The evolution of Exit planning & what is often overlooked.
- Matt Trustrum
- Mar 25
- 4 min read
Exit planning for small business owners has evolved significantly over the years, adapting to changes in economic conditions, tax laws, market trends, and business expectations. Here’s a breakdown of how it has changed and what areas are often overlooked when preparing for an exit or sale:

1. The Evolution of Exit Planning:
Earlier Approaches:
In the past, exit planning for small business owners was relatively simplistic. Many owners viewed selling their business as a transaction to occur when they were ready to retire. The focus was primarily on financial considerations, such as the price for which the business could be sold, and often overlooked the strategic planning required to maximize value and ensure a smooth transition.
Growing Sophistication:
Over time, the concept of exit planning has evolved into a more holistic process that requires thoughtful consideration of many factors. The idea of planning for an exit has shifted from being a simple financial event to a comprehensive strategy that aligns with the owner’s personal, business, and family goals.
Emphasis on Preparation:
Exit planning has also become more proactive, with a growing recognition that planning for a business exit should begin years before the actual sale. Business owners now understand that preparing for an exit involves refining business operations, optimizing financials, and ensuring that the business can run independently of the owner. This proactive approach has become more widespread, with specialized exit planning advisors and consultants becoming more common.
Tax and Legal Complexity:
The landscape of tax laws and legal structures affecting business sales has changed dramatically. Over the past few decades, the complexity of taxes, estate planning, and laws surrounding mergers and acquisitions (M&A) has increased, requiring business owners to seek professional guidance. In the past, many owners would simply sell their business without considering how to minimize taxes or how the sale would impact their personal wealth. Now, business owners are much more likely to seek advice to minimize their tax burden and plan for estate issues.
Rise of Private Equity & M&A:
As private equity firms and institutional investors have become more involved in the market, the exit options for small business owners have diversified. Instead of just selling to a competitor, small business owners may now consider selling to private equity firms, venture capitalists, or through employee stock ownership plans (ESOPs). This has led to a more complex landscape with more exit pathways, but also more planning required to determine which exit strategy best suits the owner’s personal goals.
Emotional Aspects:
There's also an increasing awareness of the emotional and psychological aspects of business exit. Many small business owners have poured their hearts and souls into building their companies, and the transition out of ownership can be fraught with emotional challenges. This awareness has led to more integrated exit planning strategies that address both financial and emotional goals.
2. Commonly Overlooked Areas in Exit Planning:
Succession Planning:
One of the biggest areas often overlooked is succession planning. Many owners fail to create a succession plan that ensures the business can continue to run smoothly after their departure. This includes identifying and training a capable management team, grooming family members for leadership, or developing strategies to make the business attractive to potential buyers. If succession is not properly planned, the business may struggle after the owner exits, diminishing its value or making it harder to sell.
Tax Implications:
While tax planning has become a more integral part of the process, many owners still fail to plan for the full range of tax consequences. Without proper guidance, business owners can be subject to capital gains taxes, estate taxes, and other liabilities that significantly reduce the value of the sale. Structuring the sale to minimize taxes—whether through an asset sale vs. a stock sale, or using strategies like charitable remainder trusts or installment sales—can make a substantial difference in the final amount the owner receives.
Valuation Gaps:
Many owners assume they know the value of their business, but they may be missing out on maximizing its value due to inaccurate valuations. Business valuation is a critical area often overlooked until the time of the sale. Owners may rely on their internal understanding of business performance without considering industry benchmarks or market trends. A professional valuation can uncover hidden value or areas of improvement that can increase the business's sale price.
Planning for Personal Wealth and Retirement:
Another overlooked area is the impact the business exit will have on the owner’s personal wealth and retirement plans. While most business owners focus on the sale price, they may neglect to consider how the proceeds will be managed for long-term financial security. This includes integrating the sale into a broader retirement plan, managing investments post-sale, and ensuring the business owner is financially prepared for life after exiting.
Employee and Cultural Considerations:
The employee impact of a sale is another frequently overlooked aspect. How the sale or exit affects employees—both in terms of their job security and their morale—can have a significant impact on the business’s value. For example, selling to a competitor or a private equity firm might lead to layoffs or cultural changes that can decrease the company’s attractiveness or disrupt its operations. Addressing employee concerns and planning for cultural alignment with potential buyers is crucial.
Exit Timing and Market Conditions:
Many owners overlook the importance of timing when planning their exit. The market for business sales fluctuates, and owners may miss an optimal sale window if they don't stay informed about industry trends or market conditions. Market timing and understanding the economic climate are critical to maximizing the business’s value.
Post-Exit Involvement:
After the sale, some owners still want to stay involved in the business to some extent. This might be as an advisor or in a transitional role. Owners often overlook the need for planning for this post-exit phase, where they still want to retain some level of influence or involvement, which can be critical in ensuring a smooth transition.
Conclusion:
The evolution of exit planning reflects a growing awareness that exiting a business is not just a financial transaction but a complex process that involves careful strategic, personal, and financial considerations. By addressing commonly overlooked areas like succession planning, tax implications, business valuation, and employee impact, small business owners can significantly enhance the value of their business and ensure a smoother exit that meets both their financial goals and personal desires. It's important to work with professionals, such as exit planners, financial advisors, and tax experts, early in the process to guide the business owner through these intricate steps.