Dear Toby: HR Advice Column: “All My People Are Contractors… Should I Be Panicking?”
- stephany520
- Jan 23
- 4 min read
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Dear Toby,
I am a small business owner and, honestly, everyone who works with me is a contractor.
When I started, it made sense. I was small, cash flow mattered, and I did not want to deal with payroll, source deductions, vacation pay, CPP, EI, and all the things I know I would probably mess up. Contractors felt simpler.
But now I am freaking out!
A friend of mine who also runs a business just got audited by the CRA. They thought they had contractors, but CRA decided those people were actually employees. Now they are facing big fines, back payments, and a ton of stress.
Now I am looking at my own business wondering if I am sitting on the same problem.
How do you actually know if someone should be a contractor or an employee? And if I got it wrong, what am I supposed to do next?
Signed, Nervous in Nanaimo
Dear Nervous in Nanaimo,
First: you are not alone in this.
Many small business owners start with contractors for practical reasons, not bad ones. Payroll feels intimidating, cash flow is tight, and no one starts a business because they are excited about remitting source deductions.
If you built your team this way, you are not reckless. You are typical.
That said, your friend’s experience highlights something important: in Canada, you do not get to choose whether someone is a contractor or an employee. The relationship does.
CRA looks at how work actually happens, not what the contract calls the person.
The Big Question CRA Asks
When CRA reviews a working relationship, they are really asking one thing:
Is this person running their own business, or are they working in yours?
If someone is truly a contractor, they operate independently. If they are an employee, they are part of your organization.
The label on the invoice matters far less than the reality of the day-to-day work.
How To Tell the Difference (In Plain Language)
CRA generally looks at a few core areas.
1. Control
Ask yourself:
Do you tell them when and how to work?
Do you set their hours?
Do you closely supervise their methods?
Contractors usually control how the work gets done. Employees are directed on both the outcome and the process.
2. Ownership of Tools
Do they use their own equipment and systems?
Or are they using yours?
Contractors typically bring their own tools, software, and setup. Employees usually rely on the company’s.
3. Chance of Profit and Risk of Loss
Can they make more money by working smarter?
Could they lose money if a project goes badly?
Contractors take on financial risk and opportunity. Employees get paid regardless of how profitable the work is.
4. Integration
Are they part of your core business operations?
Do clients see them as “your staff”?
The more integrated someone is into your day-to-day business, the more likely they look like an employee relationship.
5. Exclusivity
Do they work mainly for you?
Or do they have other clients and their own brand?
True contractors usually have multiple clients and independence in how they build their business.
No single factor decides it. CRA looks at the whole picture.
But if your contractors feel like “team members with invoices,” that is often where risk shows up.
Why Misclassification Happens
Most misclassification is not intentional. It happens because:
Businesses grow faster than their infrastructure.
Contractors slowly become permanent.
Roles evolve from project-based to core operations.
Owners keep the structure that worked when they were tiny.
What starts as flexible becomes fragile.
What To Do If You Are Not Sure
First, do not panic. Second, do not ignore it. Here are smart, practical steps
1. Review Your Relationships
List your contractors and ask:
Who controls the work?
Who owns the tools?
Who carries the risk?
Who looks like part of the business?
You will usually spot risk very quickly.
2. Fix It Forward
If someone really looks like an employee, the solution is usually not complicated: you convert them.
That can mean:
Moving them onto payroll.
Updating agreements.
Clarifying hours, pay, and benefits.
Trying to keep someone classified incorrectly is far riskier than correcting it.
CRA is generally far more forgiving when businesses proactively adjust versus waiting for an audit.
3. Do Not Let Payroll Fear Run Your Business
Many owners keep contractors because payroll feels scary.
But payroll does not have to live on your shoulders.
You can:
Use a payroll service.
Engage a part-time bookkeeper.
Work with a fractional HR or finance partner.
The cost of payroll support is almost always less than the cost of penalties, stress, and rework later.
You did not start a business to become a tax expert. You started it to build something.
4. Get Advice Before CRA Does
You do not need a lawyer for every decision, but a quick review with an HR or payroll professional can spot risk early.
It is much easier to fix quietly and intentionally than under audit pressure.
One Final Thought
If you are worried about classification, that is already a good sign. It means you care about building something sustainable, not just fast.
Contractors are a great tool when used properly.
Employees are a great investment when the relationship becomes core.
Strong businesses know when to shift between the two.
So no, you are not in trouble just for asking the question.
You are doing exactly what smart owners do: noticing when yesterday’s solution might not fit today’s business.
Signed, Toby
Disclaimer: The "Dear Toby" advice column is designed to provide general HR insights and guidance but should not be taken as legal advice. Every business and situation is unique, and employment laws vary by jurisdiction. Before implementing any advice from this column, we recommend consulting with a qualified HR professional or legal expert to ensure it aligns with your specific circumstances.
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