5 Essential Questions to Ask Your Penetration Testing Service Company

Introduction

It’s a time when cyber threats are increasing in complexity and frequency, penetration testing has become an integral part of an organization’s cybersecurity strategy. Choosing a qualified penetration testing provider is critical, as this decision can significantly affect your company’s security posture. An effective pentest not only identifies weaknesses but also evaluates the effectiveness of implemented security controls.

However, not all penetration testing services are equally effective. Asking the right questions is important for clarity in ensuring you partner with a reliable and qualified service provider. This article outlines five important questions to help you evaluate and choose the penetration testing company that best suits your security needs.

Question 1 - Are the Pentesters Full-Time Employees or Part-Time Contractors?

Why It Matters

The dedication and focus of your penetration testers are paramount to the success of your security assessment. Full-time employees, often deeply invested in the company's goals and undergoing regular training, typically provide a higher level of consistency and reliability. Their familiarity with internal processes, equipment, and procedures ensures a thorough and accurate evaluation. In contrast, part-time testers might have divided attention due to multiple commitments, potentially affecting the depth and breadth of their analysis. Additionally, full-time employees often undergo more rigorous background checks and security clearances, mitigating concerns about potential insider threats.

What to Look For

When considering a penetration testing service provider, ask them about the business environment of their pentesters. Make sure the team doing your work is a full-time professional dedicated to their role. Ask about the company’s hiring practices, ongoing training programs, and how they keep their employees up-to-date on cybersecurity issues and techniques. This gives you a sense of the level of expertise and commitment expected from the team.

Question 2 - What Credentials Do the Pentesters Hold?

Why It Matters

Cybersecurity is a rapidly growing industry, and the qualifications of the professionals you hire to protect your assets are critical.  When it comes to Penetration testing and Red teaming, certifications by offensive security in particular OSCP. However, this greatly varies from market to market, for instance, CREST certifications in particular are highly regarded in the UK market, SANS certs are regarded in the US market. Similarly, although CEH practical although is not reputable as the former certs, however 

Lead Pentesters may have additional security management and audit certifications including CISSP, CISA, CCSP and CISM certifications.

What to Look For

Ask for details of credentials and qualifications of pentesters in the group. This should include widely recognized certifications such as CISSP, CISM, and CCSP. Additionally, ask about the team’s experience in your industry and identify the unique challenges and regulatory requirements you face. This will help ensure that pentesters have not only the technical expertise but also the contextual knowledge to properly evaluate your security posture.

Question 3: Do You Have Experience in My Industry?

Why It Matters

Each industry has unique cybersecurity challenges and legal requirements. For example, the financial technology (fintech) sector is heavily regulated and is often a prime target for cyberattacks. Similarly, healthcare organizations must comply with stringent regulations such as HIPAA while protecting sensitive patient data. A penetration testing company that has experience in your industry will have great resources to identify and address the specific threats you face.

What to Look For

When considering a penetration testing service provider, ask for examples of their past work in your industry. This could be case studies, references, or examples of similar Pentecostal plays. Further, one should also ask them for their understanding of the regulatory environment in your industry and how they ensure proper standards are met. Companies with proven experience in your industry will often provide relevant insights and effective recommendations to improve your security posture.

Question 4 - Can You Provide Examples of Previous Work?

Why It Matters

Transparency is key when choosing a pentesting service provider. Reviewing examples of their prior work helps them assess their capabilities and understand the merits of their projects. A detailed report of past pentest or incident responses will reveal the methodology, accuracy, and practical value of the findings.

What to Look For

Ask the pentesting firm to provide examples of their past work, such as a detailed pentesting report or case study. Make sure these examples highlight the way they identify weaknesses, the level of detail in their findings, and the effectiveness of their recommendations. If your company has a healthcare facility, request a similar report specific to healthcare conditions. For smart contract testing, ask for reports on smart contract evaluations, if testing Web 3.0 wallets, ask for appropriate reports for that test Additionally, ask about their reporting and communication processes as they document and explain findings in time You can understand that. This will help you determine whether their offer meets your expectations and how well it meets your specific needs.

Question 5 - How do you handle false positives and negatives in your reports? 

Why It Matters

False positives and negatives can significantly impact the effectiveness of a penetration test. False positives i.e. incorrectly identifying a vulnerability can lead to unnecessary remediation efforts and inefficient use of resources. False negatives (failing to identify a real vulnerability) can leave critical security gaps unaddressed. Both can affect your overall security posture and potentially expose your organization to risk. 

False positives may stem from the use of automated vulnerability scanning tools; these tools often lack context and can generate a large number of false positives. It falls to the pentesters to manually verify these findings. Additionally, some false positives may arise from a lack of understanding of the underlying design and context, which can be due to various reasons, such as insufficient documentation explaining security controls.

For example, a pentester might submit 100 requests to a particular endpoint and report it as a lack of rate limiting, whereas this functionality might be intentional and part of the business logic, such as allowing a large number of queries to an endpoint, especially in B2B API integrations.

What to Look For

Review sample reports from previous clients of pentest companies to see if there are any findings with insufficient evidence and whether any of these vulnerabilities were rejected. Inquire about their methods for minimizing false positives and negatives, which might include using multiple scanning tools, employing experienced testers, or having a rigorous review process to validate results. Finally, ask how they use feedback from previous tests to improve their accuracy. This could involve refining their testing methods or incorporating new techniques to enhance detection capabilities.

Conclusion

The decision to choose a penetration testing service provider is critical to your organization’s security. Asking these essential questions allows you to thoroughly screen potential partners and ensure you choose the company that best fits your needs. Leverage full-time providers, certified pentesters with relevant industry experience, a proven history of transparent reporting, and a comprehensive approach to growth first This will help strengthen your security and protect your organization from cyber threats. Researching your options carefully will ensure that you find a partner who is committed to your long-term security.