How Often Should Employees Receive Cyber Security Awareness Training?

Cyber attacks are more frequent and damaging than ever, with over 60% of small businesses failing to recover from a serious breach. To counter this, businesses must consistently educate employees through cyber security awareness training. But how often should you train them, and what content should you cover?

This blog will break down the ideal cyber security awareness schedule for your organization based on different months, employee roles, and the risks they face, using the comprehensive training calendar from the spreadsheet.

Let’s dive in and explore how to keep your employees aware, engaged, and ready to tackle evolving cyber threats without overwhelming them.

Cyber Security Awareness for Employees

Cyber security awareness for employees is critical in today’s business landscape, where the majority of cyber attacks exploit human error. Employees, often seen as the weakest link in cybersecurity, need to be empowered with knowledge and skills to recognize and respond to potential threats. This training covers essential topics like phishing, malware, password management, social engineering, and safe online behavior.

Key benefits of providing cyber security awareness for employees include:

• Reducing the risk of breaches: By educating employees on common cyber threats like phishing and ransomware, businesses can minimize the chance of costly attacks.
• Compliance: Many industries, such as healthcare and finance, require regular security awareness training to comply with regulatory standards.
• Building a security-first culture: Awareness training promotes a proactive mindset where employees see themselves as critical defenders of the organization’s digital assets.

Investing in a robust cyber security awareness program ensures that all employees, from junior staff to executives, can identify and avoid potential risks, contributing to the overall resilience of the organization.

Factors influencing security awareness training frequency

The frequency of cyber security awareness for employees is influenced by multiple factors. These include:

• Business size and complexity: Larger businesses with more complex infrastructures are more vulnerable to breaches. They require frequent training—sometimes monthly—to keep their workforce aware of new vulnerabilities.
• Data sensitivity and industry regulations: Some industries, like healthcare or financial services, handle highly sensitive data. These businesses are often subject to stricter regulations, requiring frequent cyber security awareness updates to ensure compliance and prevent data leaks. For instance, healthcare organizations may need quarterly updates or annual security awareness refresher courses covering new threats targeting personal health information (PHI).

Regardless of your business size or industry, regular cyber security awareness training should be a staple. This should include annual cyber security awareness training and more frequent, bite-sized lessons throughout the year.

"Changing behavior, especially in cybersecurity, involves some cool brain science. It usually takes around 28 days of consistent practice for a new behavior to really stick—that's when it becomes automatic, almost like muscle memory. This process happens because as we keep doing something, our brain builds stronger connections in those specific areas, making the behavior more of a natural reflex over time.

So, to make secure habits second nature, we need to keep at it, repeating good practices regularly. This helps turn what might start as a conscious effort into something we do automatically. This approach isn't just about staying safe online; it’s about making security a part of who we are, making us all less vulnerable to cyber threats." Ozan UCAR, CEO of Keepnet

What is the Most Important Aspect of Security Awareness Training?

The most important aspect of security awareness training is employee engagement. Training is only effective if employees are actively participating, understanding, and applying what they’ve learned. Here’s why engagement is crucial:

1. Retention of Information: Engaged employees are more likely to retain the information presented to them. Use microlearning, quizzes, and interactive content to keep them interested and reinforce key concepts.
2. Consistency: Security threats are constantly evolving. Regular touchpoints, including monthly phishing simulations and quarterly training refreshers, keep security in employees' minds and help them stay up-to-date with the latest threats.
3. Relevance to Roles: Tailor the content to the specific roles within your organization. For example, sales teams should be more aware of travel-related risks, while C-level executives might face spear-phishing attacks.

By making security awareness training engaging, relevant, and frequent, you create a culture where employees are continuously alert to potential threats and play an active role in protecting the organization.

"Having a solid security awareness program isn't just a nice-to-have; it's essential for protecting our digital lives. It's like learning any new skill—you don't just wake up one day and you're good at it. You have to work through the stages. Interestingly, while there are nine stages in the Security Learning Curve to embed a new secure behavior, most of the stuff out there only covers about four. This is usually the basic stuff tied to what government agencies like Cyber Security Essentials in the UK or NIST in the US recommend or what regulatory bodies need, like PCI-DSS for payment processors.

What's also key in making sure these programs work is benchmarking—comparing our progress month to month. It’s like having milestones; it shows us how far we've come and what needs tweaking. This way, we can ensure our training is truly effective and isn’t just ticking boxes but is making a real difference in how we handle security day-to-day.” Joe Busto, VP of Sales US

Annual Cyber Security Awareness Training

Annual cyber security awareness training is a foundational step for every organization, ensuring all employees receive a comprehensive update on the latest threats, regulations, and best practices. This training typically covers:

• Phishing and spear-phishing: Educating employees on how to spot fraudulent emails.
• Ransomware: Explaining the dangers and prevention methods.
• Password management: Encouraging strong passwords and the use of multi-factor authentication (MFA).
• Social media security: Teaching employees to protect their personal and professional accounts.

By conducting annual cyber security awareness training, businesses can meet regulatory compliance requirements and significantly reduce the likelihood of data breaches. It also serves as a baseline for assessing where your employees stand in terms of cyber security knowledge, allowing you to address any gaps with additional resources.

Moreover, this annual training should not be seen as a one-off event but rather the core of a continuous learning program that integrates smaller, more frequent learning opportunities throughout the year.

Breakdown of Annual Cyber Security Awareness Training

An effective way to deliver consistent security awareness training is to develop a monthly training calendar. This keeps employees engaged while providing specific training that addresses the risks relevant to their roles. Below is a detailed breakdown using the monthly training calendar from the spreadsheet.

January: Information security for all employees

• Targeted risks: Information security
• Phishing campaign: “WhatsApp account has been accessed from different locations”
• Training content: Basic concepts of information security, such as recognizing common phishing attempts and keeping data secure.
• Newsletter: Weekly newsletters that emphasize privacy best practices.
• Poster: “Privacy is important for your organization”—a reminder for employees to take care with confidential data.
• Tips: “Share with care”—educate employees on sharing personal or work information only when necessary and through secure channels.

Starting the year by reinforcing the basics of information security sets the foundation for the rest of the year’s training efforts. Employees should understand how to recognize phishing attempts, secure sensitive data, and the overall importance of maintaining confidentiality.

February: Data leakage risks for C-Level executives

• Targeted risks: Data leakage
• Phishing campaign: “Twitter password has been changed”
• Training content: Phishing attacks and social engineering tactics targeting high-level executives.
• Newsletter: Focus on phishing attacks and how to avoid them. Poster: “Delete when in doubt”—remind C-level executives to be wary of suspicious emails and delete them when unsure.
• Tips: “Be careful against phishing attacks”—advice on scrutinizing unexpected emails, especially those that appear urgent or personal.

C-level executives are prime targets for phishing and social engineering attacks. In February, focus on educating them about the specific tactics used against senior leaders, like credential-stealing attempts or spear-phishing emails designed to look like official communications.

March: Travel risks for sales teams

• Targeted risks: Travel risks
• Phishing campaign: “Couchsurfing Welcome” – a fake travel-related phishing email targeting those planning trips.
• Training content: Travel safety tips, including securing devices while traveling and using VPNs on public Wi-Fi.
• Newsletter: Weekly reminders about secure travel practices.
• Poster: “Traveling? Remember to secure your devices” – ensure employees know how to stay secure on the go.
• Tips: “Flight Miller”—a reminder about travel risks like fake itineraries or malicious booking sites.

Sales teams often travel, making them more vulnerable to security risks. Whether it's public Wi-Fi or leaving devices unattended, employees must know how to mitigate travel-related security threats.

April: Online habits for all employees

• Targeted risks: Online habits
• Phishing campaign: “Ali Express Super Deals” – a tempting but fake email encouraging employees to click on suspicious links.
• Training content: Best practices for responsible internet use and being cautious with online interactions.
• Newsletter: Weekly updates on how employees can improve their digital hygiene.
• Poster: “I do my part to fight against online crime”—a visual reminder of employee responsibilities.
• Tips: “Cybersafety notification sources”—guide employees to trusted sources for cyber threat updates.

In April, focus on educating employees about the dangers of poor online habits, such as using weak passwords, falling for fake shopping deals, or oversharing on social media.

May: Identity theft for all employees

• Targeted risks: Identity theft
• Phishing campaign: “Your Twitter password has been changed”
• Training content: Protecting against identity theft and securing online accounts with strong, unique passwords.
• Newsletter: Weekly articles on password and account security.
• Poster: “Different passwords for each account”—remind employees to avoid password reuse.
• Tips: “Password security suggestions”—offer practical advice on creating strong, unique passwords and using password managers.

With cybercriminals constantly finding new ways to steal personal information, May is dedicated to helping employees protect their identities online. Reinforce the importance of using strong, unique passwords for every account and adopting multi-factor authentication (MFA) wherever possible.

June: Risk of malware infections for all employees

• Targeted risks: Malware infections
• Phishing campaign: “Someone sent a document – Excel”
• Training content: Identifying suspicious files and links to prevent malware infections.
• Newsletter: Weekly updates on common types of malware and how they spread.
• Poster: “Basic recommendations for everyone”—tips on scanning files and avoiding risky downloads.
• Tips: Basic security hygiene reminders, such as not opening attachments from unknown senders.

In June, focus on the dangers of malware, including trojans and ransomware. Ensure employees understand the risks of downloading files from unknown sources and teach them how to scan for malware before opening attachments.

July: Are you hacked?

• Targeted risks: Potential account compromise
• Phishing campaign: “DigitalOcean” – testing whether employees recognize signs of a compromised account.
• Training content: How to detect and respond to signs of a hack.
• Newsletter: Teach employees how to spot compromised accounts and respond quickly.
• Poster: “I use different passwords for each account”—another reminder of good password practices.
• Tips: “Are you hacked?”—provide a checklist for employees to follow if they suspect their accounts have been compromised.

In July, focus on helping employees identify the warning signs that their accounts have been hacked. This includes strange login activity, unexpected password changes, or unfamiliar devices accessing their accounts.

August: Social media threats for all employees

• Targeted risks: Social media threats
• Phishing campaign: “Google Hangouts” – a phishing email pretending to be a social media notification.
• Training content: Social media safety and protecting online presence.
• Newsletter: Weekly content on how to secure social media accounts.
• Poster: “Protect your online presence”—a reminder to be cautious about what is shared on social media.
• Tips: “Social networks”—encourage employees to update their privacy settings.

With social media platforms being a goldmine for cybercriminals, August is the time to educate employees on the dangers of oversharing, poor privacy settings, and targeted social media attacks like quishing (QR code phishing).

September: Seizure of accounts and data

• Targeted risks: Account takeovers
• Phishing campaign: “Sextortion Phishing Email”
• Training content: Recognizing and preventing ransomware attacks.
• Newsletter: Weekly content on account security and how to avoid takeover.
• Poster: “I back up my digital data”—remind employees of the importance of regular backups.
• Tips: “Ransomware”—tips on how to recognize and avoid falling victim to ransomware.

In September, teach employees how to recognize sextortion and ransomware emails. Emphasize the importance of regular data backups and how to avoid downloading malicious software.

October: Financial losses for all employees

• Targeted risks: Financial fraud
• Phishing campaign: “Money Transfer Decontamination Info” – a fake financial transaction notification.
• Training content: Safeguarding credit card and payment information online.
• Newsletter: Weekly content on avoiding online shopping scams.
• Poster: “Basic suggestions for online security”—remind employees of the dangers of financial scams.
• Tips: Guide employees on spotting suspicious transactions or fraudulent websites.

October focuses on financial security, including online shopping safety, protecting credit card information, and identifying fraudulent transactions.

November: Physical threats to security

• Targeted risks: Physical security risks
• Phishing campaign: “Your Sunday evening trip with Uber” – simulate how attackers might target physical security through digital apps.
• Training content: Best practices for maintaining physical security (e.g., not leaving laptops unattended).
• Newsletter: Tips on avoiding physical theft of devices and securing workplace environments.
• Poster: “Physical security is part of our life”—encouraging employees to take security seriously both digitally and physically.
• Tips: Physical security suggestions to prevent device theft or loss.

November is the time to focus on physical security threats. Remind employees to lock their devices, avoid public Wi-Fi when traveling, and report lost or stolen equipment immediately.

December: Data leakage for all employees

• Targeted risks: Data leakage
• Phishing campaign: “iPhone Trusted Device” – simulate how attackers can access sensitive information through mobile devices.
• Training content: Mobile and communication security tips, including securing mobile apps and permissions.
• Newsletter: Teach employees how to configure mobile devices securely.
• Poster: “Mobile apps and access permissions”—remind employees to review app permissions regularly.
• Tips: “Mobile apps and permissions”—guide employees on how to limit app access to sensitive data.

December focuses on preventing data leakage, especially through mobile devices. Emphasize mobile app security and ensure employees review the permissions granted to apps on their phones.

Annual Security Awareness Refresher

In addition to the main annual training, an annual security awareness refresher is essential for reinforcing key concepts learned during the year. This refresher session is a checkpoint to ensure that employees remember critical security measures and are prepared to handle new and emerging threats.

The security awareness refresher usually focuses on the following:

• Revisiting critical topics: Phishing, social engineering, secure password practices, and safe online behaviors are repeated to ensure employees haven’t forgotten the basics.
• Addressing new threats: The cyber landscape changes rapidly, so it’s crucial to update employees on the latest tactics used by cybercriminals.
• Interactive simulations: Running phishing simulations or brief quizzes during the refresher helps assess the retention of knowledge and offers opportunities to correct any recurring mistakes.

The refresher is a way to reinforce the cyber security awareness lessons throughout the year. For many businesses, this is paired with ongoing phishing campaigns or microlearning sessions that keep employees alert to potential security risks.

“To see the most significant change in behaviour which protects companies from cyber threats is to use the simulations as a training / educational tool. So employees can put into practise the key skills their awareness training teaches them. Remedial training is targeted, specific and much more powerful to insight change in behaviour. As a baseline there should be quarterly training for all employees. However, companies who have a workforce less confident in cyber security, monthly is best to ensure there's an increase in understanding and actioning best practises.” Ellie Thompson, Head of Customer Success

What is the Most Important Aspect of Security Awareness Training?

The most important aspect of security awareness training is employee engagement. Training is only effective if employees are actively participating, understanding, and applying what they’ve learned. Here’s why engagement is crucial:

1. Retention of Information: Engaged employees are more likely to retain the information presented to them. Use microlearning, quizzes, and interactive content to keep them interested and reinforce key concepts.
2. Consistency: Security threats are constantly evolving. Regular touchpoints, including monthly phishing simulations and quarterly training refreshers, keep security top of mind for employees and help them stay up-to-date with the latest threats.
3. Relevance to Roles: Tailor the content to the specific roles within your organization. For example, sales teams should be more aware of travel-related risks, while C-level executives might face spear-phishing attacks.

By making security awareness training engaging, relevant, and frequent, you create a culture where employees are continuously alert to potential threats and play an active role in protecting the organization.

“From my experience working with security teams over the years, there are 3 key pillars of security awareness training that all companies should consider.

Onboarding training - automatically assign essential cyber security training when users join the organisation. This should be included into HR's onboarding program, and will set them up for success when asked to complete cyber awareness training in the future too.

Ongoing training - Design an ongoing training campaign that covers a wide range of key cybersecurity topics. Learning paths should be defined based on the risk level of users. Higher risk users should be met with training on a monthly basis, whereas the most secure users require a lighter touch.

Remediation training - Training for users who have failed simulations should be specific to that campaign, and automated as much as possible to lower the burden on information security teams.

Covering these 3 core pillars of learning will ensure a cyber aware culture is embedded within the business.” Simon Nicholls, VP of Sales UK

Keeping employees engaged with ongoing cyber security awareness training

The key to successful cyber security awareness training is keeping employees engaged. Here’s how:

1. Phishing simulations: Regular phishing campaigns are essential for testing employee knowledge and readiness. For example, the phishing emails in this training calendar can simulate real-world attacks like fake password changes or social media notifications.
2. Microlearning and nano learning: Break training into short, digestible modules. Microlearning increases retention rates and helps employees absorb information without feeling overwhelmed. Use modules on topics like password security or social media threats.
3. Gamification: Add a competitive element to training with gamification—quizzes, leaderboards, and rewards for completing training. This keeps employees motivated and turns learning into a fun, engaging process.
4. Monthly touchpoints: Keep your employees sharp with monthly reminders through newsletters, posters, and cyber security tips that cover different risks and attack vectors.

“Employee training, no matter the content, often needs to be repeated to get lasting results. Regular repetition lowers the chance of forgetting what we learn. We increase the success of trainings by sending refreshers within three days of the initial training and holding follow-up sessions in the short term.

When it comes to behavior change, repetition is even more important. To make sure the behavior change happens and sticks, it's important to repeat the key messages of the trainings, by using visuals, clear messages, and real-life examples. From my experience, I can confidently say that repetitive sessions, together with visuals, videos, and well-crafted scenarios are essential for creating lasting and effective training outcomes.” Ece Kucukkoyuncu, HR Manager

Why security awareness training is essential

Without ongoing cyber security awareness training, employees can quickly become the weakest link in your organization’s defenses. However, with the right training schedule, they can also become your strongest line of defense. At Keepnet Human Risk Management Platform, we’ve observed that once companies implement cyber security awareness training, there is a noticeable drop in the number of employees clicking on phishing links that same month.

For example, Tiryaki, a global agricultural company, trained 1,100 employees worldwide. The result? An impressive 89% phishing identification success rate within a year. This phishing simulation program not only strengthened their defenses but also boosted their security culture. Financially, they successfully protected customer data and maintained their hard-earned reputation.

This dramatic improvement—an 89% increase in phishing detection in 12 months—demonstrates just how essential security awareness training is for your organization.