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Why Your Boss Isn’t Coming To The Office

By understanding the role of cognitive biases and fostering a culture of empathy and inclusivity, organizations can ensure that the benefits of remote work are accessible to all employees, not just the privileged few.

Dr. Gleb TsipurskybyDr. Gleb Tsipursky
November 20, 2023
in Workforce
Reading Time: 7 mins read
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Why Your Boss Isn't Coming To The Office

By the numbers stat: 48% of higher-ranking employees currently engage in remote work for at least one day per week, while only 33% of those in entry-level positions do the same, according to a recent McKinsey report.

  • A significant proportion of middle managers are adamant about maintaining their work-from-home arrangements, which is creating a ripple effect throughout the corporate landscape. 
  • A recent McKinsey report unveiled that 48% of higher-ranking employees currently engage in remote work for at least one day per week, while only 33% of those in entry-level positions do the same.  
  • Leaders need to be open to new ways of working and actively seek feedback from all levels of the organization. By doing so, they can ensure that the future of work is shaped by the collective needs and preferences of all employees, rather than just those at the top. 

In the era of hybrid work, where a combination of remote and office work is becoming more prevalent, there has been a notable transformation in the way work is perceived. The conventional five-day office week is being questioned and replaced by a more flexible approach. Surprisingly, it is the bosses in middle-management positions who are exhibiting resistance towards this shift. A significant proportion of these middle managers are adamant about maintaining their work-from-home arrangements, which is creating a ripple effect throughout the corporate landscape. 

The Boss Privilege 

A thought-provoking irony has been brought to light in a report by McKinsey about a survey of 13,000 office workers in six countries: the individuals who possess the power are using their privilege to avoid coming to the office. The report unveiled that 48% of higher-ranking employees currently engage in remote work for at least one day per week, while only 33% of those in entry-level positions do the same. This significant difference in remote work practices prompts inquiries regarding the trajectory of work in the future and the influence of leadership in shaping it. 

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When broken down by seniority, we get an even clearer disparity. 50% of middle managers – defined as directors, managers, and team leaders – said they had a strong desire to work from home, meaning they were both likely to quit their jobs if required to work at the office every day and willing to trade more than 20% of their compensation to work their preferred number of days from home. The comparable number among junior staff? 6%. When broken down by income, those making more than $150K were the ones most likely to say they have a strong desire to work from home. This trend is more common in white-collar industries such as finance and professional services, especially in larger companies. 

Similar evidence comes from a survey by Deloitte and Workplace Intelligence Research going in-depth into a specific sector: they interviewed 700 full-time executives with job titles of manager or equivalent and above. Specifically, they found that a whopping two-thirds (66%) of financial service leaders working hybrid or remote would leave their firm if required to come in full time. Leaders surveyed prefer flexible work arrangements over prescribed workplace models. Some financial services institutions now require their workforce to go into the office three to four days a week. However, only 18% of respondents say this would be their ideal arrangement. 

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And leaders with caregiving responsibilities surveyed were 1.3 times more likely than non-caregivers to say they’d leave their organization if their company eliminated their ability to work remotely. Unfortunately, caregivers are still most likely to be women, and nearly half (45%) of women respondents in senior leadership roles report being likely to leave their current employer over the next year. Of course, the ones most likely to leave are those in less flexible companies. 

The personal experiences of these executives further underscore the appeal of remote work. The Wall Street Journal reports how Deb Andrychuk, the director of global talent attraction for Sony Interactive Entertainment, walked away from a lucrative position at Lowe’s for the flexibility to work from home. The ability to balance personal responsibilities, such as caring for her aging dogs, with professional commitments has made her life “so much better.” 

Top performers hold significant influence within organizations, shaping company culture and attendance norms. Despite being a minority, their preference for remote work challenges the traditional office model and poses a potential risk of talent poaching by competitors offering more flexible work arrangements. 

The Role of Cognitive Biases 

The “Boss Privilege” phenomenon can be better understood when we consider the role of cognitive biases. These biases, deeply ingrained in our thought processes, can subtly influence our decisions, relationships, and behaviors, often without our conscious awareness. Two biases in particular, the status quo bias and the empathy gap, can shed light on this trend. 

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Status Quo Bias: The Comfort of Familiarity 

Status quo bias is a cognitive bias that favors the current state of affairs. People are generally resistant to change and prefer to maintain their current habits and beliefs. This bias can be particularly potent when it comes to work arrangements. After all, work forms a significant part of our daily routines and any change can have far-reaching implications on our work-life balance, productivity, and overall well-being. 

In the context of the “Boss Privilege”, the status quo bias can explain why higher-ranking employees, who have more control over their work arrangements, may prefer to maintain their current remote work practices. Having tasted the flexibility and convenience of remote work, these individuals may be resistant to the idea of returning to the office full-time. The familiar routine of working from home, devoid of commuting hassles and offering better work-life balance, has become their status quo, making any deviation from it unappealing. And they have the power to enact their desires. 

Empathy Gap: The Challenge of Perspective Taking 

The empathy gap refers to the difficulty of understanding others’ experiences that are different from our own, especially when we are in a different emotional or situational state. This cognitive bias can lead to a lack of understanding and appreciation for the challenges and experiences of others, particularly those who are in different roles or positions within an organization. 

Higher-ranking employees, who have the privilege to work remotely, may struggle to understand the challenges faced by lower-ranking employees who are required to work from the office. This empathy gap can lead to policies that favor the preferences of those at the top, reinforcing the “Boss Privilege.”  

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For instance, a senior executive might find it hard to empathize with the difficulties of a junior employee who has to commute daily to the office, juggling public transport schedules and peak-hour traffic, while they themselves enjoy the convenience of a home office. 

The empathy gap can also extend to understanding the different needs and preferences of employees. While some might thrive in a remote work environment, others might prefer the structure and social interaction that an office environment provides. A one-size-fits-all approach, driven by the preferences of those at the top, can lead to dissatisfaction and disengagement among those whose needs are not being met.  

Addressing the Biases 

The “Boss Privilege” phenomenon brings to light the need for a more equitable approach to remote work policies. As we navigate the future of work, it’s crucial to ensure that the benefits of flexibility are accessible to all, not just those at the top. Understanding and addressing these cognitive biases can help organizations create more inclusive and fair work environments. It’s a major challenge that I work on addressing for the organizations that I helped figure out their . 

Leaders can counteract the status quo bias by being open to new ways of working and actively seeking feedback from all levels of the organization. They can address the empathy gap by fostering a culture of empathy, where the experiences and challenges of all employees are acknowledged and considered in decision-making processes. By doing so, they can ensure that the future of work is shaped by the collective needs and preferences of all employees, rather than the privileged few. 

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Conclusion 

How do middle managers perceive and respond to the implementation of a five-day office week, considering its complexity and wide-ranging consequences? As the nature of work evolves, it is evident that the ability to be flexible and adaptable is crucial for attracting and retaining top talent. In this context, top executives face the challenge of effectively navigating this changing landscape, ensuring a balance between employee needs and business demands, while considering the issue of balance between middle managers and rank-and-file employees. 

The “Boss Privilege” phenomenon underscores the importance of addressing these challenges head-on. By understanding the role of cognitive biases and fostering a culture of empathy and inclusivity, organizations can ensure that the benefits of remote work are accessible to all employees, not just the privileged few. This approach not only promotes fairness but also contributes to a more engaged and productive workforce. 

As we move forward, it is crucial for leaders to remember that the future of work is not a one-size-fits-all model. Instead, it is a dynamic landscape that requires continuous adaptation and innovation. By embracing this mindset, organizations can turn the challenges of the hybrid work model into opportunities, creating a work environment that is not only productive but also fulfilling for all employees. 

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Dr. Gleb Tsipursky

Dr. Gleb Tsipursky

Dr. Gleb Tsipursky, called the “Office Whisperer” by The New York Times, helps tech-forward leaders replace overpriced vendors with staff-built AI solutions. He serves as the CEO of the future-of-work consultancy Disaster Avoidance Experts. Dr. Gleb wrote seven best-selling books, and his forthcoming book with Georgetown University Press is The Psychology of Generative AI Adoption (2026). Prior to that, he wrote ChatGPT for Leaders and Content Creators (2023). His cutting-edge thought leadership was featured in over 650 articles in prominent venues such as Harvard Business Review, Fortune, and Fast Company. His expertise comes from over 20 years of consulting for Fortune 500 companies from Aflac to Xerox and over 15 years in academia as a behavioral scientist at UNC-Chapel Hill and Ohio State. A proud Ukrainian American, Dr. Gleb lives in Columbus, Ohio

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