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Is your team prepared for long-term remote work? Ask these 3 questions to find out

As the remote-work routine blurs the boundaries of personal and professional lives, provide your colleagues with information and emotional support.

Is your team prepared for long-term remote work? Ask these 3 questions to find out
[Photo: Charles Deluvio/Unsplash]

As of now, two-thirds of employees are currently working remotely as a result of the coronavirus pandemic, my company included. It’s true, remote work has its benefits: From a commute to the kitchen table to the ability to have lunch with your kids, we have more time to spend on hobbies and personal interests outside of work. All of which are key factors for better work-life balance and increased productivity. For me, I have been able to spend more time with family and catch up on my reading list.

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But in recent weeks, as many companies have extended temporary plans for employees to work from home, the novelty of remote work has started to wear off. A July survey from Monster found 69% of employees are experiencing burnout symptoms while working from home—up almost 20% from early May.

As managers and leaders, we have a responsibility to help teammates adapt to their new environments as best as we can. We have to be flexible and, most importantly, ensure employees feel safe, supported, and motivated to do their best work.

To help employees adjust to long-term remote work, here are three questions leaders should ask themselves and their fellow managers.

1. Are your equipping your employees and teammates with context?

Building openness is one of our company’s core operating principles, and one that has been especially important as we grapple not only with the impact of COVID-19 but also with the critical issues of racial injustice that plague our country. It’s important to cultivate a two-way dialogue with employees to ensure everyone feels heard. One tactic we’ve found to be effective is increasing the frequency of our company all-hands from monthly to biweekly meetings, where we celebrate wins, discuss company performance, and have an open Q&A with the executive team. In engineering, we host a biweekly virtual “show and tell” where engineers demo both finished and in-progress work. We use this time to share knowledge and create a venue for feedback.

I also host a weekly “tea time” via videoconferencing for my team, which acts as a forum to hang out and discuss any top-of-mind issues with teammates. It’s completely optional but there for anyone who wants to talk or has questions. Sometimes, the discussion is focused on work projects, but other times, it’s more personal and gives my teammates an opportunity to talk about how they are feeling. I’ve also started writing and sharing weekly “Friday FYIs” with my team. These notes feature a collection of relevant updates, inspirations, challenges, and lessons learned.

2. Are you showing up for your teammates not just professionally, but personally?

Now that we have swapped in-person meetings for virtual meetings and hallway conversations for Slack messages, it’s more important than ever to tune into the needs of employees. Whether it’s a teammate seeking feedback on a project, or parents and caretakers looking for help on how to balance work and parenting, leaders should encourage constant communication to support people where needed.

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As a company, we offer resources to help with whatever situation a teammate is in and find ways to imbue wellness in our culture, even remotely. To encourage self-care, we recently hosted a Wellness Week, where we implemented a no-meeting rule and encouraged teams to take time off. We also have an online “wellness corner” available that features a curated list of wellness resources (such as recommended books, articles, playlists, and videos) for people to leverage.

3. Are you listening to employees while you plan for the future?

There are many unknowns about when it will be safe for employees to return to the office, but the future of work hinges on one attribute: flexibility. Even before COVID-19, there was a strong signal in favor of more remote work. In surveys last year, 80% of U.S. workers said they would turn down a job that didn’t offer flexible working options. Surveyed employees stated flexible work arrangements increase morale, and for leaders they can lead to lower operation costs. I see a future where employees have options, whether it’s coming into an office one to two days a week, meeting as a team once a month—or going fully remote.

As companies consider more flexibility for the future, it’s important for managers to have ongoing check-ins with employees. Ask how they’re doing in the moment, and what’s working or not working.

Surveying workers can also help a company better understand the sentiment of employees more broadly. Does your team want a fully remote office? Do they want flexible options? Have these conversations now, and start making plans proactively to build a future work environment where everyone thrives.

As leaders, we should be constantly finding ways not only to encourage our teams to do great work, but also to have a healthy work-life balance. When people can take time for themselves, they can give more of themselves to their work. Leading by example is the best way to encourage this and to set a precedent for your teammates. And, as the newness of working remotely wears off, asking yourself and fellow leaders and managers these three questions will help ensure you’re supporting employees, inside and outside of the virtual office, and showing up for them during these challenging times.


Ian Wong is the cofounder and CTO of Opendoor, where he leads a team of engineers and data scientists in modernizing the real estate industry. In the past, he has built machine learning applications for Square and Prismatic.

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