How do you teach cybersecurity professionals to use penetration testing tools?

To effectively use penetration testing tools, it's crucial to select the right ones for the specific task. Consider the tool's capabilities, the target environment, and its ease of use.

In cybersecurity, mastering the basics is crucial. From my experience, understanding the fundamentals isn’t just about knowing how to use the tools but also comprehending their underlying principles. This holistic approach enhances proficiency and problem solving abilities. Therefore, when learning cybersecurity basics, focus on both practical and theoretical understanding.

A solid foundation in penetration testing fundamentals is essential. This includes understanding network protocols, system vulnerabilities, and attack vectors. Additionally, learning scripting and automation can streamline tasks and enhance efficiency.

I believe regular practice is vital. Learning by doing when it comes o penetration testing tools is truly the best method to developing skills. It’s not enough to learn a tool, you have to become skilled with the tools. You can practice your skills with ranges, Kali simulators, etc. Practice is key, do a lot of it.

Following a structured methodology, such as OSSTMM or PTES, provides a framework for conducting penetration tests. Understanding the different phases of testing and documenting findings are critical components of a successful penetration test.

Realistic scenarios are hard to come by when learning. You have to start small and work your skills up into larger infrastructures. The larger the systems the greater the independencies. Understanding this evolves with gradual exposure and with good mentoring.

I'm still grappling with the concept of instructing a professional in tool usage. A true enthusiast comprehends the underlying logic prior to delving into the tools themselves; this is the essence of knowledge acquisition. Transitioning to the realm of instruction, grasping the nuances of tools and their requisites serves as fundamental intelligence. Knowing which tool serves which purpose lays the groundwork. Subsequently, one should embark on a thorough exploration of the tool's options and functionalities, encompassing integrations, plugins, user management, reporting, dashboards, and beyond.

Decide what tools are applicable to their role and give them a proof of value to go with them. Cybersecurity professionals is a broad term, so I think it is crucial to understand your audience and give them a meaning behind the tools they use. Tools such as Wireshark or nmap can be considered “penetration testing” tools, for example, but can be used by blue teams for understanding and defining their network scope. By understanding the application of tools to their job limits, we can enable everyone to learn within the bounds of their role.

The cybersecurity landscape is constantly evolving, so it's essential to stay updated on the latest threats and vulnerabilities. Attending training courses, workshops, and participating in online communities can help professionals stay informed and maintain proficiency in penetration testing tools and methodologies.

Learn to work in groups. Rarely are there solo penetration cases. Most often your working on a team. Buildings that house networks are geography problems as much as network problems. It takes a team for some efforts and your ability to work in teams is crucial.

Teach them ethics. The tools and the techniques you teach them can be used for good or not, strong ethical principles are fundamental to keep them safe also. A great power means a great responsability.

The best way to master any complex tool or software is to "LIVE IT". Put yourself in the position where you can't escape. Wanna learn Linux, Install Linux (Don't Dual Boot). Wanna learn AD, Start today, it's not complex. Wanna learn burp, Use it to automate. Second, after few tutorials stop watching them. Live and Search, Live and Search. If you encounter any problem while Living it then you have to search it 'cause now you can't move forward. Third, Don't follow societal expectations to do a task. - Maths for coding? Crap! - Need a ton of knowledge before AD? Crap! - Must be a genius to conquer Linux? Total Crap!