13 Jul
Most small business owners assume phishing simulations are complicated, expensive, or require a full-time IT person to manage. That assumption is costing businesses real money. According to the UK National Cyber Security Center, phishing remains the most common attack vector for organizations of all sizes, and small businesses are increasingly targeted precisely because attackers know they often lack security training programs.
The good news: setting up automated phishing simulations has become very simple. Modern tools allow you to start protecting your company in just a few steps.
What You’ll Need Before Starting
Gather these items before you begin. The prep work is very quick.
You’ll need a list of employee email addresses. A simple spreadsheet works fine, with columns for first name, last name, and email. If you have a group of employees, that is one row per person. Nothing fancy.
You’ll also want to know your email service provider. Are you using Google Workspace, Microsoft 365, or something else? This matters for deliverability settings to ensure the tests reach the intended inboxes.
Finally, decide who should receive reports. Typically this is you, as the business owner, and possibly a manager or two. These people will see who clicked on simulated phishing links and who reported them correctly.
Step 1: Create Your Account
Sign up for your chosen phishing simulation platform. When evaluating the best phishing simulation software 2026 options, buyers should look for 2026 benchmarks. Relying on 2024 evaluations may exclude vendors who have since integrated critical AI-detection and response features common in the current market. Look for platforms that focus on small businesses, as enterprise tools often come with complexity you do not need.
The signup process typically asks for your company name, your email address, and basic company information like industry and size. This information helps the platform generate realistic phishing scenarios specific to your business type.
A retail business will receive different simulation templates than an accounting firm. A construction company faces different phishing threats than a dental practice. Good platforms use this context automatically.
Step 2: Configure Email Deliverability
This step trips up many first-time users, but it is simpler than it sounds. Your email system needs to know that simulation emails are legitimate and should not be blocked by spam filters.
Most platforms provide specific instructions for your email provider. For Google Workspace, this usually means adding a few IP addresses to your allowlist. For Microsoft 365, you must use ‘Advanced Delivery’ policies for third-party phishing simulations. Simple safe-sender listing is often overridden by the platform’s automated ‘ZAP’ (Zero-hour Auto Purge) and Secure Presets, according to Microsoft Learn Documentation updated in early 2026.
The platform should provide copy-paste instructions for each major email provider. If you are using a less common provider, their support team can typically help within minutes.
Skip this step and your prepared simulations might land in spam folders, which defeats the purpose entirely.
Step 3: Import Your Employee List
Upload that spreadsheet you prepared earlier. Most platforms accept CSV files, which you can export from Excel or Google Sheets with a single click.
During import, you will map your spreadsheet columns to the platform’s fields. First name goes here, last name goes there, email address goes in the third slot. The interface typically makes this obvious with dropdown menus.
Some platforms let you add additional information like department or job title. This becomes useful later when you want to send role-specific simulations. An accounting manager should receive fake invoice emails while a receptionist might get fake delivery notifications.
For your first simulation, basic information is enough. You can always add more detail later.
Step 4: Select Your First Simulation Template
Modern platforms offer dozens or hundreds of pre-built phishing templates, each mimicking real-world attacks.
For your first simulation, choose something believable but not too sophisticated. A fake password reset email works well. So does a shipping notification or a meeting invite from a “colleague.”
Avoid starting with highly targeted spear-phishing templates. Save those for later, after your team has some training under their belts. Research published in ScienceDirect suggests employees respond differently to various phishing tactics, so varying your approach over time produces better training outcomes.
Preview the template before selecting it. Look at both the email content and the landing page that appears when someone clicks the link. The landing page should immediately reveal the simulation and provide a teaching moment, not collect actual credentials.
Step 5: Customize the Simulation (Optional)
Most templates work fine out of the box, but small customizations increase realism.
Consider changing the sender name to something relevant to your business. If you use Slack, a fake Slack notification will be more effective than a fake Teams message. If your team uses a specific project management tool, reference that instead of a generic one.
You can also adjust the difficulty level. Some platforms let you add or remove red flags like spelling errors, suspicious URLs, or mismatched sender addresses. Start with a few obvious red flags for your first test.
Don’t spend too long here. The goal of your first simulation is to set a baseline, not to trick everyone.
Step 6: Schedule the Send
Timing matters more than you might think. Send your simulation during normal business hours when people are actively checking email. Tuesday through Thursday mornings tend to work well.
Avoid sending on Monday mornings when inboxes are flooded, or Friday afternoons when people are mentally checked out. Holiday periods and company events are also poor choices.
Most platforms let you stagger delivery so all emails do not arrive simultaneously. This prevents the “hey, did you get that weird email too?” conversation that can spread through a small office in minutes.
A brief delivery window usually works well for small teams.
Step 7: Configure Immediate Training
When someone clicks a simulated phishing link, what happens next determines whether they learn from the experience.
Configure your platform to display an immediate training message. This should explain that the email was a simulation, identify the red flags they missed, and provide quick tips for spotting similar attacks in the future.
Keep this training brief. A short training session is ideal. Lengthy videos or quizzes at this stage feel punitive and create resentment toward the security program.
The goal is a quick “aha” moment, not a lecture.
Step 8: Set Up Reporting
Decide who receives simulation reports and how often. Daily summaries work for the first week, then weekly reports are usually sufficient.
Reports should show click rates, report rates (how many people correctly flagged the email as suspicious), and trends over time. Good platforms break this down by department if you’ve added that information.
Some platforms also provide a “phishing report button” that employees can install in their email client. This lets them flag suspicious emails with one click, both during simulations and for real threats. If your platform offers this, enable it now.
Step 9: Communicate with Your Team (Before You Launch)
This step happens outside the platform but matters enormously for program success.
Send a brief message to your team explaining that you’re starting a security awareness program. You don’t need to reveal exact timing or what the simulations will look like. Simply tell them that periodic test emails will arrive, that clicking isn’t a fireable offense, and that the goal is to help everyone get better at spotting threats.
This transparency reduces anxiety and increases buy-in. People who feel ambushed by simulations often become hostile to security programs. People who understand the purpose generally appreciate the training.
If you’re following a structured cyber-fraud prevention checklist, this communication step should already be on your list.
Step 10: Launch and Monitor
Hit send. Then resist the urge to watch results in real-time for the next three hours.
Initial click rates for untrained teams can often be significant. Don’t panic if your results are high. That’s exactly why you’re running simulations.
After a few days, review your first report. Note the overall click rate and identify any patterns. Did certain departments perform better or worse? Were there specific job roles that struggled?
Use this data to plan your next simulation. If everyone clicked, your next test can be slightly easier while you build up their skills. If only a few people clicked, you can introduce more sophisticated attacks sooner.
What Comes After Your First Simulation
One simulation doesn’t create a security-aware culture. Plan to run simulations regularly, with frequent tests being better for the first few months.
Vary your templates. Rotate through different attack types: credential harvesting, malware downloads, business email compromise, and social engineering. This prevents employees from developing “template blindness” where they only recognize one style of attack.
Track improvement over time. Most platforms provide trend charts showing how click rates change month over month. Celebrate improvements publicly without shaming individuals who struggle.
Consider adding supplementary training for repeat clickers. Short, focused modules on specific topics often help more than lengthy general courses.
Common First-Time Mistakes to Avoid
Starting too hard alienates your team. Begin with moderate difficulty and increase gradually.
Punishing clickers backfires. Shame-based approaches reduce reporting of actual threats because people fear getting in trouble.
Forgetting deliverability settings means your simulations hit spam folders. Always verify test emails reach inboxes before launching to your full team.
Running one simulation and declaring victory leaves your team vulnerable. Consistency matters more than any single test.
Neglecting to communicate creates suspicion and resentment. Brief, honest communication about your security program builds trust.
Measuring Success Beyond Click Rates
Click rates matter, but they’re not the only metric worth tracking.
Report rates show whether employees are actively identifying and flagging suspicious emails. A team that clicks on 10% of simulations but reports 80% is doing better than a team that clicks on 5% but never reports anything.
Time to report measures how quickly people flag suspicious emails. Faster reporting limits damage from real attacks.
Repeat clicker rates identify individuals who need additional support. Some people learn quickly while others need more practice.
The best phishing simulation software 2026 platforms track all these metrics automatically and present them in clear dashboards that do not require a statistics degree to interpret.
Your first simulation is just the beginning. With consistent testing and a supportive approach to training, even small teams without dedicated IT staff can build strong defenses against phishing attacks. The brief setup investment pays dividends every time an employee correctly identifies and reports a real threat.
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This blog offers general information about phishing and cybersecurity for small and medium-sized organisations. It is not legal, financial, or technical advice. Speak to a qualified professional before acting on any guidance you read here.