“It depends on the company, the culture and who their customers are,” said Vivian Garcia-Tunon, owner of VGT Consulting Group, an executive coaching business in midtown Manhattan. Ms. Garcia-Tunon has worked as a human resources leader in financial services, private equity, and investment banking, and noted that the communication differences at creative and conservative businesses are vast. Her client Brunch, a web design and development studio in Washington, D.C., can be sassier than banks she works with, such as Capital One. “They can’t be too edgy, because that’s when people get scared,” she said.

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It’s important for individuals to remember their audiences and what the implications are, Ms. Garcia-Tunon said: “If they’re trying to be a smartass, they need to make sure they’re comfortable in the risky approach and the consequences of their messages.” To avoid drama, she advises asking the office what it considers appropriate.

Or employees can simply follow the leader. Erich De Oliveira, 41, of Marlborough, Mass., first encountered custom vacation memos two and a half years ago when he began working for Simply Business, an online business insurance brokerage in Boston.

“Some of the out-of-office messages were really around ‘Hey, I’m going to be at the beach with my family and my children, so unless you’ve got something more important than that, I’m probably not going to be available for you’,” said Mr. De Oliveira, recalling a C-suite executive’s OOO email. “It highlights the value of what’s important to each person. For that person, it just happened to be their family.”