Planning to Sell Your Company? Ask These 5 Technology Questions Before a Buyer Does
Review ownership, key-person dependencies, legacy systems, security testing, and scalability a full 12 to 24 months before a potential transaction.
EXPERT OPINION BY BRUCE ECKFELDT, INC. 5000 CEO AND STRATEGIC BUSINESS COACH @BECKFELDT
Most founders spend the year before a sale getting their financials ready. But buyers are increasingly focused on something else. In a 2026 study by SRS Acquiom and Mergermarket, which surveyed 150 senior executives at U.S. investment banks, technology diligence ranked ahead of every other domain. Forty-seven percent called it their top priority over the past year, and 51 percent called it the single most burdensome part of the review. The concern extends beyond software companies. Buyers now treat technology documentation the way they treat financial statements: as information that helps determine the price.
I built and sold a software company, and I now coach founder-CEOs through their exits. I see the process from both sides. The founders whose companies get repriced late are rarely the ones with messy books. They are the ones who cleaned up the books but let the buyer be the first to examine the technology.
Much of what buyers look for is organizational rather than technical. Here are five questions you can answer without an engineer in the room, along with one rule about when to ask them.
1. What you own and whether you can prove it.
Buyers do not take your word for what you own. In larger deals, they scan your source code and request supporting documentation. In practice, two problems commonly emerge: Contractors never signed intellectual-property assignments, or open-source components were added years ago under licenses nobody read. A founder I interviewed who has sold multiple software companies told me large acquirers always scan the code. He has watched deals collapse late because the licensing was not clean. Build the inventory yourself. Who wrote what, and where is the signed assignment?
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2. Who is the only person who knows.
Every company has one: the developer who built the original system or the manager who alone understands the workflow. Buyers look for these dependencies because they represent a risk that money alone cannot fix. If that person leaves after the deal closes, the buyer inherits a black box. Pick your most critical system and ask who would keep it running if that person quit on Friday. If the honest answer is nobody, you have found the problem before the buyer does.
3. Which systems cannot pivot.
Legacy architecture costs money and limits the company’s potential. One founder I interviewed built his software platform before the cloud existed, so it ran in a data center. He was not technical and tried to save money on senior technology leadership. As a result, the platform could not pivot. His company stalled between $8 million and $9 million in contracted recurring revenue, and he sold to a strategic buyer with enough re
4. What a scan would find.
Three questions matter here, and you do not need to understand security to ask them. When was your last penetration test, who conducted it, and did you address the findings? A test from three years ago, conducted on code that has since been updated hundreds of times, offers little insight into the current system. If you hold customer data, expect questions about where it is stored and who can access it. These reviews can take a long time. A serious security audit can run six to 12 months, so you cannot wait until a buyer asks for one.
Source: www.inc.com
