Why Your Boss Doesn’t Want You to Telework


By Justin Draeger

But recently some major employers have been pulling telecommuters back into the office. The goal of any would-be teleworker is to show your boss how working from home will benefit him and the company.

If you’re having trouble getting your point across, here are some possible reasons he wants you in the office.

He Doesn’t Know What It Means

Don’t make the mistake of proposing telecommuting to a manager who has no real idea what teleworking is or how it works. Just because they can navigate around in Microsoft Outlook and can operate a blackberry doesn’t make managers tech savvy. Even at the risk of insulting their intelligence, it helps to provide a clear definition of what you’re asking for.

Of course that means figuring out what you want before you broach the subject. Do you want to work from home once a week, a few times a week, or full-time? Good negotiators know their end-points (what they want) and their breaking points (their bottom line).

In fact, avoid using the word “telecommute.” Even though I do it full-time, I almost always use the word telework, because it focuses on work, not my commute or lack thereof. It might be better to not use the words telecommute or telework at all, and instead just say in plain and simple terms exactly what you want.

For example:

“I get so bogged down here at the office that I end up working nights and weekends away from the office. I believe my productivity would increase if I could work from home for two days a week. I’ll still be readily accessible by phone, IM, and email during those times. Do you have any concerns with allowing me to work from home two days a week for the next three months?”

He Thinks You’re Getting Preferential Treatment

Some managers buy into the idea that everyone should be treated equally. It’s egalitarianism management and it stinks. Managers who buy into this concept care more about what their employees think about them than productivity or effectiveness.

I could give you a pep talk about changing corporate culture and management styles, but I won’t bother. Instead of wasting time trying to change management styles, it’s better to work within their framework. That means getting the approval of your coworkers and team members first, the people who will be most affected by your departure, before going to your manager. If teleworking will put additional burdens on your coworkers, they’ll let you know.

Approaching your coworkers first will also require you to take a realistic look at whether your job is a good fit for the teleworking. A production manager at an assembly plant has very little chance of telecommuting if 90 percent of his job duties require him to be on-site.

Approaching egalitarian managers with your coworkers full support tells them there’s no need to fear unpopularity or repercussions from the masses and that it’s okay to give you the green light.

He’s Old School

Many managers prefer “seeing” how hard you’re working. That includes a lot of managing by walking around, which is pretty ineffective management. Good managers know that managing by results is better for the company, employees, and ultimately themselves.

If your manager doesn’t focus on results, it’s up to you to help him start. Start reporting simple management numbers that focus on your productivity. Productivity numbers don’t just show how much you’ve completed, but shows how quickly or efficiently you tackled them. That generally means including a time component to your statistics such as tasks competed per hour, income generated per day, or product per week.

When it comes time to propose teleworking, you’ll already have management measures in place for him to ensure that you’re working hard.

He Just Loves Your Pretty Face

Some managers could forget all about you if you’re not in the office. If your manager fits this description you’ll need to retrain him or her to show that even if you’re not in the office, you’re still accessible. These managers are also less likely to allow you to work from home even on a trial basis.

For those employees, I suggest finding a reason to work from home, even if that means using a vacation day, to show just how accessible you can be. Send emails, make phone calls, or ping your coworkers and manager with instant messages. Do whatever it takes to show your boss that he’s not missing much by you not being right there with him. Most importantly, be more productive outside of the office than inside!

He Doesn’t Trust You

Stop now. You’re in trouble. If your boss doesn’t trust you then forget it. Whether the mistrust is warranted or not is unimportant because you can’t make someone trust you. Without trust you’re left with two options: build or rebuild the trust that is missing or go work somewhere else. The latter is usually easier.

Justin Draeger has been teleworking full-time since March 2008.


Nicole Bachelor

I’m surprised at the folks who say the reason bosses won’t allow telecommuting is because they feel if you work productively without them around, then they can’t justify their job anymore. I think people need to take a step back and really understand what we’re talking about here. Telecommuting is just a question of where you physically sit to work. Your boss should not need to manage anything about your physical presence (really if his only job is to make sure you dress properly for work or behave professionally in the office environment he really shouldn’t have the job). He should be managing your work – helping you prioritize, making sure you meet your deadlines, approving your decisions if needed, etc. This should be unaffected by your choice to telecommute – assuming of course you have the right skills to telecommute successfully. That’s on your shoulders to address though – learn what you need to do it right and demonstrate this and your boss is likely to let you continue.



Tsk, tsk Justin. I’ll bet there are as many female bosses as male bosses that don’t get it!

…show your boss how working from home will benefit him
…here are some possible reasons he wants you in the office?
He Doesn’t Know What It Means
HeThinks You’re Getting Preferential Treatment
HeOld School
HeJust Loves Your Pretty Face
HeDoesn’t Trust You


You can add environmental issues to your rationale for telework too! Justin’s article highlights a number of issues you may have to consider if you want to work from home, but bosses may not appreciate the positive environmental impact working from home offers either.

As background research for a book we’re writing we looked at the financial, petroleum and CO2 improvements that telework can contribute. To find specific numbers for your city or county (and other related advice) visit



Just like the 4 Hr Workweek guy said, you have to know how to negotiate with your boss in regards to this matter. And always negotiate from a position of power, meaning that you have leverage in terms of expertise, knowledge (subject matter expert), etc. Otherwise, your boss can always use that “preferential treatment” excuse on you, since you don’t really stand out among your co-workers anyway.


Moe Rubenzahl

re: As a boss, you consider telework as a privilege (your word) instead of looking at the big picture and seeing it as productivity or morale tool to the benefit of the company.

You made a presumption. I do see it as a privilege — one that benefits employee and company alike. Lest you think I am some pointy-haired boss who is clueless about telecommuting, 8 of my 14 staff telecommute part of the time. One employee had the privilege (yes, I am still using that word) revoked when their job performance suffered.

The benefit for me and for the company is that these employees appreciate the flexibility. Some of them have family or life-balance challenges and another job would not work for them.

But I’m standing by the point that employees will always benefit when they think of the boss as a co-worker and a partner, and try to see rational reasons, rather than presuming they are “old-school” or “don’t know what (tele-commuting) means.” When you presume your boss is an idiot, you have an uphill battle.

Besides, why would you choose to work for an idiot?

(I turned this into an article on my blog: http://feedme.typepad.com/my_weblog/2008/04/tele-commute-me.html).

Bloggers mosaic

first line came to my mind after reading the title is..because he is just a m..f..

most of bosses need to have people around or how the hell he gonna boss



administrative stuff

one reason is because the boss (my boss) wants to have you around so he looks important when people call, or to order you (me) around to do whatever job catches his imagination. if he has fewer people in the office, he cannot look as important. no real way around that problem while staying at the same job.


One of the standard reasons I get when I ask is that the insurance is too much. In today’s sedentary life/work style and high speed internet connections, there is very little else that would cause this to be an issue.

On the rare occasion that I, or others, work from home, there is a spike in productivity because we do not have the distractions of the office world (“Do you have a minute?”, the latest sick person in your area, or the “Hey, I have no reason to be here and chat with you, but I am gonna do it cause I have work I don’t want to do.” types.)


I agree with Arved- put your toes in the water first by testing out a day or two, maybe as working ‘sick’ days. If it doesn’t work out, now you know. If it works out, tell your boss how much more productive you were (you can load up your ducks-in-a-row jobs if you like) and try to get his approval.
I’m sorry Moe R., but you prove a point. As a boss, you consider telework as a privilege (your word) instead of looking at the big picture and seeing it as productivity or morale tool to the benefit of the company. If you remember, it is the way 60’s bosses thought about training – that it was a privilege or reward to the employee rather than a tool of the company for the company. Someday someone is going to question the astounding coincidence that most people seem to get their work done in exactly 8 hours a day and roughly between 8am and 5pm.


What’s cool for companies is all the people wanting to telecommute.

CEOs are not stupid, they’d love to have people working from home instead of renting office spaces.
But finding a system that’s working, it has a cost, and requires effort.

Thanks to all the telecommuters-wannabes, this effort is currently done by them, and not the company.

It will take time, but when a system that works efficiently is found, thanks to the telecommuters, the company will be very happy, because they will be able to fire its telecommuters and employ indians instead.

hey, if they can work with remote people, why would they pay you instead of some indian guy who’s 20 times cheaper?

Judi Sohn

You raise some excellent points, Moe. I’ve been teleworking for nearly 3 years now and I’ve always believed that I’ve had to work twice as hard as my in-office colleagues to justify the flexibility that I enjoy in their eyes.

I think it also varies greatly depending on the size of the company and how deep the chain of command is. I’ve found the larger the company, the harder it is to make it work. You would think in a larger organization individuals are more “invisible” anyway, so teleworking should be easier but in fact it’s in those companies that the face/politicking time Arved mentions is more important so you aren’t lost in the crowd.

Moe Rubenzahl

Actually, let me modulate my comment a bit since the last point of the article mentions the idea that perhaps the manager doesn’t trust you. That’s probably the most important point. While “you can’t make someone trust you,” you can -earn- trust.

There are certainly bozo bosses out there but you have to ask yourself if you’re part of the reason. If you consider your boss’s success to be part of your mission, you’ll do better. Even if this job is a dead-end, you can practice better boss-relationship skills and they will serve you throughout your career.

Moe Rubenzahl

As a boss, I have to add a couple of comments. First, you missed the number one most important way: Be a great worker. It is much easier to give telecommute privileges to someone who does their job well with minimal supervision.

Second, the reasons you cite that a boss would not want a worker telecommuting all seem to presume that the boss is an idiot. Approach the issue with that kind of attitude and you’re not likely to get what you want. Try imagining that the boss has some good reasons and I expect you’ll be more likely to succeed. And remember, your boss has a boss, too, and if we’re smart, we will look for ways to all succeed together.


A useful gauge as to whether you can telework at all (this is before you make the pitch to the boss) is, how did you do the last time you looked for work? After all, that is work. Sure, you did eventually find a new job, but how focused was your job search effort? Did you have a routine at all? Did you have lots of distractions and fail to deal with them?

Don’t forget the other dimension of telework…losing your facetime with the boss. You do lose some ability to do the required politicking and self-promotion while you’re not there.

One way to broach telework is to float the idea of flex work first. Either four long shifts a week, or days where it’s up to you when you come in and leave, so long as you nail down 8 or so hours a day. If your boss and coworkers are inimical to this idea, give up on the working from home. On the other hand, they may be OK with flex time, and if that works out, it’s a foot in the door to suggest partial telework.


Michelle got it right. Bums in seats — that’s all they care about. Granted…it is nice to be able to come into the office whenever I feel like it (6am or 10am, who cares?). The requirements I have to fill, are that I don’t miss any scheduled meetings, and that when I get in I put in my “8 Hour’s”. So, for the last 4 days, I’ve been surfing the Internet…because I finished my only assignment for the week within 3 hours — but my bum still needs to be in this seat!!!!


I tried teleworking back in the 90s and it didn’t really work for me. One, I didn’t like being isolated from my coworkers. In an office environment I could take a break and chat with other people, most of which had the same interests as I. Sure, I could have called them on the phone but I like that face to face interaction. Two, when school let out for summer break my kids and wife (she taught school back then) were around all the time and that was a huge distraction. On the other hand, I did like wearing jeans and tee shirts everyday and not having to shave if I didn’t feel like it.

Nowadays I wonder though, if you can do your job from home, can someone else do it from India?

Sean Kelly

I agree with the commenter before who said it is not in the best interest of the manager in many cases.

However, if the manager has to hover in order to make himself feel secure in his position, he needs to look at what he actually needs to do himself in order to up productivity and turn out those TPS reports. If the manager is so worried about job security, and does not feel he can defend himself against an accusation that has the “your employees perform better away from you” ring to it, he was in trouble long before he was deciding on whether or not to allow employees to work from home.


With the ever-rising costs of fuel (and food, and living…) worldwide, along with pressure for companies to “go green”, one would think it would make sense to let as many employees as possible skip the commute – as long as they’re producing the results they’re paid for. Unfortunately that doesn’t seem to register on the management mind-set. I’m currently trying to find a way to telework for a day or two a week. Not at all easy when employers focusses on bums in seats during certain hours instead of what you produce.

In addition there seems to be disparity of opinion between bosses – one is happy to have his folk turning in quality work from home daily (leading to a pretty empty section), while others don’t care what you’re really up to, as long as you don’t arrive late or leave early. Consistency would be nice, especially if it’s in favour of telework.

Cali and Jody

Today, we toil and toil under the false assumption that face time = productivity = results. Many managers believe in this equation with their hearts and souls. They don’t even realize that there are people right under their noses, that they see for 12 hours a day, that are doing absolutely nothing for the business. In their eyes, they are the star performers.

Raza hit the nail on the head. To be comfortable with employees having control over how, when, and where they work, you need to be INSANELY focused on results. If not, everything goes to…you know where.

If you’re hitting up against resistance to being able to have freedom in how, when, and where you work, our advice is to band together with like-minded co-workers and demand the opportunity to show you can produce results under that system. If it’s treated as a one-off thing, or as a perk for the privileged few, it won’t work.

We’re all adults in the workplace and if we don’t deliver results, no job, right?

Cali Ressler and Jody Thompson
Creators of the Results-Only Work Environment (ROWE)
Authors of the forthcoming book “WHY WORK SUCKS AND HOW TO FIX IT”


I’ve bumped heads with the “old school” mindset. A previous employer always rewarded my efficiency with more work. It was all about ‘putting in your time’, not performance. In fact, he would hover behind me and ask what I was working on several times a day. I used Autohotkey scripts to trim hours of labor from my day, and he couldn’t stand watching the computers doing my work for me!

If I had been in a remote workplace, poor guy couldn’t have filled my spare time with his errands! How would he retrieve his dry cleaning?

Telework is about greater efficiency and effectiveness, isn’t it? It helps companies, not just employees.

Telework has become a recent obsession for me, and I’m interested in developing a forum for the topic. If anyone else is interested, please contact me.

My current job involves litigation support, but there have been plenty of ways to use the internet away from the office to manage projects. Sick days are a great, often uncontested, way to introduce teleworking to your employer. Just don’t suggest it bed-ridden… vomit and cold sweats don’t lend to mind-blowing productivity!


I teleworked 3 days a week for 6 years while working for a large non-profit in DC. It was the ONLY reason I stayed there for 6 years.

Non-salary based compensation is the wave of the future. Companies can’t afford to pay us more so they have to find ways to keep talent.

So look around yourself; if you are the ‘talent’ then suggest once a week telework at your next performance evaluation. A trial program that works tends to become defacto working environment.

Jon Smirl

Because he knows you have young children at home. It is a rare employee that can effectively telework when young children are around. The temptation to become a baby sitter is too large. So far I’ve never encountered anyone who can handle kids being present without it impacting their work.

Anita Bruzzese

I think it’s also true that when a boss doesn’t want you out of his sight it’s often because he or she is insecure. After all, if you perform BETTER when the boss is not around, what does that say about the boss’s usefulness? It’s often a delicate balancing act…keeping a boss’s ego stroked while gaining some independence for yourself. That’s why it helps to have a co-worker be ready to sound the alarm if the boss is feeling extra insecure (like the boss’s boss is on the warpath)…that’s when you put in more face time at the office to make sure the boss feels secure again.
Anita Bruzzese


Not everyone wants to be self-employed. Being an employee for the right company, for the right pay, with the right perks (e.g. teleworking) isn’t a bad life!


I think the fear is that you’ll get over on them and start moonlighting. I can’t blame them though. I would totally moonlight if I worked for someone else. I mean if you can work for someone else from home, why couldn’t you just start a business and do the same thing and make a lot more money?

The way to rectify this is for the manager to be insanely focused on productivity and results. If an employee is delivering consistent quality, I say let ’em work on the beach if they want to.

Raza Imam


I almost forgot. There’s one more reason: cowardice. Many managers are simply too afraid to do anything they’re not 1000% certain their higher-ups will approve of. Any action that will require an explanation will be avoided to the extent that manager fears upper-level mgt.


You’re forgetting the most Darwinian of reasons. If the organization comes to the conclusion that an employee can be productive WITHOUT a manager hovering over them – then that organization might just get rid of the manager(s). Gasp. Having employees work from within the corporate hive is job security for the manager. We live in a world with state of the art tech and prehistoric organizational structures (for the most part – at least in much of the US). People typically act in their own best interest. It’s not in a manager’s best interest in most command and control org settings to let you demonstrate your effectiveness independently. sad but far, far too often true. Most companies resemble the US Post Office far more than Microsoft, Google, or Apple.


Good overview of manager resistance to telecommuting. I wanted to add to the idea that managers say it won’t be fair. Its a silly excuse considering most people don’t get paid the same or have the same benefits even when doing the same job. Raises, extra time off and other perks are earned. Telecommuting can be a perk as well.

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