Challenges of a Remote Working, Flexible Hours Setup

My company was born as a pure, unadulterated remote company. All the team works remotely right now, and it has been like that since I hired my first employee while recovering from a serious infection in Latvia.

Since the beginning, also, my employees enjoy flexible working hours. As we are also distributed through different timezones (El Salvador, Brazil, Argentina, Spain, Estonia, Ukraine, etc), that means also completely disparate working hours . One may think that a business can not work with such a setup, but we have grown from a couple of customers in 2018 to more than a thousand now.

Unavoidably, the team has been growing alongside the customers. From our humble beginnings with just a group of three people, my team has expanded to more than thirty souls now (that’s a tenfold increase in less than three years). As a result, the needs of the company have changed significantly, and now I find myself in a situation where that remote working, flexible hours setup is not working for some parts of the company anymore, and I need to rethink the way we work if we want to not just keep on growing, but progress to a new stage.

This article describes the motivation behind this change in the way I wanted my company to be structured, and the reasons why it may be critical for any business in that same scenario.

Remote First

As a digital nomad, and a strong supporter of individual freedom, I designed my company to be remote-first from the very beginning. I wanted my whole team to benefit from the freedom I enjoy.

When your company is small, its success depends on the personal commitment of its members and employees. At the beginning, it was easy. We were just three, and the business thrived thanks to our individual efforts. There was a strong sense of connection and responsibility, even if we all were in different countries.

When the company started to grow bigger, we faced a new challenge. How can we assure that the employees will be as devoted as we were, working their hours, and giving their best to make sure the business succeeded? We tested different strategies, from time management tools to task delegation, and we managed to keep our remote-first, flexible hours approach in a satisfactory way.

This has mostly worked for us so far. We’ve had some awkward moments, and there are some problems I will describe next, but it has been more or less ok until now.

Of Commitment And Flexible Hours

One of the problems when your team grows bigger is the different sense of commitment of its members. When you offer remote work and flexible hours, and your employees are distributed in different timezones, there are some people who are always “there” and some others that feel like “ghosts”.

The solution is not as simple as tracking their time or demanding them to always be online on Slack. We now have people from different cultures, ages, countries, and technical levels. Some of them work from home, some from a co-working space. Some of them have children, some are single. Some of them are millennials or even centennials, some others are less agile when it comes to computers and software tools. It’s a quite diverse gang.

Some formulas that I am considering include establishing the working hours of the team and coming with a more predictable schedule, so everybody knows when the rest of the team is available. That, of course, means depriving the employees of their flexible hours, which is something I would like to avoid.

Problems Of A Completely Remote Working Setup

In our experience, remote working setups work well in some situations… and not so well in others.

For that setup to work correctly, you need a strong leader in the department who can coordinate people working from different parts of the globe. It’s not an easy task. Not only because of the different commitments and timezones previously mentioned, but also because you need to create a sense of connection between the members of the team.

Sometimes, it is just not possible to create this cohesive spirit simply with Google Meet videoconferences and Slack. One example is our current offices in Tallinn. They are the heart of our company, and that’s where the Estonian accounting department is. So far, things have been working well. Our company encourages personal responsibility over hierarchies, people do their job, use the office at different times, and things work without major issues.

The Need Of A Corporate Culture

However, there’s still something missing. The fact that the team is not there at the same time during the whole week makes a difference. Even while the team is responsive, and you do regular meetings to talk about non-job related stuff, the connection is not completely there.

In order to get to the next level, I’ve come to the conclusion that I need to focus on bringing together the team, and sacrifice remote work for a closer relationship, where people know each other better, make jokes, talk about their weekends or favorite Netflix series at the coffee break… That will help solidify our corporate culture and bring the relationships of the members of that department to the fore.

After three years of leading a fully remote team, I know the limitations of a remote working setup. I know it works better for some areas of the business and not so well for others. That will imply a shift in our working environment and the organization of the team itself.

And that shift must not be taken recklessly. When a machine is working well, you don’t want to mess with any of its pieces. I have a period of transition in front of me. That’s exciting, but also challenging.

Always On The Brink Of Change

Owning a business is not for the faint-hearted. You are always waiting for that magical moment in which things will work flawlessly and you can spend your days answering a couple of mails and going to networking meetings. Well, it may work like that for some folks out there, but I still haven’t reached that sweet spot yet. 😅

Each one of these three years has had its own challenges, stressful situations, and problems. But also a lot of personal satisfaction and fulfillment. Having reached this point without venture capital, and having a company that’s been profitable from the beginning and has a net profitability ratio of 33% is something to be proud of.

And yet, I am still yearning for that moment of peace when everything will run smoothly without trouble, technical glitches, unexpected legislation changes, or department re-structuring processes.

But I digress…

The Perfect Remote Working, Flexible Hours Setup?

In conclusion, there’s no perfect setup, and no bulletproof answer to the question “Remote yes, or remote no?”, “Flexible hours yes, flexible hours no”. A remote working setup may be good for your company as a whole, or just for certain departments. You will need to experiment.

Also, don’t be scared of allowing flexible hours for your employees. It may work wonders for your company, keep your team happy, and bring you unexpected talent, people who just need a company that allows them to reconcile their family life or their studies with their jobs.

Your business is your baby, yes, but you should not be afraid of being bold and trying new things. Be honest and transparent with your employees, let them know when you change things why you are doing these changes, and that it may work or not. They will appreciate the honesty.