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The bossware boom

Kevin Roose
Kevin Roose
Back in 2019, I visited a call center for a big, multinational insurance company. The company had invited me to see how it was using AI to improve its customer service. It was particularly proud of a piece of software called Cogito, which it had recently installed on its agents’ computers to give them “augmented intelligence” during their calls.
Cogito’s AI worked, by, essentially, listening in on each call between a customer and an agent, and using natural language processing to notify agents when it thought they were screwing up.
If it detected that an agent sounded lethargic, for example, it flashed a coffee cup icon on their screen, reminding them to perk up. If it detected that an agent was talking too fast, it flashed a stop sign. There were at least a dozen more red flags in Cogito, including an “empathy cue” sent to agents whose voices didn’t sound sufficiently compassionate. At the end of every call, Cogito gave each agent a score, which was sent to their managers for use in evaluating their performance.
Cogito was an example of what I call “bossware” – software that is designed to surveil and evaluate workers, tracking their productivity and managing their time, doing the work that human supervisors used to do. (There’s a whole chapter in my book about this called “The Algorithmic Manager,” where I go into the bossware phenomenon in more depth.)
Bossware has existed for years in the manufacturing and retail industries, where “workforce management” tools are commonly deployed to schedule workers’ shifts, track their output, and judge their performance.
But the pandemic is fueling a boom in AI-powered bossware designed for white-collar executives who want to keep tabs on their newly distributed workforces. I’d estimate I’ve gotten at least 20 pitches from different bossware providers this year, all advertising software that is meant to replace some element of the traditional, peer-over-the-cubicle method of surveilling employees.
This week, for example, I got pitched an “AI-powered productivity platform” called Enaible. According to its website, Enaible bills itself as a way for companies to “deliver results, even while remote.” It does this by measuring how much time remote employees take to complete various tasks, and suggesting ways to speed those tasks up. It also gives each remote employee a personalized “productivity score” based on their output and time expenditure.
“Analyzing email usage, Zoom, Slack and online search histories doesn’t show a full picture of what a worker is doing,” the pitch read.
In other words, Enaible is corporate spyware – albeit the kind installed with workers’ permission, presumably on their company-issued devices. And it’s just one of many tools available to nosy executives. Here’s an article in MIT Technology Review last year that runs down the various options for bosses who want to make sure Todd in Sales isn’t spending all day playing Red Dead Redemption 2 while pretending to listen in on conference calls:
Hubstaff is software that records users’ keyboard strokes, mouse movements, and the websites that they visit. Time Doctor goes further, taking videos of users’ screens. It can also take a picture via webcam every 10 minutes to check that employees are at their computer. And Isaak, a tool made by UK firm Status Today, monitors interactions between employees to identify who collaborates more, combining this data with information from personnel files to identify individuals who are “change-makers.” 
One question you could ask about bossware is: does it actually work? I’m sure executives think it does, but I’d love to see more research on the long-term effects these apps have, not just on metrics like per-worker productivity and output, but on things like employee retention and morale. (During my 2019 call center visit, a manager proudly told me that using Cogito’s AI software had resulted in a 13 percent gain in customer satisfaction – which actually seemed like a remarkably small benefit, given the potential psychological toll on workers of having a glorified Clippy send them passive-aggressive reminders all day.)
Another question worth asking is: will remote workers accept bossware as a fair price to pay for the ability to work from home? Or will they rebel against it?
I’m starting to think the latter is more likely. Take, for example, this story by Avi Asher-Schapiro of the Thomson Reuters Foundation about an Amazon van driver who recently quit his job, citing frustrations with the AI-powered surveillance software the company forced him to use:
At first, it was Amazon’s “Mentor” app that constantly monitored his driving, phone use and location, generating a score for bosses to evaluate his performance on the road.
“If we went over a bump, the phone would rattle, the Mentor app would log that I used the phone while driving, and boom, I’d get docked,” he said.
Then, Amazon started asking him to post “selfies” before each shift on Amazon Flex, another app he had to install. 
“I had already logged in with my keycard at the beginning of the shift, and now they want a photo? It was too much,“ he said.
The final indignity, he said, was Amazon’s decision to install a four-lens, AI-powered camera in delivery vehicles that would record and analyse his face and body the entire shift. 
There are big differences between Amazon drivers and remote knowledge workers. But both groups face increasing amounts of on-the-job surveillance, and as AI technology improves, it’s possible that workers in both fields will unite to oppose new, invasive forms of performance tracking.
A common thread you hear from future-of-work pontificators these days is that workers in the post-pandemic era will have more freedom and flexibility than the cubicle-bound workers of the past. But the opposite could easily be true, too. For some remote workers, working from home, under the watchful eye of Enaible or some other app, might actually turn out to be less flexible than working from a physical office, where you can at least get up and go to the coffee machine without a robot tsk-tsking you.
When I went on Bomani Jones’s podcast last week, he mused that the rise of workplace automation might be the thing that gets white-collar workers into unions. I’ve been thinking about that a lot this week, as I comb through the pitches in my inbox. Workers have certainly put up with dehumanizing tools before. But it wouldn’t surprise me if AI-powered bossware becomes the catalyst for some kind of organized remote-worker backlash that makes executives wish they’d stuck to snooping on Slack logs and email inboxes.

Call for submissions
Do you have experience with workplace surveillance? I’ve written a bit about it, but I’m hoping to write more in a column soon. I’d love to hear some up-to-date accounts of what it’s actually like to work in a software-surveilled remote job. (And, executives, I’d love to hear a thoughtful defense of bossware.) If you have a good story, or have read anything particularly good on this subject, just hit reply to this email.
What I've been up to this week
Futureproof got reviewed in the New York Times Book Review by James Fallows, who called it “a concise, insightful and sophisticated guide to maintaining humane values in an age of new machines.” I’ll take it!
– I was on Fresh Air, which was just a total delight in every possible way. You can listen to the episode here.
– I also went on Andrew Yang’s podcast, “Yang Speaks,” to talk about the book.
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Kevin Roose
Kevin Roose @kevinroose

On life among the machines.

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