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Remote Work Challenges

In this post, GetThru's Founder & CEO Daniel Souweine talks about four key challenges of running a remote organization, along with some of the tactics we use to respond at GetThru.

Daniel Souweine

Founder & Interim Head of Product

Last year, I wrote about the joys of remote work and promised to follow up with reflections on some of its challenges. Those challenges have been especially pronounced during this past pandemic-year, so it seemed a good time to deliver on my promise. In this post, I’ll talk about four key challenges of running a remote organization, along with some of the tactics we use to respond at GetThru.  

Challenge 1: Building Camaraderie

I’ll start with how remote work makes it harder to build camaraderie -- aka mutual trust and friendship -- because it is so central to building a positive, collaborative work culture. Simply put, it’s harder to build relationships with people you rarely see outside of a Zoom meeting. There are no impromptu lunches, happy hours, or coffee runs where teammates can organically bond. Nor can we be together when a colleague is having a hard time, celebrating a life event, or departing the organization. We're hardwired to be together in moments like those, and opportunities to build connections are lost when we can’t be. 

It’s especially hard to celebrate accomplishments remotely. After the November 2020 election, I wanted nothing more than to gather our team over good food and drink to appreciate their hard work and celebrate the victories they helped make possible. Instead, I was left to express my heartfelt gratitude over Slack and Zoom, which just isn’t the same.  

Our response:

  • Slack -- Slack is an important tool for community building, and GetThru employees use it extensively to share about their pets, hobbies, what they’re watching/reading, and random tidbits from the world. We have an active “pride and props” channel for celebration and appreciation, and we take care to acknowledge work anniversaries for all employees. Some employees find remote community-building easier than in-person, as dedicated channel topics make it easier to stay in the loop and chat without feeling like you are “interrupting” someone. 
  • Retreats -- When it comes to building connections, there is no substitute for sustained time together in person to eat meals, go on outings, and get to know each other. Our current cadence is one All-Staff retreat per year and at least one departmental retreat (i.e., engineering, sales, etc.). During COVID, all retreats have (of course) been virtual, which has still been valuable, so much so that we plan to add a virtual All-Staff retreat to our calendar along with a yearly in person one.   
  • Virtual Gatherings -- We also coordinate a variety of virtual get togethers like organized coffee breaks, game hours, and “Get Acquainted” sessions that pair teammates for 1-to-1 conversations. 

Challenge 2: Communication 

Communication is hard in any organization, but it’s extra hard in a remote workplace where so much has to be written down. Between Slack, email, Google Docs, Jira, GitHub, Asana, and more, the volume of writing can be overwhelming, and it can be harder to communicate tone. Difficult conversations are also harder to have remotely. For many people, giving and receiving critical feedback is easier in person.    

A standard knock against remote work is that it makes organized brainstorming sessions less productive, but I think the bigger loss is opportunities for impromptu creativity. Some of the most important insights come when you just happen to start talking to the right person at the right time about a new idea or insight. 

But all meetings, whether planned or not, are harder in a remote setting. Zoom fatigue is real, which means each meeting “costs” more from an energy perspective. It’s also harder to be in a conversational flow over video -- internet issues crop up, people forget to unmute, etc.  And there is no way to vary the setting by going out to lunch, walking and talking, or even switching up the conference room. Variety and movement are underrated tools for improving energy and creativity. 

Lastly, having employees in different time zones creates communication challenges. Someone on the West Coast working closely with someone on the East Coast only have 5 working hours when they are online at the same time.

Our response:

  • Intentional Communication -- We try to be extremely intentional about all aspects of communication. We wrote communication norms early on and regularly update them. These norms offer general principles like “assume good faith,” and “no yelling,”  as well as detailed expectations for Slack responsiveness, calendar usage and more. 
  • Minimizing Meetings -- Minimizing meetings is smart for any organization, but especially in a remote workplace. Every meeting needs a clear purpose and process, and we regularly review our meeting cadence and structure. We are also experimenting with company-wide no-meeting Fridays to help with meeting overload and provide more focus time.  
  • Pick Up the Phone -- I personally try to use the good old telephone for many 1:1 conversations because I think it is less taxing than Zoom.  

Challenge 3: Isolation / Disconnection 

On the personal side, some people, especially extroverts, struggle with the amount of time spent alone in a remote office. It can be harder to get motivated without the energy of others to feed off of. Remote employees are also more on their own to deal with tech problems, which can be especially stressful if they have to meet hard deadlines.

From a collaboration perspective, working remotely means our day-to-day experiences are individual instead of shared.  If the office internet goes out or its plumbing breaks, everyone experiences that together. But when that happens at one person’s house, they may be scrambling to solve the problem while keeping track of work and letting colleagues know what’s happening. The same goes for the weather. On any given day we might have one employee suffering through a heat wave while another is dealing with a flood warning.    

Time zones are a factor here too. When one meeting participant is full of morning coffee and another is battling post-lunch malaise it can be harder to find the collaborative flow.

Our response:

  • Coworking Reimbursement -- We will pay for anyone to go work at a coworking space to help them get out of the house.  
  • Time Zone Conscious Scheduling -- We rarely schedule meetings before 9am PT. And on the rare occasions when we do “all day” meetings, they are actually only around 5.5 hours -- beginning at 9:30am PT and ending at 2:30 PT.
  • Virtual Gatherings -- As mentioned above, we host regular organized interactions -- coffee hours, virtual coworking sessions, game hours, and one-to-one chats -- to help provide connection for those who want it. 

Challenge 4: Blurred Boundaries 

A final major challenge of remote workplaces are their inherently blurred boundaries. If work is at home, then in some sense you are always at work. This can make it harder to put work down at the end of the day. And blurred boundaries are especially hard for parents with kids at home, which has been significantly exacerbated by the pandemic.

Our response:

  • Conscious Management of Work Hours -- We have tried hard to establish a work culture that isn't "always on." Our Slack tends to be extremely quiet during evenings and on weekends. And we reduce support hours, adjust project timelines, and give additional time off when business is slower.
  • Slack Norms -- We shy away from "pinging" people in Slack if we know they are offline, and if we do ping, we tell people whether the issue is urgent or not. We also have developed a culture of proactively letting each other know if there's something going on at home, like a tech problem or weather concern, that we need to deal with.
  • Coworking reimbursement -- As mentioned above, we will pay for anyone to go work at a coworking space if that makes it easier to create work/home separation.


When I first started working remotely, it was like any new relationship -- my excitement about the good stuff drowned out any downsides. Five years later and with a team of 50 full time employees, I’ve come to better understand remote work’s unique challenges. For me, the pros vastly outweigh the cons, both personally and from the POV of running a progressive, sustainable company. But after 18 months of a pandemic that has strained all workplaces, remote or not, I’m looking forward to when everyone at GetThru can get together in person to talk about how much we love working remotely.

Do you have remote or WFH tips & tricks to share, or just have more questions about our approach to a remote workplace? Let's talk! You can find us on Twitter, LinkedIn, Facebook, or good old email. We'd love to hear from you.


Daniel Souweine

Daniel ran the national texting program on the Bernie 2016 presidential campaign. He came away so impressed with P2P texting that he started his own company! Before Bernie, Daniel was a co-founder of Citizen Engagement Lab, an incubator for online organizing projects. He lives in Glenford, NY, with his partner Emily and their two daughters Sasha and Carina.

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