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Updated: May 5, 2025 How To

How to sell your business to maximize value and minimize regret

By Kristen Miale

For many business owners, selling their business is the most significant financial event of their lives. Yet it’s often approached with limited preparation, sometimes only after a decision to sell has already been made. But with the right planning and support, the process can lead to financial security, newfound freedom and a sense of accomplishment.

Start sooner than you think

Kristen Miale, Caswell Advisory Group

Exit planning is not the same as putting a business up for sale. It’s the process of laying the groundwork in advance to ensure a smooth transition when the time comes. The earlier planning begins, the more time there is to address potential issues, improve business fundamentals and prepare for a successful transaction.

Build your inner circle

An important first step is identifying who should be involved or informed about the process. This includes internal stakeholders, such as family members and co-owners. It could also include a key employee or two, but be cautious because maintaining confidentiality throughout the sale process is critical.

Assemble a good team

Advisors play a critical role in the planning and execution of a sale. Core members of this team typically include a CPA and/or tax advisor, a financial/wealth advisor, an attorney with experience in business transactions, and, at the appropriate stage, a mergers and acquisitions advisor.

While this may seem excessive, remember that you are navigating what is likely to be the largest financial transaction of your life. Assembling the right team early will help avoid costly mistakes and ensure the transaction is structured in a way that aligns with your personal and financial goals.

Start on tax planning

Consulting with a tax advisor in advance can result in significant tax savings. Many of the strategies that reduce tax liability require time to implement and are most effective when integrated into long-term planning. In collaboration with a financial advisor and attorney, owners can structure the sale in a way that supports their future financial needs and estate planning objectives.

Enhance business value prior to sale

Before marketing the business, it’s important to ensure the business is well-positioned for sale. This includes maintaining accurate, transparent financial records, addressing operational inefficiencies and documenting key customer and vendor relationships.

Buyers will evaluate how much a business depends on the current owner and will downgrade its value if this person is considered critical such that their exit could impact business performance. This risk can be mitigated if key responsibilities and relationships are assumed by others and business processes are formalized well ahead of the business being marketed.

Investments in necessary equipment, systems or technology should also be considered. Buyers are likely to factor needed upgrades into their offers, which can reduce the perceived value of the company.

Conduct a competitive sales process

When ready to sell, engage a proven M&A advisor to lead a competitive, confidential sales process. A well-managed process significantly increases the likelihood you will obtain a higher value for the business than if you restrict yourself to working with individual parties, and can potentially lead to multiple offers, allowing you to select between different types of buyers and deal terms.

Your life’s work

Selling a business is a complex process that requires careful planning and the support of experienced professionals. With adequate preparation, business owners can improve outcomes, reduce risk and navigate the transition with greater confidence and clarity. Early, thoughtful planning lays the foundation for a successful transaction — one that reflects the value of the business and the work that built it.

Kristen Miale is the managing director of Caswell Advisory Group, a sell-side advisory firm based in Portland.

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