Crossover Logo
Log in
  • About
    About Crossover About Crossover

    Crossover is a global recruitment company that specializes in full-time remote jobs with AI-first tech companies. We enable the top 1% of global talent to qualify...

    Companies Hiring Companies Hiring

    Some of the 70+ companies that use Crossover to recruit global talent for high-paying remote positions.

    Reviews Reviews

    Hear testimonials from some of the 5,000+ rockstars who have found a rewarding career through Crossover.

    What is WorkSmart? What is WorkSmart?

    WorkSmart is Crossover’s internal productivity monitoring tool. It helps our elite remote workers stay focused, track their time, and get paid fairly - with real-time AI...

    About

    The world's largest database of skilled remote talent

  • For Jobseekers
    Current Job Openings Current Job Openings

    Crossover matches world-class people with world-class jobs at silicon valley software and EdTech companies. Earn USD from anywhere with a full-time remote job.

    Selection Process Selection Process

    Want to qualify for awesome remote jobs? Here’s what to expect from Crossover's AI-powered system of skill assessments.

    High-Paying Remote Jobs High-Paying Remote Jobs

    Find top remote jobs that pay you what you’re worth. Browse 70+ fully remote roles that match your skills, accelerate your growth, and give you the...

    US Education Jobs US Education Jobs

    Are your big ideas too cool for school? Join Crossover to qualify for the world's most innovative (and well-paid) jobs in education technology. Work full-time...

    For Jobseekers

    The world's best remote full-time jobs, with AI-first US tech companies

  • For Companies
    Hire on Crossover Hire on Crossover

    Forget average. Use our AI-powered smart filters to tap into the world's largest database of extraordinary remote talent.

    How to Hire Global Talent How to Hire Global Talent

    Need a smarter way to shortlist global contractors? We’ve spent 10 years perfecting a process that eliminates barriers, guarantees outstanding matches, and saves you time-to-fill.

    How to Manage Distributed Teams How to Manage Distributed Teams

    Streamline everything from contracts and payroll to productivity management.

    Remote Software Developers Remote Software Developers

    Find and hire the top 1% of remote software developers in the world through Crossover. Tap into a global talent pool of 7 million rigorously tested...

    For Companies

    Get the world's best AI experts on your team, in 5 mins a day

  • Reviews
  • Resources
  • Help
Crossover Logo
🕓 Are you guilty of time theft? | Ep25 OoO

Share

  1. Home
  2. Resources
  3. Out of Office
Out of Office

🕓 Are you guilty of time theft? | Ep25 OoO

Andrew Allen by Andrew Allen
  VP of Content Marketing
🕓 Are you guilty of time theft? | Ep25 OoO
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 It’s Worth It
  • This Week’s 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.

👩🏽‍⚖️ NPR: Woman Found Guilty of Time Theft

🚔 The Guardian: Bossware is Coming for You

👁️ Productivity Monitoring: Say Yes to Trust

🤞 Language Matters: Extremes Help No-one

Hey, Welcome Back!

Ever heard of time theft? What about bossware? They’re making headlines again.

It’s 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.

I’m going to take you through one of the biggest remote stories of 2023 so far, and why it’s a landmark story for all of us. Then, we’ll 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?

Let’s start the clock -

Karlee Besse: In the Nick of TimeCamp

Time is money, as they say.

If you’re a remote worker this is a literal truth, especially when you have to log hours. Karlee Besse found this out the hard way.

She’s at the center of a landmark court decision that impacts everyone who works remotely, and uses productivity monitoring software.

If you’re ever caught in a dispute with your employer about what you may – or may not – have been doing on company time, well.

😵 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 wasn’t 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.

🏴‍☠️ 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.

Image

That spike means it’s official – time theft isn’t just another fun phrase, it’s 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.

😡 People get incredibly worked up about the topic.

Zoe Corbyn writes,

“Tracking technology can [also] log keystrokes, take screenshots, record mouse movements, activate webcams and microphones, or periodically snap pictures without employees knowing.”

I believe time theft and bossware may be the most critical conversation impacting the future of work right now. To ignore it, isn’t going to make it go away.

So, let’s 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 I’m crazy because I work for a company who takes photos of me every 10 minutes. They wouldn’t dream of it.

Image

It causes a visceral response in a lot of people – I get it. And it is challenging, I’d be lying if I said it wasn’t. But for me there’s no question that the pros outweigh the cons.

Here are two objective truths:

😎 I have the right to do whatever I want in my own home

🧐 I don’t have the right to do whatever I want when I’m on the clock and my boss is paying me

Do you agree with those statements? Most people would. The time theft – bossware conversation falls somewhere between those truths.

You’ll also agree that both extremes are bad:

👻 Companies shouldn’t be tricked into paying someone to play PlayStation instead of work

👀 Employees shouldn’t be watched when they’re 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 they’re defending one of those terrible extremes.

Now consider:

😇 Most employees are good people who work hard every day

It doesn’t matter if they’re 10 feet from their boss, or 10 feet from their shiny new PlayStation 5.

😈 But some people suck.

It’s the sucky, dishonest people that ruin it for everyone else. They can’t or won’t refuse the temptation. At the office, their boss would see them and know. “Ah, there’s the office blackhole,” they would think.

If that employee worked from home – how would they know?

Employee Language vs Boss Language

That’s 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.  

Image

And

Image

A stalemate is reached that can’t be resolved with objective facts. And that’s because something this subjective has a lot of moving parts.

⏳ Too much trust is time theft

🕵🏼‍♂️ Too little trust is bossware

So how much trust is the right amount? There must be a goldilocks ideal out there somewhere. What you’ll find is that everyone’s answer is different. There’s too much nuance around work to simplify this into a ‘trust me’ or ‘don’t’ situation.

🤔 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, there’s no easy, objective answer.

But what we do know is:

🤨 No-one should be monitored without their consent (that’s creepy and invasive)

😉 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 they’re willing to live with.

Nobody in their right mind wants to be watched – but what if it was worth your while?

Everyone has their price. That’s a fact.

For me it was three incentives:

1.     💰 The job must pay at least 20% more than other jobs available to me

2.     🤩 The job role had to be better than other roles out there

3.     🛫 It must come with complete flexibility to choose my own location & hours

Image

Those were three non-negotiables that I’d never had before.

Because they’re 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.     📸 Still selfies and screenshots were fine during work hours, never on personal time and never a full video feed

2.     🤳🏻 I could review the images captured and delete any if they caught me doing something I didn’t want my boss to see

3.     ⏲️ No timecard micromanagement, I’d be measured on the quality of my output not the quantity of my inputs

Image

That last one was important, I’d just left a job that would ding me if I was 4 minutes late, even if I’d been at my desk until 10pm the night before. If I worked hard, stayed on task and prioritized my workflow – 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. I’m glad I saw past my knee-jerk reaction to say no to being monitored.

Sure, it’s hard – but it’s not that hard.

It’s 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 isn’t enough focus time at the office. Let’s be realistic about context.

🌟 I’ve never regretted my decision to say yes. Not for a single moment.🌟

The Future is Monitored: And Sometimes It’s Worth It

Wherever you decide to fall on this issue, I’d encourage you to look past that knee-jerk reaction to say ‘hell no.’ 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 it’s worth it.

Don’t sign up for anything you’re not okay with – but don’t 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!

🐯 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.

That’s it for this week folks – and remember, the future of work is Out of Office.  

Andrew

This Week’s Shareable

  • Where do you draw the line with productivity monitoring software? When #remoteworkers demand trust, and companies insist on proof-of-work - it’s 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: 🚧

💥 Chief of Staff at Trilogy, $100k ($50/hour)

💥 Demand Generation Marketing Manager at IgniteTech, $100k ($50/hour)

💥 Senior Project Manager at Aurea Software, $100K ($50/hour)

Similar post
📢 Breaking news: The FINAL episode of Out of Office with Andrew Allen | Ep84 OoO

Hey, Welcome Back! One. Last. Time. You probably thought I’d keep going forever, likeMarvel spin-offsor awkwardZoom meetings that should’ve been emai...

Read more
Out of Office Logo
PODCAST SERIES
Out of Office
The least boring remote work news source on the planet. Meet expert and ordinary remote workers from around the world.
View All Episodes

Share

Andrew Allen
ABOUT THE AUTHOR

Andrew Allen

  VP of Content Marketing

Andrew lives in Auckland, New Zealand and has worked full-time remotely for Crossover since early 2021. His superpower is using storytelling and humor to make interesting and memorable insights on complex topics. He's known for hosting the world's most-viewed remote work vlog (Out of Office), co-creating one of the most-subscribed newsletters on LinkedIn (Radically Remote), and contributing to Forbes. Beyond work, Andrew has visited over 100 countries, seen all seven wonders, and starred in a few high profile TV shows and musicals in New Zealand. You can hear a bit more of his backstory (and meet his dogs) here.

Return to Top
Read Next
🛺 A call to remote leadership with Rahul Subramaniam | Destination India Part 1 OoO
Section Separator Top

Blog

View all blogs

Want to read more?
We have a lot more where that came from

Achieving Excellence
3 AI Home Schooling Programs to Try in 2026
The notion of a 'good school district' means nothing in the face of AI home schooling. The U.S. education system is buckling under chronic t...
Read more
3 AI Home Schooling Programs to Try in 2026
The Future of Work
7 AI in Education Statistics To Reshape Your Hiring Strategy
Fresh AI in education statistics have revealed a serious disconnect between traditional hiring and the types of teachers needed in the AI ag...
Read more
7 AI in Education Statistics To Reshape Your Hiring Strategy
The Future of Work
4 Top Private High Schools in the US Using AI
Every private school in the US claims to be 'future-ready.' But scroll past the glossy headers and you'll find the same classroom structure ...
Read more
4 Top Private High Schools in the US Using AI
The Future of Work
What Does AI in EdTech Look Like on the Ground?
Ask what AI in EdTech looks like in the classrooms, and you're likely to receive two radically different answers. The first comes from the c...
Read more
What Does AI in EdTech Look Like on the Ground?
Achieving Excellence
Startup Founders are Limiting Growth by Staying Locally Remote
Startup founders just LOVE to brag about being fully remote. But if everyone on your team still lives within door-dash distance, you’re not ...
Read more
Startup Founders are Limiting Growth by Staying Locally Remote
The Future of Work
How to Call Out AI Workslop (+Win Respect Doing It)
Has your remote team become a one-stop AI workslop shop? Emails suddenly only make partial sense. There’s something off about the latest rep...
Read more
How to Call Out AI Workslop (+Win Respect Doing It)
The Way We Work
Why Top Performers Use Both X and LinkedIn
Do you have a multi-platform approach to AI information? Most people will say yes! But they're wrong. And if you're one of them, I have some...
Read more
Why Top Performers Use Both X and LinkedIn
The Future of Work
48 Remote Work Comics That Capture the Future of Work
Two years ago, Andrew and I had an idea. What if we could create a single panel comic that could capture moments in time that showcased the ...
Read more
48 Remote Work Comics That Capture the Future of Work
Achieving Excellence
Crossover’s Basic Fit Check [Official AI Screening Guide]
Are you fit for the role you’re applying for? We get it – our jobs are flexible, AI-forward and highly paid. Who wouldn’t want to apply to a...
Read more
Crossover’s Basic Fit Check [Official AI Screening Guide]
Building a Remote Workforce
3 Ways Remote Work Innovation Improves In-Person Work
Most people make the mistake of thinking remote work is ONLY about where you work. But they're missing the real workplace update happening r...
Read more
3 Ways Remote Work Innovation Improves In-Person Work
Achieving Excellence
7 Flexible Remote Work Hacks for Time-Poor Workers
Flexible remote work handed you back 3 precious hours from your old soul-crushing commute. But your days still feel like they're running on ...
Read more
7 Flexible Remote Work Hacks for Time-Poor Workers
The Future of Work
How to Survive the 2026 AI Skills Rollercoaster
Another AI-fueled tech shakeup is coming. If you’ve spoken to anyone working in local tech lately, you’ve heard the same exhausted confessio...
Read more
How to Survive the 2026 AI Skills Rollercoaster
Software Engineering
Will AI Replace Software Engineers? Not If You Do This
Will AI replace software engineers? This is the question hanging over the heads of every engineering team right now. Engineers have lived wi...
Read more
Will AI Replace Software Engineers? Not If You Do This
The Way We Work
Remote Office, Real Visibility: Stand Out From Anywhere
Working from a remote office should mean more work life balance, less synchronous distraction, and a global career built on your terms. But ...
Read more
Remote Office, Real Visibility: Stand Out From Anywhere
The Future of Work
How AI-Led Remote Work Made Leadership Honest
Nominate a Remote Work Leader! The best place to hide bad management is at the office. At least – it used to be. But when the pandemic struc...
Read more
How AI-Led Remote Work Made Leadership Honest
Achieving Excellence
3 AI Home Schooling Programs to Try in 2026
The notion of a 'good school district' means nothing in the face of AI home schooling. The U.S. education system is buckling under chronic t...
Read more
3 AI Home Schooling Programs to Try in 2026
The Future of Work
7 AI in Education Statistics To Reshape Your Hiring Strategy
Fresh AI in education statistics have revealed a serious disconnect between traditional hiring and the types of teachers needed in the AI ag...
Read more
7 AI in Education Statistics To Reshape Your Hiring Strategy
The Future of Work
4 Top Private High Schools in the US Using AI
Every private school in the US claims to be 'future-ready.' But scroll past the glossy headers and you'll find the same classroom structure ...
Read more
4 Top Private High Schools in the US Using AI
The Future of Work
What Does AI in EdTech Look Like on the Ground?
Ask what AI in EdTech looks like in the classrooms, and you're likely to receive two radically different answers. The first comes from the c...
Read more
What Does AI in EdTech Look Like on the Ground?
Achieving Excellence
Startup Founders are Limiting Growth by Staying Locally Remote
Startup founders just LOVE to brag about being fully remote. But if everyone on your team still lives within door-dash distance, you’re not ...
Read more
Startup Founders are Limiting Growth by Staying Locally Remote
The Future of Work
How to Call Out AI Workslop (+Win Respect Doing It)
Has your remote team become a one-stop AI workslop shop? Emails suddenly only make partial sense. There’s something off about the latest rep...
Read more
How to Call Out AI Workslop (+Win Respect Doing It)
The Way We Work
Why Top Performers Use Both X and LinkedIn
Do you have a multi-platform approach to AI information? Most people will say yes! But they're wrong. And if you're one of them, I have some...
Read more
Why Top Performers Use Both X and LinkedIn
The Future of Work
48 Remote Work Comics That Capture the Future of Work
Two years ago, Andrew and I had an idea. What if we could create a single panel comic that could capture moments in time that showcased the ...
Read more
48 Remote Work Comics That Capture the Future of Work
Achieving Excellence
Crossover’s Basic Fit Check [Official AI Screening Guide]
Are you fit for the role you’re applying for? We get it – our jobs are flexible, AI-forward and highly paid. Who wouldn’t want to apply to a...
Read more
Crossover’s Basic Fit Check [Official AI Screening Guide]
Building a Remote Workforce
3 Ways Remote Work Innovation Improves In-Person Work
Most people make the mistake of thinking remote work is ONLY about where you work. But they're missing the real workplace update happening r...
Read more
3 Ways Remote Work Innovation Improves In-Person Work
Achieving Excellence
7 Flexible Remote Work Hacks for Time-Poor Workers
Flexible remote work handed you back 3 precious hours from your old soul-crushing commute. But your days still feel like they're running on ...
Read more
7 Flexible Remote Work Hacks for Time-Poor Workers
The Future of Work
How to Survive the 2026 AI Skills Rollercoaster
Another AI-fueled tech shakeup is coming. If you’ve spoken to anyone working in local tech lately, you’ve heard the same exhausted confessio...
Read more
How to Survive the 2026 AI Skills Rollercoaster
Software Engineering
Will AI Replace Software Engineers? Not If You Do This
Will AI replace software engineers? This is the question hanging over the heads of every engineering team right now. Engineers have lived wi...
Read more
Will AI Replace Software Engineers? Not If You Do This
The Way We Work
Remote Office, Real Visibility: Stand Out From Anywhere
Working from a remote office should mean more work life balance, less synchronous distraction, and a global career built on your terms. But ...
Read more
Remote Office, Real Visibility: Stand Out From Anywhere
The Future of Work
How AI-Led Remote Work Made Leadership Honest
Nominate a Remote Work Leader! The best place to hide bad management is at the office. At least – it used to be. But when the pandemic struc...
Read more
How AI-Led Remote Work Made Leadership Honest
Achieving Excellence
3 AI Home Schooling Programs to Try in 2026
The notion of a 'good school district' means nothing in the face of AI home schooling. The U.S. education system is buckling under chronic t...
Read more
3 AI Home Schooling Programs to Try in 2026
previous
next
Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs
  • Companies Hiring
  • Resources
  • About Crossover
  • What is WorkSmart?
  • High-Paying Remote Jobs
  • Reviews
  • Selection Process

Join the world's largest community of AI first Remote WorkersAI-first remote workers.

Find your dream job
Hire top talent
© Crossover, 2025
Website TermsContractor TermsPrivacy PolicyLegalCookie Settings