Top Five Most Important Things to Ask Before Hiring a Pentest Company

If you follow cybersecurity news, you’re likely no stranger to stories about giant breaches. In fact, according to IBM's Cost of a Data Breach report, the average global cost of a data breach has reached a staggering $4.88 million, a significant jump from the previous year. 

It’s never been more important to truly know if your organization is secure against threats. 

This is where a talented penetration testing firm can help you. Think of pentesters as ethical “burglars” who you hire to try to break into your environment. Pentesters can identify your weak spots, so you can defend them from real criminals. 

And yet, choosing a pentest firm can be difficult if you don’t know the right questions to ask.

Read this blog to discover the top five most important questions to ask a potential pentest firm and why each question is vital to your success. 

See Also: Why Some Penetration Tests Cost $10K and Others $3K

See Also: How Much Does a Pentest Cost?

See Also: 6 Steps to a Penetration Test

The Five Most Important Questions to Ask Your Pentest Firm

Question 1: What is your methodology and approach? How do you balance automated and manual testing?

Why it's important: 

Understanding a penetration testing firm's process (e.g., planning, execution, reporting) is crucial for assessing the quality of your pentest. 

Automated tools are a great starting point, but manual testing by skilled human testers is essential for finding complex vulnerabilities and business logic flaws.

Key points to cover:

• Do they follow recognized frameworks (e.g., NIST, OWASP, PTES, OSSTMM, SANS 25)?
• What is their process for defining scope and rules of engagement?
• What is their typical timeline for engagement?

It’s important to know that automated scanners, while helpful, often miss complex vulnerabilities like logical flaws or authorization bypasses. 

In one notable case, an automated scanner repeatedly dismissed timeouts on an endpoint, only for manual investigation to reveal a massive JSON array exposing every single user in a customer's database because the server was simply too slow for the scanner's default timeout. 

An actual human ethical hacker performing your penetration test can be a valuable asset. 

See Also: Penetration Testing Timeline Checklist

Question 2: What are the qualifications, experience, and certifications of your testing team?

Why it's important: 

The quality of the pentest depends heavily on the people performing it. You need skilled, trustworthy, and ethical professionals with certifications to back up this knowledge.

Key points to cover:

• What certifications do their testers hold (e.g., OSCP, PNPT, BSCP, CRTO, GPEN)?
• What is the average experience level of their team members?
• Do they use in-house experts or third-party contractors (and if contractors, how are they vetted)?
• What are their continuous training and professional development programs?
• Do they conduct thorough background checks on their personnel?

Did you know that there's a global shortage of cybersecurity professionals? This scarcity makes verifying the credentials of your pentest team even more vital, so you don’t get someone who’s overstating or masquerading their pentest knowledge. 

Question 3: Can you provide a sample report, and what does your reporting process entail?

Why it's important: 

A pentest is only as valuable as the insights it provides. 

The report should be clear, actionable, and comprehensive. A sample report can help you see how detailed your pentester is in informing you of their findings, and what kind of level of report you can expect to receive. 

Key points to cover:

• What information is included in their standard report (e.g., executive summary, vulnerability details, risk scoring, remediation recommendations, evidence/screenshots)?
• How do they prioritize and categorize vulnerabilities?
• Do they offer a debriefing session to walk through the findings?
• Is retesting included to confirm fixes, and what are the terms for retesting?

A penetration testing report is your roadmap to strengthening your cybersecurity posture. 

The most effective reports go beyond simply listing issues; they provide clear, actionable recommendations and evidence of exploitation, transforming your data into a defense plan.

Question 4: How do you ensure the security and confidentiality of our data during and after the test?

Why it's important: 

You're giving them access to your highly sensitive information so their firm’s internal security practices are crucial.

Key points to cover:

• What internal security controls do they have in place (e.g., ISO 27001, SOC 2 compliance)?
• Do they have a clear incident response plan in case something goes wrong during the test?
• Do they carry adequate liability insurance? 

Question 5: How do you customize the scope to our specific needs, industry, and technology stack?

Why it's important: 

Your pentest should be tailored to your unique environment so you get the pentest you actually need. An inflexible or one-size-fits-all penetration test is a red flag when choosing a firm. 

Key points to cover:

• Do they have experience in your specific industry (e.g., healthcare, finance, e-commerce)?
• Can they test your specific assets (e.g., web applications, mobile apps, network, cloud, IoT, APIs)?
• Are they able to work within your budget and timeline constraints?
• How do they collaborate with your internal teams throughout the process?

Generic penetration testing often falls short because it lacks context. For example, a firm who only specializes in web application pentesting might miss critical vulnerabilities unique to an industrial control system (ICS) or a highly regulated healthcare environment. 

Tailoring the test to your specific industry and technology stack ensures that the most important weaknesses are identified.

What to Know When Choosing a Pentest Team

Asking the right questions when choosing a penetration testing firm is key to getting the best pay off for your investment. However, don’t forget that getting a pentest is only the first step, the next step is securing your environment based on the identified vulnerabilities. 

One SecurityMetrics Penetration Testing customer shared: 

“SecurityMetrics’ team of penetration test analysts gives us the manpower necessary to perform a deep analysis of our application, setting us free to focus on building the best product possible.” 
-Shawn Neibaur,
Systems Administrator
BambooHR

Whoever you decide to choose, make sure they have the skills and experience necessary to give you the best penetration test possible.

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