reviewing which decision makes the most sense for you and your company, the seasoned advisors at Final Ascent are here to help.