Oops.

Donald Trump’s personal attorney Marc Kasowitz wound up in the headlines yesterday after it emerged that he sent several expletive ridden emails to a stranger who had called on him to resign. After receiving an email from a retired PR exec urging him to quit advising the president for the “long-term interest of your firm,” Kasowitz responded with a note saying: “I’m on you now. You are f—-g with me now Let’s see who you are Watch your back , b—h.”

He then urged the sender, who he called a “piece of s—t” to call him. “I already know where you live, I’m on you. You might as well call me. You will see me. I promise. Bro,” Kasowitz wrote. After the emails were first reported on by ProPublica, a spokesman for the New York lawyer said that he intended to apologize for them.

Kasowitz is not the first person to be publicly embarrassed for having sent awkward emails. Earlier this week, Anand Sanwal, chief executive of data firm CB Insights, revealed that an unidentified venture capitalist randomly emailed him from a corporate email account calling him an “indian brownie” and a “mofo.”

That people who really should know better slip up is proof that the rest of us really also shouldn’t conduct sensitive conversations over email, especially with people we don’t know well. That’s key for job seekers, who in the pressure of the hunt may be more susceptible to sending off emails they later regret. “They’re frustrated people are not responding to them when they’re interested in an opportunity, but can come across as more aggressive than intended,” says Howard Fox, a Chicago-based careers coach.

Instead, experts say you should conduct sensitive conversations over the phone or in person. This has two benefits. Firstly, the need to arrange a time convenient for both parties gives them time to cool down and think through what they want to say. “It’s about being measured in your response and giving yourself time to think about what you want to achieve,” Fox says. He adds that having visual or audio cues also helps, since things like tone can come across strangely via text. “It’s not like we’re novelists copyediting. We’re not thinking of the repercussions,” he says. “For anything that’s sensitive, it’s better to just take some time to chat on the phone. “

Secondly, even if you do make a faux pas in a phone call or in-person meeting, it’s likely that it’ll just stay within the parties who were actually there. “Emails never really go away,” says Debra Benton, co-author of “The Leadership Mind Switch.” “They’re so permanent and they’re really easily shareable.” The same goes for public platforms like Twitter and more private ones like Slack and Facebook Messenger, since screenshots of conversations can easily be captured these days. Just ask the staff of alt-right website Breitbart, whose internal Slack deliberations have leaked to CNN and BuzzFeed in recent times.

If you do make the mistake that Kasowitz has owned up to, the key is to apologize quickly, sincerely and publicly. Benton recommends doing so in the medium in which you originally committed the mistake. The reason? “It can be easily shared” with the rest of the world, she says. “If you tweet out a mistake, you should also tweet out the apology.”

And when in doubt, leave out the “bro,” unless, of course, you’re emailing your brother.