5 Questions to Ask Yourself Before Starting A Remote Company

Evelin Andrespok
Jun 12 · 9 min read

The future of work and remote work are some of the hottest business buzzwords in the recent years. We transitioned to remote work at Toggl five years ago and never looked back, so sometimes I feel like we must be living in the future. It has become the new normal to us. Buzzwords or not, but it is evident that there is growing demand among the global workforce to have more flexible schedules. Because of this I have received quite a lot of questions about if and how more companies could offer the option to work remotely. If you are one of the entrepreneurs thinking about starting a remote company or simply want to offer more work-from-home options to your team, here are some key questions to ask yourself before making the leap.


1. What is your motivation for going remote?

It is not going to work if your main goal as a founder is to save money on keeping an office (although it is a likely side effect). You have to really want it, because you think it brings value to your business and your employees.

Stanford professor Nicholas Bloom revealed in a study that employee attrition was 50 percent lower among China’s largest travel agency’s remote workers, because among other thing they take shorter breaks and had fewer sick days. From what I hear from others and based on our experience at Toggl, remote setup helps attract and retain amazing talent from all around the world. You know that a strong team is what makes the business flourish and this is the motivation that should guide you.

What is more, studies have proven that above all else remote workers appreciate the better work-life balance that comes with flexible work and from not having to commute for hours every day. Many are even willing to take a pay cut in exchange for the option of telecommuting. Remote workers are more productive and engaged, because they can fit work into their life not the other way around. Feeling trusted to get work done regardless of location creates loyalty. You should go remote if you believe it will be a win-win situation for both your company and your team members.

2. What type of remote company do you want?

There are many types of remote work and you should decide, which one suits you best. Think about how deeply you are willing to commit.

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The most liberal approach is going fully remote (also known as remote-only or all-remote), which means not having an office at all. Your team can be located in a single country or you can go all in and give your team members the freedom to live anywhere on planet Earth as long as they have internet access. You can choose to limit your working hours to a certain time or you can hire across countries and time zones.

This is the most “future or work” approach and will surely make you stand out among the other employers. You should take into consideration that you will have to re-think a lot of the traditional approaches to management and team building. Not being able to see your colleagues on a daily basis means you will need to find new and innovative ways to hold meetings, making plans and creating fun moments the build the necessary human connection. The unknown territory may scare you, but I guarantee that it is an extremely rewarding experience if you give it your all.

Examples of fully distributed companies are Automattic, Basecamp, Buffer, Doist, GitLab, Help Scout, InVision, Toggl, Zapier and more than 150 others.

You could also opt for the more commonplace remote-first hybrid approach, where your communication and collaboration is set up in a way that completely enables working remotely, but you still have a brick and mortar office for some of the meetings, collaboration and socializing. In this setup going to the office is not required, but is possible and encouraged for those who want or need it.

The main premise is that every person on the team gets to choose where and how they do their best work. The CEO of Litmus has listed the top 10 tenets of remote-first and points out that the number one element is committing to being remote-first 100% of the time and making sure every person can participate in the work regardless of their location. Remote people should never feel like second class citizens for not coming to the office.

Some examples of remote-first companies are Amazon, Litmus, Netguru, Owl Labs, Salesforce, Stack Overflow and Stripe.

The mildest option is being remote-friendly and allowing your team members to work from home once in a while. Often such companies do not have clear systems for remote communication and the work-from-homes days are spent on independent deep work. The remote days are taken ad hoc and are usually “need”-based.

On the one hand, this is an easy and likely the most popular way for companies to start experimenting with remote work. You can test how remote work affects your company culture and productivity as a team. On the other hand, you need to be extra clear when setting up the communication channels and expectations, so that everyone is included in the important discussions and feels like a part of the team. You should make sure working remotely does not create exclusion — rather it should signal to your people that the company offers the best possible working environment for each person and appreciates work-life balance.

3. Does your team want it, too?

If you already have a co-located team and you are thinking of transitioning to a remote setup, you need to ask your team how they feel about it. Your team members are likely to have concerns about working from home and you should find answers to their question as a team. Some people might not be able to work from their homes due to personal reasons, others might not be comfortable with the new communication tools and yet others might need help with establishing borders between work and personal life. At Toggl, even after years of working remotely, we are constantly discussing how to make this modern way or working easier on the body and the mind.

If you are just starting a company and decide to be remote from the beginning, it is still necessary to have a constant conversation with your team about how remote work works for them. Ask your HR team to make building a remote work culture part of their mission.

Involving your team in these discussions will unveil any possible problems faster. It will also give everyone ownership of the process and increases team spirit through tackling a common challenge. Communicating honestly and openly about the good, the bad and the ugly is a cornerstone of remote work and you should embrace that from day one.

4. Are you willing to trust your team members?

“How do I know people will actually work when they are not in the office?” is by far the most common concern managers have about going remote. My answer is always the same: you know it the same way you would if they were in the office — you look at their results.

Brenna Loury has written an excellent article about her best practices of managing remote employees as head of marketing at Doist. She says that managing is not about monitoring the amount of time your team members spend online, but about building and supporting a team that doesn’t need to be micromanaged in the first place.

It all comes down to trusting the people you have hired. Seeing someone sit on a chair all day is no proof of work getting done. You need to clearly identify the goals and tasks, so everyone knows what is expected. Then you need to treat people as adults and trust them to be responsible. That is why you hired them in the first place, isn’t it? If you can’t tell if work gets done or not, then you have to rethink your goal-setting strategy as a manager first and only then suspect your team members of slacking off. Be really honest with yourself when answering this question.

5. Which tools will your team need to succeed?

The first thing you need to figure out before going remote is how daily communication will take place. Decide if you want synchronous or asynchronous communication or some kind of a hybrid model and then choose the appropriate tool. There is an abundance of collaboration tools out there like Slack, Twist, Skype, HipChat and others. In addition, you can find services for video calls (i.e. Zoom, Google Hangouts) and for managing projects and tasks (i.e. Asana, Trello, Teamweek). Make sure everyone in the company knows what tools you have and how they should be used.

You would be surprised to see how much communication and productivity technology has advanced over the past few years. In fact, many of the new tools have been built by remote companies for themselves first and then shared with the world. Examples of this are InVision for designers, Twist for team communication, Teamweek for project management, Happy Tools by Automattic for team scheduling and the list keeps growing as more and more companies embrace remote work.

Another pragmatic thing to think about is how much you can support people with setting up their home offices or finding a co-working space. You will learn almost immediately that having a good internet connection is super important for remote workers and in the interest of work not dragging due of technical obstacles, you should consider reimbursing internet expenses. Having a productive and healthy home office or co-working space setup is just as important as providing ergonomic chairs and equipment at a regular office, so do not skimp on that part either.


To sum it up, before starting a new remote company or transitioning your existing to that path, ask yourself why and how you will go about it. However, regardless of which type of remote company you choose to build, the leadership must be behind it 100% and understand the ‘why’ behind the decision. Mixed signals from the leaders will erode trust faster than a hot knife cuts through butter. Keep in mind that you will have higher chances of success with transitioning to remote work if you involve your team in the debate. Trust your team to tell you how they work best and provide them with the support and tools they need to succeed.

Last but not least, remember that while any type of remote work seems completely new and different — it is still just good old work. Entrepreneur and angel investor Hiten Shah has explained this beautifully:

“People tend to overemphasize the fact that it’s different, and then all of their conversations start by focusing on the difference. So then remote work gets treated as something completely different by everyone. We’re still all working together. We’re still one company. Everyone’s still getting a paycheck.”


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Evelin Andrespok

Written by

People ops team lead at Toggl herding cats in a growing team distributed across 30+ countries.

The Startup

Medium's largest active publication, followed by +539K people. Follow to join our community.

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