Move over traditional working there’s a new method in town – Remote working!

A significant part of the world has been forced to change their way of working with the onslaught of COVID-19. For some organizations they’re making that change kicking and screaming, but know if they’re to survive they have to adapt.

In the Caribbean, there has always been pushback when it comes to remote workers – “How will I know they’re doing their job?” “How can I say they’re at work when they’re at home?” “I need to know that they are working and I can’t do that if they’re not in the office?”

So many excuses, but if you look carefully most are due to a lack of trust.

As a leader I learnt long ago, that to effectively lead I had to focus on the real objective – the output! Whether that was creating a product or delivering on the numbers, it was achievement of the target not necessarily the process to get there that was important.

This is the change of mindset required for any leader new to remote working.   

This new reality raises a multitude of questions and challenges for team leaders that they’ve never had to consider – How do I communicate effectively with a workforce that I can’t see or spread out across multiple locations? Beyond day-to-day workflow, what does a performance evaluation for a remote worker look like? How do I keep my team members happy and on track to complete major projects? How do I trust them to deliver? How can I lead when my team is in not in front of me? 

This is where you need to establish a clear set of best practices for managing your remote workforce to complete projects on time, build team morale, and feel confident in your leadership.

Communicating With Your Team

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

Set up the right tools – Larger organizations will most likely have some Microsoft product for messaging. For smaller organizations, get in touch instantly with your team on messaging services like Slack and encourage your team members to message each other there – it’s free for small teams.

Set up sub groups for individual projects or teams making it easy for your team to see who’s working on what – and how things are going. Try to avoid communication via WhatsApp, people still need to retain a level of privacy. 

Regular communication around projects will most likely happen through a combination of email, video conferencing, and phone, utilize tools like Skype and Zoom to host meetings, which can help put your team all on the same page. To maintain the team environment use video or phone conferencing for all-team meetings or check-ins to ensure team members remain connected.

Establish a check-in routine that works best for your team – Yes, managing a remote workforce has its disadvantages and it can be tough for bosses who are used to hands-on management. Strike a balance between regular check-ins and team meetings and letting employees come to you with problems. For instance, schedule a morning buzz brief or end of day debrief, try setting up daily/weekly email check-ins for each employee and a weekly/monthly all-team video conference call. You can scale up or back as needed.

Encourage open lines of communication between you and your team – This is all about building trust and empathy. If your team don’t feel comfortable coming to you with questions, you could wind up with a bunch of missed deadlines. Just like you, it’s a new way of working for them, so impress upon them your ‘open door’ policy and encourage them to reach out with questions, concerns, or problems.

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 service like 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.

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 they won’t receive these same contextual clues while working online, it’s up to you – the leader to provide clear team expectations about everything from deadlines to individual responsibilities.

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, projects online and expected availability.

Establish a clear chain of command – If you have to delegate some of your responsibilities, ensure the rest of your team understand the chain of command, who they should email with questions, and how often they can expect check-ins from you.

Discuss how to resolve problems or questions – It can be easy to misinterpret tone in an email or intention online or via phone. Again they no longer have the physical cues or opportunity to discuss on the fly. 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.

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. Aligning everyone’s goals through a common goal or objective and regularly recognizing individual  contribution to that goal is imperative for team building. Not only will your team be more effective but they’ll more apt to support each other too.


Both you and your team have been used to creating that team camaraderie and there’s a chance that they will struggle with 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 track.

Provide opportunities for remote social interaction – You don’t have to get straight down to business in every meeting, structure ways for your team to interact socially (that is, have informal conversations about non-work topics) while working remotely, virtual coffee dates, pizza breaks (there’s a boom in food delivery services across most islands). The adjustment to remote working can take time, but particularly so if your team have been abruptly transitioned out of the office.

These types of activities may sound artificial or forced, but can help reduce feelings of isolation, and promote a sense of belonging.

Provide encouragement and emotional support – Especially in the context of an abrupt shift to remote work, it is important for you to acknowledge stress, listen to employees’ anxieties and concerns, and empathize with their struggles. If an employee is clearly struggling but not communicating stress or anxiety, ask them how they’re doing, just like you would at any other time. Even a general question such as “How are you adapting to this new work situation so far?” can elicit important information that you might not otherwise hear. Once you ask the question, shut up and be sure to listen carefully to their response, briefly restate what you heard back to the employee, to ensure that you understood correctly. Let the employee’s stress or concerns (rather than your own) be the focus of this conversation.

Continue with your One-to-one meetings – These will be even more critical for morale and while it can seem like a hassle to schedule one-to-ones with every team member, they make workers feel valued and are an opportunity to give feedback on work performance. If these meetings aren’t conducted regularly or get rescheduled, it can make remote workers feel out of touch with what’s happening in the company and unsure of where they stand.

Managing workflow

In an office environment, it’s easy for your team 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 can get lost in translation in remote environments, it’s important for leaders to clearly communicate priorities – and when those priorities or deadlines shift.

Use task management tools – Depending on your business, you may already be using tools such as Asana or Trello to manage projects. If not a good old Excel Gantt chart can help you with assigning responsibility for tasks, and can progress can be updated via your regular check-ins to ensure project completion.

Create a check-in culture – Your team should already feel comfortable communicating with one another and with you about their progress. But set expectations from the get-go by establishing a check-in culture, a quick message will feel natural, rather than overbearing. Don’t feel like you have to check in every hour – trust that your team is getting work done behind-the-scenes.

Addressing Accountability and Performance

This is probably the biggest aspect most leaders are worried about. 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 processes that help your employees excel remotely. 

Focus on output not input – As a leader ask yourself what’s the real end goal – how long someone is sat at their PC or the completion of that report? For most roles your focus can be on the deliverables and not necessarily the process (at least for the short term). Also bear in mind that most workers can actually be more productive because they don’t have the constant interruptions of impromptu meetings, constant phone calls and peers stopping by for a chat. Trust is two way street –

Assign clear deadlines and communication pathways – Clearly define your deadlines, some are non- negotiables what are they? Make sure your team know what they are. Missing a deadline for a small task may not seem like a big deal, but it could escalate and impact the entire team. Establish protocols around what your team should do if they face hurdles that would impact delivery times. 

Create a culture of positive feedback – Accountability isn’t just about critiquing someone’s performance. In this new environment, it can be difficult for employees to know if they’re on track or doing a great job. Make sure your team know when they’re knocking it out of the park – they need to hear praise too.

Don’t wait to address poor performance – If you sense that someone on your team is struggling to adjust, they’re missing deadlines or haven’t quite come up to speed, it’s important to address issues right away. Make your expectations clear, ensure they understand any consequences and give them the support they need to get up to speed.

Evaluating Performance

Both you and your teamwould be used to receiving multiple forms of verbal feedback – from co-workers, other managers and collaborators, as well as regular input from their superior. Since there are fewer real-time interactions on virtual teams, it can be difficult for your team to know how they’re performing.

Schedule regular feedback – Now, more than ever your team need to receive regular feedback. Hearing about their performance will help them to feel like they’re contributing to the team. Use your regular check-ins, briefings or calls to encourage employee feedback and questions. You can also use this time to evaluate ongoing progress on projects.

Encourage employee self-reflection before a review – How long your remote team will be operational is an unknown at present but just because your team is now remote doesn’t mean that their quarterly/semi-annual or annual review is cancelled! Just as you would have done irl (in real life), this activity continues. 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 management tools. Consider their responses when you evaluate your own job as their leader. What can you do to make your teams’ remote work lives even better?

Don’t blindside them with negative feedback – When your team is remote, it’s especially important to address problems as they come up – even if it seems easier to turn a blind eye and 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.

The challenges of managing a remote workforce aren’t that dissimilar to leading your team in the office, it just takes a flex of both your skills and mindset. Treating your newly remote team any differently could lead to trouble.

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If you need more support leading your remote team join me in Effective Leadership In a Remote World – a 4 week group coaching program specifically for leaders who would like more guidance and support. With live hands on calls 3x per week via Zoom, we’ll address real challenges and create solutions that deliver real results. Secure seat and register today.