Evaluate automation by the task it changes
When a proposal includes automated ticket handling, suggested answers or scheduled workflows, ask what the system actually does. Establish which actions need approval and how staff reach a person when the ordinary route doesn’t resolve their problem.
A demonstration should use a relevant business request, such as a new starter needing access to an application. Follow the request through assignment, approval and completion. This reveals more than a broad claim about efficiency.
For tools that process support messages, clarify what information they receive and who can review it. Keep confidential business information out of demonstrations until appropriate handling arrangements are agreed.
Plan support around where work happens
Describe your actual working arrangements rather than choosing a support model because it sounds modern. Office-based staff, remote workers and people moving between locations may have different support requirements.
Ask which issues the proposed remote arrangement covers and how work requiring physical access would be handled. Confirm the responsibility for home working devices and business applications where those boundaries are unclear.
Include cloud systems in the handover
If email, shared files or applications are changing, the support discussion should include what happens after the project. Who handles access requests? Who contacts the application supplier? Who approves later changes?
The cloud and workplace IT page provides a starting point for describing the project and its ongoing support needs.
A specialist application may retain a separate support route. Make that dependency visible even if other workplace systems move into one arrangement.
Ask what proactive support would mean in practice
Replace the word proactive with named tasks, review dates and responsibilities. Ask what is checked, what information is reported and who decides what action follows.
For security planning, include backups, device and account protection, and awareness of scams. Those subjects appear in the small organisations guide (ncsc.gov.uk) from the National Cyber Security Centre, the UK’s national technical authority for cyber security.
At your next support review, request a description of one ordinary task and one difficult exception. The exception will expose decisions that a technology forecast can leave unanswered.