Contents
- Hey, Welcome Back!
- Karlee Besse: In the Nick of TimeCamp
- Procrastination: Not the Only Thief of Time
- The Guardian: Bossware Makes You Easy to Fire
- Productivity Monitoring: My Journey to Saying Yes
- Employee Language vs Boss Language
- The Future is Monitored: And Sometimes Itβs Worth It
- This Weekβs Shareable
- Latest Remote Jobs
Karlee Besse was - and it's set a precedent for all remote workers. This week we chat about where to draw the line with productivity surveillance, and why I said yes to being monitored at work.
π©π½ββοΈ NPR: Woman Found Guilty of Time Theft
π The Guardian: Bossware is Coming for You
ποΈ Productivity Monitoring: Say Yes to Trust
π€ Language Matters: Extremes Help No-one
Hey, Welcome Back!
Ever heard of time theft? What about bossware? Theyβre making headlines again.
Itβs episode 25 and this week we tangle with ethics and the law, delving into a topic that makes a lot of remote workers furious: productivity surveillance.
Iβm going to take you through one of the biggest remote stories of 2023 so far, and why itβs a landmark story for all of us. Then, weβll get a bit more personal as I share what made me choose to work for a company that uses productivity monitoring software.
Come armed with your opinions, this is one topic that you want to do justice (before it does justice on you). Ready to face facts?
Letβs start the clock -
Karlee Besse: In the Nick of TimeCamp
Time is money, as they say.
If youβre a remote worker this is a literal truth, especially when you have to log hours. Karlee Besse found this out the hard way.
Sheβs at the center of a landmark court decision that impacts everyone who works remotely, and uses productivity monitoring software.
If youβre ever caught in a dispute with your employer about what you may β or may not β have been doing on company time, well.
π΅ This case will likely affect the outcome of yours.
Procrastination: Not the Only Thief of Time
Karlee got a remote job at an accounting firm in British Columbia, Canada. Five months later, they fired her, and she decided to sue for wrongful termination.
What came to light was that Besse had misrepresented over 50 hours of time. Apparently, this time wasnβt used for work-related tasks.
The surveillance app TimeCamp provided the courts with the evidence. It had tracked her activities while she was on the clock.
Details have been disputed, and no-one knows if the time was mislabeled on purpose or by accident. But in the eyes of the law: she lost.
And the really big deal - the court ordered her to repay the time back to her employer!
The ruling got a flood of media coverage because it was the first ruling of its kind. What it did was set a precedent for using time-tracking software in legal proceedings.
π΄ββ οΈ The term coined for it is: time theft.
Now the term has been around for a minute, but not like this. A trend chart over the last 5 years shows a steep upward leap after the Besse court case ruling.

That spike means itβs official β time theft isnβt just another fun phrase, itβs an unethical practice that will stand up in court.
The Guardian: Bossware Makes You Easy to Fire
According to data published by the Guardian, 60% of companies with remote workers implemented some variation of bossware last year. And 9 out of 10 of those companies has terminated someone since then.
π‘ People get incredibly worked up about the topic.
Zoe Corbyn writes,
βTracking technology can [also] log keystrokes, take screenshots, record mouse movements, activate webcams and microphones, or periodically snap pictures without employees knowing.β
I believe time theft and bossware may be the most critical conversation impacting the future of work right now. To ignore it, isnβt going to make it go away.
So, letβs strip away the rollercoaster of emotions and focus on the facts.
Productivity Monitoring: My Journey to Saying Yes
In my personal life, some of my friends think Iβm crazy because I work for a company who takes photos of me every 10 minutes. They wouldnβt dream of it.

It causes a visceral response in a lot of people β I get it. And it is challenging, Iβd be lying if I said it wasnβt. But for me thereβs no question that the pros outweigh the cons.
Here are two objective truths:
π I have the right to do whatever I want in my own home
π§ I donβt have the right to do whatever I want when Iβm on the clock and my boss is paying me
Do you agree with those statements? Most people would. The time theft β bossware conversation falls somewhere between those truths.
Youβll also agree that both extremes are bad:
π» Companies shouldnβt be tricked into paying someone to play PlayStation instead of work
π Employees shouldnβt be watched when theyβre home alone and not on company time
Both extremes are outrageous, and nobody wants that.
Of course, now that the line between work and home is blurred, both sides are painting the other as though theyβre defending one of those terrible extremes.
Now consider:
π Most employees are good people who work hard every day
It doesnβt matter if theyβre 10 feet from their boss, or 10 feet from their shiny new PlayStation 5.
π But some people suck.
Itβs the sucky, dishonest people that ruin it for everyone else. They canβt or wonβt refuse the temptation. At the office, their boss would see them and know. βAh, thereβs the office blackhole,β they would think.
If that employee worked from home β how would they know?
Employee Language vs Boss Language
Thatβs why a lot is assumed when either side moves to communicate. When one group says one thing, the other takes it the wrong way. Everyone is on the defense.

And

A stalemate is reached that canβt be resolved with objective facts. And thatβs because something this subjective has a lot of moving parts.
β³ Too much trust is time theft
π΅πΌββοΈ Too little trust is bossware
So how much trust is the right amount? There must be a goldilocks ideal out there somewhere. What youβll find is that everyoneβs answer is different. Thereβs too much nuance around work to simplify this into a βtrust meβ or βdonβtβ situation.
π€ Every remote worker and company will need to decide where they stand on trust
How much is reasonable? Where do we draw the line?
Is the line drawn between privacy and surveillance in sand or cement?
Like I said, thereβs no easy, objective answer.
But what we do know is:
π€¨ No-one should be monitored without their consent (thatβs creepy and invasive)
π No-one would choose to be monitored if they had the choice
So, companies should be transparent about their monitoring practices and people should make up their own minds about what theyβre willing to live with.
Nobody in their right mind wants to be watched β but what if it was worth your while?
Everyone has their price. Thatβs a fact.
For me it was three incentives:
1. π° The job must pay at least 20% more than other jobs available to me
2. π€© The job role had to be better than other roles out there
3. π« It must come with complete flexibility to choose my own location & hours

Those were three non-negotiables that Iβd never had before.
Because theyβre incredibly difficult to find. When I found this job at Crossover more than 2 years ago, it ticked all the boxes. Moving from New York to New Zealand would have meant a pay drop in this market. But I was nervous!
I outlined three deal breakers that would send me running for the hills.
1. πΈ Still selfies and screenshots were fine during work hours, never on personal time and never a full video feed
2. π€³π» I could review the images captured and delete any if they caught me doing something I didnβt want my boss to see
3. β²οΈ No timecard micromanagement, Iβd be measured on the quality of my output not the quantity of my inputs

That last one was important, Iβd just left a job that would ding me if I was 4 minutes late, even if Iβd been at my desk until 10pm the night before. If I worked hard, stayed on task and prioritized my workflow β that had to be enough.
Looking back after two years at Crossover, the incentives turned out to be true and none of the deal breakers ever happened. Iβm glad I saw past my knee-jerk reaction to say no to being monitored.
Sure, itβs hard β but itβs not that hard.
Itβs not harder than constant requests from colleagues, being asked to stay late, or spending most of your free time at home on work, because there isnβt enough focus time at the office. Letβs be realistic about context.
π Iβve never regretted my decision to say yes. Not for a single moment.π
The Future is Monitored: And Sometimes Itβs Worth It
Wherever you decide to fall on this issue, Iβd encourage you to look past that knee-jerk reaction to say βhell no.β The best things in life are never easy.
Society once raged against televisions, dial-up internet, and most recently AI. What was once unimaginably invasive, is now painfully mundane.
So, stop asking yourself if its hard, and start asking yourself if itβs worth it.
Donβt sign up for anything youβre not okay with β but donβt rule out a great opportunity either. The only people who have anything to fear are the ones planning to play PlayStation all day, or do whatever the heck Karlee Besse was doing.
In that case, I wish you the best of luck finding a clueless boss, or a decent lawyer.
Before I go, tell me what your three incentives are!
π― What would make you accept a job that requires productivity monitoring software?
It will be interesting to see if your bar is higher or lower than mine.
Thatβs it for this week folks β and remember, the future of work is Out of Office.
Andrew
This Weekβs Shareable
- Where do you draw the line with productivity monitoring software? When #remoteworkers demand trust, and companies insist on proof-of-work - itβs easy for both sides to lean on extremes. This week we strip away the emotions and take a fact-based look at #timetheft and #bossware. Read about it on OOO.
Latest Remote Jobs
Are you waiting for a sign to apply? Here it is: π§
π₯ Chief of Staff at Trilogy, $100k ($50/hour)
π₯ Demand Generation Marketing Manager at IgniteTech, $100k ($50/hour)
π₯ Senior Project Manager at Aurea Software, $100K ($50/hour)






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