Selecting an M&A Attorney

One of the most important roles we play as Exit Guides is helping business owners assemble the right team of advisors for a successful transition. While business brokers, M&A advisors, accountants, and wealth planners all have critical responsibilities, few advisors can impact the outcome of a transaction as directly as an experienced M&A attorney.

For many owners, the sale of a business is a once-in-a-lifetime event. Yet one of the most common mistakes we see is relying on a trusted attorney who lacks meaningful deal experience. A strong general business attorney may be highly competent in their field, but M&A transactions require a distinct set of skills, technical knowledge, and negotiation experience.

Put simply: hiring a non-M&A attorney to lead a business sale is like hiring a dentist to perform heart surgery. Both are professionals, but only one specializes in the procedure at hand.

An attorney without the right experience can significantly delay negotiations, create unnecessary friction between parties, and in some cases jeopardize a closing altogether.

So, how do sellers select the right attorney for their exit?

First, sellers should be on the lookout for some important signals. Potential attorneys can be identified by:

• Specific M&A experience noted on their website
• A dedicated M&A resources or articles page
• Real example transactions listed as proof

And this doesn’t mean any attorney with M&A experience is guaranteed to be the seller’s best bet. After identifying a few attorneys to pursue, sellers should interview their options. The attorney a seller selects will be the legal support in the sale of their life’s work; they should feel empowered to investigate their options with scrutiny. We recommend that sellers interview each potential attorney and ask:

How many M&A deals have you closed in the last 12 months?

• Red Flag: Fewer than three completed transactions.
• Recent deal activity matters. Active practitioners are more likely to understand current market dynamics, buyer expectations, and evolving transaction trends.

What share of your work is for transactions under $10 million* in purchase price?

• Red Flag: Less than 30% of their practice is dedicated to this market segment.
• The needs of privately held lower-middle-market businesses differ from those of large corporate transactions. Experience within the seller’s size range often leads to more practical guidance and greater efficiency. 
• *When asking this question, use a transaction size that aligns with your expected sale price. The goal is to determine whether the attorney has meaningful experience handling transactions of a similar size and complexity to yours.
• For example, transactions with purchase prices below $5 million often involve SBA financing and owner-operator buyers. Transactions between $5 million and $50 million are more likely to attract private equity firms and strategic acquirers, both of which typically engage more sophisticated legal counsel.
• An attorney who regularly works on transactions within your expected value range and with your likely buyer type will be better positioned to protect your interests and navigate the transaction effectively.

What percent of your M&A deals actually close?

• Red Flag: A closing rate below 70%.
• Not every deal reaches the finish line, but attorneys who consistently navigate transactions to closing demonstrate an ability to anticipate and work through obstacles.

Can you introduce me to 3 clients from the last 5 years?

• Red Flag: An unwillingness to provide references.
• References provide valuable insight into an attorney's communication style, responsiveness, negotiation approach, and overall effectiveness.

The best M&A attorneys do far more than review contracts. They serve as strategic advisors throughout the transaction, helping owners understand risk, navigate complex negotiations, and maintain momentum when challenges arise.

While sellers can significantly improve their chances of a successful outcome by following these guidelines, they do not have to make this decision alone.

Experienced exit advisors often have firsthand knowledge of attorneys with proven success in specific industries, markets, and transaction sizes. They can help evaluate candidates, participate in interviews, and ensure legal counsel is aligned with the objectives of the transaction.

By taking the time to identify qualified candidates, ask the right questions, and assess real transaction experience, business owners can significantly improve their chances of achieving a successful and efficient exit.