Waypoint — Agentic Rollout Planning

Waypoint

Agentic rollout planning, with guardrails

Signed in as

Priya Shah

IT Admin — planning a phased Microsoft 365 Copilot rollout, one department at a time

Department

Adjust org data — Finance

Rollout mode

Shadow mode

Agent proposes & logs — a human executes

Problem: admins are asked to delegate rollout planning to AI, but a recommendation isn't the same as permission to act. Without a hard boundary between reasoning and execution, delegation isn't safe.

Differentiation: Conditional Access and Intune enforce policy at the point of access. The Copilot Dashboard reports adoption after the fact. Waypoint reasons through the whole rollout plan before anything executes, with a full decision trail.

Non-goals (v1): no live Graph/M365 integration, no roster/file upload — org data is edited in-app instead, single persona, single tenant, no live license sync, no execution — plan & guardrail simulation only.

Roadmap — workload-specific guardrails: a workload selector (Teams, SharePoint, Copilot Chat, etc.) shapes the plan today, but guardrail rules are still department-scoped, not workload-scoped. The JD's own scope spans Exchange, SharePoint, Teams, Copilot, Commerce, Message Center, and Service Health — each with different DLP and access-control profiles. Next iteration: a guardrail matrix keyed by department × workload, not department alone.

Approval, risk-tiered: a policy pass alone never finalizes a step. Elevated-access steps, near-license-cap steps, and any step in a department without an established trust record need an explicit admin confirmation. Only low-risk steps in a department the ramp has already vetted "ready" auto-confirm — and every auto-confirmation is logged exactly like a manual one, so nothing is final without a visible, attributable decision.

Plan quality: plans are also scored for coverage against a lightweight golden checklist, separate from policy — a plan can be fully compliant and still be incomplete.

Rollout request

Add a bit more detail about the rollout request before generating a plan.

Workload

Shapes the plan's wording and scope. Guardrail rules are department-scoped in this version, not yet workload-specific — see roadmap below.

Reasoning through a plan…

Decision log

Time	Step	Department	Status	Rule / note

Plan a rollout

Decision log