Why Do Bosses Resist Telecommuting? Common Concerns & How You Can Respond

Increased productivity and satisfaction, enhanced employee engagement, higher retention rates… With study after study touting these benefits (and more) that result from workplaces offering employees flexibility, why do bosses resist telecommuting? 


There is no empirical data to suggest that working remotely makes a team less effective overall- it’s just a different way of working together. And that is exactly what causes friction between managers and employees when it comes to telecommuting requests. 


The 2017 State of Telecommuting in the U.S. Employee Workforce Reportpublished by FlexJobs and Global Workplace Analytics— asserted that, in 2017, 3.9 million U.S. employees worked from home at least half the time, a more than 200% increase from 1.8 million remote workers in 2005. 


The entire telecommuting population is 10 to 15 times larger than these data suggest since the data focus only on employees who work from home full-time. Excluded from the data are those who are self-employed, those who split their time between work and home, those who work extra hours at home, or those who work at home less than half the time.


Concern #1: “We don’t have the support or infrastructure necessary to support a distributed workforce.”

Concerns about the company’s technological shortcomings

    • Short-term telework arrangements (an hour here or there, from time to time) require minimal tech: a laptop with necessary software and Internet connection. 
    • Long-term telework arrangements (day to day) require more devices, secure software, and additional tech tools to help them keep in touch with colleagues (Zoom, Slack, etc.). There is a budgetary impact once these tools are taken to scale. 

Concerns about the manager’s own, or the employee’s own, technological shortcomings

    • Your manager may be fearful about exposing his or her own insecurities around how technology works. 
    • Your manager may not trust your own abilities to reliably trouble-shoot technological problems remotely without hands-on, in-person support.

Concern #2: “Employees who work from home oftentimes miss opportunities for casual feedback and praise.”

  • Your manager may prefer to offer casual feedback whereby advice is given in the moment. He/she may be insecure about how or whether his/her management style will need to change when you are not face-to-face to receive guidance.

  • Your manager may be heading off anxieties felt by some remote workers, such as questioning the quality of their performance or their dedication to the team. 

Concern #3: “Remote employees become disconnected employees when they cannot join impromptu meetings.”

  • Your manager may not be in the habit of planning ahead; he/she may prefer to “gather when the mood strikes” or call ad hoc brainstorming sessions. 

  • Your manager a) may not want to change this pattern while also wanting you to be present, or b) may not want to invite technology to interrupt these spontaneous conversations (i.e., “can you hear me now?”).

Concern #4: “Gathering in-person builds trust and collaboration”

  • Your manager may have never had an opportunity to practice building trust via long-distance relationships or virtual face-to-face meetings (via Zoom or otherwise). 

  • Your manager may have concerns about whether you will feel as if you are not as valued a teammate as others, which in turn can lower productivity and engagement. 

  • A common complaint made by remote workers is feeling – or, worse, unintentionally being – left out of the office camaraderie. This leads to an undercurrent of mistrust and feelings of disrespect.

Concern #5: (Unspoken) “I’m not sure I trust you to be productive when you’re not in the office where I can see you.”

Your manager has become accustomed to judging his/her workforce not just by how productive they are, but how productive they appear to be. People in an office may look busy when they are clicking away on their keyboards or taking calls, but this can mask what is actually getting done – or not.

Concern #6: “How will working remotely work affect Employees B, C, and D who are not working remotely?”

  • Will the team’s morale take a hit when a portion of its members work remotely? If morale is fragile at your workplace, your boss may not want to risk upsetting it. 

  • Your manager may feel uncertain about picking up on signs that morale is suffering. If changes are indeed evident, how will your manager respond?

Concern #7: (Unspoken) “Does our policy need to be ‘all or nothing’?

Some workplaces insist on a “one size fits all” approach to management. In this case, your manager may not be concerned about YOUR productivity, but rather, that of your coworkers. 

Concern #8: “How will stakeholders perceive remote workers?”

While a manager may have the authority to approve a telecommuting arrangement for her workforce, she may be concerned about her boss’s perception of her decision. For instance, if she takes a day off and her boss cannot find her and does not see evidence of her work-from-home subordinate, she may have a perception issue on her hands.

Concern #9: “Who will track your hours, and how?”

The perceived productivity of office staff is higher than the perceived productivity of remote workers, whether accurate or not. In a salaried position, working hours are not as much of a concern theoretically; however, a manager may be concerned with your whereabouts and accessibility during normal business hours. Without seeing you face-to-face, they may grow anxious about your presence and dedication- whether warranted or not.

Concern #10: “How will employment necessities like training, supervision, performance management, and retention be handled?”

  • Teleworking requires more from managers: better planning, communications, and an emphasis on performance.

  • If managers are accustomed to relying on “things unsaid” – nuances of their communication and directives – and/or body language to communicate prioritization of projects, that is a sign of weak management rather than a sign of a teleworking problem. Employees thrive when they have clear performance goals and metrics, not lessons in interpretative communication.

Concern #11: “How will we ensure the strength of our cyber security?”

  • An employee’s laptop may have all the latest patches and be secure when connecting to the company’s network from home; however, an employee’s home device may not be as well secured and could introduce malware or a virus to the network. 

  • Copies of confidential files left open on shared home computers could present security risks.


1. Employees are happier: they are available for the needs of their family, easing stress and leading to increased creativity 

    1. Need a study to show your boss? Here ya go
    2. Need quick data from the study? Full-time remote workers say they are happy in their job 22% more than people who never work remotely.

2. Employees are more productive and dedicate more time to work- eliminating the commute and lunchtime errands 

    1. Remote workers work > 40 hour weeks to support their team and because they enjoy what they do. 
    2. In contrast, when onsite workers work long hours, it is because it is required of them. 
    3. Poor middle managers measure performance based on time in the office (face-time focus). Telecommuting, in contrast, is about how much work you get done (productivity focus).

3. Reduction in turnover

    1. Need a study to show your boss? Grab it here
    2. Need quick data from the study? Remote workers say they are more likely to stay in their current job for the next five years 13% more than onsite workers.  

4. Employer gets credit for being “green”

  1. Having a remote workforce reduces the company’s carbon footprint attributable to commuters
  2. A remote workforce reduces the employer’s real estate footprint (and cost)

5. Employer saves money on office space and potentially salary 

  1. 34% of survey respondents would take a pay cut of 5% in order to work remotely; 24% of survey respondents would take a pay cut of 10% in order to work remotely. 
  2. Companies spend $18,400 on average, per person, per workplace. Remote set-up costs $2,000/year on average or a savings of $16,400.

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6. Employer has an easier time attracting and retaining talent 

7. Employer can dip into a broader talent pool

Rather than being limited by talent that is within a 30-mile radius, employers can source talent worldwide.

8. Disaster preparedness- companies will be ready to relocate or work remotely


Asking for a flexible working arrangement, such as telecommuting, sometimes results in employees (particularly women) suffering a “perception penalty” in terms of their professional standing and/or compensation.

  • Performance reviews may take a hit, which can impact promotions
  • They may attract an unwanted professional stigma of being less committed when in actuality, it is their commitment to their jobs that initiates the conversation. The press depicts women as “opting out” when it reality, many are pushed out when they ask for what they need.

Experts say that telecommuting does not create management problems; rather, it makes existing problems more apparent. 

Before making a request for a telecommuting arrangement, take an honest look at your relationship with your boss: what problems exist currently, and how might those manifest in a telecommuting arrangement?

The disconnection work-from-home employees sometimes experience is often about culture rather than technology. 

In preparing your request, give dedicated thought to when certain tech tools will be used, what is the appropriate response time for correspondence, and what media for correspondence is primary (i.e., Slack) vs. secondary (email, phone).

Confirm employees’ performance is based on clear and measurable goals, not time and attendance. 

Check your employee handbook, schedule time with HR, and take a look at your past performance appraisals. Will your performance and value shine through in a remote arrangement? Would it be to your benefit to attend some meetings in person?

Remote workers value their boss’s availability to them during working hours. If the boss is inaccessible, the employee’s stress rises and job satisfaction diminishes.

Discuss a weekly standing meeting with your boss and a quarterly in-person meeting. Discuss and agree to expectations for your availability to one another in the interim. 


If you have a strategy for how to overcome the potential drawbacks to telecommuting and you want a taste of the benefits, you now need to plan for how you will make your request to your boss.

1. Start small

Ask to work from home one or two days a week, or one or two afternoons a week, to start. Establish trust and a track record of productivity first.

2. Demonstrate how the COMPANY will benefit – use data!

  • Improving your productivity benefits the company; any claims that you make about productivity must be delivered upon. Now is the time for follow-through: over-deliver, be reliable, available, and responsible.

  • A meta-analysis of 46 studies comprised of more than 12,000 employees indicates that telecommuting had small but mainly beneficial effects on outcomes such as perceived autonomy and lower work-family conflict, and beneficial effects on job satisfaction, performance, turnover intent, and role stress.
    • It is widely known and accepted that employee churn causes upwards of twice the employee’s salary to find, hire and train their replacement. The silent cost that also takes a toll is the damage to morale when employees leave. 
    • Remote employees have increased autonomy, which leads to employees making an emotional investment in the projects they are tasked with. Building an engaged team of employees who care about a company’s outcome is the “secret ingredient” that successful companies have mastered.
  • Remote workers are 13% more productive (almost an extra day of output per week) 
    • They experience a quieter environment with fewer “break room” distractions. 
    • They work more hours- they start earlier, take shorter breaks, work until the end of the day, and don’t run errands at lunch.
    • Remote workers have 63% fewer unscheduled absences than their onsite colleagues. 
    • Less expensive for the company
      • Employees without access to flexibility are 2x more likely to leave their job for a more flexible alternative, according to this study published in 2018 by Werk.co
      • Companies that remove barriers to wellness and preventative health reduce absenteeism and reduce health care costs overall. Flexibility allows employees to prioritize preventative health care. 
      • Telecommuting allows employees to structure their day around sustainable optimal performance. 

    3. Work out the details ahead of time 

      1. Get with IT to understand the VPN or other connection to your network; do a test run at home to make sure your connection is stable (and for how long). 
      2. Review your employee handbook to make sure you haven’t overlooked any provisions or expectations for telecommuting arrangements. 
      3. Overcome concerns about cyber security with a combination of technology and policy

    4. Document everything 

    1. Write down your understanding of the agreement and ask your boss to sign off on it. You want to ensure you start off seeing eye to eye. 
    2. Having an agreement in writing gives you something you can fall back on so future bosses will understand the arrangement should your current boss leave.

    5. Answer manager’s concerns about equity 

      1. Rotate the days at home so that a certain percentage of workers (your peers) are always in the office, OR
      2. Schedule mandatory, in-the-office days

    6. Show up! 

      1. Demonstrate a willingness to come into the office when necessary- for important meetings, company gatherings, and other opportunities.
      2. Use the video chat feature during team meetings so colleagues can “see” you- this helps build trust

    7. Customize your plan

    1. Rather than all-or-nothing thinking, such as “the entire company needs to have one policy”, or that “everyone in one department must work from home or no one can”, consider the policy role-by-role. You are unique and your request is unique- it may not be a fit for someone else. 
    2. Remember the potential for hybrid solutions (e.g., work from home 50% of the time, one day a week, or other).

    As a manager of a remote team, check in with telecommuting staff more often rather than less in order to build trust. Creating a team virtually is different than doing so in person- it is not impossible. Keep in mind that 60-80% of communication is nonverbal- so, when you ask your subordinate to turn their video feed “on”, make sure you do the same.

    Questions? Visit the Contact page to discuss your unique situation. 

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