Senior executives
Practice pausing and using known advisers or approval routes for unusual high-impact requests across email and messaging.
For Executive Teams
Phishing Simulation Planning for Executive Teams
Executives and their support teams have public visibility, broad relationships, sensitive information, approval authority, and limited time across email, messaging, travel, and mobile devices.
Their simulations should practice high-value verification and escalation without exploiting personal details, creating market confusion, or disrupting consequential business decisions.
Enterprise governance • Role-based scenarios • Controlled delivery • Contextual reporting
01Map the enterprise
Design around how executive and leadership teams actually operate
Start with the entities, roles, systems, decision rights, and support teams involved in the selected workflow. Enterprise scale makes ownership and local conditions as important as message content.
Executive assistants
Reflect delegated calendar, travel, document, payment, and communication responsibilities without using live arrangements.
Board support
Use fictional governance documents and meetings outside the actual board portal and confidential board calendar.
Travel and mobile use
Pilot supported mobile experiences and reporting routes without collecting precise location or personal-device information.
02Choose the scenario
Use a role-specific request with a controlled response
Give every scenario one observable learning objective. Use fictional people, organizations, transactions, systems, and incidents, and keep the campaign outside production and privileged environments.
Confidential document request
Practice validating an invented requester, business purpose, authorization, and approved sharing destination.
Unusual payment approval
Ask leaders to use the established independent confirmation and finance approval process for a fictional transaction.
Board meeting invitation
Reinforce checking the organizer and opening the known governance service independently.
Travel support message
Practice verifying a fictional itinerary or account request through the approved travel channel.
03Govern the campaign
Resolve ownership, authority, and data questions before launch
| Consideration | Question to answer | Required preparation |
|---|---|---|
| Authorization | Who approves scenarios involving executive names, roles, delegated authority, and communications? | Document sponsor, executive-support, legal, communications, and security approval before launch. |
| Sensitive events | Could the message imply an acquisition, layoff, investigation, litigation, crisis, or market-moving event? | Exclude consequential themes and use a routine fictional workflow. |
| Delegation | Do assistants or other employees receive and act on requests for the executive? | Include the actual verification and escalation chain without exposing personal schedules or contacts. |
| Result access | Who needs individual event data, and how will it be protected? | Restrict access, define retention, avoid public reporting, and focus review on workflow and control improvements. |
04Run the exercise
Coordinate one enterprise workflow end to end
- 1
Write the campaign brief
Define the behavior, authorized audience, exclusions, scenario, permitted data, delivery windows, owners, reporting route, stop conditions, and intended use of results.
- 2
Confirm decision rights
Map central and local approvals, system and data owners, response teams, providers, and the real verification or escalation process employees should use.
- 3
Pilot representative environments
Test entities, locations, roles, devices, languages, email controls, landing pages, event records, reports, and follow-up material included in scope.
- 4
Brief response teams
Prepare security, privacy, legal, communications, HR, operations, local support, and relevant providers while preserving normal handling of real incidents.
- 5
Debrief and assign owners
Explain the expected action, provide relevant private learning, and record every process or control improvement with a responsible owner and review date.
Source: NIST SP 800-50 Rev. 1: Building a Cybersecurity and Privacy Learning Program
05Measure responsibly
Report enterprise results without hiding local conditions
Record intended recipients, exclusions, successful deliveries, unique recipient events, verified reports, response handling, and completed follow-up. Reconcile automated inspection and repeated events before attributing activity to employees.
Executive populations are small and often identifiable, making percentages and rankings inappropriate. Use restricted case-level review of expected controls, reports, response handling, device context, delegation, and process findings.
Use findings to improve real verification, reporting, identity, access, email, provider, and support processes. One interaction is not an employee risk score, and an enterprise-wide percentage does not establish program effectiveness.
Common questions
Common questions about Phishmake's features, onboarding, and support, answered to help you get started with confidence.
Should executives receive harder phishing simulations?
Difficulty should follow a defined learning need and the executive's real authority, not an attempt to trick or embarrass. The expected action must remain realistic and available.
Can a campaign imitate an acquisition or board crisis?
Avoid acquisitions, layoffs, litigation, investigations, health events, family emergencies, and other consequential themes that can cause harm or trigger business action.
Should executive assistants be included?
Include them when they operate the relevant delegated workflow and are within the approved scope. Tailor scenarios to their actual verification and escalation responsibilities.
How should executive results be reported?
Use tightly restricted, contextual reporting focused on use of expected controls, response handling, and process improvements. Avoid rankings and broad distribution of identifiable events.
Sources & further reading
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