How To Turn Remote Work Pitfalls Into A Formula For Success
Illustration: Eric W
Articles - 6 min read
Published on June 28, 2021

How To Turn Remote Work Pitfalls Into A Formula For Success

Remote work isn’t all a bed of roses. We highlight key areas that leaders should take note of when transitioning to the future of work, and how to turn them into success strategies to help organizations win at remote work.

Jillian Wong
Contributing Talent


International borders are closing and reopening every few weeks as the global economy bears the brunt of a virus that is mutating quickly in various parts of the world. Perhaps just as swift as governments’ decisions to close and reopen borders, some companies are equally quick to invest in technology in order to embrace the remote work path. Other more traditional companies may find it a challenge to take up this less conventional work approach.

Remote work, however, isn’t new. It's simply accelerated by the coronavirus. The speed at how remote work further evolves will be nothing short of rapid, even after the fine particles of this pandemic settle. Upwork’s “Future Workforce Report” reports that 73% of all teams are expected to have remote workers by 2028. As we expect the trend to continue, the remote work phenomenon guarantees a bumpy transition for countless organizations. The way to win at this remote game is to anticipate potential pitfalls in order to safely step over to the other side.

After all, it is only through a better understanding at how we can fail at remote work, that we are better equipped for its success.


Let’s face it, there will be growing pains resulting from an office decoupling. Some employees will find this new way of working difficult. There will be new technology and collaboration tools to master and, not to mention, inadequate social interactions and frustration at new processes. The list goes on. Unless organizations start laying the groundwork for this future work model, remote work will fail.

When making the switch from office to remote work, today’s leaders must pay close attention to these five key areas in order to ensure a successful transition towards remote working.


1. Top executives must be the first to adopt a remote work mindset.

In order for remote work to be successful, the key group of employees supporting the shift towards the ‘work-from-anywhere' model must be the C-suite executives. The reasoning behind this is simple. If the leadership team is still located in a physical building, then middle management will flock there in order to be visible to the bosses. The office should no longer be the command post of power or decision making. It is only when top executives practise remote-first practices that a clear mandate for remote work is understood as the future and taken seriously by everyone in the organization.

2. Develop a handbook on the new remote culture, and share it.

A company’s culture can be described as the values that employees believe in, how they feel about the work they do, where they see the company going and how they are going to get there. When an organization is thrust into a new and unfamiliar way of working, employees will be confused and unsure of what to expect. A company culture built over decades can be lost when the physical workplace is suddenly no more.

When an organization gears towards a remote work model, it needs to have its remote culture documented, updated constantly and shared in a handy guide. It is always better to over communicate than to assume that newly-turned-remote-employees are aware of where the company is heading. A handbook documenting the best practices and processes of remote working will help employees continue their work in the most efficient and productive manner. It should cover topics such as how to set up a dedicated workspace, what collaborative/productivity tools to use, how to conduct remote meetings, technical requirements, mental health/wellness and even time management tips. The objective is to prepare employees or new hires to be familiar with challenges and new habits that accompany the dynamics of remote work - allowing them to thrive in an unfamiliar setting and for the organization to operate with uninterrupted efficiency. An organization that fails to do this will risk having their employees repetitively seeking answers everywhere in the wrong places, creating unnecessary interruptions to work processes and resulting in mediocre knowledge sharing.

3. Having the right digital tools and knowing how and when to use them.

Read this: Having digital tools doesn’t guarantee a successful remote work environment. Firstly, you’ve got to have the right tools. Not all communication tools are the same. Some platforms are great for quick exchanges or chit-chat,  some work for urgent matters, some for non time-sensitive matters, while others are used for issues that require lengthy discussions and shared access. Use the right channel for communication.

Secondly, there must be a consensus on how and when to use such tools. Set boundaries such as availability hours so that communication doesn’t become disruptive to others. Remote collaboration tools come with notifications, which can inundate employees with unceasing pings and end up disrupting their productivity. Create rules around keeping the communication respectful, concise and considerate.

4. Trust that your employees are working.

Top leaders must advocate remote work as real work. To put that bluntly, remote managers must trust their employees to do the job. In a study conducted by Harvard Business Review, 617 workers were surveyed on their experiences while working from home. 34% felt that their supervisors expressed a lack of confidence in their work skills, doubted their ability and whether they had the required knowledge to perform at their jobs. An even larger number of employees felt that they had to be available at all times and are expected to have instantaneous responses, even after work hours. The impact of constantly being monitored can have repercussions on employees’ mental health and work-life interferences. Cut back on unnecessary meetings. Instead, schedule short bi-weekly progress catch-ups to check in and provide frequent feedback to help employees work towards the goals you have set as a team and as individuals. Trust and empower your employees to carry out their duties.

5. Create community bonds to fight isolation.

In a remote setting, employees no longer have physical office hallways or shared pantries to chit chat or have informal conversations, and social relationships can erode and loosen quickly. As executives leading change and transformation for a remote work environment, efforts have to be intentional around building alternative modes of community bonding for all. Whether it is work-related or just getting to know your co-worker better, a sense of community is important for employees’ wellness, morale and confidence. Recreate coffee breaks online, have ‘get-to-know-each-other’ sessions where employees can even pick up a skill or two from each other. Share recipes, exchange plants, swap fashion. Get creative to tighten the bonds and develop a sense of togetherness.

While remote work champions workplace flexibility and worker independence, organizations have to work hard at providing the openness, support and infrastructure for this work practice. As it turns out, we have proven that we can accomplish our work from anywhere.  Will the future be all-remote or hybrid-remote? It’s still too early to tell. What we do know is that we aren’t going back to the working world that we knew before. The earlier we start investing in the future of work, the surer our returns will grow ahead.

Do you have a strategy to win at remote work in your organization? Share them with us on our social media platforms.

You may also be interested in this: Is remote working for you? 5 questions to help you decide.

You may also like to browse through our e-shop for some ‘conversation-starter’ tees when you next return to the office.


There’s a better way to grow. And it’s not the traditional way.

It’s about rethinking traditional employment archetypes. Can we progress from an economy built on full time employment habitually enslaved by unemployment fears, to one where individuals have greater autonomy and are self motivated to do work that inspires them? And as a result,  benefit the economy as a whole?

You can’t own full time employees. But you can build a winning team with talent management companies. As businesses demand more, external talents are emerging as the sure forerunners of an agile workforce. At Chance Upon, we partner businesses to get a head start over competition by creating collaborative work between companies and the right talents.

Hire anytime, hire anywhere. Hire exceptional.


Katie Evans, Third Annual “Future Workforce Report” Sheds Light on How Younger Generations are Reshaping the Future of Work, Upwork Press Release, (5 Mar 2019)

Eric Rosenbaum, The biggest work from home mistakes: Harvard Business School remote expert, CNBC (17 Nov 2020)

Dan Marzullo, Maintaining an Employee Handbook In The Age Of Remote Work, Workest by Zenefits, (24 Apr 2020)

Sharon K. Parker, Caroline Knight and Anita Keller, Remote Managers Are Having Trust Issues, Harvard Business Review, (30 July 2020)

remote work
future of work
work trends
remote handbook
remote culture
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