The Ladder

Is Your Boss Reading Your Email?

We all know our work computers aren’t private—but we use them as if they were.

boss emails.
Even if our bosses aren’t reading every word, we could all stand to be a little more thoughtful about what we say on our work computers, and how we say it.


Everyone knows that you shouldn’t do anything on your work computer that you wouldn’t want your boss to know about. Legally, employees have no expectation of privacy when they’re on the clock or using a company-owned device. “If you work on an office computer, your bosses can not only legally monitor your company email and internet browser history, they can also log keystrokes to check your productivity and even see what you type on private services like Gmail, Facebook, and Twitter,” explains the Week in a recent explainer of the phenomenon it dubs “workplace spying.”

But how many of us always behave as though we’re being watched at work? I sometimes use my work computer for recreational Web browsing, and I’ve detailed personal problems and expressed unpopular opinions in work emails and Slacks to colleagues. That’s because I’m assuming that my boss isn’t actually scrutinizing my communications and online activity, even though she could if she wanted to. If I thought my superiors were actively surveilling everything I do on my work laptop, I’d avoid checking my Gmail at work, think twice about booking yoga classes from my work laptop, and stop using Slack to tell my closest work friend how much I love Borgen. I’d also feel less comfortable at the office, more paranoid around my boss, and resentful at the company’s lack of trust. 

Standards for computer use are more flexible in online journalism than in most fields—believe it or not, I had a work-related reason for Googling “leonardo dicaprio secret son” last week—but I suspect many white-collar workers would be stricter about the wall between private and professional computing if they thought their boss was watching their every keystroke.

According to a 2007 survey, 43 percent of companies monitor employees’ email, and 66 percent monitor employees’ Internet connections—but the term monitoring is vague enough to encompass activities both invasive and benign. Most of the companies that monitored email did so automatically, using “technological tools”—which might mean scanning for inappropriate language or just storing backups that supervisors could review if they had a specific reason. Only 17 percent of the companies surveyed “assign[ed] an individual to manually read and review e-mail”—and I suspect that percentage has gone down as monitoring software has improved over the past nine years. (It’s much more efficient to have a robot reading employee emails than to have a human do it.)

So should you be worried about your boss reading your email? After talking to people who’ve monitored their employees’ computer activity, and people who’ve been monitored, I’m convinced that most bosses aren’t poring over every word their underlings type over the course of the day—but we could all stand to be a little more thoughtful about what we say on our work computers, and how we say it.

If your boss is a good manager, he’s probably not reading your email or monitoring your Internet browsing unless you give him good reason to. “I’ve never read emails of my employees or co-workers,” said Bob, a software executive, although employees’ at Bob’s firm are required to turn over their email accounts when they leave the company to make sure information doesn’t fall through the cracks. However, Bob says he did once look at an employee’s Internet history. “A couple of years ago I had a very underperforming employee who was on probation (from a previous performance review) and I just couldn’t explain why his performance was so bad,” he said. He asked IT to review the employee’s computer activity—and discovered that he had been spending lots of time on an adult dating site and a sports betting site. “We fired him pretty much immediately,” said Bob. “He was on probation, after all.”

So—to state the obvious—if you know your work is being monitored because your boss is unhappy with your performance, expect him to take a closer look at your computer activity, too. But there’s another reason your boss might be watching you at the keyboard, even if your performance is excellent: his own narcissism.

Several years ago, Daniel (his middle name) was working for a startup, for a boss who “didn’t seem to really know what he was doing and was much more interested in what other people thought of him and name-dropping and traveling around to meet with people than in actually focusing on the company.” Daniel and his colleagues often used instant messenger to communicate about projects and, occasionally, to gossip about their boss. “We were human, so sometimes it was about work and sometimes it would be like, ‘Ugh, can you believe what this person did?,’ ” said Daniel. After a couple of years, Daniel got a new job and gave notice. He didn’t think anything was amiss until the afternoon of his last day at the startup, when his boss asked him for a meeting:

He calls me into his office and he says, “I know what you think about me.” I said, “Well, what do you mean?” He just took out a printout, a piece of paper, and started reading conversations between me and other people at the company. And of course in these messages I wasn’t saying very nice things about him, so I was just kind of like a deer in the headlights. I wasn’t even thinking about the ethics of reading someone’s private messages, I was just kind of horrified. Even though I didn’t really respect this guy as a boss, I don’t think anyone deserves to read such horrible things about themselves. … I said, “Well, I’m sorry that you read those things,” and I just apologized a bunch, and he said, “OK, you can go.” And I left and I never talked to him again.

Daniel later found out from the IT manager that the boss had installed spyware on all the company laptops—“software that was just recording everything that was on our screens all day.” Daniel warned his former co-workers to be careful about what they did on their work computers, and he says the experience changed the way he approaches communicating online. “I definitely think I have been less frivolous in the things I’ve said online about any subject since,” Daniel told me.

Daniel’s boss’s habit of reading everything his employees typed had no professional justification—he used surveillance to dominate his employees, not to strengthen the company. But we could all take a page out of Daniel’s book and be more careful about where we talk about people behind their backs—because a gossipy aside in an email could end up making things uncomfortable around the office, even when your boss isn’t actively spying on you.

Jacqueline (her middle name) started out as an assistant in publishing, and her job required her to read her bosses’ emails to find information and take care of business when they were out of the office. While sifting through her superiors’ inboxes, Jacqueline found conversations in which they called her “awkward.” Once she saw that they were talking about her, “I did look for more, which was a terrible idea,” she said. “The word ‘ungainly’ was used once, I remember. … They forgot that I would be reading it, I guess.” Jacqueline, who was in her early 20s at the time, says the experience hurt her feelings and “made me want to leave, but I also worried I was too ‘ungainly’ to find another job.” She did eventually find a new job that does not involve reading other people’s emails.

Bob’s, Daniel’s, and Jacqueline’s stories show that a healthy workplace dynamic around computer monitoring requires restraint on both sides. Morale can suffer when employees feel that they’re constantly under surveillance, but it can also suffer when people find out their colleagues’ unflattering opinions of them. So if you have access to another person’s email account or Internet history, don’t snoop unless you have a compelling reason. (Curiosity is not a compelling reason.) And if you know someone else—like Jacqueline—has access to your email, don’t say anything there you wouldn’t say to her face.

But if you’re simply an average office drone, like me, a more relaxed attitude might make sense. It’s possible that your boss, or someone else, will read your email or look at your browser history. For some people, that possibility is enough to make them avoid any hint of unprofessional language or behavior on their work computers. For others, though, the pleasure of gossiping with co-workers and the convenience of checking your Gmail at your desk outweigh the slight chance of a nightmare scenario like Daniel’s. I doubt I’ll purge all personal activity from my work laptop. Maybe this habit will someday come back to haunt me. But it probably won’t.

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