As much as distributed teams are becoming more common, there are still plenty of “traditional” companies out there who aren’t all too excited about allowing remote work. Here are a few tips on handling the situation of having to ask for more flexibility.

Whether you want or need to work remotely for a one-off time for traveling, a few days a week to take care of your kids, or go all out and fully remote, the initial discussion can be hard. It’s an unknown territory for a non-remote team, and there are a couple of things to keep in mind when bringing it up.


Before Teleport, I’ve been in a situation of having to ask my boss to let me work away from the office three times. The first two times it was a week every month when I knew I had to travel, and the final time was when I requested to go fully remote in a completely non-remote team. Here’s what I learned from these negotiations.

Understand the apprehension about remote workers

I wrote a post a while ago about the main roadblocks of remote work. Long story short – working remotely, especially if you’ve never done it before, is not easy. It requires a lot more self discipline than being in an office, plus better time management and independence skills. And your employer knows that. In 2011, Microsoft published a white paper entitled Work Without Walls, which also stated the main aspect of employers and employees viewing remote working differently – even though 62 percent of employees believe their productivity increases when they work remotely…:

“Business leaders assume employees who work remotely and take advantage of the policy are not really working. This is because of the loss of control. Employers lose direct oversight and cannot witness productivity firsthand.”

Nobody is being a control freak just for the sake of it. The real problem is that in a “traditional” work environment, someone going remote is a huge change and nobody (including you) can be a hundred percent sure how well you’ll be able to handle it – if the employer has no previous experience of having remote employees, they’re not sure what to expect.

From their perspective, letting you do this is a huge leap of faith that, as far as they’re concerned, might or might not seriously damage the team dynamics. Make an effort to truly understand those fears before you even bring it up.

Talk about what they will gain

One of the golden rules of making someone do a favor for you is not going on about what you will get out of it, but rather letting them know what they’ll be gaining. Using statements like “I want to travel the world” or “I get to see my family” won’t excite anyone besides yourself.

Try and think about what your company will gain from letting you have this extra freedom – will you be happier and therefore more productive? Will your time away score you some extra skills or knowledge you can use to benefit the entire team? Can you do some extra work or meet up with partners/clients/investors you wouldn’t be able to in the office? Will you save the company money? And don’t just think about it because you need a good argument to butter your boss into saying yes, genuinely think about how the company will benefit – you should care about that, too.

This was one of my biggest lessons when requesting for remote time – as much as I was only thinking about what I was getting out of it, my employers were only thinking about what they might lose. Sit down and talk about both sides – their side first.

Even if you want it all, start out in bits

Waltzing in and announcing you would like to work from home all the time from now on is not cool. Especially if you work in a company that has no previous remote working experience, try and ease into it gradually. Instead of going fully remote, propose giving it a test (using the same technique of letting them know what they’ll get out of it that I mentioned before). Say – work remotely for a few days, and see how it goes. If it works, you can think about extending that time.

Be patient – you can’t have everything you want and need right away. This decision isn’t affecting only you, it’s affecting your coworkers as well. Carefully sliding into the new situation helps everyone cope with it better and creates less barriers all at once.

Make an solid action plan

Words aren’t enough. First of all, figure out a system that you think or know will help you stay productive while away – whether it’s time tracking and management to make sure you do your hours, a task management system you can use to show progress and completed assignments, a good backup supply of coffee, ear plugs to eliminate distractions, or all of that combined.


Secondly, if you’re going away on a one-off occasion for a very specific time on specific dates and you know what you should be doing during that time, make a task list, plan your time for each assignment, set deadlines. Make up a very detailed plan of what you’ll be doing and when, and then present this system to whoever you need permission from.

This whole process shows that you’re not taking your responsibilities any more lightly when you’re away than when you’re at the office – you’re taking them even more seriously and are willing and able to plan ahead and track your own progress.

Communicate and deliver

If after making a plan, explaining your reasons and motives and being a decent human being about it, you get a yes to your request, don’t ever take that as a permission to kick back and relax. You’ve made a promise to stay productive and check yourself (before you wreck yourself) and you need to keep to it. Don’t ever abuse the trust you’ve been granted. According to the aforementioned Microsoft whitepaper:

“Information workers top two pet peeves with colleagues working remotely are inability to speak face-to-face and lack of a quick response.”

Give as many updates as you can to whoever you work for as well as your teammates – clarity and communication are extra important when you’re not in the same physical space as others – make sure everyone knows what you’re up to at all times. Make a writeup of your plans each morning, let people know what you’ve accomplished by the end of the day, and be available when you should be. Don’t go AWOL no matter what, especially if you know your non-remote team members depend on you.

Being aggressive doesn’t benefit anyone

Like I said before – employers can be wary of letting you do this, no matter how much you want to. If they say no, your first reaction should never be to be pissed off. Remember the “try to understand their side” point? Roll on that now – instead of storming out, talk it out. Ask why they’re against it. Don’t start an argument – start a discussion, and explain your side of things again, calmly.

Even if nothing comes out of it, you’ll hopefully at least have a better understanding of how your employer feels, and there will be little to no hard feelings. If you are still upset – be an adult and keep it to yourself – unless you really feel like you’re being treated unfairly, but then you need to think long and hard about whether it’s actually unfair or not. If your job wasn’t a remote one to begin with, then remember that your employer doesn’t owe you anything, and they have every right to turn you down.

The one time I got rejected to fulfil my remote working dreams, I was so horribly butthurt it clouded every bit of reasonable thinking I had. I sulked for a good amount of time, and it only made things worse – until I realized it’s not worth damaging my relationship with my workplace. Your employer makes their decisions for a reason, and if the answer is no, it’s a no. It might seem harsh, but back-talking, complaining or throwing a hissy fit isn’t going to improve your situation. There’s no point – you don’t want to have to stay working in the office and piss people off.

If everything else fails, consider an actual remote job

So, the answer was a no. All you have left to do now is to make the decision of how important gaining that extra bit of flexibility is for you. If it was a one-off thing you wanted to do, you’ll probably swallow it up and get on with your life. However, if remote work – whether all the time or part-time – is something you feel like you need or truly want to do, you’ll have to consider if you’re willing to let go or not.

I was in that situation with my previous workplace – after a long and strenuous discussion and process (including all of the points I mentioned before) I got a resounding no to my request. I had a think, and realized I needed that flexibility in my life – needed, not wanted. So, I quit. Two months later I found Teleport and am now a full-time happy remote working camper.

If you truly think you want to take the plunge and find yourself a real remote job, do it! Remote working isn’t the odd out thing it used to be – more and more people and companies are embracing working from home:


Also, have a look at this talk by Coby Chapple from GitHub about remote work being the future (we believe it is, too) and how to make it not suck. Working in remote companies is fun – we promise!

Inspired? To start out, have a look at our review and comparison of the best remote work sites out there, and get applying.

All in all – if you work in a non-remote team, bringing this topic up probably isn’t going to be easy – and if it is, please don’t take it for granted. It’s a big change for both you and your team, and the best way to go about it is to stay calm and rationalize your own motives as well as your employer’s. Good luck!

What are your experiences with asking to work remotely in a non-remote team and what’s the best advice you’d like to share with people in the same position? Join in on the discussion in the comments!

Elen Veenpere is part of the Teleport team, spending most of her time writing all kinds of content for everything Teleport. When she’s not busy typing, she likes to travel around the UK doing stand up comedy and drinking coffee.