TL;DR SUMMARY: As cyber threats evolve continuously, cyber security training needs to move beyond annual, tick-box exercises towards ongoing, contextual learning that supports people in making safer decisions within the flow of their working day.
The problem with annual cyber security training
For many organisations, cyber security training has become a familiar part of the calendar. Once a year, employees are asked to complete a course, watch a series of videos, answer some questions and confirm that they understand the organisation’s security policies.
It’s an established approach, and it gives people a foundation for understanding the risks they might encounter at work. The difficulty is that the threat landscape doesn’t operate on an annual cycle.
Cyber threats are evolving continuously, with AI giving threat actors new ways to create convincing phishing messages, automate activity and adapt their approaches. By the time an organisation has designed, approved and rolled out a training module, some of the examples and behaviours it covers may already feel distant from what employees are encountering in their day-to-day work.
There’s a further gap between understanding a security principle in a training environment and recognising when it applies in the middle of a busy working day. Knowing what phishing looks like and spotting a convincing phishing attempt arriving in your inbox are two different experiences, particularly when it appears alongside legitimate messages and competing demands for attention.
Security training has become a timing problem
The traditional model assumes that knowledge can be delivered in advance, stored in someone’s memory and retrieved when it’s needed. Human behaviour is rarely that straightforward.
People forget information, particularly when it isn’t used regularly. They also behave differently depending on their workload, attention, environment and the task they’re trying to complete. An employee who carefully works through a security scenario during a training session might approach an unexpected request very differently when they’re rushing to finish something important.
Training can tell someone what to look for, while the moment of risk arrives somewhere completely different, often weeks or months later, embedded within an ordinary working task. The useful information may have faded while the pressure of the immediate situation has taken over.
Organisations can create more frequent opportunities for people to encounter, absorb and apply relevant information as part of their everyday work, rather than concentrating security education into a single annual intervention.
People shouldn’t have to choose between security and their job
Employees have jobs to do. Their attention is directed towards customers, colleagues, deadlines, projects and decisions, alongside the countless other things that keep an organisation running.
When cyber security training is presented as another substantial task that needs to be fitted into an already busy schedule, it can feel disconnected from the work people are actually trying to accomplish. An employee might be expected to spend an hour completing a training module during a week when their attention is already stretched across competing priorities.
Security becomes another demand on finite attention, rather than something that supports the work they’re already doing.
A different approach brings security learning into the working environment itself. Instead of waiting for an annual training session, organisations can give people small pieces of relevant information when they encounter situations where that information is useful. The learning becomes connected to an action, giving the person an opportunity to understand the risk while they’re experiencing it.
The shift towards learning in the flow of work
The idea of learning in the flow of work has gained traction well beyond cyber security. Digital products have become increasingly good at delivering small amounts of information at the point where people are most receptive to it, while education platforms have embraced microlearning through smaller, repeated interactions.
Apps such as Duolingo have made frequent, short learning sessions part of the experience of acquiring a skill. Platforms such as 7taps have taken a similar approach into workplace learning, breaking information into small, accessible units that can be consumed without requiring people to set aside large blocks of time.
Cyber security can apply the same principle. People need useful information in a form they can absorb and apply, particularly when it relates to something they’re actually doing.
Behavioural science offers another way forward
A nudge can provide a small intervention at the point where a person is making a decision, bringing relevant information into their attention when it has a direct connection to what they’re doing.
Instead of relying entirely on someone remembering what they learnt months earlier, an organisation can support their decision-making in the moment. That might mean prompting someone to pause before interacting with an unusual link, drawing attention to a potentially risky action or providing a short piece of relevant guidance based on what’s happening on their device.
The intervention can be deliberately small, with its usefulness coming from its timing, context and relevance.
For Redflags, this means taking a contextual approach to security behaviour. Rather than treating every employee and every situation in exactly the same way, Redflags can respond to what a person is doing and the context surrounding that behaviour, providing a nudge when there’s an opportunity to encourage a safer decision.
The individual remains part of the process. They’re given a moment to recognise what’s happening, consider the potential risk and make their own decision, while the intervention becomes part of the work rather than another task sitting outside it.
Training becomes part of behaviour
Cyber security learning can happen through repeated experiences, timely prompts and small moments of reflection that gradually build someone’s ability to recognise and respond to risk.
Someone who receives a relevant nudge when they’re about to perform a potentially risky action gets an opportunity to connect the behaviour with the underlying security principle. Over time, those interactions can reinforce awareness and help people develop stronger instincts around security.
People are often more receptive to information when it has an obvious connection to what they’re doing. A lesson about suspicious links might be useful in isolation, but a prompt that appears when someone is about to interact with an unfamiliar link has a direct connection to the decision in front of them.
The context becomes part of the learning experience, making security guidance easier to understand and apply.
The stakes have changed, too
Sensitive information is no longer concentrated within a small number of large enterprises. Even relatively small organisations can hold substantial amounts of customer information, employee data, financial details, intellectual property and commercially sensitive material.
A security breach can have serious consequences for organisations of many different sizes. Financial costs can be accompanied by operational disruption, reputational damage, regulatory consequences and a loss of trust among customers and employees.
Employees interact with email, cloud services, documents, payment systems, customer information and internal platforms every day. Their accounts and devices can become routes into wider organisational systems, making human behaviour an important part of an organisation’s security posture.
That puts greater emphasis on preparing people for the decisions they’ll actually encounter, rather than relying on knowledge delivered at a single point in the year.
The first line of defence needs ongoing support
It’s tempting to describe employees as the weakest link in cyber security, but that framing overlooks the complexity of the environment people are working within. Employees are often the people closest to the information, systems and relationships that organisations need to protect, while also making security-relevant decisions throughout the day without necessarily thinking of them as security decisions.
A more useful approach is to equip people with support that reflects that reality. Annual training can establish foundational knowledge, policies can provide a reference point and technical controls can prevent or limit certain types of activity. Contextual learning and behavioural nudges can connect those layers to the decisions people make in real time.
Together, these approaches create a more continuous form of security awareness, where learning happens alongside the work rather than being separated from it.
Rethinking what cyber security training looks like
The pace at which the threat environment changes creates a growing gap between a yearly training course and the situations employees encounter throughout the rest of the year.
Shorter learning interventions, timely prompts and context-specific guidance can give people opportunities to build on what they already know while helping them respond to new situations as they encounter them.
For Redflags, behavioural science provides a practical way of putting that approach into action. Contextual nudges and microlearning can turn security awareness into something that happens continuously within the flow of work, while people are making the decisions that have a bearing on cyber security.
Instead of asking employees to step away from their work periodically to demonstrate what they remember, organisations can build learning into the environments where security decisions actually take place.
As cyber threats continue to evolve, keeping security awareness connected to the reality of how people work offers a more responsive way to prepare them for the risks they’ll encounter.
Key takeaways
- Annual training can’t keep pace on its own. Threats and working environments change continuously, so security learning needs to continue beyond a single yearly session.
- Timing can matter as much as content. People are more likely to apply security guidance when it appears alongside the decision or behaviour it relates to.
- Small interventions can fit around real work. Microlearning and contextual nudges can support safer decisions without asking employees to step away from their day-to-day responsibilities.
- Security awareness should become part of everyday behaviour. Training still has a role, but it works best alongside policies, technical controls and ongoing support at the point of decision.
