That sounds like a great initiative! Penetration testing is an essential step in assessing the security of a product or system. Designing a worksheet to guide product owners through the process and collect necessary information is a practical approach. To help you with this task, I can provide a general framework for your worksheet. You can customize it based on your specific requirements and the nature of the product or system being tested. Here's a suggested outline for your penetration testing worksheet:

    General Information:
        Product name and version.
        Product description and purpose.
        Product owner's name and contact information.
        Date of the worksheet completion.

    Scope and Objectives:
        Define the scope of the penetration test, including the specific components, networks, or systems to be tested.
        State the objectives of the penetration test, such as identifying vulnerabilities, assessing the effectiveness of security controls, or validating compliance with security standards.

    Assumptions and Constraints:
        List any assumptions made during the penetration test planning.
        Identify any constraints or limitations, such as restricted testing hours or specific compliance requirements.

    Target Identification:
        Provide details about the target system(s), including IP addresses, URLs, or other relevant identifiers.
        Specify the technology stack used in the product (e.g., web application, mobile app, database).

    Testing Methodology:
        Describe the methodology or approach that will be followed during the penetration test (e.g., OWASP Testing Guide, OSSTMM).
        Outline the different testing techniques to be used, such as network scanning, vulnerability assessment, or social engineering.

    Credentials and Access:
        Provide necessary login credentials or access tokens for the tester(s) to access the target system(s).
        Specify any additional access requirements, such as VPN or two-factor authentication.

    Test Schedule and Timeline:
        Define the proposed test schedule, including start and end dates.
        Indicate any critical or high-risk periods during which testing should be avoided.

    Reporting and Communication:
        Specify the expected format and delivery method for the final penetration test report.
        Identify the stakeholders who should receive the report.
        Establish a communication plan for reporting interim findings or critical vulnerabilities.

    Legal and Ethical Considerations:
        Highlight legal and ethical guidelines that should be adhered to during the penetration test.
        Include any necessary agreements, such as non-disclosure agreements (NDAs) or authorization letters.

    Additional Notes:
        Leave space for any additional comments or notes relevant to the penetration test.

Remember that this is a general framework, and you should tailor it to fit the specific needs of your penetration testing process. Additionally, it's crucial to consult with legal and security experts to ensure compliance with relevant laws and regulations and to conduct the penetration test ethically and responsibly.