Overnight transition to remote work for leaders

Overnight transition to remote work for leaders

Has the latest once-in-every-50-years species-threatening pandemic confined your team to your respective homes? Do you still need to ship product, make customer calls and maintain a regular meeting cadence to avert chaos? Don’t we all.

Every team faces a set of common and entirely predictable issues in the switch to remote work, and I want to share a few core practices that worked well for us at Freckle. We started remote work around 2015 when, as a tiny K-12 education startup, we struggled with hiring locally the kind of talent we wanted on our team. Since then, 70-80% of the company has become remote, allowing us to build an exceptional team we would have never put together in the Bay Area alone. Remote-accepted became remote-preferred, and eventually remote-only, with the unfortunate occurrence of COVID-19.

Here are the basics.

Prepare the new home workspaces

Photo by JC Gellidon on Unsplash

If you spend 16 hours a day in front of your home computer screen like I do, you might find it hard to believe that not everybody already has a dream workstation setup at home. Mind blown, right? A desk, a quiet room, an ergonomic monitor setup, and a stable Zoom-friendly internet connection aren’t a given for many, but are essential for productive work sessions at home. The last thing you want is to fight your environment.

What can you do, then, to support your team members who aren’t properly set up yet?

If you still have access to your office, then I recommend reimbursing last-minute Lyft rides to pick up whatever supplies your employees might want to move to their homes. For anything less urgent, an overnight Amazon or Monoprice delivery will take care of basics such as monitors, cables, and office chairs. Consider going the extra mile and providing your suddenly-remote employees with a home setup budget.

Reimburse your employees for part, or the entirety, of their internet bill. Some will not have a connection that can consistently handle a Zoom video call. This is critical for your customer-facing team members. Encourage them to upgrade their internet speed if they’re maxing out their bandwidth.

Employees who share their living spaces with others will also benefit from a headset with a directional boom mic. At Freckle, we’re partial to the Jabra Evolve 40 UC model, which does a great job at isolating the speaker’s voice in a loud office or call center.

This all assumes that all of your employees have access to an assigned work laptop that they can take home with them from the office. When that’s not the case, you will want to consider renting or acquiring devices ASAP.

Standardize communication tools

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Wearing PJs unfortunately does not exonerate you from meetings, team syncs, status reports and ad-hoc group debates. Among many of the social work processes, you still need to run your all-hands and get your teams informed, inspired and motivated to do their best work.

Good news: when everyone is remote, meetings are actually easy. There’s no fiddling with conference webcams, awful large room acoustics — huh, what did the quiet guy in the back mumble? — and having to remember to regularly pause for your remote attendees to make sure they get a word in over people vigorously arguing in the room.

Bad news: you have to overcommunicate. Before, gaps in shared information might have been accidentally overcome through hallway whispers, overheard conversations and lunchtime catch ups. Now, getting the full story to your whole team must be a concerted effort. Many books have been written on company-wide communication alone, so I won’t attempt to squeeze that into a couple of paragraphs. A simple guideline is that you will not be able to overdo it; too much information is better than not enough. Also create a regular cadence for sharing info with your team, if you’re past the point where you can get away with one single Slack channel for all the latest company news.

What about tools, though?

Email is always there for anything that must not be missed, and requires more careful reading and permanence. Good old email is still your Swiss Army knife of information dissemination. For anything less ethereal, group chat tools like Slack are a time-tested solution — at least in startup dog-years. Tandem or Slack video calls can be great for impromptu chats, just be considerate about how and when you pull people out of their flow.

For video conferencing I’m biased toward Zoom, with its gallery view feature. It’s consistently fast, has miraculously not collapsed yet under the extra Coronavirus-induced traffic, and it’s free for K-12 schools impacted by the virus.
Tip #1: the Zoom calendar integration for O365 or G Cal is essential to making sure there’s always an associated Zoom link with every meeting. The last thing you want is for people to roam your Slack channels asking for a meeting link. It must, must be there in the calendar event itself.
Tip #2: the /zoom integration for Slack is also nothing to laugh at and adds a quick pathway to starting an impromptu video call.
Tip #3: this should go without saying, but it’s still pervasive: make sure your video is on during calls. Many teams will devolve to audio-only, but that removes a lot of important communication information that we (mostly) hairless primates rely on to interact with each other.

You should let teams pick their tools, but your company’s core communication infrastructure is something you want to standardize.

Brace for distractions

Photo by ROBIN WORRALL on Unsplash

Unless you’ve done this before, your first impact with the new work environment is going to be full of character-building lessons. Family members and pets will be confused about why you’re stepping on their routine. Your brain will associate home with fridge runs, naps and refreshing Twitter, not with staying focused on the task at hand. Motivation sags, the natural accountability of the office goes away. You wonder how anybody gets work done like this. And if you still have that last stick of string cheese left in the fridge.

Turning home-mode into work-mode is not easy, but it can be done. Set up your desk in a way that screams “work”: keep it clean of distractions and unrelated items. Just your laptop and your notes. Consider keeping your personal phone somewhere else to avoid the temptation. If you’re fancy, have a separate desk or room just for work. It’s tough for those of us who live in 500-square-foot studios in San Francisco, but your situation might be more conducive.

This is trite, but it works: dress as if you were going to work. Don’t go full suit unless you have to, but consider tech-casual or business-casual. It’s hard to negotiate budgets or fix a network outage in your datacenter with no pants on.

Set expectations with those around you that, despite being at home, you’re actually working and your job expects you to be available with minimal distractions. Again, looking like you’re working helps with this. Your cat won’t care, but there are exceptions to every piece of advice.

Hold space for feedback

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Let’s go meta. At Freckle, we get a lot of value from having a #remote channel on Slack for surfacing concerns, feedback and ideas on how to make our remote workflows better. It’s a great place to raise issues likely affecting several people and see if anyone has found a workaround.

For example, when we still had an office, our remote staff couldn’t hear one of the conference rooms that well. People didn’t want to bring the issue up, concerned it might be only a problem on their end and it was maybe their fault. Receiving confirmation from others in the feedback channel helped show enough traction to warrant upgrading the mics in that room to a different system.

Additionally, consider having a biweekly or monthly remote hangout, and put feedback exchange on the agenda. With the team no longer having a physical space to voice concerns, having an allocated time to exchange ideas is going to pay dividends over time.


Switching to remote work in a pinch can be confusing, but if you address these four broad categories, you’ll have the fundamentals handled, and will be able to iterate further from there.

  1. Set up your new work environment for optimal ergonomics and availability for video conferencing
  2. Standardize all communication tools across the company
  3. Expect distractions, and to deal with them one at a time.
  4. Share feedback about your experience with remote work with the rest of the team, and iterate on it together.

(Featured image: Photo by Anna Auza on Unsplash)

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