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Tim Cynova Post by Tim Cynova

By Tim Cynova on March 13th, 2020

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How to Transition to a Virtual Workplace Overnight

Big Ideas | How We Work | Remote Working | People Operations | COVID-19

The question that I’m increasingly asked nowadays (and something the team at Fractured Atlas who helped manage our own transition have been discussing) is: now that we’re an entirely virtual organization, having evolved into it over 4-5 years, what if we had to do again, overnight?

Our planning and transition to an entirely virtual organization evolved over years. We went through multiple stages that lead us almost naturally from one iteration to the next. I’ve detailed that journey here

However, with the global spread of COVID-19, many organizations no longer have the advantage of time on their sides. They need to transition to a virtual organization now. Below are suggestions to do this quickly (even if not “overnight”), recognizing that this piece itself came together quickly; every organization’s specific needs and requirements differ slightly to wildly; and some organizations have employees who quite simply must work in a physical space and possibly risk not being compensated if they don’t. We know that this process is challenging. We’ll be adding to this piece and have more resources dedicated to crafting virtual workplaces on our website Work. Shouldn’t. Suck.

A Spirit of Experimentation in the Virtual Workplace

First, approach this transition from a place of experimentation. Articulate that explicitly and openly with everyone in your organization. Say, and mean, that we will iterate and adjust as we discover the things that don’t work (and we need to find alternatives) and the things that do work (that we want to make sure become fundamental to this new work arrangement). But, unless something is definitively not working, stick with something for at least a month before iterating. Doing otherwise will send people bouncing in all directions and further exacerbate the negative impacts of change.

Talk openly about the stress and uncertainty of change, and that this is on top of the stress and uncertainty and worry that most of us are experiencing right now simply as human beings on this planet during a pandemic. Highlight things like SCARF to acknowledge the very human impact of change, and what altering how and where people do their work means for flipping those Freeze, Fight, or Flight switches. Refer to this piece for more of what can be expected as humans experience change initiatives.

When Work and Life Get Harder to Balance

Balancing work and life, becomes exponentially more challenging when both are in the same location. Especially as school districts shutter for weeks and students are expected to suddenly e-learn, caregivers are faced with not just the prospect of trying to figure out how to work remotely themselves, but helping others and balancing competing demands. When your “office” is also your kitchen table, or you need to make meals for people during what is typically the team stand-up, it can make balance a near impossibility.

For some, working in an office provides safety and security that they might not have at home. They might not have the physical space to set up an office or the capacity to install fast enough internet. And, please, please, please as you proceed with plans, don’t further burden people by expecting them to disclose, or to divulge this if you ask them. Craft plans from a place where this might be an issue, and continue to iterate towards solutions.

Research also shows two significant differences when people work remotely: (1) they work longer hours because they don’t have the physical cue of arriving and departing the office to punctuate their date, and (2) people become isolated and lonely.

As employees, we need to work to help create our own boundaries and routines, when possible, to delineate when we’re “on the clock,” and when we’re not. As leaders and managers, we need to be proactively mindful of what might happen when in the virtual setting we send requests outside of “normal” business hours. Previously people couldn’t do anything about that email sent at 9PM until they got to their office computer in the morning. Consider using a tool that allows you to schedule emails to send during business hours so there’s no question, and no implicit or explicit pressure, for people to respond outside of work hours.

Default to “Virtual First”

Don’t stand in the middle of the road. This is sound advice when you’re walking across a road, and when you’re quickly transitioning to a virtual workplace. Take this opportunity to go virtual first in meetings and your communications. Everyone going “in” on this right now will create a shared experience and shared learning. Those who wait will be left to figure it out themselves after their colleagues have already made it a consistent way of working. The process of going virtual first all together begins with documenting things virtually (and online) before you don’t have access to in-person meetings or the documents that are on your desk. 

Going virtual first collectively creates a shared experience and prevents having to bring on more  people in a later learning wave. I often think about the Stages of Grief here and how it’s better to go through this together than have some people exiting that process while another is just in the Denial stage. And, as a note from one organizational leader to the next: If you’re an executive director or CEO, lead by example here.

Virtual first also means that if anyone isn’t attending a meeting in 3D but joining by video, everyone joins individually using their video. It equalizes the experience.

If you’ve ever been the one person on a video call when everyone else is meeting in person you can attest that the experience usually sucks. It’s a less than inclusive experience, to say the least. When people laugh in the room, it floods the microphone so you just have to sit there pretending like you know what was funny. You then wait your turn only to get a slice of “air time” for your poignant comment 15 minutes after it would’ve been really useful for everyone else to hear and consider it.

Virtual first video calls also give people more practice leading and participating in inclusive group video meetings. This is one of the *most* underrated skills of the 21st century.

ProTip: You’ll quickly discover this if you don’t do it, please, default to muting everyone on a video conference call, especially if some people are joining from the same room. Once we went virtual first at Fractured Atlas, we started to realize that we were creating unspoken meeting procedures organically. One such procedure was that everyone muted themselves and, if someone had something to say, they would unmute themselves as a signal to the group that they would like to speak. As the meeting facilitator, we’d scan the group to see who was unmuting to queue up a comment, much in the same way that in the 3D setting you’d keep a pulse on the room.

The Video Meeting Exhaustion Coefficient 

Those who frequently participate in meetings by video experience something that I’ve begun to call the “Video Meeting Exhaustion Coefficient.” It’s ~2X. Virtual meetings and convenings are roughly twice as exhausting as their 3D counterparts. You’re sitting still in a chair positioned in front of a camera and screen filled with tiny heads in a Brady Bunch-like grid. Staring and concentrating in that way is exhausting. 

It’s not socially acceptable in the same way as a 3D meeting to get up and stretch or even gaze out the window. That signals you’re possibly not paying attention and/or you’re being disrespectful to your fellow meeting participants. To counteract this, include stretch breaks. Default to 45-minute meeting lengths rather than an hour. And take a moment to simply check in with people as humans to see how they’re doing (but be careful not to overdo that last one, nobody likes long meetings). 

We've also shared some other suggestions for improving video meetings here.

Lighten the Financial Burden of Having a “Home Office”

Always lead with putting the financial burden on the company. If it’s important for this person to work remotely, figure out how the company credit card can pay for things like phone minutes and internet connections rather than assuming people have, or can use, enough minutes and megabytes to cover their work. 

Unless it’s absolutely impossible — in which case explore other “workarounds” like who truly, absolutely needs to use the phone — lead by asking for consent. Don’t simply assume your team is able to subsidize this transition with their own money. Give them a stipend upfront (figure out the pennies later) or, if it’s really not possible, have whoever does the finances prioritize processing reimbursements to people within the week. Please don’t ask people to shoulder additional financial burden during times of crisis and/or significant uncertainty.

When all is said and done, or at least a little more settled, consider reimbursing staff for all or a portion of their home internet access if they use(d) that to work. At Fractured Atlas, we currently reimburse staff for up to $100/month to maintain a high-speed internet line. Besides providing people with a work-issued laptop, keyboard, and mouse, that’s the one work condition that’s absolutely required, so we cover or greatly subsidize it for staff. (Aside from that, remote workspaces are often bespoke to the individual.)

Now Let’s Move to Communication Tools for Virtual Work

Email is not the best tool for communicating virtual at scale. It’s clunky and confusing to follow once more than a few people start responding to threads. If you’re not using a chat application like Slack, Flowdock, or Mattermost prioritize that adoption right now. Also, Zoom, Bluejeans, or needs to be at the top of the list too for video meetings. 

Full disclosure: Fractured Atlas currently uses Zoom and Slack; although, as an organization, we previously used Bluejeans and Flowdock. My personal preferences are Zoom (certainly for the group video experience) and Flowdock. See more about the tools we use to communicate here.

Virtual Meeting Participation & Project Management

Sometimes you can’t simply print out meeting agendas or handouts and pass them around the conference table so everybody can “take one.” It’s additionally difficult to coordinate complex projects and activities with people distributed across space and time where you aren’t able to spin your chair around and ask.

Several helpful tools for both project management and remote meeting facilitation and participation include Trello, Basecamp, Team Gantt, and Jira. Over the years Fractured Atlas has used all of these tools; although, for the moment, we primarily use Trello to manage meeting agenda and projects within and across teams. If you’re someone who likes to see and work visually and you have a rainbow of Dry Erase pens always at the ready, then check out Mural. It’s a tool for visual collaboration in the digital workspace.

Remote File Access for Virtual Workers

If time is not on your side, and for many it’s not, just start putting necessary files online using applications like Google Docs, Box (tip from our Senior DevOps engineer whose accompanying comment was “like Dropbox but WAY better”), or Nextcloud. Don’t let perfect be the enemy of good with this option. Just start using something that isn’t your physical file server in the office. Once the dust settles, you can go back and make sense of which document version needs to be stored where, and whether this is the right app to use.

Now most mission-critical and everyday operating files are accessible and you can communicate with your team and coworkers.  

Remote Desktops to Access Files Virtually

Sometimes people need to the access of an office-based computer because a specific application is only accessible from inside of the office. For instance, maybe your donor database or accounting software is located on a physical server in the office. If you’re working, say, on the finance team and the only way you can access the accounting software is by using your computer in the office, consider using something like GoToMyPC (GTMPC). It’s another quick and easy solution for remote desktop access that you can iterate on later if necessary.

You can now work from almost anywhere that has an Internet connection. When pulling up the  GTMPC application it will look like you’re sitting down at your office computer, sans the pictures of family and friends on your desk. When I’ve used it in the past with computers that have the same background images, one of the “problems” was that I got confused if I was working on my home machine or my work machine. (Pro tip: Change a background image.) 

Over the years, I’ve even used GTMPC from my phone while on a plane so that I could increase a coworker’s credit card limit who was stranded in a snowstorm and needed to book a hotel. Not a great experience looking at a double monitor set-up on a tiny iPhone 6 screen, but it worked out and felt like I was living in the future. 

Phones for a Virtual Workplace

This can get tricky, especially if you have an “old school” phone system and a physical server in the office that manages your email. If you have more time to plan the transition (or once you get a stop-gap in place move to this), consider VoIP services like Dialpad, Twilio, and Skype. (We’ve used both Dialpad and Twilio over the years at Fractured Atlas, and have used Skype to make international calls when our previous phone system didn’t allow.)

Hopefully, your current phone option allows you at least the ability to forward lines to other numbers. This buys you some time. You might even be able to set up Google Voice numbers so that staff doesn’t need to call from—and possibly expose—their personal numbers. Using an interim solution like Skype can allow the company to pay for minutes so that staff doesn’t need to use their personal phone and data plans for work use. 

Email for the Virtual Workplace

If you can’t access your work email from a home computer because it uses a specific client that’s computer or physical server-based (and this suggestion doesn’t create a security breach), consider creating a work-adjacent email that you can use to correspond with people. And, if it’s an option, have your work email forward to that address for the time being. Create something like (which is a completely fake email address that I just made up here for illustrative purposes), but one that you can use until a better solution is found. 

Security in Virtual Offices

Be mindful of where you’re working, who’s around, what you’re sending over a (possibly unsecured) internet connection, and who might be listening to you “read back that donor’s credit card information” in the coffee shop (Hi, everyone within 15 feet of me in this Starbucks).

If you’re out and about, consider getting and using a MiFi. Or, at least get one for those who do the most sensitive work like access your organization's bank accounts. You can also use a VPN.  Some to consider include: ProtonVPN and Mulvad. A piece of advice from our Senior DevOps Engineer Andrew Hanson about selecting a VPN is to do a Google News search for the one you plan on using to see if there’s anything that might concern you about the specific service provider (e.g., recent data breaches, etc.).

If you’re going to be working from a laptop in various public spaces consider getting a privacy screen like this or this. If you’ve ever sat in the aisle seat on a bus, train, or plane, you most likely have noticed just how easy it is to read someone’s laptop screen who’s sitting even five rows in front of you.

Also, so it’s explicit, consider the privacy of your staff’s personal information. I’ve mentioned personal phone numbers and email addresses here as two examples. Home addresses are another. It’s the organization’s responsibility to help protect and keep employee information confidential. Consider the scenario where everyone gets along fine now—that donor is great!—and then things sour or there’s a falling out. Proactively help people think about protecting their information.

Moving Money in a Virtual Office

One of the things I hear quite frequently is that remote work doesn’t work for every position. That’s completely true. There are some positions that simply can’t do the work they need to do without being in the physical space. I’m thinking about stagehands and building maintenance staff right now, but there are many others.

However, I think in many cases that is used as an excuse for not putting in the thought to discover new ways of working and alternative processes. For instance, I’ve stopped counting the number of times people have said their finance teams can’t work fully remote because they need to be near check stock and the check stock is kept in an office safe. Meaning, part of their job is to sit in the office and feed checks into a printer so someone can physically sign them. Here are our suggestions for moving money without a physical office.

Turning a finance role virtual requires a bit more planning and intentionality than other roles might, but we live in the 21st century. You don’t need check stock, you just need a way of moving money. And with that reframing, a whole host of options become available. Bank checks created and sent through your online banking portal. Wire transfers. Heck, in an emergency you could use PayPal, Venmo, or Zelle. As I can feel our Controller’s head starting to explode due to my last three suggestions, bank checks through the bank website often affords you the ability to institute important controls like daily limits, secondary approvals, etc., so start there first.

You could also explore using an application like Expensify. We started using Expensify a few years ago, and now all of our staff reimbursements are processed through it. Each of us have a separate, secure account that we pair with our personal banking information. When we have expenses we upload receipts to provide the necessary back-up, and within a day or two have the money sitting in our personal bank account. Expensify works well, but is probably one of the items to do after you’ve figured out the above, and doesn’t work for everyone. 

This by no means the full list of how to be an entirely and solely virtual organization from a tech standpoint. (Our Chief Technology Officer Shawn Anderson will be writing more about those shortly.) Some of the things on the non-tech extended playlist include, what happens with your mail and how do you process and deposit checks in a way that doesn’t include any staff member? For that, you can use “caging services” to receive, process, and deposit checks, and companies like Earth Class Mail to act as the address where you receive company mail that then is automatically emailed or physically redirected to you, wherever you might be at the time. 

People standing in a row in suits considering whether or not virtual work suits them.

Remote Work Doesn’t Suit Everyone

Now you have the basic technology infrastructure and processes in place. 

But this last section isn’t about that. It’s a reminder that we need to remember we’re human beings working with other human beings and to be human. The tech is the relatively easy part. However, we’ve spent decades upon decades figuring out how to work together in a physical space and now, seemingly or literally overnight, we’re working distributed from each other. (Check out this piece and this podcast episode if you want to dive into that more).

Some high performing, amazingly talented people just can’t work in a virtual setting. They’ve found that it just doesn’t suit their style of working and what they need in a workplace to be successful and thrive. Many in this group have actually given it a solid try; more than just those few days they worked from home because they were sick.

This requires some personal introspection and managerial understanding. It requires us to meditate on when and how we do our best work. What do we need to feel supported. For some of us, we just find the Venn diagram doesn’t overlap enough with the virtual workplace in ways where we can be successful in that environment over the long term. Related, it requires managers to understand that some amazing people are unable to work remotely for reasons that they might not want, feel comfortable, or should feel at all obligated to discuss with their supervisor.

Explore this series about how others approach their virtual work experience

When we finally made the last leg of our transition into being a fully virtual company we acknowledged that not everyone would be with us when we got to “the other side.” Some people opted out in advance because they knew it wasn’t the best environment in which they could thrive; others gave it a try but found it didn’t, or couldn’t, work. It’s a different way of working than what most people signed up for. As leaders, it’s worth pausing to acknowledge that this changes the unwritten employee/employer contract that governs the employment relationship for many of us.


The virtual workplace is different than the physical workplace, and not just for the obvious reasons. It’s a different experience and, to be successful in the long run, it requires intentionality and thought and iterating and adjusting and reinventing and retooling things we seldom give a second thought to if we’re in a physical space. What does a conference room or whiteboard or cubicle allow us to do? What does having a physical separation between work and the rest of our lives do? And in the absence of those things, how can we capture the essence — the positive essence — of them in a virtual setting? How do we avoid toxic workplace tendencies?

Earlier in my career I worked for dance companies. Something that the cultural sector has been wrestling with for years is the role of technology in disseminating performance. From a tech standpoint, it’s relatively simple these days to live stream a performance, especially if image and audio quality aren’t primary concerns. But a piece of art created to be performed in a theater with a live audience often falls flat when streamed online, even with the best video crew filming it. Art experiences that are designed to be experienced online first (or solely) are far more successful at making the connection with their intended audiences.

So, the above list is essentially the live streaming version of a performance. If you can’t be there in person, and really want to see it, it’s better than nothing. But to truly level up to be a work of art it takes approaching it from a place of deconstructive discovery. What is the essence of this thing? What are we trying to achieve? How can we create and craft structures to support it so that it can thrive?

And that my friends is where things really get exciting and awesome and liberating. Many of our cultural sector organizations are filled with creative administrators working to fulfill missions — putting incredible art on the stage, the screen, the public space — in environments that have changed little since the 1980s. The workplace is operated with some of the least adaptive and resilient structures that exist. This is that moment in our lifetime — *ring ring* the phone’s for you — born out of necessity and uncertainty and fear, when we get to unleash and direct the creativity we possess internally to craft workplaces that fit how and where we want to work, and in ways that allow people to thrive. Godspeed in your journey.  

For those with questions about how to turn your physical team into a successful, creative, collaborative virtual team, we’ll be offering several webinars hosted by both People Operations staff and also Engineering staff. 

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Other questions? Hit me up at (and yes, *that* one is a real email address.) 

More posts by Tim Cynova

About Tim Cynova

Tim wears a multitude of hats, all in service of creating anti-racist workplaces where people can thrive. He currently is co-CEO of Fractured Atlas (an entirely virtual organization with staff spread across multiple states and countries) and a Principal of the consulting group Work. Shouldn't. Suck. He serves on the faculty of Banff Centre for Arts & Creativity and The New School teaching courses in People-Centric Organizational Design; he's a trained mediator, and a certified Senior Professional in Human Resources (SPHR). Earlier in his career, Tim was the Executive Director of The Parsons Dance Company and of High 5 Tickets to the Arts in New York City, had a memorable stint with the Cincinnati Symphony Orchestra, was a one-time classical trombonist, musicologist, and for five years in his youth he delivered newspapers for the Evansville, Indiana Courier-Press. Also, during a particularly slow summer, he bicycled 3,902 miles across the United States.