The Top 3 Unexpected Events CEOs May Encounter During the Selling Process

By Michael D. Rubin, CEO & Founder · Updated September 2026 · 743 words

The three surprises that catch most CEOs off guard in a company sale are first bids lower than expected, the amount of their own time the sale consumes, and the approvals needed from other people before anything can close. None of them should derail a well-prepared sale. All three can if they arrive unannounced.

A fourth risk sits behind all three: while the CEO is absorbed in the sale, the business itself starts to slip, and buyers notice.

Surprise one: the first bids are low

Early indications of interest often land below what the owner hoped for. Some buyers open low to test the seller; others simply have not seen enough to justify more. Those first bids rest on the offering memorandum, the confidential document that describes the company (also called a confidential information memorandum), so a thin or unconvincing memorandum produces thin offers.

Do not react to a single low number. Ask what assumptions sit behind it, fill the information gaps and let competition work. Prices move most when several buyers know others are interested, and when management meetings show them a company that is better than its paperwork.

It also helps to know what the company is really worth before the first bid arrives. An owner who has seen an honest opinion of value can tell a lowball from a fair opening, and does not waste weeks on a buyer who was never going to get close.

Surprise two: the sale is a second job

The CEO usually knows the most about the company, so the sale leans on that person heavily, often for months, on top of running the business. Most CEOs underestimate it by a wide margin. The work typically includes:

• Supplying and checking the financial and operating information for the memorandum
• Preparing and giving management presentations, often several times to different buyers
• Answering follow-up questions and hosting site visits
• Working through due diligence requests, which can run to long lists
• Reviewing letters of intent and the purchase agreement with advisors and attorneys

Keep the business performing

The biggest danger of that workload is what it does to results. Buyers watch monthly sales and margins through the whole process, and a dip after the memorandum has gone out invites a lower price or an attempt to renegotiate. Hand day-to-day decisions to your managers before you go to market, set a weekly review of the key numbers, and let your advisor carry the process so your time goes where only you can add value. Our answer on how to maintain business performance while the company is being marketed covers this in detail.

Preparing the heavy documents before launch helps too. A data room, a secure online folder of financial, legal and operating records, built in advance means diligence questions can be answered in days rather than weeks. That keeps momentum and shows buyers a well-run company.

Surprise three: other people must agree

A CEO can negotiate a deal but often cannot approve it alone. Depending on how the company is owned and financed, the sale may need written consent from the parties below. Find out who they are before you sign an engagement letter, not after a buyer has signed a letter of intent; a holdout who appears late gains leverage over the whole deal.

Minority shareholders and co-founders deserve special care. If they hear about the deal only when asked to sign, they may feel ambushed and resist even a good offer. Brief them early and in confidence, and agree how the proceeds will be divided before negotiations with buyers begin.

• The board, and the shareholders or members under the bylaws or operating agreement
• Minority owners with approval or first-refusal rights under a shareholder agreement
• Lenders with liens on company assets, who must be paid off or release them
• Landlords, key customers or licensors whose contracts require consent to a change of control
• A spouse, where marital property or estate plans are involved

How MDR & Associates takes the load off

MDR & Associates prepares the confidential marketing package, the financial recast and a professionally produced HD marketing video, so buyers arrive better informed and first bids start closer to the mark. We screen buyers before they take up your time, negotiate multiple letters of intent at once, and coordinate diligence with your attorney and CPA. A principal of the firm is in every negotiation. See how it works in the ten-step process and our videos, then contact us.

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Questions owners ask next

How much of my time will selling the company take?

It depends on how organized the company is, but the heaviest periods are preparing the marketing materials, the management meetings and due diligence. A good advisor runs the process and filters buyers, so your time goes to meetings and decisions rather than logistics. Plan to hand daily operations to managers during those stretches.

Should my management team know about the sale?

Usually one or two key managers need to know, because buyers will want to meet them and diligence depends on them. Tell them early enough to prepare, under a confidentiality agreement, and consider stay bonuses. The wider team is typically told at or near closing.