5 Things That Kill Deals and How to Avoid Them
November 6, 2025From poor financials to valuation disputes, Optima M&A outlines how to build buyer confidence and keep deals on track with early planning, clear communication, and expert advisory.
What’s worse for the sale of a business than when the prospective buyer finds a big, potentially expensive surprise in their due diligence review? The answer is easy: when that same discovery also surprises the seller. When preparing for the sale of a business, consider due diligence as a two-phase process: the first phase is internal due diligence, conducted by and for the seller; the second phase is external due diligence, conducted by and for the buyer. The best way to prevent potential problems from due diligence and to make the whole process a positive one for owners selling their company is to conduct early, thorough sell-side due diligence with enough lead time to identify and address any potential issues before undergoing buy-side scrutiny.
A sell-side advisor’s prepping of a company to be marketed for sale is like prepping a home for an open-house showing, and internal due diligence is like a sell-side home inspection. In the same way that a home inspection would uncover any issues that have the potential to affect pricing or process for the sale transaction, sell-side due diligence is far more thorough than merely staging the home to look good on the surface. Thankfully, internal due diligence is a great opportunity for company leadership to take a detailed look at the business in a way that they may not otherwise, and the benefits can reach far beyond merely a better, smoother sale transaction.
How detailed should the internal phase of due diligence be? The goal is to compile everything that is ‘material to the business’. Due diligence requests from buyers and their attorneys are commonly qualified with a materiality standard –a request for all “material supplier contracts”, for example. As a baseline, ‘materiality’ is an accounting principle describing any item that can reasonably impact a business’s financial statements. In mergers and acquisitions, materiality should be viewed more broadly as anything affecting a buyer’s investment decisions or valuation, and the standard for what is material varies widely from business to business.
For example, a faulty compressor in the soft drink refrigerator of a small-town takeout pizza parlor may be material, but a similar compressor in one of numerous staff break rooms of a very large trucking company may not be. Notably, materiality is not necessarily determined by actual cost – fixing the trucking company’s broken refrigerator may not be expensive, but doing so may be a requirement for the business’s compliance with a material labor contract.
Understanding what is material for each individual enterprise is one area where the value of expert sell-side advisors like the team at Optima M&A cannot be overstated.
The emergence of virtual online data rooms as a repository for due diligence materials has been a major improvement for mergers and acquisitions. Having all necessary diligence materials in one well-organized and easily-accessible digital space is still time-consuming and costly, and yet it continues to be an essential part of preparing for any M&A transaction. In addition, knowing at the outset that a data room will be the end-product of the internal due diligence phase helps keep everyone organized and detailed in their work before turning to face prospective buyers. The resulting good impressions made on buyers, their advisors and legal counsel can dramatically improve their confidence in every aspect of the transaction and, therefore, their impression of value being received for price.
Buy-side attorneys often provide itemized due diligence requests that are exceptionally detailed and may not be tailored to the seller’s business. Those requests can feel onerous, so organizing the sell-side internal due diligence effort into subject areas keeps the process achievable, productive, and on track.
Litigation history, regulatory correspondence, and compliance documentation, however routine or unflattering, are essential. As much as negative outcomes of regulatory reviews may be unflattering, a willingness to remedy them and engineer the enterprise for compliance is a strong complement to any business. A good example would be a restaurant whose business performs better after remediating a health code violation.
Investing time and effort into thorough internal due diligence is essential for a successful sale. By working with experienced sell-side M&A advisors at Optima Mergers & Acquisitions, you’ll be able to prepare well in advance, identify potential issues early, and ensure a smoother, more successful sale. Get in touch with us today to start preparing your business for a seamless transition.
From poor financials to valuation disputes, Optima M&A outlines how to build buyer confidence and keep deals on track with early planning, clear communication, and expert advisory.
Optima Mergers & Acquisitions has been nominated for three 2025 M&A Advisor Awards for its role in the Acquisition of Texas Ecogrow by NextGen Partners.
Choosing the right sell-side M&A advisor is critical. Learn what to ask, what to expect, and how Optima M&A helps business owners sell with confidence and clarity.