You can agree on a price and still be talking about two different deals.

The buyer expects enough working capital to keep the business running. The seller expects to take certain funds at closing. One assumes the seller will stay involved for a year. The other is ready to leave in a month.

Everyone feels good about the agreement. Until someone starts asking questions.

Those are the kinds of issues we explored during a recent workshop Nancy Stabell led at Vanderbilt University’s Owen Graduate School of Management. With students, buyers, clients, and industry professionals in the room, we worked through letters of intent and the decisions that shape a business purchase.

The starting point was a document. The larger conversation was about judgment: what to ask, what to verify, and what to resolve before a deal starts moving quickly.

What does the seller think you are buying?

A letter of intent (LOI) outlines the proposed terms of a transaction. It also tells the seller how you are thinking about the business they built.

Price matters. So do their employees, their reputation, and what happens after they hand over the keys.

A buyer who understands those concerns can have a more productive conversation from the beginning. That includes being specific about the seller’s future role. Will they help with the transition? For how long? Doing what?

Those questions can feel premature when everyone is excited. They become much harder when both sides have already built plans around different answers.

What will this business actually cost to operate?

One example we discussed involved a business paying rent well below market rates.

That detail changes the questions a buyer needs to ask. Will the rent continue? For how long? What do the lease terms actually provide?

The answer affects how you evaluate the business’s earnings and the expenses you should expect after closing. You need to understand both the current arrangement and what you can rely on going forward.

The same discipline applies to personal expenses running through the company, unusual revenue timing, and other items that deserve a closer look.

Before debating what multiple to pay, understand the earnings you are multiplying.

What obligations come with the money?

Imagine buying an event venue that has already collected deposits for future weddings.

There is money in the account. There are also events still to deliver.

That raises practical questions: Who keeps those deposits? Who pays the costs of putting on the weddings? How will the transaction account for those obligations?

Receivables, customer deposits, and working capital deserve clear treatment in the deal documents. Each can affect what the buyer receives and what the business needs to operate after closing.

An assumption that sounds reasonable in conversation can become an expensive disagreement when it reaches the closing table.

Who is connecting the decisions?

A business purchase brings legal, financial, tax, lending, and operational questions into the same conversation.

A decision about the transaction structure can affect taxes and risk. A proposed payment arrangement can affect financing. A transition plan can affect the people responsible for keeping the business running.

Your advisors need enough context to see how their recommendations fit together.

That is why we encourage buyers to build a coordinated deal team early. You want people who can explain the tradeoffs, identify gaps, and help you understand what a decision means beyond their own part of the transaction.

For an owner, these choices may also affect family wealth, employees’ livelihoods, and plans for the next chapter. There is a great deal behind the purchase price.

Have the conversation before the pressure arrives

What we enjoy about workshops like this is the opportunity to connect a provision on the page with a decision someone may actually face.

A discussion about rent becomes a discussion about value. A question about customer deposits becomes a conversation about obligations. A seller’s transition period becomes a question about expectations, relationships, and the future of the business.

These conversations matter whether you are preparing to buy, thinking about an eventual sale, or helping an owner make those decisions.

You do not need a live deal to start asking better questions. In fact, that is an excellent time to begin.

Thank you to Joe Steigman for bringing this group together.

Preparing for a business purchase? Email info@woodstabell.com to request the due diligence matrix shared during the workshop.

The information provided in this article is for informational purposes only and does not constitute legal advice. No attorney-client relationship is formed by virtue of this article. For specific legal advice related to your situation, please consult with a qualified attorney.