From Identification to Remediation: A Security Leader's Pre-Engagement Checklist for Penetration Testing

20 must-ask questions to transform your penetration test from a checkbox exercise to a powerhouse of actionable insights.

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With 48.8% of executives expecting an increase in cyber events targeting their organisations’ accounting and financial data in the year ahead*, the stakes have never been higher.

This checklist serves as more than just a preparatory guide; it’s a tool for aligning crucial variables between you and your pen testing service provider.

As you delve into the questions that follow, keep in mind that the aim is to drive a focused, efficient test that yields actionable insights—insights that directly contribute to strengthening your cyber security measures. You’ll notice that we’ve omitted some of the more obvious questions, such as establishing primary objectives, outlining target assets or defining the type of penetration test. We’re confident you’ve already tackled these in your planning. Let’s get started.

Download your copy of the pre-engagement checklist below



Aligning Business Goals and Cyber Security Objectives

Harmonise the mission-critical aspects of the organisation with cybersecurity imperatives.


Outlining Stakeholder Engagement and Alignment

Develop communication plans to keep all relevant parties informed and invested.


Navigating Legal and Regulatory Complexities

Avoid legal snags and ensure full compliance with industry standards.


Defining Test Complexities and Timelines

Specify the scope, methods, and deadlines to maintain project focus.


Evaluating Team Expertise and Dynamics

Scrutinise skill levels and collaboration effectiveness within the assessment crew.


Managing Complex Risks and Incidents

Preemptively identify and plan for potential challenges and unexpected outcomes.


Navigating Legal and Regulatory Complexities

Avoid legal snags and ensure full compliance with industry standards.


Navigating Post-Test Complexity

Streamline the steps to take following the assessment for prompt remediation.

The questions in this checklist are crafted to elevate your cyber security planning, aiming for a holistic and rigorous approach. At recon, we excel in creating penetration tests that transcend mere vulnerability scans. We invite you to engage with us for a tailored, actionable strategy to fortify your cyber security measures. 

We thank you for considering recon as your trusted cyber security partner.