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TD Magazine

How Remote Organizations Can Instill Thriving Workplace Cultures

Monday, February 28, 2022

FlexJobs, a fully virtual business since 2007, knows what it takes to maintain company culture for a remote workforce.

In the years before the pandemic, remote work was running its own race, often to the side of larger workforce trends. The pace of remote work's growth for the past two decades has been slow and steady—but two years into a pandemic, it's clear that remote work is winning the race.


As a job search service focused on remote work since its founding 15 years ago, FlexJobs has had a front-row seat for remote work's seemingly overnight success, the roots of which began growing many years ago. One of the things we've been particularly focused on during that time, and perhaps even more so during the pandemic, is remote company culture.

Our leadership team is people focused, thoughtfully building programs and initiatives to support and extend the company culture out to the remote workforce. The culture is guided and aligned to the company's overall mission with intention and a sense of mindfulness. Those efforts have resulted in not only a company that is focused on a holistic approach to culture but also multiple years being named among the top 25 small-company cultures by Entrepreneur magazine and one of the best places to work by Outside magazine.

What is remote company culture?

An organization's culture, whether remote or otherwise, can be defined as how the people in the company work and work together to accomplish their tasks. Culture comprises a mission, attitudes, norms, behaviors, expectations, and overarching principles and values.

FlexJobs, for example, is focused on helping people find a better way to work through remote and flexible work, and we are guided by integrity, communication, and care. Those are the building blocks of our company culture. But that's only the beginning. As employers with remote workforces think more deeply about the culture they are intentionally or unintentionally creating, there are many opportunities to build strategy and process around culture—to weave the who, what, when, and where of the company's daily work with the why of it all.

Note that developing a remote company culture is somewhat different from building an in-person company culture. For decades, traditional in-person businesses used a set of cultural and managerial practices that relied on physical proximity as a big indicator of productivity and cultural health. Facial expressions, body language, the presence of someone physically at their desk; high fives, handshakes, pats on the back—with remote work, those indicators (regardless of whether each is a worthy indicator) are not available.

Therefore, to build a remote company culture, the focus must be on different practices: clear and open communication in all directions, a focus on results and the processes that get them, and trust.

Maintaining and strengthening remote culture

One of the most difficult aspects of remote work is the lack of spontaneous interactions among staff members who don't regularly work together. That spontaneity builds small but meaningful connections—the ones that foster trust and make you think, "Hey, I know someone on that team" when the need arises to reach out for a work-related situation.

FlexJobs has tried to solve for that in several ways. One simple addition to our company-wide Slack channel is the platform's Donut app, which pairs employees at random to schedule a virtual meetup and get to know each other. People from vastly different teams and career areas schedule 30-minute chats to talk about their career paths, interests, hobbies, and anything else that comes up in their casual conversations. The key is encouraging people to opt in to the app on Slack. One way we do that is by inviting staff who have used and enjoyed the app to share their stories in the general Slack channel to show others it's a fun and worthwhile experience.

Related to that, the more you can have employees share their experiences, tips, and tricks with others, the more the company's culture grows and evolves. Managers and leaders should regularly and enthusiastically encourage openness, trust, and the free sharing of information and ideas.

Our monthly all-staff Zoom calls are one way that the company shares information from the top down. CEO Sara Sutton, who co-hosts the calls, sees them as an opportunity to connect with everyone at the company. During the first few minutes, everyone is on video getting settled in. Meanwhile, Sutton makes a point to say hello to different team members, mostly individuals whom she otherwise wouldn't interact with much on a daily basis. Those small but significant interactions are an important part of strengthening the underlying fabric of a remote team.

During each meeting, leaders share company information and news, discuss ideas and issues, and spotlight different teams and contributions. The meetings are also a time to celebrate birthdays and work anniversaries happening that month and to welcome new staff members.

Less-formal activities are additional ways for colleagues to interact. Our people and culture team (which houses the HR function) organizes virtual lunches, Zoom trivia events, and other casual get-togethers. During those events, we use breakout rooms to help smaller groups of employees come together. That helps individuals develop stronger connections with each other.

Aside from live virtual meetings, we use Yammer as an asynchronous way for team members to connect around a virtual watercooler of sorts. We use it with intention in a variety of ways to engage staff. For example, we pose a Question of the Week such as:

  • What was the first record or CD you ever bought?
  • Coffee or tea?
  • How many states have you been to?
  • Yoga or running?

Those simple prompts garner lively responses every time, and the replies illustrate what different employees have in common with others from across the company (and encourage fun debates when they differ).

We also have used Yammer to create groups for connection over shared interests—for instance, pet corner, book club, crafts, cooking, exercise, parenting, and health and wellness.

It's important to encourage such discussions to take place. Don't underestimate the value of giving employees the opportunity to see both what they have in common and how they are different. It all goes toward reinforcing trust and strengthening relationships. Sometimes workers bond over creamy versus crunchy peanut butter or make a connection based on the commonality of caring for a parent in their final stage of life. In a remote company, it's more paramount to make spaces for such bonds to develop—and to repeat the process over and over.

Building culture through onboarding

A strong virtual onboarding program can also contribute to a positive company culture. As with in-person onboarding, a disorganized process can leave a lasting bad impression on new employees. We have found that two of the most important aspects of onboarding remote workers are communication and time.

Open and regular communication from day one is vital to successful remote worker onboarding. Managers should have three critical communication objectives when onboarding a new employee:

  • Use a combination of communication methods.
  • Explain how the team uses each of the communication methods.
  • Share their own communication preferences and ask the new hire how they prefer to communicate.

Communication must be both personal and professional. In addition to making sure a new hire learns how to operate in their job, managers should want to get to know their new team member as a whole person with a big life outside of work and enable them to get to know their new team in that way.

Giving new hires the time to get adjusted to working remotely on the team and setting clear time expectations is another big piece of successfully onboarding remote employees. FlexJobs workers are largely able to set their own schedules each day. In that type of environment, make it clear to new hires what they should be spending their time on, for how long, how often, and when so that they know how to structure their new schedules. Have new employees discuss schedule ideas with seasoned staff so they learn best practices and what works well.

Typically, each FlexJobs manager works with their team to create a training outline that details the overall training process and what the new hire should be focusing on each day. An essential piece of that is giving the individuals plenty of time to digest all the new things they're learning. Managers should schedule time to talk to their new hires about each training piece and help them gain clarity where they're confused or learn how everything fits together.

Finally, introduce new staff to and immerse them in other parts of the company. In remote work, it can be easy for employees to stay heads-down and remain siloed in their part of the company. To combat that, make sure new remote workers get to interact with staff from other teams, both related and unrelated to their day-to-day work. For example, FlexJobs assigns new team members a buddy—an employee in a different part of the company—who can show them the ropes and answer their questions about the organization. In many cases, buddies have become strong connections long into a new person's tenure.

Best practices for leadership and managers

Remember that remote leadership requires more intention than in-person leadership. Great cultures and thriving employees do not happen by accident.

Day to day, managers and company leaders are central to imparting a remote company's culture. They should devote regular time to keeping their fingers on the team's pulse, actively exploring opportunities to engage them in meaningful work and discussions about work, and demonstrating the value they bring to the company.

Just as with on-site companies, each team in a remote company develops its own culture based on its shared professional focus, values, and needs. Team-level managers at FlexJobs foster strong cultures in different ways. For example, there's a lot of common ground in the work our career coaching and client services teams do. Those teams' managers held a cross-team get-to-know-you meeting to create bonds, share knowledge, and brainstorm ways to solve shared pain points.


Afterward, individuals from both teams said they were thrilled to have the chance to connect more deeply with the other team's members. Moving forward, the managers plan to hold similar meetings once or twice a year.

For remote company cultures to work every day, managers should lead by example every day. Our team managers make a point to do small things such as saying good morning and goodnight to their teams on Slack; asking about people's lives outside of work; sharing about their own lives; and posting pictures of their kids, pets, hobbies, messy home offices, and funny memes. It's easy to get stuck in work mode, especially for managers with multiple big responsibilities. But those small, daily interactions are vital to healthy remote team cultures.

FlexJobs routinely refines and improves methods to boost engagement, productivity, and happiness. Feedback and input from team-level managers are especially helpful in these fluid endeavors because employees in that position can more easily see what works well and what doesn't than senior-level managers.

Policies and guidelines

Companies should have some structure around any guidelines they put in place so that those guidelines will be effective. Having flexible work options doesn't mean it's a free-for-all. Everyone will feel more confident when there are guardrails and guidelines to go by.

One place to start is in developing policies around the platforms employees should use for different types of communication. FlexJobs managers have created guidelines for communication norms within teams and across the company. For instance, Slack may be the best place for teams to casually chat throughout the day, but email is better for questions that require some thought before responding.

Further, we have a general policy that if an email chain goes back and forth more than three times without getting closer to clarity or a solution, the staffers involved should stop and think: Would this be more productive as a voice conversation? Synchronous communication can help employees get in sync.

While remote work is overall a more productive, focused way to work, we are human and mistakes will happen. Company-wide, staff talk regularly about assuming "mistake rather than malice," which means that employees start with the assumption that someone did their best and tried to do the right thing. Starting with that assumption makes it easier for staff to address the issue proactively, gain buy-in from everyone involved about the best path forward, have managers check in regularly as the improvements proceed, and continue to use proactive communication to reinforce the new approach. One way to open difficult conversations is with something such as "Our goal for this meeting is to find a good solution" so that the focus is on the problem, not the person.

It takes a reasonable level of empathy to build a healthy workplace culture remotely, as well as a certain amount of humility and vulnerability. Nobody will get it right 100 percent of the time. Starting from a place of trust, plus acknowledging difficulties and being open to feedback, is required of leaders and managers who aspire to build successful remote work cultures over the long term.

Culture is a living, breathing entity

Perhaps the greatest strength of remote workforces is their understanding that work and life are not mutually exclusive. Work and personal responsibilities, interests, and goals will always be vying for similar time and attention, but when those things happen in the same space, the tension between those aspects of people's lives becomes more obvious. And throughout the pandemic, hundreds of millions more professionals have felt that push and pull acutely in their daily lives.

FlexJobs is a workplace where staffers feel empowered to arrange their daily lives in a way that makes sense to them. The company gives team members control and freedom in when, where, and how they work, which helps everyone determine the best ways to make their work lives and personal lives coexist more peacefully. And that control and freedom exists within a cultural framework that supports and promotes proactive communication—starting with trust—and regular reflection and improvement, from the time they interview for a position throughout their life cycle as a team member.

Managers need to appreciate the fact that what works to grow a healthy culture is ever-changing. What may be effective for a period of time can change, so regularly reconsidering how things are working is important. Culture is not stagnant but a living, breathing part of the company that needs steady attention.

The future of work involves remote workers, and workplace culture must reflect that trend. Healthy remote companies proactively build culture in a virtual environment so employees can feel supported and do their best work.

About the Author

Carol Cochran is vice president of people and culture at FlexJobs, leading the company’s human resources functions. She focuses on team and leadership development, engagement and retention strategies, and organizational management. In 2020, she was honored to be named among the 20 Most Inspiring HR Leaders by Business Insider.

With nearly two decades of experience working with teams and companies, Cochran has extensive background in creating and implementing operational and leadership training programs; recruiting, hiring, and onboarding staff at all levels of an organization; and helping to scale operations and culture for growing companies.

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