Bossware: The Motivation Behind Monitoring Software

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Due to the fierce market competition, it is natural for businesses to want to boost their productivity by any means possible. Among other factors, a company’s overall financial health is largely contingent on individual workers’ contributions. However, employees are not always at the top of their performance. In fact, according to InterGuard (2018), US businesses alone lose up to $178 million due to workers’ Internet misuse. Employees’ self-reports only confirm the facts: apparently, more than one-third of them (37%) browse the web for purposes other than work.

I would like to point out that browsing is not just an innocuous waste of work time. Going on unreliable websites can cause cybersecurity issues and data breaches. Townsend (2018) reports that more than 18 million websites are infected with malware and ransomware, which is 1% of all the websites on the Internet. While it may seem like the odds are low, in reality, an average website is attacked 44 times a week (Townsend, 2018). So next time, a formerly safe page can become a source of danger. I should note that people at all levels can compromise the information security of a company, be it entry-level employees or CEOs.

Considering all these facts, it seems that monitoring software is the key to resolving all these problems. InterGuard (2018) goes as far as to say that all industries could benefit from it. Yet, I cannot help but wonder about the ethical side of things. Therefore, the topic I have chosen for this assignment is BossWare.

BossWare is software that is used to monitor CEOs on what they do at work. I will be doing research on the ethical issues it may bring or what it has done. The reason I chose this topic is that I am always curious about software that can monitor you, and the privacy it invades. Privacy is always a big concern for me when it comes to any new technology or software coming out. With this software, I have the same concern as I do with other software. I am convinced that we need to balance technological progress with ethics to protect people from unnecessary harm.

BossWare: Main Concerns

I have a few questions about BossWare and its implications. My biggest concern is what information it can gather. I have this concern because the CEO’s board of directors shouldn’t have full access to what their CEO does at work. They shouldn’t be able to see emails, what they search, what they post on social media, personal information like credit cards, social security, and what they order online. If it can gain these types of information what more can it gain? Will it have full access to anything done on the computer or is there limitations?

Another question I have is can it be installed without the user knowing? This is a concern because if it can then I feel like that is a big invasion of privacy of the CEO. Is there a way to tell if they have it on their system? If not this could mean that any board of directors could spy on their CEO, and the CEO will never know. That can be a huge ethical issue waiting to happen.

The last question I have is can this be applied to employees within the business? If so, does this invade the employee’s privacy, or can they make it so that when they sign up for the job, they have to be aware they’re being spied on? I personally wouldn’t like that to happen to me, but others might find it to be great to find a leak within the workplace.

BossWare: Pros

Despite being ethically controversial, brassware has promising potential to meet some of the most relevant business needs. First and foremost, bossware seeks to reduce the incidences of employees wasting time on something that is not related to work. Slacking at work is more common than you may think. Rampton writes that 89% of people in the workplace waste time in one way or another. How much time they spend doing something else varies a lot. According to Rampton, it is 30 minutes for the majority of people but three hours and more for the top 10% “wasters.” In the latter case, it translates into 15 hours of lost time per week and immense financial and HR losses on a large scale. Bossware helps to prevent these losses by exposing slack and misuse.

Secondly, bossware can help enforce safety practices on CEOs. Koulopoulos (2017) reports that cybersecurity attacks are one of the top reasons why businesses fail. Recovering from an attack takes a lot of money and other resources. What is more, some incidents are “lethal.” For example, 60% of small businesses go off the market six months after a cyberattack (Koulopoulos, 2017). Bossware helps to see whether CEOs actually put safety guidelines into practice. If they do not, it is a good time to mentor them again.

Lastly, bossware helps to spare a lot of HR resources. Managers and executives who supervise others are at an increased risk of a burnout. The bigger the company, the more difficult it is to control how people spend their time at work. Bossware offers an automated solution that renders constant supervision unnecessary. It frees up people to invest their efforts into something more productive.

BossWare: Cons

For all its advantages, bossware does have some major flaws that we cannot overlook. Firstly, a decision to supervise CEOs and employees can be psychologically difficult for them. Surveys show that companies perpetually misjudge people’s motivation. 89% of them think that money is what drives them (Smart & Chamberlain, 2016). However, turnover studies show that the majority of cadres who quit wished for more understanding and flexibility (Smart & Chamberlain, 2016). Bossware will signal mistrust and cause CEOs and employees to take a defensive position against their managers/ board of directors.

Secondly, bossware gives businesses a false sense of security, which is dangerous in the long-term. For starters, bossware cannot just function on its own. It needs at least minimum maintenance and involvement to make it efficient. This means that managers or directors will still have to put in some effort to gain insights from bossware and make sure that it works as intended. On top of that, like any software, bossware is not immune to cyber attacks, which I discuss further in this presentation.

Ethical Concerns: Gathering Information

My Initial concern about BossWare is what information it gains, and according to an article (Raicu, 2020) found that:

BossWare includes all the features of other nontraditional monitoring products: it logs applications and websites that the CEO accesses and uses, social media posts, email, and other messages; it also uses location tracking via GPS (para. 4).

This software gains a lot of information on the CEO. To me, this information gathering is invasive and should be frowned upon. This is a huge invasion of privacy. Why would a board of directors need to know every website, all social media posts, and their location? The answer is they don’t need this information. Unless the board is aware of leaks, and they found it to be coming from the CEO, then I could see the use of it. Then according to (Cyphers & Gullo, 2020) found:

Most bossware also records levels of input from the keyboard and mouse—for example, many tools give a minute-by-minute breakdown of how much a user types and clicks, using that as a proxy for productivity (para. 5).

This is also invasive of what the CEO does. Anybody can just click randomly, and type stuff, and not be productive at all. BossWare is just invasive and should only be used for specific reasons. Reasons like if the CEO has been doing shady stuff or has caused leaks.

Ethical Concerns: Installation of Bossware

The next concern I have is will the CEO be aware of the software being installed on their systems? In the same article by (Raicu, 2020) found that:

the EFF advertises the fact that it “can be silently and remotely installed, so you can conduct covert investigations… and bullet-proof evidence gathering without alarming the suspected wrongdoer.” (para. 5).

This means that whenever they want, they can spy on their CEO, and the CEO will have no knowledge. This can be a huge privacy and PR problem for the business. It is a privacy problem because the CEO is being spied on without their knowledge which is not ethical. It is also a potential PR problem if word got out that a board of directors is spying on their CEO. People will assume that the CEO has been doing something, and the reputation of the business could be tarnished. if the public finds it odd for the board to spy on their CEO it could lead to loss of sales, money, and business opportunities. It will also be hard for the public to re-establish trust in the business, and it could be what burns the business to the ground.

Ethical Concerns: Tracking Employees

The answer to my last question is yes it can be used on employees. If the business implements the policy in their business, then they can. According to (Cyphers & Gullo, 2020):

  1. Is installed on the device the employee uses (laptop, PC, smartphone, tablet);
  2. Collects any data regarding the use of this device – running programs, keystrokes, activity in apps, etc.;
  3. Sends collected data to the boss. (para. 5).

Just like for CEOs, employees can be spied on by their bosses. This can go two ways. One where the workers don’t mind, or new employees/potential employees might not like the policy, and look for work elsewhere. It may seem too invasive for new workers/potential hires and could make it hard for the business to hire new people.

Cybersecurity Issues

Like any other software, bossware is potentially vulnerable to cyber attacks. Hackers could exploit a vulnerability in the software itself and be able, for example, to view a random person’s actions. In addition, they could use social engineering tactics to extract administrator passwords from the employer or an employee. By doing that, they can get access to their streaming, browser history, private corporate data, account logins and password, and many more. This information could be exploited by the hackers or sold to a third-party. Data breaches typically make it to the press, and customers lose their confidence in a business. Thus, bossware cannot be trusted as is, and its maintenance should become a part of the information security strategy.

Summary & Conclusion

Monitoring software is gaining attraction as businesses seek ways to boost their productivity. On the one hand, software such as bossware can reduce wasted time on the job. In addition, it can help enforce safety practices and remove some managing responsibilities through automated supervision. On the other hand, bossware may be psychologically daunting and signal mistrust. Besides, it can give a company a false sense of security. Some may say it gathers to much personal information and can go under the user’s radar, which makes me think about consent issues.

After researching possible ethical concerns, I came to the conclusion that BossWare is invasive of CEOs, or employee’s privacy. However, it can be implemented to not be extremely invasive. I think the best way an ethical issue could be avoided is to let any party that is going to be subjected to BossWare or any software like it be notified, and give the outcomes if they didn’t abide by it. Anybody should feel safe in their workplace, and not feel like they’re being spied on.


Cyphers, B., & Gullo, K. (2020). Inside the Invasive, Secretive “Bossware” Tracking Workers. Eff. Web.

Employee surveillance & Bossware – what exactly are employees okay with? (2020). Kickidler. Web.

Koulopoulos, T. (2017). 60 percent of companies fail in 6 months because of this (it’s not what you think). Inc. Web.

The stats: Employee monitoring a must for all industries. (2018). InterGuard. Web.

Raicu, I. (2020). BossWare: An Introduction On remote employee monitoring tools. Scu.Edu. Web.

Rampton, J. (2018). Wasted employee time adds up: Here’s how to fix It. Entrepreneur. Web.

Smart, M., & Chamberlain, A. (2016). Why do workers quit? The factors that predict employee turnover. Glassdoor. Web.

Townsend, K. (2018). 18.5 million websites infected with malware at any time. Security Week. Web.

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