How to Prepare Your Team for an Upcoming Penetration Test

Introduction

When asked whether organizations are ready for a penetration test, one leading cybersecurity firm stated: “A lack of preparation is the common denominator in pen tests that don’t deliver value.”

If your team isn’t ready, the test can become a disruption, yield misleading results, or fail to uncover the most relevant risks. In this article you will learn how to prepare your team for a pen test what must be understood, who needs training, and how to structure communication and responsibilities. We’ll focus on how to prepare your team for an upcoming penetration test, with practical actions, checklists and best practices.

By the end you’ll be ready to:

  • Define the objectives and scope of the test in a way your team understands.
  • Assign roles and train the relevant participants.
  • Manage logistics, environment, communications and follow-through so the testing engagement adds maximum value.

The main keyword appears here naturally: prepare your team for a penetration test.

Why Team Preparation Matters

A penetration testing engagement is not just a technical exercise, it’s a team event involving stakeholders across security, IT operations, developers, business owners and potentially external partners. Without coordination your test may:

  • Run outside business windows and cause unintended downtime.
  • Hit blind-spots because asset inventory or roles weren’t clear.
  • Fail to turn results into action because no one was prepared to respond.

According to industry checklist guidance:

Employees should be aware, trained and ready to respond.” A-LIGN

Another firm lists communication and expectation-management as a top preparation item:

“Communicate the purpose and scope of the penetration test to all relevant stakeholders… Socialise the test and manage expectations.”

In short: If your team does not understand the ‘why’, accept the ‘how’ and commit to the ‘what’s next’, the test may feel disruptive or worse, pointless.

Step 1: Define Scope, Objectives and Internal Roles

Objective: Ensure all team members understand what is being tested, why it’s being tested and who is involved.

1. Clarify the test’s purpose

Are you testing external perimeter, internal network, web applications, cloud, APIs or social engineering?
What business or regulatory drivers exist (e.g. compliance, M&A, new product release, risk reduction)?
Industry advice emphasises this first step strongly.

2. Define the scope

List assets/ systems in-scope and out-of-scope.
Identify environment (production vs test), time window, permitted techniques.
Document Rules of Engagement (ROE) and share with your team and the vendor.
Role
Key responsibilities
Executive sponsor
Ensures funding, strategic buy-in
Internal project lead
Coordinates schedule, resources
System owners & Dev teams
Provide access, context, monitoring
Incident response / Ops team
Monitors for unintended disruptions
Legal / Compliance
Reviews ROE, data-handling rules

Step 2: Prepare Your Environment and Asset Inventory

Objective: Ensure the team understands the environment and that the test can proceed smoothly with minimal surprises.

Inventory and documentation

Your team should provide:

  • Complete list of hardware, software, cloud assets and network zones.
  • Details of architecture, trust boundaries, user access roles.

    As noted: “The first and most important step … is to have a comprehensive understanding of your IT environment.”

Pre-scans and baseline checks

  • Run internal vulnerability scans (authenticated) ahead of time to reduce “low-hanging fruit”. (
  • Confirm backup, change freeze periods, business-critical windows.
  • Prepare test accounts, logging/monitoring channels so your team can track what the testers do.

Communication with your team

  • Notify operations, dev, help-desk about the upcoming test and potential impact.
  • Set a schedule and share contact points for escalation.
  • Establish a “war-room” or channel for live updates during the test.

Step 3: Train and Align Team Participants

Objective: Make sure each participant understands the test, their role and how results will be consumed.

Developer/Engineering training

  • Review common vulnerabilities (OWASP Top10, business logic flaws).
  • Explain how testers may exploit issues and how remediation will be prioritised.
  • Encourage developer teams to consider the forthcoming test as a learning opportunity, not a pass/fail exam.

Operations/Support training

  • Prepare ops teams to monitor for unexpected behaviour or alerts during the test.
  • Decide in advance how to respond if a tester accidentally causes disruption.
  • Clarify escalation paths and communications (e.g. via the ROE who to contact).

Business and stakeholder alignment

  • Ensure business leaders know what the test will deliver (report, risk-ratings, remediation plan).
  • Emphasise that goal is improvement of security posture, not pointing fingers.

Step 4: Engage with the Pen-Test Team and Manage Logistics

Objective: Create friction-free engagement with your third-party testers and internal team.

Select and brief the testing team

  • Ensure the vendor understands your scope, business context, critical assets, and change freeze windows.
  • Share asset inventory and architecture docs so they can move faster and avoid wasted time.

Logistics and scheduling

  • Lock in date/time. Avoid critical release windows or major change freeze periods.
  • Confirm test environment (prod vs staging), data sets and replicate realistic conditions.
  • Agree on reporting schedule (interim updates? final report?).

If you’re unsure how to schedule or define your testing engagement, explore DeepStrike’s penetration testing services to see examples of structured testing engagements and timelines.

Communication plan

  • Define primary points of contact inside your team and at the vendor.
  • Set a live channel (Slack, Teams) for progress and issues.
  • Pre-plan how you will capture lessons learned and how your team will respond after.

Step 5: Post-Test Team Actions and Remediation Readiness

Objective: Ensure your team treats the test as a starting point for action, not an endpoint.

Receive and distribute results

  • Expect an executive summary + technical details.
  • Share findings with developers, ops, and business stakeholders according to their needs.
  • Prioritise findings: critical risks first, then medium/low.

Action planning

  • Your team should be ready with a remediation backlog and owners assigned.
  • Consider a retest schedule: once fixes are applied, confirm vulnerabilities are addressed.
  • Use the results to update training, processes and perhaps adjust your security roadmap.

Continuous improvement

  • Make penetration testing a recurring process within your security lifecycle.
  • Share lessons learned across the organizations to raise security awareness.

Conclusion

Preparing your team ahead of a penetration test is as important as choosing the right vendor or tool. With the right preparation your team will understand the scope, be aligned in roles, ready for the engagement and able to act on the results. By following the steps above you will prepare your team for a penetration test in a structured way that maximises value and drives real security improvement.

FAQ

Q1. Who should be involved in preparing for a penetration test?

All relevant stakeholders: security, dev, operations, business owners, legal/compliance.

Q2. How far in advance should we start preparing?

At least one to three months ahead is recommended, especially for more complex environments.

Q3. Should we perform vulnerability scans before a pen test?

Yes, internal scans help identify obvious issues ahead of time and allow testers to focus on deeper risks.

Q4. What if our team or environment changes mid-test?

Notify the testing team immediately, update the ROE if needed, and ensure the internal contact remains aware.

Q5. How do we ensure the test delivers value, not just a list of issues?

By aligning business objectives, ensuring roles are assigned for remediation, tracking results and scheduling a retest.

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