Phishing Training That Actually Works (And Doesn't Waste Everyone's Time)

A couple of winters ago I was reading a survey from the Canadian Federation of Independent Business: nearly half of small businesses had experienced random cyberattacks, but only 11% had offered mandatory cybersecurity training in the past year.

That stuck with me.

Around the same time, federal and Chamber-style guides were saying the same thing: phishing is one of the top threats, and basic awareness training is one of the cheapest ways to lower risk.

So on one hand you've got attackers pounding on inboxes. On the other, most SMBs are either:

• Doing no training, or
• Doing training so boring that nothing sticks

Let's fix that.

Why Phishing Training Matters More Than Another Gadget

StatsCan's 2024 release on cyber incidents in Canadian businesses said scams and fraud (which includes phishing) increased compared to 2021.

You can have:

• Firewalls
• Endpoint security
• Backups

…but if someone in the office sends money to a fake "vendor" or hands over email credentials, you're still in trouble.

Government and industry guides aimed at small businesses all repeat the same idea: human error is the weak link, and training is how you harden it.

Why Most Training Flops

Here's what I see when I get called into businesses from Stoney Creek to Burlington:

• Slide decks copied from a U.S. vendor, full of jargon
• One long annual session, usually jammed into December
• No local examples, no numbers, no follow-up

Staff walk out thinking, "Don't click bad links, got it," and then click the next polished fake CRA email they see.

CIRA's 2023 report found 97% of organizations say they conduct cybersecurity awareness training. The CFIB survey I mentioned earlier shows how weak that can be in small business reality. There's a gap between "we did training once" and "our people can spot trouble."

What "Good" Phishing Training Looks Like

Let's keep this practical. For a 10–50 person shop along the QEW, good training should be:

• Short and regular – 15–30 minutes, a few times a year
• Concrete – screenshots of real phishing emails
• Local – "This is how a fake CRA / Interac / Bell / Rogers message looks"
• Tied to process – "Here's exactly what you do when you're unsure"

Pulling from Get Cyber Safe's phishing guidance and small business material, here are the key signs to teach: urgent language, odd links, attachments you didn't expect, sender addresses that are 'almost' right, and requests to bypass normal process.

How to Build a Simple Phishing Training Program

Think in phases, not perfection.

Phase 1 – The "coffee and examples" session

Gather your team (in person or remote) and walk through 4–6 real phishing examples:

• Fake shipping notifications
• Fake CRA or bank messages
• Fake CEO / supplier payment requests

For each one, ask:

• "What looks off?"
• "What would you do if this landed in your inbox?"

Use examples from Canadian-focused resources and industry writeups, not random U.S. cable companies.

Keep it under 30 minutes. End with one clear rule: "If you're unsure, stop and ask. You will never get in trouble here for double-checking."

Phase 2 – Simulated phishing (the right way)

I'm a big fan of safe phishing tests, as long as they're not used as a "gotcha".

Basic rules:

• Start simple, don't try to trick people with pixel-perfect fakes on day one
• If someone clicks, the page should teach, not shame
• Use the results to see where to focus (finance? front desk? remote staff?)

Several Canadian guides recommend ongoing training and simulated phishing as part of a small org's basic security program.

Phase 3 – Tie it to business process

Phishing risk plummets when you tie email decisions to real-world procedures. For example:

Payments:

• No bank detail change based on email alone
• Always verify by phone using a known number

Gift cards / urgent payments:

• Any "urgent" payment request from a "boss" must be confirmed verbally

Password reset links:

• Staff should go directly to the site (e.g., office.com, cra.gc.ca), not through links in email

Write these rules down. One page, plain language, part of your onboarding.

Tools That Can Help (Without Buying Half of Bay Street)

You don't need some fancy learning management system to start.

Comfortable options:

• Short internal sessions using examples pulled from trusted Canadian sources
• Low-cost phishing simulation platforms (or modules from your MSP)
• Occasional posters or email reminders with one tip at a time

Just make sure whatever you use:

• Covers phishing, spear-phishing, and business email compromise (fake CEO/vendor)
• Reinforces MFA, strong passwords, and "verify big money moves"
• Is tracked, so if anyone ever asks "What have you done?", you have proof

How to Measure If It's Working

Don't get lost in dashboards. Track things you actually care about:

• Click rate on simulated phishing over time
• Number of staff reporting suspicious emails
• Time it takes for someone to report a real phishing attempt

Between StatCan's numbers, the CFIB survey, and Chamber/CIRA guidance, the picture is clear: phishing isn't going away, and training is one of the few levers you control that doesn't require new hardware.

If you can get your team in Hamilton, Burlington, Oakville, and Stoney Creek to go from "click first, think later" to "stop, squint, and ask," you've already moved the needle more than any glossy brochure from a vendor.