Unexpected Lessons From 4 Years of Remote Work

It’s been more than four years since the Covid-19 pandemic changed how and where knowledge workers interact with their workplaces. Today, we see a dynamic mix of remote, hybrid, and in-person attendance models, proving that 2020 permanently changed our collective outlook on work, flexibility, and talent. But if there’s anything the past four years have taught us, it’s that the idea that people need to be at an office from 9 to 5, Monday through Friday, to be productive is an outdated way of thinking. In fact, recent data reveals only 16 percent of white-collar workers feel they’re more productive in the office, compared to 46 percent who said they’re more productive at home. The shift to remote work proved that geographical differences are not the limitations they once were. Broader geography allows companies to access a wider range of talent, all while meeting talent exactly where they’re at. As the CEO of Oyster, a fully remote company of more than 500 employees in 70 countries, I like to think that we’ve truly mastered the art of remote work—but that didn’t come without learning lessons along the way. Here are five of the best lessons to come out of those years. 1. Remote work is not just about the tools—it’s about the rules, too. In early 2020, at the onset of the pandemic, my co-founder, Jack Mardack, and I had just started our new business: a global employment platform to enable cross-border hiring. While the world was on lockdown, we had to launch, fundraise, and go from no product to a minimum viable product in a matter of months. All during the pandemic; all across two continents; and all over Slack and Zoom. Collaborative tools like Slack, Zoom, Loom, and Notion, helped us stay connected during our company’s infancy. But building the “tools and rules” early on allowed us to create necessary structures and internal cultural norms that are still in place today. As we’ve grown across many time zones, the tools and rules have never been more necessary. For example, we branded our way of working as “follow the sun,” meaning that employees should not feel pressured to work “global hours” just because they work for a “global company.” Prioritizing asynchronous workflows and communication, team members ending their days can hand off work to those starting their days in other parts of the world and trust that it’s being carried forward. This enables teams to be productive no matter the location of their members, helping us collaborate across time zones more effectively, and making it possible for our company to have a 24-hour workday for ultimate customer service around the globe. 2. When it comes to remote, track results, not hours. “It’s easier to trust people are working if we can physically see them working.” How many times have we read headlines, RTO policies, and quotes from business leaders in the past few years that boiled down to this outdated approach to management? Before I became a remote CEO, I’d spent the majority of my working life in offices with leaders who strongly believed that the more employees were physically in seats, the more productive they were. This overreliance on superficial measures of productivity often resulted in missed opportunities, inefficiencies, and work/life imbalances for employees. Remote work has effectively shifted the focus from hours worked to results achieved. This priority shift is a driving force that lends to a more logical and satisfying work approach that’s good for your business and good for your people. As a CEO, it’s not my job to ensure that people are at their desks by 9 a.m. It’s my job to set the vision and overarching business goals for the company. Instead of focusing on how many hours an employee spends on idle in the office messaging app or their number of keystrokes, connect their work to high-level objectives and key results. For example, if you set a company goal of “increasing the share of new business from enterprise companies by 15 percent,” individual teams and departments have a North Star objective that they can track, measure, and work towards. This hasn’t always been my approach, even as a remote CEO. But one of the most important lessons I’ve learned is that when you prioritize alignment, productivity tends to follow. 3. Don’t be afraid to adapt your leadership style. Your leadership style isn’t set in stone, even if you’ve been an executive for half of your career. When it came to leading a remote company, adapting my leadership style for a virtual environment was necessary. Early on, I learned that we always need to assume good intent from our people. In a remote setting, it’s easy to become paranoid and feel the need to over-communicate to gain a greater sense of control. The right approach is the opposite: hire talent that aligns with your values and mission and trust them to do their best at all times. To counteract the instinct to micromanage in a remote or hybrid environment, leaders should adopt more supportive and coaching-oriented management styles. Focus more on providing clear objectives and removing obstacles for their teams, rather than hovering and following up with non-stop Slack messages. Manage 1:1’s and updates in a flexible but results-oriented way. Get into the habit of giving continuous feedback so your reports know where they stand and how they’re performing. 4. Remote-first doesn’t mean remote only. There is a popular misconception that remote-first companies have to miss out on the human touchpoints that come with in-person work. One of the most surprising lessons I learned as a remote CEO is how organic these touchpoints can be. While a work environment can be remote-first, it doesn’t—and shouldn’t—mean your organizational culture exists only virtually. At Oyster, meeting people in person is a part of our culture. With colleagues and friends all around the world, you may be surprised by how often our people get together—co-working with colleagues who live in the same city or who are vacationing, or just passing through. Leaders in a fully remote or very distributed company may also find it especially helpful to meet once a year (at least) for executive offsites—both to have the most complex strategic conversations and to build trust within the team While Oyster will always be a fully remote, very distributed company, none of us are limited by the idea that every interaction, connection, and collaboration must be either entirely virtual or entirely in person. 5. Self-discovery meets personal growth. One of the most impactful things I’ve seen come out of the remote work revolution is the opportunity to become the most authentic version of ourselves. Gone are the days of keeping up with office dress codes and social pressures. Remote workers can show up every day exactly as they are, allowing them to explore their personal style and interests more freely. Over the years I’ve worked remotely, I saw the most personal growth—both in and outside of my work. I’ve gleaned a better understanding of my work habits like when I do my best work (at night, after my kids have gone to sleep), as well as my personal strengths and weaknesses. Because if we can altogether reach a deeper level of self-knowledge, we can optimize our work schedules and improve our overall performance and well-being. It’s 2024, and it’s time we all make work work for us. EXPERT OPINION BY TONY JAMOUS, CEO AND CO-FOUNDER, OYSTER @JAMINGO