In late 2008, Google found itself under intense scrutiny. Facing antitrust concerns tied to an advertising agreement with Yahoo and lawsuits involving intellectual property disputes, its leadership sent a confidential memo to employees.

The memo emphasized that while “information is good,” careless communication could be leveraged by competitors or regulators. To mitigate legal risks, employees were advised to avoid speculation, sarcasm, and premature commentary on sensitive topics. The directive: “Think twice” before writing about controversial matters and ensure facts were verified before commenting. Google even modified its internal messaging system, setting chats to “off the record” so that messages would automatically disappear.

This marked the beginning of a 15-year strategy aimed at limiting internal communication trails. While Google amassed the world’s information, it cultivated a culture of internal discretion, using tactics such as labeling communications “attorney-client privileged,” regardless of actual legal relevance, and imposing self-restrictions on its technology. Employees were regularly reminded that casual remarks could jeopardize the company.

Details of Google’s internal practices came to light during three recent antitrust trials involving the company. Plaintiffs, including Epic Games and the U.S. Department of Justice, sought to prove monopolistic behavior, reviewing thousands of emails, memos, and chat logs. Evidence showed that Google took deliberate steps to limit document retention. Instant messaging was excluded from legal holds unless employees manually activated the feature, which few did.

This approach is not unique to Google. Modern corporations often grapple with balancing communication tools’ convenience against the risks of legal exposure. Decades ago, incriminating remarks might have been exchanged verbally, leaving no trace. Today, digital records persist, and regulators argue these should be fair game in court. Companies, however, prefer instant messages to mimic the transience of casual conversations.

Google’s document practices have faced sharp criticism. Judges in its antitrust cases accused the company of fostering a culture that suppressed evidence. Judge James Donato, overseeing the Epic Games trial, described Google’s behavior as an “assault on justice,” vowing further investigation. Judge Leonie Brinkema, presiding over another case, criticized Google’s document retention policies as irresponsible, asserting that significant evidence had likely been destroyed. The Justice Department has even requested sanctions, proposing that missing materials be presumed damaging to Google’s defense.

In its defense, Google claimed to fulfill its obligations by educating employees about legal privilege and producing millions of documents for litigation. However, critics argue that its obsessive deletion policies created an impression of dishonesty. Agnieszka McPeak, a legal scholar, noted, “Google’s policy of not saving anything potentially damaging ironically makes it look worse. If there’s nothing to hide, why act like there is?”

Google’s cautious communication culture appears to be a reaction to Microsoft’s antitrust struggles in the 1990s. Back then, damning internal memos played a central role in the government’s case. Determined to avoid a similar fate, Google implemented measures to reduce its paper trail. Kent Walker, Google’s chief lawyer, admitted during testimony that the company sought to manage its burgeoning email volume, which far exceeded industry norms.

Yet the strategy extended beyond technical solutions. Employees were instructed to avoid certain language entirely, refraining from metaphors related to war or competition. Even innocuous phrases like “reaching new customers” were deemed risky. Over time, invoking attorney-client privilege became standard practice, even in non-legal matters—a move critics described as “fake privilege.”

Despite these efforts, Google could not entirely shield itself. Judges and regulators increasingly scrutinized its behavior, with Judge Amit Mehta remarking in a recent case that Google’s efforts to avoid leaving evidence were blatant. While finding Google guilty of monopolistic practices, he warned the company against further document mishandling.

As antitrust cases continue, Google’s approach remains under fire. From disappearing chats to reliance on obsolete methods like fax machines, its paranoia about documentation seems entrenched. While employees may believe discretion protects their careers, regulators argue that transparency is non-negotiable in the pursuit of justice.