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Entitled “Boss” Spends All Her Time Spying On An Employee, Ends Up In A Disciplinary Meeting
Older woman in a red shirt using a smartphone, illustrating a boss struggling with technology and workplace issues.

Entitled “Boss” Spends All Her Time Spying On An Employee, Ends Up In A Disciplinary Meeting

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In theory, the existence of human resources, rules, managers and a separation of professional and home life should mean that workplace drama stays at a minimum. The reality is that petty jealousies, entitlement and just unhinged human behavior can still show up even in the most inappropriate settings.

A woman turned to the internet for advice on how to deal with an older boss who would constantly diminish her work and even literally spy on her. We reached out to the person who made the post via private message and will update the article when she gets back to us.

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    A boss spying on you is a great way to diminish a worker’s morale

    Older woman in red shirt struggling with smartphone, representing a boss bad with technology trying to spy on coworker.

    Image credits: Linoleum Creative Collective / unsplash (not the actual photo)

    So one woman had to escalate things when her boss asked a coworker to report on her activities

    Text excerpt about a boss caught spying on a 25-year-old coworker, highlighting workplace issues with technology.

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    Older woman in her 60s labeled as boss showing incompetence and poor technology skills at the workplace.

    Alt text: Young woman expressing frustration at boss caught spying and struggling with technology in a public sector workplace.

    Woman boss struggling with technology, looking thoughtful in a modern office setting, holding a tablet with concern.

    Image credits: Getty Images / unsplash (not the actual photo)

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    Text excerpt showing a coworker describing conflicts with a boss who tries to micromanage and act like a boss.

    Text discussing a boss who is bad with technology and tries to spy on a 25-year-old coworker while playing the victim.

    Text discussing a boss caught spying on a coworker due to being bad with technology and trying to play victim.

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    Text excerpt about a boss bad with technology spying on a 25-year-old coworker during work from home.

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    Boss struggling with technology trying to use smartphone in a meeting room with coworkers around a conference table.

    Image credits: Getty Images / unsplash (not the actual photo)

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    Screenshot of a text message about a boss caught spying on a coworker, revealing workplace conflicts and deleted messages.

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    Middle-aged woman in pink lace dress wiping tears, depicting a boss struggling with technology and emotional stress.

    Image credits: Alexander Mass / unsplash (not the actual photo)

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    Text excerpt describing a boss caught spying on a coworker, causing trust issues and workplace tension.

    Alt text: Boss struggling with technology caught spying on coworker, then plays the victim in disciplinary meeting.

    Text on a plain background asking if the person is wrong for reporting their boss caught spying on a coworker.

    Image credits: Familiar-Plantpot-9

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    Some people are still suspicious when people work remotely

    Woman using laptop on bed in cozy room while golden retriever dog sleeps nearby, illustrating boss bad with technology concept.

    Image credits: BRUNO CERVERA / unsplash (not the actual photo)

    Some entitled ageing workers will have to snoop on their colleagues, particularly folks who work from home, because of a centuries-long lack of trust in modern ways of working and the view that productivity must be monitored if it is to be real. Having created their professional careers in traditional office environments where professional growth was measured by time spent at the desk, punctuality, and visible work, they can struggle to adapt to a more results-focused and self-managed attitude of remote or blended work. For them, the absence of face-to-face management can result in feelings of losing discipline and accountability. They may think that others will take advantage of the system in their absence, a thought based less on reality than on projection.

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    A good number of times, this need to observe others is caused by insecurity and fear of being left behind. As the professional world trends towards digital literacy and flexible working, some of the veterans may feel their accrued experience is now less valued. As younger colleagues learn to pick up collaboration tools with ease, juggle tasks asynchronously, or perform well without micromanaging, it disrupts the established status quo that had long defined their value. Rather than try to adapt, some push back against change, by inserting themselves into others’ processes, inquiring intrusive questions masquerading as “concern,” or unofficially monitoring when people are online, present, and even the cadence at which they respond to messages.

    This kind of behavior is also a function of generational power relationships. Older workers will assume a management function, even when they lack formal power over fellow workers. They will assert the privilege of monitoring, reporting on, or “fixing” colleagues who are not doing things right in their eyes. To them, they are enforcing standards or “serving the company” by doing so. But in fact, much of the time, this is really about imposing traditional norms and creating status in an increasingly horizontalizing, more trusting workplace.

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    As in this story, a lack of trust in one’s boss is bad for everyone

    Boss struggling with technology looks over coworker's computer in a modern office setting with headsets on.

    Image credits: Getty Images / unsplash (not the actual photo)

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    The damage caused by this sort of informal monitoring is often undervalued. It creates a culture of distrust and erodes psychological safety, the sense that you can work freely without risk of judgment, monitoring, or misrepresentation. It even leads to passive-aggressive conduct, undue tension within colleagues, and even formal action if the management reacts to information based on supposition rather than fact. When someone feels watched, they’re bound to start performing defensively rather than creatively, concerned with image at the expense of effect. That’s a setback for everyone.

    If you feel that a co-worker, particularly one who seems rooted in old office habits, is observing your work, recording your steps, or subtly undermining you with management, you need to address it skillfully but firmly. The first step is to document what is occurring. Note events, comments, or patterns that make you suspect the behavior is inappropriate or invasive, especially if the actions expose you or are unreasonable. Gather details, dates, times, interactions, and any communication that did not feel right or felt inappropriate or overly inquiring. Do not rely on nebulous impressions, details matter if it’s going to come up to someone higher up.

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    So what should someone do?

    Boss struggling with technology confronts coworker in office, sitting across a desk with laptop and smartphone nearby.

    Image credits: Andrej Lišakov / unsplash (not the actual photo)

    If you have to report this to management or HR, frame the issue clearly in terms of how it affects your performance, doing your job. Confine yourself to professionalism issues, not personal attacks. Maintain an objective tone, not emotional, and be prepared to clarify how the behavior affects team morale or productivity.

    Where you can, propose a positive solution. You might propose a reminder to staff from management about boundaries, expectations, and trust in a remote work culture, or propose more specific guidelines around performance expectations and communication that apply to everyone equally. Managers might be unaware of tensions lurking, especially if they’re passive or informal monitoring. Raising it responsibly enables them to remind staff of good work norms before things become an issue.

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    Most of all, remember that the feeling of being spied on or monitored by a peer is not something that you just have to accept, especially when it is driven by entitlement, resentment, or inability to adapt. Organizations excel when autonomy and trust are values, not fear and control. If you’re being made to feel as though you need to answer every hour or defend yourself as working hard enough, the issue isn’t your performance, it’s the old-fashioned mentality of those attempting to project their own insecurities onto others.

    Most thought she did the right thing

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    Screenshot of an online comment accusing a boss of toxic behavior and highlighting issues with employer’s management.

    Comment from Reddit user moew4974 discussing a hostile work environment caused by a boss bad with technology.

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    Alt text: Screenshot of online comment warning about incompetent boss spying on coworker and advising to document everything.

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    Poll Question

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    Justin Sandberg

    Justin Sandberg

    Writer, BoredPanda staff

    Read more »

    I am a writer at Bored Panda. Despite being born in the US, I ended up spending most of my life in Europe, from Latvia, Austria, and Georgia to finally settling in Lithuania. At Bored Panda, you’ll find me covering topics ranging from the cat meme of the day to red flags in the workplace and really anything else. In my free time, I enjoy hiking, beating other people at board games, cooking, good books, and bad films.

    Read less »
    Justin Sandberg

    Justin Sandberg

    Writer, BoredPanda staff

    I am a writer at Bored Panda. Despite being born in the US, I ended up spending most of my life in Europe, from Latvia, Austria, and Georgia to finally settling in Lithuania. At Bored Panda, you’ll find me covering topics ranging from the cat meme of the day to red flags in the workplace and really anything else. In my free time, I enjoy hiking, beating other people at board games, cooking, good books, and bad films.

    What do you think ?
    Lee Gilliland
    Community Member
    Premium
    4 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    This woman got that job by having something on somebody. OP needs to leave.

    Crystalwitch60
    Community Member
    4 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I’m that woman’s age , n omg I’d never act like her in no way shape or form, if she’s taking bribes ,that is a prison sentence , it’s fraud ,basically and if your working with the public purse as it’s called in uk , you should be doing time end off !! NTA op for reporting her , polish up your cv n get job hunting , , then report her to the police , I so want an update on this one

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    Roberta Surprenant
    Community Member
    4 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    When she makes misogynistic comments, ask if she judges ALL women by her own incompetence?

    Lee Gilliland
    Community Member
    Premium
    4 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    This woman got that job by having something on somebody. OP needs to leave.

    Crystalwitch60
    Community Member
    4 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I’m that woman’s age , n omg I’d never act like her in no way shape or form, if she’s taking bribes ,that is a prison sentence , it’s fraud ,basically and if your working with the public purse as it’s called in uk , you should be doing time end off !! NTA op for reporting her , polish up your cv n get job hunting , , then report her to the police , I so want an update on this one

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    Roberta Surprenant
    Community Member
    4 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    When she makes misogynistic comments, ask if she judges ALL women by her own incompetence?

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