Insights for Working, Leading, and Learning Remotely

Sixty-nine percent of companies intend to involve some sort of “hybrid” in their workforce location plans for the fall of 2021 and into 2022. Yet, these setups are uncharted territory for many teams. Finding what works for your organization will involve experimentation. But, you can learn from those who have done this before. We reached out to experienced hybrid teams to ask about the practices they’ve established to ensure their teams are inclusive and productive.

We specifically wanted to focus on how teams overcome challenges that can make hybrid work harder, such as:

• In-office vs remote workforce inequities
• Remote employees left out of decision-making
• Unprepared leaders
• Executives out of touch with workplace realities

Here are some routines from a wide range of teams worth considering as you experiment with your own setups.

“At Loom, our very own asynchronous video messaging tool is foundational to how we communicate, collaborate, and...

Hrishikesh Pardeshi is the co-founder at Flexiple, a fully remote bootstrapped company with $2 million+ revenue. He's passionate about remote working and has also built Remote Tools and Remote Clan.

We're grateful to Hrishikesh for sharing his expertise. Any opinions expressed within this blog post are those of the author and not necessarily held by Workplaceless itself.

It’s been a while since the world had to go through a sudden shift to working remotely. As the COVID-19 pandemic forced companies to go remote, the reception was mixed. Companies had to restructure their teams, find remote practices that work well and ensure that there was no loss of productivity, all at the same time. Given the suddenness of the situation, this definitely wasn’t easy.

In a remote environment, the way a team functions is very different from a co-located setting. Teams have to find what works best for them and effectively coordinate with each other. Processes such as hiring and...

Estimated reading time: 3 minutes, 30 seconds

Organizations continue to tackle remote and hybrid work challenges like overwork, Zoom fatigue, burnout, disconnection, and interruptions. Leaders, managers, and their teams recognize that finding the right balance between async and sync communication is critical. But coming from a work context where decision-making, creative thinking, and connection all take place in a co-located office environment, professionals often struggle to shift to this new paradigm of async-first work.

Before you start to learn how to implement asynchronous communication and collaboration, it’s critical to understand both:

• what is asynchronous vs synchronous communication
• why asynchronous communication is beneficial to teams

But HOW can teams implement impactful async communication? Here are the seven fundamental steps to implementing effective asynchronous workflows, collaboration, and communication:

1. Establish a Placeless...

Originally published June 2019. Just as relevant in July 2021.

As of June 2019, Remote work is on the rise and expected to grow exponentially in the coming years. Yet, some companies are changing course by banning and limiting remote opportunities, finding comfort in supposedly having more controlled work environments in brick-and-mortar offices.

An article published by SHRM (“Why Are Companies Ending Remote Work?”) discusses the reasoning behind the shift of large corporations such as IBM, ATT and Yahoo to recall remote employees. Specifically, the author identifies the following concerns with remote work:

• Employers allow people to work remotely without giving them the proper training or resources to do so productively.

• Supervisors—untrained on how to properly manage and monitor remote workers—find it easier to manage someone face-to-face.

• Some supervisors—perhaps because they feel they must be in control or don't trust their...

Successful remote teams understand the need to develop the fundamental skills necessary to function efficiently and effectively in a distributed environment, but they also iterate on best practices that work for their particular organization. We reached out to fully remote teams and companies to ask “what are some habits or rituals your team uses to stay healthy or productive?”

Here are some habits they shared that we can all learn from.

“Schedule flexibility is key to health and happiness, and GitLab is consistent about prioritizing time away from work. Every Friday is a meeting-reduced Focus Friday; About once per month, the entire company shuts down for Friends and Family Day. 

In 2021, we piloted an experiment in Async Weeks: every sixth week, my team clears all non-critical meetings from our calendars to create space for deep work and innovation. It’s a breath of fresh air to have a wide-open calendar and all the time you need to...

Corine Tan is co-founder of Kona, the wellness platform for remote teams. Her Slack app has helped teams at Asana, Medium, HelpScout, Coffee Meets Bagel, Happy Money, and more improve their emotional health and build trust. The Kona team has interviewed over 550 remote managers since January 2020 and compiled their findings in their annual Remote Manager Report.

The State of Remote Training in 2020

When my team at Kona first started interviewing remote managers in January 2020, we had no idea how soon the world would dramatically change. In a span of two months, we witnessed a worldwide remote experiment unfold as entire countries fell into lockdown. We scrambled to record the immediate experiences of managers and documented our findings in our 2020 Remote Manager Report. Three major takeaways emerged from our data:

1. New and experienced remote managers struggled disproportionately with relationship building (46.7%) and miscommunication (30.2%).
2. Emotional intelligence was the...

Estimated reading time: 3 minutes, 25 seconds

"If someone comes in five days, and another person three days, let me tell you I'm giving a promotion to the five day and I'm sidelining the three day." This sentiment is further reinforced in The Atlantic’s reporting of a series of studies that revealed “people will assume that those who put in a lot of office time are go-getters, even if they’re not.”

Unfortunately, leaders feel more comfortable when they can “see” employees working. If this is the leadership mindset when shifting to a flexible, hybrid, or fully remote structure, your organization is set up to fail.

Instead, organizations that are concerned with remote employee performance should evaluate the impacts of:

• Too many synchronous meetings
• Inefficient work that lacks async structure and practices
• Interruptions due to lack of boundaries or documentation
• Disengagement stemming from overwork and a lack of autonomy

Our ...

By Barbara Jovanovic, the Head of Content at SafetyWing.
SafetyWing (YC W18) is here to remove the role of geographical borders as a barrier to equal opportunities and freedom for everyone, by creating a global social safety net for remote workers and nomads worldwide. It’s your home country on the internet. 

We're grateful to SafetyWing for sharing their expertise. Any opinions expressed within this blog post are those of the author and not necessarily held by Workplaceless itself.

SafetyWing has been a fully remote company from day one. We strongly believe that remote work is the future of work. We also believe that all problems are solvable. Once the pandemic hit, we wanted to make sure we were solving as many problems as possible for the remote community. We did that by offering resources and advice to other companies that were forced to suddenly go remote. The number of teams and leaders that managed to maintain a healthy company culture and motivate...

Estimated reading time: 5 minutes, 45 seconds

Jamar is in the flow of work when a notification pops up that he’s received a new email from his manager. Even though he’s extremely focused, he steps out of his workflow to respond. His manager has asked him to connect with finance to confirm a budget number, but doesn’t specify a timeline. Jamar wants to prove his worth so he picks up the phone to call his finance colleague, Chantel. When Chantel answers, Jamar expresses an urgency to his request and he waits on the line while Chantel stops her work to dig through reports to find what he needs. After finishing the call and sending his manager a response, Jamar realizes he needs to head to a meeting, and won’t be able to finish up his original project work like he intended.

This scenario of regular demands on synchronous time plague many workforces today. Employees experience non-stop phone calls, messages from coworkers expecting a speedy response, and...

Our Workplaceless team is proudly fully remote and globally distributed. However, we still get giddy whenever we get the chance to connect in person, and we normally aim to meet in person once or twice a year. With the travel restrictions in 2020 and into 2021, we weren’t able to make it happen, but we all needed the opportunity to connect as if we were together. So we set out to plan a synchronous and asynchronous virtual team retreat.

Planning the Retreat.

We started planning two months prior to our targeted retreat timing.

• Select a planning committee. We wanted elements of our retreat to remain a surprise, so we selected a small planning committee and delegated responsibilities for organizing activities based on expertise and interest.
• Set goals. Outlining goals for the retreat will help team members see value in the event and help them focus on the aspects that are most important. Thinking about purpose first makes planning easier, because you’re less likely...