Dealing with Inexperience Can Ruin the Deal

By Michael D. Rubin, CEO & Founder · Updated September 2026 · 769 words

Inexperience ruins deals because a company sale is full of steps whose importance is only obvious to someone who has done them before: confidentiality agreements, buyer screening, a credible offering memorandum, deadlines for offers, and a transaction attorney who knows what a purchase agreement should say. Skip any one and the sale can leak, stall or close at a lower price.

Owners are often tempted to save the fee by handing the sale to a bright relative, a friend with a business degree or the company's long-time general attorney. The motive is understandable. The results are frequently expensive.

A familiar pattern

Picture a successful owner ready to retire. An experienced intermediary has quoted a fee, but a family member with a business degree offers to run the sale for less, confident after studying plenty of case studies. The owner agrees. Within weeks the company's name has been shared with anyone who asked, including competitors. There are no confidentiality agreements and no deadline for offers, because the owner is in no hurry. Buyers are invited straight to the business. The financial package is assembled quickly from unreviewed numbers, with no projections and no explanation of adjustments, and a pending lawsuit is buried in the text. The company's regular attorney, capable but new to acquisitions, will handle the legal work.

Each of these choices is common. Any one of them can end a sale or trigger a leak; together they put most of an owner's net worth in untested hands.

The mistakes, one by one

• Leaving the CFO out. Buyers expect to meet the person who owns the numbers, and that person must be available in due diligence. Bring your CFO or controller in early, under a confidentiality agreement and usually with a stay bonus tied to closing.
• Naming the company too soon. Revealing the name before buyers sign agreements invites competitors and idle browsers to your door, and news travels quickly from there.
• No screening and no timetable. Without checks on buyers' finances and deadlines for offers, a sale drifts, leaks and loses the competition that sets the price.
• An unreliable offering memorandum. Unreviewed figures, unexplained adjustments or a missing transaction produce low offers or none, and hidden problems such as litigation surface in due diligence and destroy trust.
• A general-practice attorney. Purchase agreements involve representations, warranties, indemnities, escrows and working capital adjustments. A lawyer who has not negotiated them before may miss points that cost far more than a specialist's fee.
• The owner making every call alone. Decisions made without experienced counsel tend to be the ones buyers exploit.

What experience actually adds

An experienced intermediary has seen which buyers close and which do not, what a fair letter of intent looks like, where due diligence tends to break, and how to hold a price when a buyer pushes back. That judgment is hard to learn from books, because much of it is about sequence and timing: what to disclose when, which issues to raise early, when to press and when to wait. An experienced transaction attorney plays the same role on the legal documents, and a CPA with deal experience on structure and taxes. The three work as a team; our answer on the advisors to have on your sale team besides the M&A firm explains who does what.

Experience also changes how buyers behave. A buyer facing a seasoned advisor knows that the process is organized, that other buyers are in it, and that weak tactics will be recognized. That alone tends to produce better offers.

How to test for experience

Whoever you consider, ask plain questions. How many sales of companies like yours has this person or firm completed, and how recently? What happened in the ones that did not close? Who will actually do the work, and who negotiates? How do they keep a sale confidential, and how do they screen buyers? What does their standard engagement letter say about fees and terms? Relatives and friends can still play a valuable role, as sounding boards or by helping pull records together, but the process itself belongs with people who have done it many times.

The experience MDR & Associates brings

MDR & Associates has represented owners since 2008 and has closed more than 250 transactions. A principal of the firm is in every negotiation, and the work follows a ten-step process refined over those years. Founder Michael D. Rubin wrote Sell Your Company for Maximum Value, drawn from that practice. The firm works alongside your own attorney and CPA rather than replacing them. To talk with someone who has done this many times, contact us.

Where this fitsHow a business sale works, step by step →

Questions owners ask next

Can my company's regular attorney handle the sale?

Only if they have real experience with acquisitions of your size. Many excellent business lawyers rarely draft or negotiate purchase agreements. A common approach is to keep your regular attorney involved for background and history while a transaction specialist leads the sale documents.

Is it ever sensible to sell without an intermediary?

Sometimes, for example when a trusted buyer approaches you directly and you already know the value. Even then, an experienced advisor can test whether the offer is fair, bring in other buyers to compare, and protect you through due diligence. Selling alone is usually most costly for a first-time seller.