How should organisations design phishing exercises for finance and executive teams?

Design exercises around the real requests finance and executive teams receive

Phishing exercises work best when they mirror the kinds of business requests those teams handle under time pressure. For finance, that usually means payment instructions, bank-detail changes, invoice queries, or urgent approvals. For executives, it often means board documents, deal materials, travel changes, or requests that appear to come from assistants, counsel, or other senior staff.

That realism matters because the exercise is trying to measure decision quality, not just link-clicking. If the scenario is too generic, you learn little about how the team behaves when the message matches a real workflow and the stakes feel high.

Scenario design should also reflect the channel mix those teams actually use. A credible test may involve email, collaboration tools, SMS, or a callback request, but the key is that the pretext fits the recipient's normal working pattern. For a broader exercise design reference, see Phishing Guide.

What the exercise should measure, and what it should not

The central control objective is whether the recipient verifies an unusual request through a trusted channel before acting. That means the scenario should encourage a pause: confirm the sender, validate the request out of band, or seek a second approver where policy requires it. The exercise should reveal whether those checks happen naturally or only when the message is obviously suspicious.

It should not be built to capture real credentials, interrupt live financial operations, or create unnecessary confusion for assistants, approvers, or payment processors. A good exercise avoids crossing from assessment into harmful interference. If the scenario is meant to assess approval discipline, then the success criterion should be verification behaviour, not whether the person can be tricked into completing a real transaction.

For finance and executive audiences, it is also useful to test the points where authority is assumed rather than checked. Requests that appear to come from a senior leader, a known vendor, or an internal finance contact are especially instructive because they probe trust shortcuts, not just technical awareness. That is where Tabletop Exercise Guide is useful as a planning model for injects, roles, and after-action review.

How to keep the exercise realistic without causing disruption

Good design balances realism, safety, and measurable outcomes. Use realistic wording, familiar attachments or document references, and plausible urgency, but avoid content that would trigger actual transfers, legal sign-off, or customer-impacting actions. The exercise should be easy to grade and safe to run repeatedly, not a one-off stunt.

It also helps to align the scenario to the approval path the team is expected to use in real life. If an unusual payment change should be verified through a known internal contact, the exercise should test that exact behaviour. If an executive assistant is expected to validate a request before forwarding it, the scenario should place that validation step at the centre of the test. That keeps the exercise tied to process, not just awareness messaging.

Where organisations want a stronger benchmark, they should track whether staff follow the intended verification path consistently across repeated exercises and whether the control holds when the sender appears senior, the request is urgent, or the business context looks legitimate. The value is in spotting weak approval habits before an attacker does.

Risk and Threat Considerations

Finance and executive teams are attractive targets because they can authorize payments, disclose sensitive information, or accelerate decisions. The main risk is not only a click on a malicious link, but a believable request that bypasses normal scrutiny and moves money, data, or authority through an unsafe channel.

Failure mechanism: The attacker relies on urgency, authority cues, or workflow familiarity to get the recipient to act before verifying the request through a trusted channel.

Impact: That can lead to unauthorized transfers, disclosure of confidential documents, credential exposure, or follow-on impersonation attempts against other staff and vendors.

Practitioner Guidance

What to verify: Design the exercise around the exact verification step you want to reinforce, then confirm that the team knows which channel counts as trusted for payment changes, approvals, and executive requests. If the control depends on callback validation or second-person approval, the scenario should make that step observable.

Common mistake: Avoid generic bait that only tests curiosity. For finance and executive groups, the meaningful failure is usually trust in a plausible request, so the scenario should look operationally real without creating genuine business risk.

Practitioner takeaway: The best phishing exercise for these teams is one that pressures real decision habits, not one that maximizes trickery, because the real control is disciplined verification under urgency.

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