Questions to Ask the Penetration Testing Company

When you are hiring a cybersecurity company for penetration testing, it is important for clients to ask the right questions to make sure they receive the service that they need. These questions can help clients get a better understanding of the testing process, set clear expectations, and make sure the security company has the skills needed to get the job done right. This guide outlines questions to ask a penetration testing company.

Qualifications and Experience

Clients need to evaluate the team’s qualifications and experience to assess what they can do.

• What certifications do your penetration testers hold (OSCP, CISSP, CEH)?

• How long have you been conducting penetration tests?

• Can you share case studies or examples of successful projects in our industry?

• Do your testers have experience with systems or applications similar to ours?

• Are your team members full-time employees, or do you rely on contractors?

• Have you handled projects involving highly regulated industries (e.g., healthcare, finance)?

Methodology and Approach

It is important for you to understand the company’s testing methodology to ensure their approach aligns with industry standards.

• What penetration testing frameworks do you follow (OWASP, PTES, NIST)?

• Do you tailor your testing approach based on the organization's risk profile?

• What types of tests do you provide (internal, external, application, network)?

• How do you determine the scope of the test, and how flexible is this process?

• Will you provide a clear timeline and roadmap for the test?

• How do you ensure testing does not disrupt day-to-day business operations?

• What steps do you take if critical vulnerabilities are identified during the test?

Tools and Techniques

The tools and techniques used can significantly impact the quality of the testing.

• What tools do you use for testing (Metasploit, Burp Suite, Nessus)?

• Do you use automated tools, manual testing, or a combination of both?

• How do you simulate real-world attack scenarios to test our defenses specifically? 

Note: The pen test company should work with your organization to stimulate attacks regarding what industry your organization focuses on. It will relate to the offerings of the client’s organization.

Compliance and Legal Considerations

Compliance with laws and regulations is critical when conducting pen tests.

• Are your tests compliant with industry standards (PCI DSS, HIPAA, GDPR)?

• How do you ensure the testing process adheres to legal requirements?

• Will you provide a letter of authorization to protect us legally during the test?

• Have you ever encountered legal issues during a penetration test? If so, how were they resolved?

• How do you document and address compliance gaps discovered during the test?

Communication and Reporting

It is important to have clear communication so you as clients stay informed throughout the whole process.

• How will you communicate with us during the test? Will there be regular updates?

• What information will your final report include (executive summary, technical details, risk rankings)?

• Will you provide recommendations for remediation and prioritize identified risks?

• Can we schedule a debriefing session to discuss the findings?

Risk Management and Mitigation

Penetration testing can cause disruptions or expose sensitive information. It’s important to understand how risks are managed.

• How do you minimize the risk of disrupting critical systems during testing?

• What safeguards do you have in place to protect sensitive organizational data?

• Are you insured for liability in case of accidental damage or data breaches during testing?

• What steps do you take if a test inadvertently impacts production systems?

• Can you perform tests in a controlled environment to reduce risks?

Post-Test Support and Follow-Up

The true benefit of pen testing is the steps taken to resolve the vulnerabilities that are found during the process. Finding the weak points is just the beginning. It is most important to take proactive measures to remediate these issues and strengthen the overall security framework.

• Will you provide assistance in remediating identified vulnerabilities?

• Do you offer follow-up testing to verify that vulnerabilities have been resolved?

• How long will you provide support after the test is completed?

• Are you available for ongoing consultations to help us improve our security posture?

• Can you provide training for our internal team on addressing and mitigating vulnerabilities?

Cost and Deliverables

The most important questions. Understanding the cost structure and deliverables makes sure you stay within your budget and meet expectations.

• What is the cost of the test, and what factors influence the pricing?

• What deliverables can we expect at the end of the engagement?

• Are there any additional fees for follow-up testing or extended support?

Your organization can better evaluate penetration testing companies with these questions. You can make sure you are hiring a service provider that aligns with your organization's needs and expectations. Asking the right questions and thorough preparation will result in a more effective testing process and a better relationship with our testers here at Last Tower Solutions.