A Guide to Testing Executive Resilience Against Social Engineering

Executive leaders often have broad access, public profiles and demanding schedules, making them attractive targets for phishing, impersonation, business email compromise and phone-based scams. A controlled assessment can reveal whether an organisation’s senior decision-makers, assistants and security teams are prepared to identify and report these attempts.

A well-designed exercise tests people and processes without humiliating individuals or creating operational risk. The goal is to understand how an attack might unfold, which controls would detect it, and whether staff know how to escalate a concern quickly.

Australian organisations must also account for privacy obligations, the Notifiable Data Breaches scheme and industry requirements. Financial services firms may need to consider APRA CPS 234, while many organisations use the Australian Signals Directorate’s Essential Eight as a practical security baseline.

For an independent assessment, a specialist such as Infoziant Security can combine social engineering simulations with vulnerability testing, monitoring and incident response expertise. The result should be a useful security improvement program rather than a one-off stunt.

Establish Executive Sponsorship And Boundaries

Testing should begin with written approval from the board, chief executive, risk owner or another authorised executive. The document should define the objectives, target groups, permitted channels, testing period, exclusions and rules for stopping the exercise.

Senior assistants, family members, reception staff and external suppliers may unintentionally become involved, so the scope must be carefully designed. Personal accounts, private phone numbers and home addresses should be excluded unless there is a compelling legal and business reason to include them.

Australian privacy law makes data handling particularly important. Collect only the information needed to assess behaviour, store results securely and establish how long evidence will be retained. Legal counsel and the privacy officer should review the plan before any contact is made.

Select Realistic Attack Scenarios

A credible exercise reflects the organisation’s actual threat profile. Examples include a fake invoice request, a request to approve an urgent payment, a simulated Microsoft 365 sign-in prompt, a phone call impersonating a supplier, or a message claiming to come from a board member.

Scenarios should use publicly available information responsibly. LinkedIn profiles, company announcements, conference appearances and supplier relationships can make a test realistic without resorting to sensitive personal details. For an Australian audience, references to an EOFY approval, a Sydney client meeting or a Brisbane office relocation may feel plausible, but the scenario must remain proportionate.

Use several channels when appropriate, such as email, SMS and voice calls, while avoiding excessive pressure. A message written in familiar Australian business language can expose weaknesses in verification procedures without relying on caricature or slang.

Protect People And Business Operations

The exercise must never cause a real payment, account lockout, malware infection or disclosure of confidential information. Use harmless landing pages, dummy documents and controlled callback numbers. Any credentials entered into a simulation should be captured only as a non-sensitive event, such as “attempt recorded”, rather than stored in readable form.

Create a live safety process. The testing team should have an emergency contact, a clear stop command and a way to notify the security operations centre if an employee reports distress or a genuine incident is triggered. Testing outside peak periods, such as late Friday afternoon or during a major public event, can reduce disruption.

The assessment should also test detection. Security teams can monitor whether suspicious messages are reported, whether identity controls generate alerts and whether executives follow the organisation’s incident response process. A managed security provider can help correlate these events through SIEM monitoring and threat intelligence.

Measure Behaviour And Response Quality

Click rates alone provide a limited view. Stronger measures include reporting time, verification behaviour, escalation accuracy, use of approved channels and the time taken to contain a suspected compromise. Record whether an executive independently contacts an assistant, supplier or security team using a trusted number.

The quality of the response matters more than individual scores. An employee who pauses, verifies the request and reports it should be recognised even if the message was opened. Conversely, a low click rate may hide a serious weakness if staff ignore the message but fail to notify anyone.

Compare results across business units, locations and channels, while protecting individual identities in reports. Trends can show whether executive assistants need additional support, whether payment approval controls are clear, or whether staff in a Perth office face different operational pressures from teams in Melbourne or Canberra.

Convert Findings Into Stronger Controls

Every finding should lead to an assigned owner and a measurable remediation action. Improvements may include payment verification by voice, stricter executive impersonation controls, phishing-resistant multifactor authentication, privileged access reviews and clearer reporting buttons in email clients.

Training should be short, practical and role-specific. Executives may need guidance on travel-related requests and urgent approvals, while assistants may require deeper practice in identity verification and secure calendar handling. Conducting a follow-up simulation after remediation shows whether new habits have become routine.

The report should distinguish between human behaviour, technology gaps and process failures. If a leader bypassed a control because the process was too slow, changing the workflow may be more effective than repeating generic awareness training.

Priorities For A Responsible Program

A repeatable social engineering assessment works best when it is treated as part of enterprise risk management rather than an isolated phishing campaign. Plan a baseline exercise, remediate weaknesses, and retest at sensible intervals using different scenarios.

Keep the tone professional and respectful. In Australian workplaces, a direct explanation and a quick debrief usually land better than public call-outs or “gotcha” language. Leaders should model the expected behaviour by reporting simulated attacks and discussing lessons learned.

• Obtain documented approval and define legal, privacy and operational limits.
• Test assistants, finance staff and trusted suppliers where the risk justifies it.
• Use harmless infrastructure and never collect real passwords or payment details.
• Measure reporting, verification and containment, not just clicks.
• Provide role-based coaching immediately after the exercise.
• Retest critical weaknesses and report progress to the board or risk committee.

Executive resilience improves when leadership participates visibly in the security culture. Arrange a controlled assessment, review the findings with your security and privacy teams, and turn the results into specific improvements across people, processes and technology.