Is a Completely Remote Organization Possible? Here’s What We’ve Learned So Far

I waited until the last possible second, but it’s now my turn. I take a deep breath – gather my emotions – and reach for an invisible pen. What I’m about to say is incredibly uncomfortable, and I’m terrified of how others will respond.

I quietly say, “I’m overwhelmed. I feel frustrated and inadequate.”

We’re in the middle of our fully remote company check-in process, and it’s my turn to speak. This is a routine that we’ve used to start our meetings for the past two years, and it’s a method that helps us tap into some the human element that’s often missing when working from home.

There’s no actual pen, and grabbing it is an action that’s more symbolic than anything. It demonstrates the transfer of attention from one person to the next and is our version of a “talking stick.” When someone takes the pen, they have the floor – and for this check-in, I was sharing my raw emotions about where I was at that moment in time.

You see; our digital check-in process is not just a way for us to see how we’re doing with work, it’s a way for us to share our feelings and honest emotions about our lives outside of It’s a safe space for us to share our real thoughts and feelings about the pandemic, our personal relationships, and even our inadequacies.

Remote work is not easy, and when I launched the completely remote organization,, I knew that it’d take some time to work out the kinks. Now, in the wake of COVID-19, many companies across the globe are going through some of the same struggles I’ve faced over the last two years.

So, can you actually run a successful and completely remote company? Let’s find out.

Creating a Safe Environment for Remote Employees

The major downside of running a remote organization is that you miss out on a lot of the real human interaction you get from an office setting. Whether it’s body language, handshakes, or being able to look someone in the eye when you’re talking to them, we use these in-person social cues in order to gauge how people are doing emotionally.

Even if you’re just making small talk at the water cooler, you get a lot more insight into how a person is actually feeling when they say, “I’m fine”, when you ask how their week is going if you can see their expression and body language clearly.

These subtle interactions help develop a culture within the workplace, improves rapport, and strengthens relationships. As a completely remote organization, and as many others are learning through this pandemic, finding ways to generate “human interactions” with people on the other side of your screen can be difficult.

It is very hard to solve this dilemma, because you need to reach a high level of trust and safety within an organization to be able to let people feel comfortable enough to open up in a genuine way. What you can hear in someone’s voice if they have an issue is not what will typically be said in a weekly call with a group.

At, we’ve worked to solve this issue through our routine check-in process. We start every meeting with a check-in and have people delve into how they feel – not allowing a simple “I’m fine.”

The goal of these check-ins is to provide the opportunity that people need to describe their emotional wellbeing. Whether it’s “I’m stressed” or “I don’t feel well today” or “having my kids home all the time is stressful”, allowing your team to express openly will give you a better picture of how people are doing overall.

I always like to have people end their turn by giving a number between 1-100 of their general wellbeing. Whenever someone says a number below 50, that’s a big red flag that they are experiencing stress or burnout, and we stop the meeting to address that person’s needs – allowing them to withdraw themselves from the call or simply listen-in without the expectation of participating.

I’m proud to say that after two years, we’ve gotten to a really incredible place, and our employees are very open and honest during the check-in about their emotional state. Even as a remote organization, we’ve prioritized mental health and employee wellbeing, making it a safe environment that placed mental health and employee satisfaction over profits.

However, mental health isn’t the only roadblock a remote business comes with. Technology and process are also a big adjustment. 

Getting Buy-In for New Processes, Systems, and Tools

I started freaking out while on a walk recently – screaming with excitement. I began recording a video to send on Slack to our team and specifically, Angelica.

Why am I so excited?

I was thinking about Trello and how we could use it to improve Becoming Great, an entrepreneur podcast I co-host. I know what you’re thinking – “Why am I that excited about Trello?”

Well, Angelica has been pushing to get me and the rest of our team to integrate Trello into our systems for over a year now, and I was already resistant. Eventually, I gave in. Now, I can’t see running a business without it. I even use it in my personal life.

This story illustrates an issue that many organizations, remote or not, face which is getting buy-in for new tools, systems, and processes. However, operating a remote team makes acquisition more difficult and unfortunately, more important.

We’ve struggled to get buy-in for many of the tools that we now rely on such as Trello, Slack, and Google Drive. Most of the time, the issue was with me more than anything or anyone else.

As an owner, manager, or leader, it’s your responsibility to drive change in your organization. It’s taken me a while to understand this – but now, I’m much more receptive of new tools and solutions.

Remote companies need to embrace collaborative tools, communication solutions, and data management systems to improve business inefficiencies that are further strained while working from home. These technology platforms and improved processes can streamline your organization and make your remote team more agile and effective.

You can imagine how confusing and difficult it would be if you had some employees using Outlook calendars and the rest using Google calendars. Even worse, what if you had important conversations going on inside Slack, Skype, Microsoft Teams, and email?

Remote teams need buy-in and consistency with new tools and systems.

So, what’s the hurdle when adopting a new tool or solution? Consistency and adoption from the top, down. You and your team need to use the tool, use it correctly, and use it often to truly see its value and viability.

And, as a leader or manager, it starts with you.

Take the time to really learn the tool so you can understand and communicate it to others. Then, implement a company-wide initiative to adopt and use it for a set period of time. This “trial period” will help everyone acclimate themselves to the tool or process and will give your organization ample time to assess whether it’s worth using full-time.

Is a Fully Remote Organization Possible? 

While there are definite setbacks to an entirely remote workforce, there are also positives — and I believe that when you implement check-ins and add the right technology, you can be just as efficient as you would be in-office.

As many organizations are moving to more flexible work schedules and remote opportunities, you can expect to see many new tools and solutions designed to make the home office more successful. Keep in mind, fully remote organizations need to continue to place a priority on employee satisfaction and wellbeing as well as productivity. Finding a balance between employee health and employee production are the keys to building a successful company regardless of where and when your employees work.

Erik Bergman

Erik Bergman cofounded Catena Media and helped grow it to over 300 employees and a $200 million valuation before stepping away to start, an iGaming organization that donates 100% of its profits to environmental charities. Erik inspires change and positivity through his work, social channels (@SmilingErik), and his podcast Becoming Great.

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