The short answer
A personal-context assistant should begin with one bounded job, such as summarizing a meeting note or drafting a follow-up from selected material. The pilot should not start with broad mail, calendar, file, and third-party access simply because the product can request it.
A four-part rollout
Name the task, the approved data sources, the person who reviews outputs, and the action that always requires confirmation. Confirm locale and feature availability before promising a workflow. Keep a small log of failed answers, unwanted data access, and cases where the user over-trusted a suggestion.
Measure the permission cost
The gain is not just minutes saved. Ask whether the assistant reduced rework, whether users could correct it quickly, and whether a narrower permission scope would have produced the same result. Remove access that is unused; permissions should have an expiry or a review date.
FAQ
Is more context always better? No. More context may improve relevance while increasing exposure and error impact. What should be automated first? Reversible, reviewable work with a clear source of truth.