According to Made in CA, approximately 22% of Canadians are remote workers, a significant increase from 4% in 2016. Part of the reason remote work has become more popular is because of the COVID-19 pandemic. More Canadians worked from home during this time, leading many employers to see the value of having their employees work outside the office.
Even though the pandemic has ended, remote work seems here to stay, which has led to a need for remote team management for a small business. Remote work is no longer seen as a temporary response to disruption but rather as a solution and permanent operating model, especially for small businesses in the country.
In today’s blog, our team at Bizfund shares what we know about managing remote employees in Canada so you have a better idea of whether it’s the best model for your business. Usually, if management isn’t a concern and remote work promotes compliance, productivity, culture, and profitability, it’s a good option. Let’s dive in.
Setting Up for Remote Success
Before you can begin to look at remote team management for a small business, you need to set yourself up for remote success. This means you need to ensure your business has the essential tools and software, while also accounting for communication expectations and security considerations.
Essential Tools And Software
We know it may seem like it’s necessary, but you don’t need 15 subscriptions for your remote workforce. It’s usually best to stick to a handful of applications or fewer because you want to use tools and software that actually solve problems.
For example, many small businesses find Teams, Slack, or Asana is the best solution for communication and meetings, while Clickup or Monday.com is the best for project management and task overviews.
In addition, on the financial side, cloud-based accounting platforms like Intuit and document storage like Google Drive are usually the best bet. With these, employees aren’t relying on personal devices or unsecured transfers.
Communication Expectations
One of the biggest reasons remote work fails is that communication expectations are not established early on in the process. That’s why it’s incredibly important that you define your expectations with remote employees.
For instance, define response windows for messaging and email, and specify when you expect real-time communication. It’s also important to clarify escalation processes so that your remote employees know when something is routine versus urgent.
With clear communication policies, you can better manage your team, prevent burnout, and maintain decision-making speed.
Security Considerations
According to 2025 data, about 43% of all cyberattacks targeted small businesses, underscoring the serious risk to these organisations. We tell you this to say that Canadian businesses shouldn’t take cybersecurity considerations lightly, even with small remote teams.
It’s important that you require remote employees to use multi-factor authentication, secure wifi connections, and company-managed devices when possible. It’s also important to limit sensitive client data and financial system access to only those roles that need them.
It’s also essential to update software routinely and educate staff about phishing risks. After all, a data breach will cost your small business more than the cost of preventive controls.
Hiring Remote Employees
Remote team management for a small business also involves correctly hiring the right employees to work from home. Let’s have a look at what to look for, interview techniques to follow, and onboarding tips:
What To Look For In Remote Workers
Knowing what to look for in remote workers can help ensure your business can build a strong team, which in turn makes managing them easier. You’ll want to look for:
- Employees who are adept at self-direction and who can take ownership of tasks. Since remote employees have to work forward without awaiting daily instruction, you need go-getters who are comfortable pushing themselves. The easiest way to ensure they can do this is to ask candidates how they prioritize tasks when multiple deadlines overlap.
- Exceptional written communication. Given that remote workers often communicate by written word, you need to hire individuals who can clearly explain ideas in email or project commentary. This can help minimize friction across teams.
- Exployees comfortable being accountable. For most small businesses, remote roles require measurable outcomes. This means that you need to look for individuals who understand that the flexibility they enjoy comes with performance expectations that adapt.
Interview Techniques For Remote Roles
Hiring for a remote role can be quite challenging, especially if you’re putting together a new team. Here are a few simple interview techniques that you can use to make sure you’re hiring the right people:
- Use scenario-based questions, like asking how they handle missed deadlines or unclear instructions.
- Ask the candidates to explain their process, as this often matters more than the ‘right’ answers.
- Have candidates describe tools they have used before when collaborating to assess their digital fluency. If they seem comfortable, you know they can better grasp remote communication.
- Clarify your business’s performance expectations early. The last thing you want is to hire a candidate, and their performance goals don’t align with what you need. So, discuss measurable outcomes during the interview so both parties understand one another.
Onboarding Remotely
If you’ve ever been a part of a remote onboarding process before, you know exactly how difficult it can be. After all, remote onboarding requires far more intentional structure than in-office training. In many instances, this is where your management truly begins.
So, with this in mind, here’s how to manage things the right way from the beginning:
- Offer your remote employee a roadmap: The best remote teams follow a 30-60-90-day onboarding plan. This staggered approach offers new hires clarity on early priorities and measurable goals.
- Assign a designated contact person: There’s nothing worse than a new hire not knowing who to reach out to for clarity surrounding questions. That’s why it’s important to ensure you assign a contact person to avoid undermining their confidence when questions go unanswered for days on end.
- Schedule structured check-ins: You shouldn’t rely on new remote employees to reach out when they need support. Instead, it’s best to schedule check-ins to build early role consistency and independence later on.
Day-to-Day Management
The day-to-day management can get tedious at times, but if you nail down the right processes early on, things tend to fall into place. Of course, there is always the chance of a curveball appearing from left field, but generally, things stay the course.
Tracking Work Without Micromanaging
You don’t want to micromanage your team, even though this can be quite an easy trap to fall into with remote employees. To avoid micromanagement, it’s best to define deliverables and deadlines upfront so expectations are measurable. You can easily do this by sharing project boards or task trackers to create visibility without interrupting workflow.
Regular Check-Ins That Work
We cannot stress enough how important regular check-ins are with remote teams. In these meetings, which you should hold weekly, you should be discussing priorities, obstacles, and support. What you shouldn’t be doing is discussing performance updates; those should be in special meetings so employees can better prepare. You should also be sending meeting summaries to eliminate confusion about next steps.
Managing Across Time Zones
In the modern day and age, it’s common to have remote team members spread across different countries. If you hope to manage these employees, it’s best to establish clear overlapping hours when you expect real-time collaboration.
It’s also important to document this when it’s the case, to avoid confusion. We also recommend you create workflows that allow for asynchronous progress through recorded updates and shared documents. This way, no one is waiting on anyone else, and there is no holdup with deliverables.
Building Remote Culture
When you have a small business, remote culture matters far more than you might expect. This is because company culture can directly affect employee morale, performance, and retention rates. So, you need to better manage employee culture to ensure these don’t become problems down the road.
To manage employee culture, you should consider setting up practical virtual touchpoints, such as short knowledge-sharing sessions or collaborative problem-solving meetings tied to real projects. These culture-building solutions can help you keep everyone on the remote team aligned without disrupting productivity.
It’s also important to make it clear to remote workers that company values guide promotion, performance review, and hiring decisions. This can help them understand that expectations are consistent. In addition, address signs of disagreement early, as they can severely impact company culture, even in remote environments. The easiest way to address these signs is to conduct regular one-on-one discussions.
Legal Considerations in Canada
Legal considerations are a huge part of remote team management for a small business. This is because effective team management also requires protecting the business from compliance risks. So, if you have a remote team, just bear in mind that provincial employment standards still apply, including statutory holidays, overtime, and termination requirements.
It’s also important to define reimbursement policies for things like internet and equipment costs, and to understand the CRA documentation requirements. And although it may be surprising, occupational health and safety obligations still apply even in remote settings. This means you still must offer guidance on safe work practices and document reasonable efforts to support your remote employees’ well-being.
Measuring Remote Productivity
To know whether your remote team management is working, you need to learn how to measure productivity. Below we share a few of the best ways to measure how well your team is performing…or isn’t:
- Output vs hours worked: With your small business, your remote team management should prioritize results over screen time. What we mean is that you should have a team that meets agreed standards and completes deliverables, rather than simply ‘being present’ when they’re needed. So, don’t simply look at logged hours when measuring management; also look at what has actually been achieved.
- KPS that make sense: Depending on the industry within which you operate, there are likely many different KPIs you can use. However, not all KPIs matter. You would do best to use KPIs that measure revenue growth, turnaround time, client retention, and cost-efficiency. By focusing on a limited set of metrics, you’re better positioned to glean meaningful insights for your small business.
- Signals things aren’t going well: There are many signals you need to watch for that can tell you immediately that your management isn’t working. For example, when work quality declines, deadlines are missed, and communication breaks down, these usually indicate that your team management strategy needs revision. When you notice these signals, it’s important to address the concerns as soon as possible.
Remote Can Work for a Small Business
For some small businesses, a remote team is the best choice as long as clear expectations are set, compliance is a priority, performance is measurable, and the appropriate individuals are hired. If you can get this right, remote work can improve your productivity, reduce overhead costs, and expand your hiring reach without you ever feeling like you’re sacrificing control.
If you do decide to expand your team and invest in tools, software, and security systems, but you don’t quite have the capital, it might be time to consider financing. At Bizfund, our team offers merchant cash advances of up to $300,000 to help you fund and grow your remote team. If you would like to learn more, you can contact us here.
