Key Prescreening Questions to Ask for Successful Penetration Tester Postion

What prior experience do you have as a penetration tester?

Penetration testing requires hands-on experience. By asking about the candidate's previous experience, we can gauge their practical knowledge and capability to handle real-life situations in the domain of cybersecurity.

What certifications do you hold in cyber security or related fields?

There are numerous certifications that validate an individual's proficiency in cyber security. Examples include Certified Ethical Hacker (CEH), Offensive Security Certified Professional (OSCP), and Certified Information Systems Security Professional (CISSP). Holding such certifications is a good indicator of a candidate's dedication and formal knowledge in the field.

Can you briefly explain your understanding of a Penetration Testing Execution Standard (PTES)?

A good understanding of PTES is a must for every penetration tester. PTES offers a basic framework and guidelines for conducting penetration tests which help ensure the consistency and standards of work.

Have you worked on any projects manipulating system and application vulnerabilities?

Identifying and manipulating system and application vulnerabilities are staples in penetration testing. A positive answer to this would demonstrate a candidate's capabilities in conducting active penetration tests.

Can you describe your experience with tools such as Metasploit, Nessus and Wireshark?

These tools are among the most commonly used in penetration testing. Any tester worth their salt should be familiar with, if not proficient in, these tools.

Do you have experience in developing scripts in languages such as Python, Perl, or Bash?

Scripting enables penetration testers to automate tasks, customize attacks and manage data. It's important that the candidate has experience in this area to be able to develop and adjust tools to their specific needs.

How experienced are you with both the Unix/Linux and Windows operating systems?

Linux, Unix, and Windows all have unique structures and vulnerabilities. A well-versed tester should be comfortable working with these platforms to secure a diverse range of systems.

Can you explain your understanding and experience with wireless penetration testing?

With more and more devices connecting wirelessly, this area of penetration testing is becoming increasingly important. Assessing a candidate's experience and understanding in this area is thus key.

How good is your understanding of web application logic and its security vulnerabilities?

Web applications are often a weak-link in security chains. They can be complex and riddled with vulnerabilities. A solid understanding of application logic and its associated security vulnerabilities is crucial to ensure robust testing.

What do you do to stay updated on the latest cybersecurity threats and hacking techniques?

The world of cybersecurity is ever-evolving. In order to stay ahead of potential attackers, it's crucial to keep up-to-date with the latest threats and techniques.

Have you ever identified a security risk or vulnerability that was previously undetected during a penetration test?

This question can give an idea about the candidate's capability to scrutinize and the attention to detail they give in their line of work.

How do you typically document and report the findings from your penetration tests?

This is an important part of a penetration tester’s job. The ability to communicate complex technical threats in clear and impactful ways can mean the difference between a business taking action or ignoring a threat.

Can you describe your experience dealing with cross-site scripting and SQL injection attacks?

These are two common and damaging threats to web security. Inquiring about specific knowledge of these will give reference points about the applicant’s hands-on experience.

Have you ever had to create a custom exploit?

A candidate who has needed to create a custom exploit will likely have a deep understanding of vulnerabilities and will be able to think like an attacker. This can be a valuable perspective in securing systems.

Do you have experience in auditing network devices in order to enhance system security?

Regular audits of network devices are critical to maintaining system security over time, so a candidate's experience with this can be an important indicator of their ability to maintain secure systems in the long term.

Do you have any experience managing client expectations during a penetration test?

Client interaction and expectation management are important but often overlooked aspects of penetration testing. A candidate with experience in this area may have a more well-rounded skill-set and be better equipped to provide a comprehensive security service.

Could you describe your knowledge of and experience with OWASP?

The Open Web Application Security Project (OWASP) is an important resource for anyone providing IT security. It contains helpful guidance, including the list of the Top 10 Most Critical Web Application Security Risks. Proficiency with OWASP is crucial for any penetration tester.

Do you hold any industry recognized security certifications such as OSCP or CEH?

Certifications from industry-recognized bodies can lend credibility to a candidate's skills and can be indicators of their dedication to keeping up with the latest techniques and trends.

Do you have experience in penetration tests for mobile platforms?

Nowadays, consumers tend to use their mobile devices for several tasks previously carried out on desktops. That’s why a penetration testing process also needs to cover mobile platforms. Asking about experience in testing mobile platforms can ensure the candidate’s ability to deal with these threats.

Can you explain a difficult technical challenge you had to overcome in previous penetration tests and how you resolved it?

This question not only tests the technical capability of the applicant but also their problem-solving skills and ability to work under pressure. Highlights from their past experiences will provide a candid view of their way of working and approaching problems in varying situations.