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Common challenges for remote companies & solutions

Table of Contents
I.Here are the most common remote work challenges for companies
1. 1.Problem 1: Maintaining company culture while growing
1. 1. 1.How can you solve it?
1. 2.Problem 2: Effective Communication and Collaboration
1. 2. 1.How can you solve it?
1. 3.Problem 3: Social Interaction
1. 3. 1.How can you solve it?
1. 4.Problem 4: Hiring
1. 4. 1.How can you solve it?
1. 5.Problem 5: Time Off
1. 5. 1.How can you solve it?
1. 6.Problem 6: Onboarding
1. 6. 1.How can you solve it?  
1. 7.Problem 7: Employee feedback
1. 7. 1.How can you solve it? 
1. 8.Problem 8: Asynchronous communication
1. 8. 1.How can you solve it?
1. 9.Problem 9: Time zone differences
1. 9. 1.How can you solve it?
1. 10.Problem 10: Trust and accountability
1. 10. 1.How can you solve it?
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.

Here are the most common remote work challenges for companies

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 remote work communication 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.
  • Provide context around existing systems in the company through knowledge-sharing software like Notion.
There are many available tools for better remote team collaboration and communication to choose from. So do your research and find the ones that serve you best.
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 a big remote work challenge for companies with 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. 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 challenge many companies face with remote work. 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 Pilot.co 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. 

Problem 6: Onboarding

With the sudden change in the way people are approaching employment and acquiring employees, the process of onboarding staff has completely changed. These changes have brought with them many different challenges that need to be solved remotely. In the former working landscape, companies were able to have direct and sociable interaction with their new staff in a physical location. Nowadays, this is a fully remote, and oftentimes largely asynchronous process.
Remote companies are having to overcome this lack of physical connection during the onboarding process. Successful onboarding can increase employee retention by an incredible 82%.
With all this being said, remote companies still struggle with this process. Older methods of integration often fall short due to the remote nature of the worker. This can then lead to a sense of detachment, leading to poor performance and a lower desire to stay with the company.

How can you solve it?  

There are many ways for solving the modern problem of onboarding remotely, and these range from the culture of the company and its practices to a more software-based solution.
One of the best solutions is to have a designated person in-house that will focus on the role of onboarding new arrivals - acting as a go-between the new employee and the inner working of the company. This will allow the new employee to see a friendly face, who can then introduce them to the company's mission, roadmap and the rest of the team. 
In our team at SafetyWing, the Head of Culture takes on this role. For us, this was the perfect choice for a first introduction to the culture and processes of the company. Through the onboarding process, the Head of Culture will take the new arrival through an onboarding checklist. This checklist makes sure that the new employee has a clear understanding of the mission and vision of the company, enabling them to know the culture of the company from day one.
Next, the onboarding process should ensure that the employee is introduced to a clear roadmap of how their time at the company will look during the next year and in the long term. This allows the new recruit to see a clear path ahead and what they can expect from the role. 
Another way to make the onboarding process successful, and something that has proven to work at SafetyWing, is to arrange a one-to-one introductory meeting with each of the existing team members. 
However, this can be difficult to arrange as your company grows and expands its team. If this is the case, it is arguably more advisable to set up one-to-one introductory meetings with people relevant to their role that they will closely work with. Initiating an onboarding process such as the one Nicole Vasquez, the Co-Founder and Chief People Officer of Deskpass has introduced proves that you are able to continue good onboarding practice, even when scaling up your business.
As well as efficient onboarding practices, you should also use software to your advantage. Using a communication platform such as Slack allows you to get to know others and how the company is functioning. It also gives your team the opportunity to connect. In our workspace on Slack, we have something known as the “window-of-life”, a Slack channel where people post random day-to-day photos of what they’re up to. For new hires, this is a great way to get to their new teammates.
Overall, it's important to make an effort towards creating a feeling of welcomeness, inclusion and answering any first-day-at-work questions. It is also important to remember that having a wide range of people in your workforce, especially a remote one, will mean that you will undoubtedly have people from all walks of life, backgrounds, cultures and personalities. Adapting to all of this and making everybody welcome will ensure a great onboarding process.

Problem 7: Employee feedback

As I mentioned earlier, under the older and more traditional workspace, it was easier to get immediate feedback from your employees. Being in one building or office ensures the line for communication is practically always open and clear. 
With the birth of remote work, it has become a common problem for remote companies to get direct employee feedback. No matter how small or large your team is, it is essential to have some kind of process in place for it.

How can you solve it? 

Solving this issue simply comes down to good leadership qualities. It’s important for founders, managers and team leaders to have an openness to honest criticism and feedback.
This also has a lot to do with your own curiosity about improvement, something that is only ever going to help your company grow and succeed. Growmotelty’s CEO and founder Sarah Hawley highlights the need for this in her recently published book Conscious Leadership: A Journey from Ego to Heart.
There are a number of things you can do to improve and solve the challenges of remote employee feedback. For example, creating feedback buddies, where employees pair up with co-workers and talk at regular intervals. Within these bubbles, employees can chat and mention any feedback they have for each other throughout the year.
When it comes to direct feedback to team leaders and founders, it's a great idea to set up one-to-one meetings, monthly, bi-monthly or quarterly. In these meetings, managers come with an open mind and create a space where employees can provide honest and open feedback.
Having to give feedback or criticism face-to-face can be an uncomfortable experience for many people and often pushes them to sugarcoat or hold opinions back. To overcome this, why not create an anonymous forum for the company. This way, those who don't wish to make open criticism or give direct feedback can post on the forum anonymously, without self-editing. 
Conducting an end-of-year survey where everyone gives feedback to the group is also a good idea. This allows each member to choose something that was done well and something that could be improved on.

Problem 8: Asynchronous communication

In the usual setting of a remote company, communication between employees at any level can be more or less instant and direct. Simply being able to pull someone aside or send an email within the same building once allowed us to have this instant line of communication. Now, with working remotely with people in different time zones, this is often impossible to do. 
Many companies have tried to adopt a hybrid work model, but this doesn’t solve the issue.

How can you solve it?

If you are planning to alter your business’s approach to a hybrid working model, it’s still best practice to have remote-first practices and policies in place. Regardless of those employees that will be working in a psychical location, you remote workers must be able to keep in contact and use successful asynchronous communication. This means you must adopt a remote work culture and have this at the heart of your business.
Remote companies that have a worldwide workforce may even choose to go fully asynchronous. To help you achieve this, there are a swathe of different platforms and software you can use to achieve this. The platform of Loom is a popular option for those looking to bring a bit of face to face interaction. By using the software for Loom video recording, you are able to record video messages to you and your workforce. As it is well known, the majority of communication is nonverbal. This then allows the subtlety of communication that only body language and facial expressions can bring.  
Another hugely popular platform is Slack, the business communication platform. This allows bubbles and groups to form and have interactions over different time zones, which brings successful asynchronous communication.
Notion is another platform that can help create smoother asynchronous communication. This platform allows businesses to help their company or organisation coordinate deadlines, objectives and assignments for the sake of efficiency and productivity. 
The software Almanac is a super helpful tool that will allow you to synchronise documents and objectives. This helps different employees who work on the same project who are maybe working in different time zones and hours. All of these platforms will take the stress and hassle of coordinating information across huge groups, leading to a healthy and workable culture of asynchronous communication.
Although we have seen a boom in the use of software such as Zoom over the past few years, having real-time instant video communication isn't always the best approach. A phenomenon that can only be called Zoom fatigue can bring down productivity levels and leave employees with a sense of constant communication requirements. Asynchronous communication allows you to truly make the most out of working remotely and allows you the freedom of working whenever you feel most motivated. This also means you dont waste time on too many meetings unless it is wholly necessary.  
Before booking another meeting, take yourself through a number of points and assess whether you need yet another face to face meeting. You can do this by first reaching out to a team member and telling them your thoughts or asking for their help. This may allow you to get an instant result without bringing the whole workforce together for a synchronised meeting.  
It’s also important to question why you’re having the meeting in the first place. If there's not a topic of definite reason to be calling the meeting, then it is simply a waste of time and productivity. If the meeting isn’t going to resolve a problem, bring clarity to the situation or advance your business in any way, then simply don’t call one for the sake of one.
If you still don’t want to be fully asynchronous then there are some things you will have to do without. You won’t be able to hire in time zones that can’t accommodate those meeting times. If you’re in the US or Europe, the only way to work with someone in Asia is to be fully async. If you do wish to call a meeting, it is also important to communicate to everyone when they’ll be expected to be on a certain recurring meeting.
Making this transition to asynchronous communication and as a fully remote business can sometimes be a frustrating and difficult transition to make alone. Consider hiring a Head of Remote or someone to help specifically with this transition.

Problem 9: Time zone differences

One of the most dramatic changes to come out of the remote work revolution is the way in which global workforces are coming together to work within one company and towards one goal. Remote work allows you to hire from a pool of talent that stretches across the seven continents. Although this has had a fantastic effect on the ability to hire the best of the best, certain problems have arisen. 
One of the most dramatic changes to come out of the remote work revolution is the way in which global workforces are coming together to work within one company and towards one goal. Remote work allows you to hire from a pool of talent that stretches across the seven continents. Although this has had a fantastic effect on the ability to hire the best of the best, certain problems have arisen. 
One of the biggest of these is the sheer difference in time zones between workers across the globe. As the working day is ending for one of your employees, it's more than possible that it’s just about to begin for another. Bridging the gaps between these vast time zones is a problem that must be overcome before you can make a true success of a remote business. There are a number of ways in which this can be overcome, with much of relying on an ethos and culture, as well as creating an agreeable structure that works for everybody.     

How can you solve it?

Solving the issue of vast time differences comes down to using the platforms and software you have to their utmost advantage. This means setting down rules for each one, whereby each employee knows how long they have to respond, creating a perfect balance of asynchronous communication. 
If you are operating over email, agree that a response will be needed within a few days. This allows those in different time zones to both read the email, take the necessary actions and reply within their own working hours. If you are conducting communications over on the platform Slack, this is seen as a far more personal and direct method; you can expect a reply within 24 hours. It’s important in this instant communication day and age to allow employees to have a sense of disconnection. This being said, it's seen as quite unprofessional to contact staff directly through personal message services such as Whatsapp unless it is an emergency.
As well as thinking about communications over time zones, remote work challenges for companies working over vast time zones can include organising meetings. It is important to implement a healthy work-life balance for all employees, regardless of where they are working in the world. 
This being said, it's good practice not to arrange meetings past 7 or 8 pm, no matter where they are. Remote working also honours the age-old pleasure of having weekends off for most companies. This being the case, it's not good practice to arrange meetings over the weekends, where your employees are striving to keep that work-life balance.   
Although we are working in a hyper-connected environment as remote companies, it’s wise to not always assume that people are online all day and available just as a given. Even where you may share time zones, don’t assume that they are always free and available for meetings; communication is the key. 

Problem 10: Trust and accountability

The historic and cliche image of the prowling manager, with one eye on the workforce, is fastly becoming a thing of the past. Employee’s work was once overseen by management and team leaders, ensuring they were working at the most efficient level and giving it their all. 
Now, unsurprisingly by its very nature, remote working has taken this element away. What you are left with is a gap that can be exploited by those who aren't as professional as we all may wish them to be. There are a number of ways to overcome this problem, and again, it's born out of good people management trust on both sides and developing a culture where trust and accountability is only second nature.

How can you solve it?

As many of us may have seen, there is a plethora of software available that will enable you to monitor screen time and activities. We would argue that this isn't the best road to go down if you want to create a long-lasting feeling of trust. Alongside this, it will not create a happy and motivated remote team, and it’s not a direction we want to be heading in as the builders of the future of remote work.
To be able to trust your employees to bring about the best in themselves and dedication to the company, the management themselves must trust their employees. Trust is one of the most central components of a company and without it, there is no integrity or stability to allow your company to grow. So, be generous with your trust.
Finding the right person who you can trust should be a strong integral part of your hiring process. A hiring process that may take much longer but strives to find those who are trustworthy will be far more beneficial in the long run. Management and company founders must be aware of the trapping of home life and working remotely. Having an understanding of how things such as children, pets, noisy neighbors, family and much more can be a distraction to productivity will create trust in those who experience it.
You are within your right to expect the best out of your employees, yet making their life easier to see this through can also make the world of difference. Providing employees with a home office stipend that they can spend on better office equipment, noise-canceling headphones and other helpful resources will also encourage mutual trust. 
This world of mutual trust between companies and their remote employees has become one of the most talked-about challenges of remote work and has raised many different opinions and approaches. Podcasts, articles and studies all have taken this problem in hand, bringing about a dialogue that is only ever-growing.

The route to approaching and solving these challenges with remote work is to understand and never let go of the human elements. The gap between global workforces and humanity as a whole becomes ever smaller thanks to technological innovations. This may force many to forget the human emotional and personal core behind the faceless screen. Being open to these unchanged social and emotional needs will only bring remote workers ever closer to one goal and eventual company success.
Whether this is understanding communication needs, the currency of time or the need to forget what has gone before, the world of remote working is only going to grow.   
Is there another challenge with remote work you are facing? If there is a topic you would like to see covered on Building Remotely Podcast or Blog you can reach out to me via jakob@safetywing.com. 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.