What Sellers Don’t Expect When Selling Their Companies

By Michael D. Rubin, CEO & Founder · Updated September 2026 · 752 words

Most owners are surprised by the same things: how much of their time a sale takes, how much they must rely on their managers, how hard it can be to align co-owners and family, how far the first offer may be from their number, and how much of the deal is give-and-take. Knowing these in advance does not make them disappear, but it keeps them from derailing the sale.

Many sales are triggered by events, not plans

In an ideal world an owner plans a sale years ahead. In reality, many sales are prompted by an event: a partner dispute, a divorce, a health scare, burnout or a strong new competitor. An owner who starts in a hurry meets every surprise below with less time to absorb it and less room to wait for a better offer. That is the best argument for preparing before you need to.

Even owners who plan carefully are often surprised by how personal the process feels. Buyers question decisions you made years ago, test numbers you know to be right and probe the weak spots you would rather not discuss. None of it is personal to them. Expecting that tone, and letting your advisor absorb much of it, keeps you focused on the decisions that matter.

The time it takes, and who else must be involved

Gathering information for the marketing package, answering buyer questions, attending meetings and supporting due diligence all take time away from running the company. An advisor carries much of the load and screens out buyers who are curious rather than serious, but the owner still has real work to do.

Founders who make every decision themselves often find this hardest. At some point a trusted manager, often the controller or sales manager, has to help with information and buyer questions, because they hold details the owner does not. Deciding who knows, when they learn and what they are asked to keep confidential is a real decision; see when to tell employees the business is being sold.

Other owners and family members

Many privately held companies have minority shareholders or family members with an interest in the business. They may have legal rights over a sale and strong views on price. Bring them in early, agree on the goal and the minimum acceptable terms, and keep them informed throughout. Leaving them until the end is one of the surest ways to lose a deal at the last moment.

Where owners disagree about value, an independent valuation or a fairness opinion, which is an outside assessment of whether a price is reasonable, can settle the argument before it reaches the buyer.

The offer, the negotiation and the leak

Most owners have a number in mind, and first offers often come in below it. The instinctive reaction is to reject them on price alone. Look at the whole offer first: cash at closing, seller financing, earnouts, your role after closing and the buyer's ability to close. Structure can close a gap that price alone cannot.

Owners are used to calling the shots, but a sale is a negotiation. Hold firm on the points that matter most to you and give on the rest. Let your attorney advise on legal risk, but keep the business decisions for yourself.

Finally, plan for a leak. Even with strict confidentiality, rumors can start. Have a short, truthful explanation ready, such as that you are exploring growth capital or strategic options, and a plan for talking to key employees if it becomes necessary.

Keep your eye on the business

With all of this going on, the company still needs you, arguably more than ever. Buyers follow monthly results to the day of closing, and a dip can reopen the price. Keep selling, keep hiring where needed and keep the ordinary disciplines of the business, from collections to maintenance, exactly as they were. Delegating the routine work of the sale to your advisor is what makes that possible. Our answer on maintaining performance while the company is marketed has practical steps.

How MDR & Associates takes the surprises out

MDR & Associates tells owners what to expect at the first discovery meeting and handles the time-consuming work of marketing, buyer screening and coordination. Our VP of Client Engagement is your main contact during marketing, and a principal of the firm is in every negotiation. Every offer is presented to you in person, with its structure explained. The ten-step process shows what happens when. To talk through your situation, contact us.

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Questions owners ask next

How much of my time will a sale take?

It varies, but plan for concentrated effort while the marketing package is prepared, during buyer meetings and throughout due diligence. An advisor handles outreach, screening and coordination, and a capable manager can help gather information, which keeps most of your time on running the business.

What if a minority shareholder opposes the sale?

Their rights depend on your company's governing documents and state law, so ask your transaction attorney early. Many disputes are resolved by agreeing on price expectations up front, sharing an independent valuation, or buying out the dissenting owner before or at closing.