Most of what surprises a first-time seller is already in documents they signed early and read quickly: the listing agreement that ties up their only exit, the letter of intent that quietly fixes the price, and the tax allocation that decides how much of it they keep.
The listing agreement, before the broker
Exclusivity length, the tail clause and how you get out. A tail makes you owe the commission if you sell to a buyer the broker introduced, for a period after the agreement ends, and the definition of an introduction matters. None of the eight firms read for the record on this site publishes any of these terms, so they are a first-call question rather than a research question.
The letter of intent is not the deal, but it sets it
By the time an LOI is signed the price, the structure and the exclusivity period are usually fixed in the buyer's mind, and everything after it is a negotiation about reductions. Read it as though it were binding even where it says it is not.
How the price is split matters as much as the price
In an asset sale the buyer and seller must both report how the purchase price is allocated across asset classes, on IRS Form 8594, and the two filings have to agree. The split changes what each side pays in tax, so it is negotiated, not clerical. Get your accountant into that conversation before the purchase agreement is drafted, not after.
Questions people ask about things to consider when selling a business
Asset sale or stock sale?
Buyers usually prefer an asset sale and sellers often prefer a stock sale, for tax and liability reasons that differ in every case. That is a question for your own accountant and attorney; nothing here is advice on it.
What should I not agree to?
An indefinite non-compete, an earnout you cannot influence after you leave, and a tail clause with no time limit. All three are negotiable and all three are easier to change before signature than after.
What is an earnout and should I accept one?
Part of the price paid later, conditional on how the business performs after you have gone. It can raise the headline and it depends on a business you no longer control, so weigh it on what you are likely to actually receive rather than on the total.