Penetration Tester Interview Questions and How to Crush Them

Penetration Tester Interview Questions and How to Crush Them

To land your dream job as a pentester, you need to ace your penetration tester interview questions. These questions test your technical knowledge, interpersonal skills, and problem-solving abilities. They filter for the best candidates, and you must conquer them to become a professional penetration tester.

This article dives into the types of penetration testing interview questions you will likely be asked, from the technical to non-technical ones that tell the company if you’re a good fit. You will see examples of these questions and how you can discover the answers so you’re ready to crush your interview.

Let’s start exploring what to expect as you continue your journey to become a professional penetration tester.  

Types of Questions

Questions will vary from non-technical to very technical, each designed to assess how well-suited you are for the job and the likelihood that you will be successful as a penetration tester for their company. 

You must be prepared to answer all of the interviewer's questions, not just the technical ones. Companies look for well-rounded candidates who can demonstrate their soft and hard skills during the interview process. As such, it is vital you understand the types of questions you are likely to face and have your answer prepared. 

The common types of questions you are likely to be asked during a job interview for a penetration tester role include:

Let’s look at each category of questions and gain an understanding of what the interviewer is really asking in their questions.

Personal

Personal

An interviewer will typically start off by asking you personal questions. These questions are designed to ease you into the interview process and allow the interviewer to get a better sense of who you are as a person, what motivates and inspires you, and what type of personality you have.

Where do you research the latest vulnerabilities?

As a penetration tester, you must keep up to date with the latest vulnerabilities in technology. This shows that you know what is exploitable, that you are passionate about pentesting, and you are devoted to continuously learning. You can learn how to research the latest vulnerabilities in 10 Top Places to Practice Ethical Hacking on Your Own.

Do you have a favorite hacker/blogger/YouTuber?

It is important to keep up to date with the latest trends in security and technology so that you are not left behind in the ever-evolving cyber world. You can stay up to date by following tech influencers on social media, Youtube, or on their blogs. Check out The Best Cyber Security Podcasts for You and The Top 15 Cyber Security Blogs to Start Reading Today for some great sources to follow.

What are your thoughts on ChatGPT for penetration testing?

Artificial Intelligence (AI) is a trending topic in technology. You will be expected to have a general understanding of major trending topics like this, and a good way to demonstrate this knowledge is by having thoughts on how tools like ChatGPT may affect penetration testing. To find out how ChatGPT can be used for hacking, read Unlock ChatGPT for Hacking: Jailbreaking Ethical Restrictions.

Additional personal questions include:

  • What are some of your favorite penetration testing tools?
  • Have you ever participated in Capture the Flag (CTF) or other online hacking games?
  • Do you know any programming or scripting languages?

Behavioral

Behavioral

To assess if you have the soft skills necessary to be a penetration tester, the interviewer will ask questions to understand how you will handle workplace situations based on past experiences. These questions allow you to showcase non-technical challenges you have previously overcome through your problem-solving abilities and soft skills.

How have you communicated complex ideas with other teams, departments, or clients in the past? 

Communication is a key part of being a penetration tester. You will need to write reports and give presentations that communicate the findings of your testing to your client. A good way to demonstrate this skill is to draw on previous experiences where you have had to communicate with others and how you were effective at this. You can learn how to communicate with the SOC team in this article on What Is a Purple Team? (And How It Can Strengthen Security).

Describe a situation where you have worked with frustrating clients or colleagues in the past and how you have managed this?

Conflict resolution and adaptability are two soft skills required to flourish in any work environment. You may have to work with difficult clients, and having the ability to handle these situations effectively is an important skill. If you don’t have a relevant professional example demonstrating how you have performed this behavior, you can draw from experiences outside of work. This could include school, sports, or community events.

Additional behavioral questions include:

  • Your initial penetration test proposal is heavily criticized by your manager. How have you adapted to negative feedback in the past?
  • Describe a situation where you were able to use persuasion to successfully convince someone to see things your way.
  • Can you think of a situation where innovation was required at work? What did you do in this situation?

Culture Fit

Culture Fit

It’s not just important to have the technical knowledge to fulfill the role of a penetration tester; you must also be a good fit for the company’s culture. Your values, work style, and personality need to align with the company’s culture and the team you are planning on joining.

Do you prefer working independently or as part of a team? 

Penetration testing often involves working independently when performing testing and working collaboratively when communicating your findings and improving the security of your client’s organization. You should be able to give an example of each scenario by drawing on previous experiences to demonstrate you possess these abilities and are a good fit for the pentest team.

How do you adapt your communication style when working with different personalities and team members with diverse backgrounds?

You will be expected to interact and work with these diverse personalities daily, which requires strong communication, teamwork, and emotional intelligence skills. Discussing how you’ve changed your communication style in the past to interact with different people is a good way to demonstrate these skills.

Additional culture fit questions include:

  • What attracted you to our company and its culture?
  • What do you value most in a workplace and its culture?
  • How do you handle failure or setbacks in your work? Can you provide an example?

Knowledge Based

Knowledge Based

To succeed as a penetration tester, you need foundational knowledge about cyber security. The interviewer will assess this by asking about well-known cyber security frameworks, practices, and terminology. 

Differentiate between a vulnerability and an exploit.

You need a strong understanding of cyber security fundamentals to succeed as a penetration tester. These questions uncover if you have this fundamental knowledge, and you should be able to answer both easily. If not, consider taking an entry-level cyber security certification that teaches this knowledge, such as CompTIA’s Security+. For more information, read What Is CompTIA Security+? An Essential Guide (2023).

Define the CIA Triad, and provide an example of each component.

Just like above, this question tests your basic knowledge of a popular cyber security topic. You should be able to list the components of this information security model and describe each in detail with an example. You can learn about the CIA triad here.

What is the difference between a blue team and a red team? 

Another common question used to assess your fundamental cyber security knowledge quickly is to define the different teams involved in protecting an organization. You should be able to define these two teams, list their responsibilities, and describe their job roles. You can find the answer to this question in Red Team vs Blue Team: Which Is the Best Choice for You?

Additional knowledge based questions include:

  • What is the difference between intrusion detection systems (IPS) and intrusion prevention systems (IDS)? Name an example of each.
  • Describe symmetric and asymmetric encryption.
  • What is a threat modeling system?

Technical

Technical

To determine if you have the requisite skillset, the interviewer will ask you questions about the technical areas relevant to performing the role of a pentester. Often these questions are asked in a separate interview by a specialist.

How would you discover hosts on a network you are unfamiliar with?

Host discovery is one of the first steps when performing a penetration test. To do this effectively, you need to understand how networks work and how you can use tools like Nmap and Zenmap to discover hosts. You can learn how to do this using Nmap in Nmap Host Discovery: Your First Step in Ethical Hacking.

Can you explain Kerberoasting as if I was 10 years old?

Kerberoasting is a common attack used against Active Directory environments. You will need to possess the ability to explain this attack (and others) to a non-technical audience, such as C-Level executives. By explaining this to a 10-year-old, you can demonstrate your ability to simplify complex topics into an easily digestible format for clients. To learn about Kerberoasting, read How to Perform Kerberoasting Attacks: The Ultimate Guide.

Additional technical questions include:

  • Explain what cross site scripting (XSS) is and how you would test for it.
  • List three ways of maintaining access to a system during a penetration test.
  • How do you test the security of wireless networks?

TIP:

If you are unsure how to answer a technical question, it is best to admit you do not know the answer but will research it as soon as the interview finishes. This demonstrates your honesty and eagerness to learn. 

Situational

Situational

These questions put you in a hypothetical scenario, similar to ones you are likely to encounter when performing your role, and ask how you would handle such a situation. They assess your problem solving skills and ability to adapt to complex situations quickly.

You are placed on an internal penetration test. How do you discover vulnerabilities and attack paths in an Active Directory environment?

Windows Active Directory is used by around 90% of Fortune 1000 companies, and because of this prevalence, you will be expected to have in-depth technical knowledge of how it works and how to hack it. You can learn more in How to Use BloodHound to Hack Active Directory: A Full Guide.

What is the first thing you should do before testing begins?

You will be expected to know the fundamental steps of a penetration test, how to perform each technically, and how to communicate these steps to a non-technical audience. This question lets you list these steps and describe why they are important. To answer this question, read Penetration Testing Steps: A Comprehensive Assessment Guide.

Additional situational questions include:

  • What is social engineering? Describe a situation you would use it to gain initial access during a penetration test.
  • After gaining access to a vulnerable system, what are the privilege escalation vectors you first check for?
  • You get simple command injection on a web server through the address bar. What would you do to get a shell?

TIP:

To discover what situations you may find yourself in as a penetration tester, check The Very Best Books on Ethical Hacking for You in 2023. They cover everything from interview skills to advanced techniques!

Problem Solving

Problem Solving

In addition to having knowledge of the technical areas of penetration testing, an interviewer will also ask you questions focused on assessing if you can solve technical problems that arise when performing pentesting. 

These questions assess your analytical and critical thinking skills and are usually included in the separate technical interview.

You have discovered a web application that appears vulnerable to SQL injection, but you cannot use an automated tool to verify the vulnerability (e.g., sqlmap). How would you go about manually verifying the vulnerability?

Junior penetration testers often rely on hacking tools that automate the exploitation process without actually knowing how the vulnerability is being exploited. You should know how to manually exploit vulnerabilities without relying on these tools and be able to describe this process. To find out how to exploit SQL injection vulnerabilities, read Blind SQL Injection: An Expert’s Guide to Detect and Exploit.

You gain low-privileged access to a Windows machine within a target network. How do you pivot through this network to target other machines using stolen credential data?

This question asks you to combine several pieces of knowledge to solve a problem. You need to know how to escalate your privileges on a Windows machine to obtain credential data, and you need to know how to use this credential data to pivot to other machines within the network. You can learn how to do both in How to Use Windows Privilege Escalation: Elevate Your Skills and Pass the Hash Attacks: How to Make Network Compromise Easy.

Additional problem solving questions include:

  • How would you try to bypass an intrusion detection system you encounter on a penetration test?
  • Where would you got to find out if a software you encounter has any security vulnerabilities you can exploit?
  • During a penetration test, you discover a lack of data protection around a company's cryptographic keys and can steal these keys. How could you exploit these keys to access other network devices or cloud services?

TIP:

Take a pen and paper to your penetration tester interview so you can jot down ideas when trying to solve these types of questions.

Interview Advice

Penetration testing interviews can be hard, especially if you are new to the process. To help you succeed, here are some Do’s and Dont’s that you should remember when preparing for your interview.

Things to do in a penetration tester interview:

  • Research the company: You should research the company to find out its values, culture, services, and recent events. This will show your interest in joining the company and sets you apart from other candidates.
  • Dress appropriately: Determine the company’s dress code ahead of time and dress to match. This shows you care about the company culture. If you cannot find the dress code, dress professionally.
  • Be enthusiastic: Showcase your desire to be a penetration tester by being enthusiastic about the opportunity to join the company and the work you will be doing.
  • Showcase your successes: Plan what stories you want to share with the interviewer that showcases your talents and previous workplace successes.
  • Ask questions: Ask questions throughout the interview about the company, the role, and the team you will be joining to demonstrate your genuine interest in joining the company.

Things not to do in a penetration tester interview:

  • Lie or exaggerate your previous experiences: Be honest about your current skillset, previous experiences, and accomplishments. It is easy for employers to find out if you’ve been dishonest, which will destroy your credibility. 
  • Speak negatively of former employers: Try to maintain a positive and professional outlook throughout the interview that focuses on your skills or positive outcomes from past experiences.
  • Interrupt the interviewer: Never interrupt the interviewer. Instead, showcase your soft skills by actively listening to the interviewer and maintaining attentive body language. 
  • Avoid acting too informally: Always remember you are in a professional setting. Maintain a warm but professional demeanor that is indicative of how you want to be perceived in the workplace.

Conclusion

To land your dream job, you need to be well-prepared to answer any penetration tester interview questions that might get thrown at you. This article described the types of questions that may be heading your way and why an interviewer may ask them. You discovered where you can learn the answers to these questions and some useful interview advice to help you succeed. 

Always prepare for your penetration tester interview by rehearsing the questions you might get asked beforehand. This lets you develop a great answer to showcase your talents and blow the interviewer away!

To ensure you are best prepared to land a role in cyber security, check out the StationX Accelerator program. This program provides personalized career roadmaps, dedicated mentorship, and courses to build your interviewing skills. We will provide you with everything you need to land a cyber security job.

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  • Adam Goss

    Adam is a seasoned cyber security professional with extensive experience in cyber threat intelligence and threat hunting. He enjoys learning new tools and technologies, and holds numerous industry qualifications on both the red and blue sides. Adam aims to share the unique insights he has gained from his experiences through his blog articles. You can find Adam on LinkedIn or check out his other projects on LinkTree.

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