Play podcast

5 most common problems for remote companies

Table of Contents
I.Problem 1: Maintaining company culture while growing
II.Problem 2: Effective Communication and Collaboration
III.Problem 3: Social Interaction
IV.Problem 4: Hiring
V.Problem 5: Time Off
Over the last two months we reached out to over 300 remote companies to find out what are their biggest challenges when building and scaling a company remotely. Here’s what they shared with us.

Problem 1: Maintaining company culture while growing

Most of the challenges mentioned in this research fall under the umbrella of “culture building.” Creating a sense of belonging and collaboration for a remote team, as well as preserving one's culture as a company grows, can be incredibly difficult for remote organizations. 
How can you solve it?
According to Darcy Boles - Head of the award-winning culture at TaxJar - remote does not necessarily make it harder to create a thriving culture, but reveals when a company is not taking culture seriously.
“Values and culture in a co-located space can easily just be glass-plaques on a wall. And when you go remote it does not kill culture it reveals it, very quickly.”
Her biggest tips for creating a sense of belonging among your employees is to actually focus on the employees themselves:
  1. Determine - and live -  your values as a company and hire people that fit those values. 
  2. Ask your employees what you could improve through regular surveying, while you scale
  3. Create a sense of belonging by finding common interests in your team.
“If your intrinsic values match that of the company (you work for), you don’t need external motivation, because you are naturally driven in the work that you do.”

Problem 2: Effective Communication and Collaboration

Effective communication is one of the most important assets of a remote company, and that might be why this is one of the biggest challenges mentioned in our survey.  Possibilities to facilitate critical conversations being missed. Founders are struggling to communicate the company culture, vision and values. 
How can you solve it?
When discussing effective remote communication with Uri Bram from The Browser, he mentioned the concept of tacit knowledge: 
“(Tacit knowledge) is, for me, the difference between watching someone cook and reading a recipe book. No matter how good the recipe book is, it just can't explain the entire process.”
So how can you effectively replicate the experience of communicating with someone else in person? While accepting that there will always be certain limitations to human interaction online, here are some starting points:
  • Use Loom: Introducing new people to your company and giving/requesting feedback are just a few of many other use-cases
  • Document what you can: From your values and mission to processes of your company and decisions made, documenting every part of your company is key to functioning remotely and will be a great asset once you scale. GitLabs handbook is a great example of this practice
  • Provide context around existing systems in the company through knowledge-sharing software like Notion.
According to Rajiv Ayyangar - the founder and CEO of Tandem - the world of e-sports can be a great inspiration for effective remote communication: 
“For the world that has just gone remote there is still this question: can you actually form the same level of trust as you would in person? And the thing that gave us a lot of confidence, is when you look at an entire generation making friends through playing games and talking on Discord.”

Problem 3: Social Interaction

Especially in the last year, working remotely has been more challenging than usual as social interaction was impossible for most of us (both in and out of the workplace). 
Whereas many remote companies had physical meetups at least once a year, many teams did not see each other physically for over twelve months. For a company that is scaling, half the team or more may have never met anyone in person. This is posing an extra challenge for teams that transitioned from a hybrid or fully co-located model to fully remote. They subsequently miss physical brainstorming and watercooler moments. 
Since the beginning of the pandemic, households with symptoms of Anxiety and Depressive Disorders increased by 30%.
How can you solve it?
If you are a remote company that did not have any physical meetups before the pandemic, we would definitely recommend doing so once it is possible again. Until then, there are a lot of fun ways to host a virtual team gathering. 
Furthermore, virtual offices like Tandem or Teamflow, or software like Focusmate make it possible to work together in a virtual space, which makes a big difference in terms of creating a sense of belonging. It works great for us at SafetyWing!
Rather than an obstacle, Flo - the CEO of Teamflow - sees remote as an opportunity for social interaction and the office itself:
“It's very effective to have a room that is dedicated to a project in which the whole team can come together and put all the artifacts they need in it. You would imagine, now that we have gone remote and that we have infinite real estate, we would use it to create infinite working rooms. But instead we have zero of them.”
According to Rajiv Ayyangar, in a remote team “everybody's talking all the time and nobody sees anybody talking.” This can be extremely demotivating because employees feel less encouraged to voice what's on their mind and can have the impression that they are the only ones actually working (or the concern that no one sees them working). 
A virtual office is vital because it not only gives better possibilities to collaborate but also gives a stronger sense of collaboration. Using software like Tandem or Teamflow is definitely a better solution than having hour-long working sessions via Zoom or Google Hangouts. 
Finally, it is just as important to be very mindful about informal communication when you are remote. According to Darren Murph from Gitlab:Remote companies need to be very intentional about informal communication. This is something co-located companies get a pass on.
Bring employees together through shared interests. At TaxJar, Darcy and her team created dedicated informal Slack channels and organized mutual teaching sessions among the team as well as an annual bake-off. At SafetyWing we have a book club, a writing club, and other ways for people to share their interests through their work. 

Problem 4: Hiring

Not everyone is a perfect fit for working remotely. Even if you find a great candidate, it can be a whole different challenge to set up an international contract and onboard employees effectively. That makes it a double sided problem. It’s hard to find that talent you want to hire, and almost just as hard to actually hire them once you’ve found them. 
How can you solve it?
To hire great people you need to find and attract them first. This is big enough of a challenge for most companies, which is why we wrote up a guide to beat big tech to the best remote talent.
When discussing this topic with Austen Allred - the founder and CEO of Lambda School - he mentioned that, while the competition for talent is bigger, the talent pool accessible to you has increased ten, if not a hundredfold. 
To capture this talent it is important to:
  1. Be attractive: Determine and communicate your values as a company. Create a great company culture people feel drawn to and want to join.
  2. Hire effectively: Don’t neglect great candidates because they might be in a different jurisdiction, timezone or country. Being open to hiring talent in unconventional ways is still a competitive advantage. Not doing so will soon be a fallacy.  
Darcy Boles recommends to clearly determine the values of your company first and then hire based on those values to determine the “culture fit” of your employees. Many companies actually have their values written on their webpage and if you have not done so already, you definitely should! 
Here is Darcy talking about how you can clearly determine values in a job interview: 
“A question that we use sometimes in our shared values interview is, ”Talk to me a little bit about a time where you totally messed up and you got negative feedback and how you handled it.” What does that show us? Does it show us that the person is humble or does it show us that they didn't care and they didn't take responsibility? So it showed us that they're willing to learn and grow, or does it show us they just thought that it was somebody else's fault. I've heard that answer multiple times. And so you can really start to design the right questions and not have to ask a lot of them to discover the underlying layers of how people actually live their values and what their values are.”
Services like make it increasingly seamless to hire and offer benefits to remote employees. When talking with Matt Drozdzynski from Pilot, he brought up an interesting question:
“The moment that you have folks that are in different time zones, then you start thinking why am I okay hiring someone in New York, but not someone in Sao Paulo, Brazil where the time difference is effectively the same.”

Problem 5: Time Off

Creating a balance between work and play, as well as general mental health issues have been mentioned as one of the top challenges from the participants of our survey. 
And while the fact that we experience a global pandemic probably has a role to play in these results, finding time to unplug has always been a challenge for remote teams. According to Buffer, 22% of remote workers faced this challenge in 2019 (which has since decreased to 18%). 
How can you solve it?
We outlined some ways how you can give yourself a mental health boost earlier this year, which includes tips for structuring your day and balancing your life while working remotely. 
When it comes to managing a remote team, Danielle Morrill from Gitlab mentioned that it is important to acknowledge and celebrate when a goal is reached: 
“My goal is to manage teams that hit their goal. And when they do hit that goal, how do we celebrate that win and actually stop and reset?”
Other ways you can employ to motivate your team to take a rest:
  1. Mandatory time-off: Create a minimum amount of days every employee needs to take off each year/quarter 
  2. Allow your team to take a Meeting Sabbatical
  3. Make it impossible to work when you should not work. Take the company offline on weekends and holidays. Don’t use Slack, don’t check your mails. If the company is offline, employees will follow. 
  4. Take mental health seriously. Give employees the possibility to seek help if they need it. Not only does that create a direct employee benefit but gives employees a sign of support and safety. 

Is there a challenge you experience with working remotely? If there is a topic you would like to see covered on Building Remotely Podcast or Blog you can reach out to me via I look forward to your message! :)

About the author

Jakob Bodendieck

Podcast Production Manager
Jakob is a startup-oriented nomad, recently completed his BA in Creative Business in the Netherlands. He joined SafetyWing as a Podcast Production Manager and helped create and grow the Building Remotely podcast. As the host of his own podcast, The Self Employed Student, he is offering a valuable resource for other young people with an entrepreneurial mindset.