11 mins read

How to Overcome the Challenges of Managing a Remote Workforce

overcome challenges managing remote workforce
Daphne Blake

By Daphne Blake

Corporate America has already ditched the cubicle for the conference room, and water cooler small talk for a string of Slack chat notifications. When rapidly-shifting work cultures make leading a team challenging during the best of times, how do you manage a remote workforce on top of everything else?

Entrepreneur reported that as of last year, as much as 43% of the U.S. workforce was expected to telecommute . This new reality raises a host of questions for team leaders- How do managers communicate effectively with a workforce that could be spread out across multiple states – or countries? Beyond day-to-day workflow, what does a performance evaluation for a remote worker look like? How do you keep your team members happy and on track to complete major projects?

As your team expands, establish a set of best practices for managing a remote workforce to complete projects on time, build team morale, and hire the right people.

Challenge-1- Communicating With Your Team

communicating with your team

Whether you have staff across multiple time zones or multiple countries, communicating with direct reports – and helping your employees communicate with one another – can be two of the most challenging aspects of working remotely.

Action Step-1- Set up the right tools

Get in touch instantly with your team on messaging services like Slack , Jostle , or Ryver , and encourage your team members to ping each other there, too. Slack offers separate 'channels' for individual projects, making it easy for your team to see who’s working on what – and how things are going.

Regular communication around projects will most likely happen through a combination of email, video conferencing, and phone. Tools like Skype, Google Hangouts, and GoToMeeting offer free high-quality video or audio conference calls, which can help put your team all on the same page. Since remote employees don’t often have the opportunity to feel like part of a team, using video or phone conferencing for all-team meetings or check-ins can be a great way for team members to become more familiar with one another, too.

Need more guidance on how to use these tools effectively? Check out this helpful resource from HubStaff.

Action Step-2- Establish a check-in routine that works best for your team

Managing a remote workforce has its disadvantages, but it can be especially tough for bosses who are used to hands-on management. It’s best to strike a balance between regular check-ins and team meetings and letting employees come to you with problems. For starters, try setting up weekly email check-ins for each employee or team and a monthly all-team conference call. You can always scale up or back as needed.

Action Step-3- Encourage open lines of communication between you and your staff

If remote employees don’t feel comfortable coming to you with questions, you could wind up with a backlog of uncompleted projects. As you onboard new staff, impress upon them your 'open door' policy and encourage them to reach out with questions, concerns, or problems.

Action Step-4- Create space for staff to communicate with one another

Chatrooms are a great space for staff to encourage one another, ask questions, and manage projects to completion. Whether you choose Slack or a project management servicelike Asana, make it clear that staff members should interact with one another regularly and establish the hours when they should be available to respond to one another.

Challenge-2- Setting clear expectations

setting clear expectations

In a traditional office setting, your employees pick up on visual and behavioral clues – say, how their co-workers dress, or what it feels like to be part of a collaborative or team meeting.

Since remote employees don’t receive these same contextual clues while working online, it’s up to the manager to provide clear team expectations about everything from deadlines to individual responsibilities and billable hours.

Action Step-1- Create detailed onboarding documentation

Make sure all of your employees have easy access to company expectations and protocol . In addition to details about individual roles, including how often your teams communicate, how employees are expected to manage deadlines and projects online and expected availability.

Action Step-2- Establish a clear chain of command

Ready to delegate some of your supervisory tasks to a project manager? Ensure the rest of your employees understand the chain of command, who they should email with questions, and how often they can expect check-ins from you.

Action Step-3- Discuss how to resolve problems or questions

Anyone who’s read a confusing text understands how easy it is to misinterpret tone or intention online or via phone. Give your employees proactive tools for handling problems and questions, whether that’s encouraging them to pick up the phone and talk it out, or specifying a team turn-around time for project-related emails.

Action Step-4- Explain how individual tasks contribute to the company’s goals or culture

When team members understand how their day-to-day roles fit into the company’s big picture, things get done more quickly, says Obie Fernandez , author of The Lean Enterprise.

'Aligning everyone’s goals through a common purpose and regularly recognizing each person’s contribution to that purpose is essential for team building,' Fernandez writes at The Muse. Not only will your workers be more effective with these goals in mind – they’re more apt to cheer each other on, too.

Challenge-3- Team-building

team building

According to Forbes , remote workers struggle most with three major aspects of working on their own- feeling isolated from their co-workers, exhibiting a lack of productivity, and being unable to set clear work/life boundaries. Make it a priority for your team members to feel comfortable with one another, in order to improve morale and stay on deadline.

Action Step-1- Use project management tools to foster systems of support

Often project management tools or online chat are only used to push a project across the finish line. Encourage employees to use these systems to provide positive support – feedback, encouragement, and virtual high fives help build relationships and morale.

Action Step-2- Find time to meet in personDepending on how to spread out your team is, it may be worth holding monthly in-person meetings. Not possible? How about a monthly video chat where you all get to see one another and touch base on your projects?

Action Step-3- Get social

The team that plays together stays together. Fitness challenges, book clubs, and other outings help put the Kayako team on the same page, and Zapier hosts weekly hangouts, ranging from talks to demos. Plenty of these activities take place virtually, but the social nature of them helps team members feel more comfortable and confident in one another.

Challenge-4- Managing workflow

managing workflow

In an office setting, it’s easy for employees to get a sense of the company’s priorities, keep the big-picture goals of the company in mind, and know when they should accommodate a new request or task on the fly.

Since these elements of work tend to get muddied in remote environments, it’s important for managers to clearly communicate priorities – and when those priorities or deadlines shift.

Action Step-1- Use task management tools

Asana, Basecamp, and Trello each offer professional solutions for moving projects through the pipeline. Not only is it easy to assign responsibility for tasks, but there are also plenty of chat functions in Asana and Basecamp that allow team members to check in regularly with one another around project completion.

Action Step-2- Create a check-in culture

Team members should feel comfortable communicating with one another and with you about their progress. If you establish this culture from the get-go, a quick ping on Asana will feel natural, rather than overbearing. Of course, managing a team remotely can make some supervisors feel like they have to check in too often. Trust that your team is getting work done behind-the-scenes – or institute something like HubStaff’s employee monitoring software .

Action Step-3- Use team meetings to have a group huddle about ongoing projects

When your team is scattered, it’s important to use what little time you have together to get on the same page. If you have a big deliverable, this becomes even more important. Schedule regular team or project meetings to ensure everyone is clear on their tasks. Encourage report-outs on progress and make it clear that you need to know if things are moving along according to schedule.

Challenge-5- Addressing Accountability

addressing accountability

Working from home means employees have the luxury of working out of your sight. Some employees thrive with this kind of independence, while others can falter. Create systems that help your employees shine from afar.

Action Step-1- Assign clear deadlines and communication pathways

There are always soft and hard deadlines, but make sure your employees know the difference between the two. Missing a deadline for a small task may not seem like a big deal, but it could snowball and impact the entire team. Establish protocol around what employees should do when they hit snags, especially around completing projects on time.

Action Step-2- Create a culture of positive feedback

Accountability is about more than critiquing someone’s performance. In a remote environment, it can be tough for employees to feel like they’re on track. Especially if you work in client services, make sure your staff and project managers know when they’re rocking it – they need to hear praise , too.

Action Step-3- Don’t wait to address performance with struggling employees

If you sense that someone on your team is struggling with deadlines or doesn’t quite have the technical skills you need, it’s important to address this right away. Make your expectations clear, and give them a pathway to follow to get up to speed.

Challenge-6- Hiring & HR

hiring and hr

Finding an employee who works well remotely can be tricky since working remotely requires trust, effective communication skills, and worker independence. Often this means hiring workers who have a high level of skill in their area of expertise, rather than employees who might develop in their roles.

Action Step-1- Understand the skill sets of good remote employees

These skill sets include both technical and soft skills . The best remote workers are action-oriented, have good problem-solving abilities, and are able to prioritize tasks. They’re also often highly skilled in their field, which means they require less day-to-day supervision.

Action Step-2- Interview via video chat

You wouldn’t hire someone just based on their resume in corporate culture – so why do that for a remote team member? A video chat will give you a better sense of the applicant’s social skills, which they’ll need to be successful on your highly-communicative team.

Action Step-3- Require work samples

Not only are work samples a good indication of ability, but you can also see how the applicant handles communicating via the tools your remote team logs onto every day. How well do they navigate your virtual culture?

Action Step-4- Initiate a paid trial period

Make sure the hire is a good fit before you bring them on full-time. Since finding the right employee is even more important on a virtual team, write the paid trial period into the contract . You can part ways after a few months if it doesn’t work out, or address issues early before they become bad employee behavior.

Challenge-7- Evaluating Job Performance

evaluating job performance

In a traditional office setting, employees receive multiple forms of verbal feedback from their coworkers and collaborators, as well as regular input from their supervisor. Since there are fewer real-time interactions on virtual teams, it can be difficult for employees to know how their performance stacks up.

Action Step-1- Schedule regular feedback

Whether you send regular feedback once a quarter or once a month, remote employees need to hear about their performance to feel like they’re contributing to the team . Use your regular check-in meetings or calls to encourage employee feedback and questions. Managers can also use this time to evaluate ongoing progress on projects.

Action Step-2- Encourage employee self-reflection before a yearly review

This is a common enough practice for in-person teams, too. To make the review especially useful, ask your employee to evaluate how they manage their time on their own and their comfort level with your company’s set of communication and project management tools. Consider their responses when you evaluate your own job as a manager. What can you do to make your employees’ remote work lives even better?

Action Step-3- Don’t blindside employees with negative feedback

When you have remote employees, it’s especially important to address problems as they come up – even if it seems easier to let things slide. If you save all of your negative feedback for the yearly review, you’re not giving your remote workers a fighting chance to adapt to your virtual culture and expectations. That takes time – and practice.

While there are technical challenges to managing a remote workforce, it’s important to treat remote workers just as you would your office colleagues or supervisees. In fact, says organizational behavior expert Mark Mortensen , thinking about your remote employees as 'different' could lead to trouble.

'We have a tendency to overcompensate and approach remote workers and virtual teams as these mythical beasts,' Mortensen told Harvard Business Review. 'But you shouldn’t think about them in a fundamentally different way. They are still people working in an organization to get stuff done. Treat them as such.

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