Executive Time is Slate’s pop-up blog about bosses.

According to a 2017 report from the Brookings Institute, nearly 90 percent of “good jobs”—defined as jobs that “have the potential to help workers without a four-year college degree earn enough to support themselves and begin to move toward the middle class”—require medium- or high-level familiarity with digital tools. The omnipresence of computers at work raises concerns for desk jockeys everywhere, the specter of surveillance not least among them. From key-tracking software to the panopticon technology of Slack to the prospect of actual microchip insertion, the shift of work to largely digital spaces provides more and more opportunity for workers to be tracked … or at least to wonder who’s watching.

To find out if my boss actually knows how often I check Twitter, I sat down with Slate’s IT admin and advice columnist Shasha Léonard.

Rachelle Hampton: So what exactly can a boss track on your computer?

Shasha Léonard: It really depends on where you work, and the size of the company usually is a big factor. Some places only care about what you do on their network in the office. You take the computer home, you go on your home network, and they don’t care what you’re doing. If you accidentally download malware or something like that, sometimes there will be systems in place so that the minute you get back onto the office network, IT is pinged about it. Sometimes employers cannot remote into a work computer when it’s not on the company network, while other companies, if they feel like it, can totally do that. There is also GPS tracking for when computers are lost or stolen, and sometimes there might be software on the work computer that allows for a remote wipe, to protect the company’s assets.

Ultimately, the computer and the network are company property. If you quit your job, you can erase your data if you want. I understand why someone would do it, but it may also look a little suspicious. If your company uses an email system, the employer owns it and is allowed to go through it if they wish.

“Do we know a lot of things about you? Yes. Could we find out more? Sure.” — Shasha Léonard, Slate IT admin

So if I were to join a company that had the highest level of workplace surveillance, what could they do?

Anything you do on company property can be surveilled, and with the highest levels of security, we could easily enter Big Brother territory. You could Google something, and the network could be set up to ping IT for that criteria, whether that’s porn or something specific to that company you shouldn’t be looking up. Some places equip their computers with keylogging software, which means everything you type is recorded and can be reviewed. Basically, if it’s not your computer, there’s probably surveillance and security software on it that you have no idea about because they’re hidden, and you wouldn’t know where to look for them.

Fascinating.

In addition to your email being company property, your phone calls can also be quietly monitored (unless you live in the state of California). I wouldn’t do or text anything personal on a company-provided cellphone either.

So it’s a possibility that your boss can find out all the online stores you gave your email to for a 20-percent-off coupon?

It’s totally a possibility.

If you delete something in Slack, is it actually gone?

Depends on your company’s retention policy in Slack. If the settings are made to retain edited and deleted messages, then what’s Slacked is Slacked.

If not?

It’s gone.

OK.

And contrary to popular belief, getting a transcript of your Slack DMs is not as easy as pressing a button. Technically your workspace admin will need to request a Corporate Export from Slack with legitimate reasons to back it up. That takes effort and time, so unless it’s a crazy scandal, I highly doubt that would happen. There’s no need to be paranoid.

So what about personal email on a work computer? Can a boss see that?

If you left or were fired and your computer was returned to IT or HR and you had not logged out of your personal Gmail, it’s possible. For integrity’s sake, if someone else’s personal email falls into another person’s hands, that person should ideally log them out of their personal email on their work computers when that happens. It seems illegal for a company to go through your personal email, but I don’t have a law degree.

Good to know.

If it’s on your work computer and someone glances at it, that’s not illegal though.

Can your boss tell how often you’re on Twitter?

I would say if they want to, probably. If you’re on the company’s network, it will most likely generate reports of where and how long exactly that bandwidth is being used.

So you can technically see how often I’m online shopping?

No, I don’t have time to police y’all.

Is that just this company or all companies?

There’s more in-depth reporting, or application fingerprinting, that we could do, but yes, every company has its own prerogative. You’ll find different companies are sensitive to different things and their networks will be restricted accordingly. A writer asked me why they couldn’t access any video gaming websites, and it was because our firewall blocks that kind of content. But that was one of her beats, so we changed it accordingly. If you ever can’t access a website at your workplace, don’t blame the computer or your phone. It’s probably because of the network you’re on.

And is that for security reasons?

For the gaming example, that’s for productivity. I’m pretty sure we also block porn, but I’ve never tried to search.

What other measures for productivity do you have?

Well, that’s the thing. Because we’re a small company, but not the smallest, we don’t spend all day auditing our users. We have other shit to do. When I worked at the Apple Store, people always asked, “What do you do when you take my phone in the back? Do you go through all my shit?” And it’s like, we’re so busy, we don’t have time for that. Do we know a lot of things about you? Yes. Could we find out more? Sure, but I’ve got a million other more important things to do. It’s a pretty chill working environment here.

So you’re saying it depends on the company size—would a bigger company do more or less?

I think a bigger company might have more stringent security protocols, especially older places still using Windows computers because all that stuff is super complex. (I’m an Apple person.) Bigger companies may be stricter because they can be, and maybe because they have to be because they have a lot of employees. Bigger companies might definitely put keyloggers on your computer. If you have a doubt, or you feel guilty about anything you might be doing, don’t do it. Or just do it on your phone or your personal computer.

Read more from Executive Time, Slate’s pop-up blog about bosses.