Experts on leadership communications call it the New York Times rule or the “front page test.” It's one of the most common aphorisms of advisers and attorneys who counsel executives on their business ethics, legal strategies and crisis management: Don't put anything in an email that you wouldn't want to see on the cover of the New York Times or another major newspaper.

Securities lawyers use it to remind corporate directors to think about what gets written down in board minutes. Law professors use it to remind people it has the power of the written word if the informality of verbal speech. Consultants traffic in it often. Warren Buffett has long used it as a reputation guide for his managers, at least since he became chairman of Salomon Brothers amid a bond-trading scandal in the early 1990s.

And yet, legally questionable or merely embarrassing examples bubble up again and again, from Hollywood (consider the racially insensitive jokes made by Sony executives) to Wall Street (recall those damaging emails from the Great Recession). Now Trump Organization executive vice president Donald Trump Jr., the president's eldest son, has released a stunning example: An email exchange in which he is offered the chance to meet with someone promising information that was “part of Russia and its government’s support for Mr. Trump” and replied that “if it's what you say I love it especially later in the summer.”

The New York Times reported that after Trump Jr. was told the Times was about to publish the content of the emails, he shared images of the emails himself via Twitter on Tuesday. That followed reports from the Times in recent days that the meeting had taken place. In The Washington Post's coverage of the emails, it called the exchange “the most concrete public evidence to date suggesting that top Trump campaign aides were eager for Russia’s assistance in the campaign.” 

On Monday, Trump Jr. sent a tweet suggesting he was hardly alone in taking meetings on political opposition research, and tweeted on Tuesday that “Media & Dems are extremely invested in the Russia story. If this nonsense meeting is all they have after a yr, I understand the desperation!” In a statement he released with the exchange, Trump Jr. said he was doing so to be “totally transparent.”

Whatever the ultimate conclusion from these emails may be — whether they crossed the line on collusion or are an overblown story about a rookie mistake, as some have suggested — they are a blaring reminder of the high-risk perils of putting sensitive information in email form. Not only do they spell out an executive's exact words, but they put a time stamp on how quickly one responds. (The Times noted he responded “within minutes.")

That may be one reason why on Wall Street, some high-ranking executives still don't use email. Trump himself has said: “I'm not an email person myself. I don't believe in it." But he has also said that he loves them because you “can't erase emails.”

But for most of us, it's a way of life, a part of the workday that is constantly there, an ever-present risk to organizations, reputations and careers. And it's the reason the simple, common-sense “test” or “rule” has become such a constant refrain from business advisers for everything from decision-making to corporate governance to communications strategy. It gives executives working in the nonstop whirl of a big deal or a critical decision — or, ahem, a presidential campaign — a quick way to pause, ask a basic question and, one hopes, make a wise choice.

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