Inventory
Separate interviews with the principal and the assistant. Task list, system list, and the informal workarounds that have accumulated around missing access.
DAGR‑400 · Engagement Brief
Almost every executive support arrangement runs on impersonation. A shared password. Full-mailbox delegation because full was the only setting. An AI tool holding a token that grants everything, because everything was the only checkbox on the consent screen.
It works — right up to the moment someone needs to know who actually did something.
The distinction
The difference is invisible day to day and decisive afterward. Under impersonation, the audit log says the executive sent the email, approved the invoice, opened the file. It says that whether the executive did it or not, and there is no forensic way to separate the two. Every action the assistant takes lands on the executive's record — including the mistakes, and including anything done by someone who should no longer have had access at all.
Delegation grants the assistant a narrower set of permissions, held under their own identity, with the executive's authority attached to the action rather than to the login. The work gets done the same way. The record is materially different.
If you can't answer all four, you don't have delegation. You have a shared password with better manners.
Signals
Deliverables
Every task performed on your behalf, the systems each one touches, and the narrowest access that actually completes it. Built from separate interviews with you and with your assistant — because the list of what they do and the list of what you think they do are never the same list.
What is granted right now across mail, calendar, files, finance, and connected applications — including standing grants nobody remembers making and tokens issued to tools that are no longer in use.
Per system, the specific mechanism: shared mailbox versus delegate access, calendar availability versus full detail, folder-scoped document permissions, spend ceilings, and hard approval gates on anything financial, contractual, or legal. Configuration you already own and have not used.
In writing, countersigned by both of you: what the assistant does alone, what requires your explicit confirmation, and what is never delegated regardless of how convenient it would be. The document that protects the assistant as much as it protects you.
Every action traceable to exactly one principal, with logging retained long enough to matter. No shared credentials anywhere in the design — not as an exception, not for the one legacy system, not temporarily.
Not a document describing how revocation would work. A rehearsed procedure, executed once in front of you, with a measured completion time. Offboarding an assistant should take minutes and leave nothing behind.
The AI extension
A human assistant with too much access is bounded by working hours, attention, and the social instinct that stops them from opening the thread marked Board only. An AI agent holding your token has none of those brakes. It has your authority at machine speed, around the clock, and it will follow an instruction into a mailbox a person would have known not to touch.
The controls are the same controls. What changes is the tolerance for getting them wrong — and the fact that most organizations have no lifecycle for non-human identities at all: no owner, no review interval, no expiry, no inventory of which tools currently hold a key to what.
This engagement treats an AI assistant as what it is: a principal that needs its own identity, its own narrow scopes, a named human owner, a review date, and a kill switch someone has tested.
How it runs
Separate interviews with the principal and the assistant. Task list, system list, and the informal workarounds that have accumulated around missing access.
Enumerate what is actually granted today — delegates, shared mailboxes, folder permissions, OAuth grants, service accounts, and anything with a password in a shared vault.
Working alongside your IT or Microsoft 365 administrator. Scopes narrowed, impersonation retired, approval gates put where the money and the contracts are.
Written authority limits, the delegation map as a living register, and the revocation drill run end to end while you watch the clock.
Not an identity platform rollout, and not a product you have to buy. The large majority of this engagement is configuration you already own and have never turned on, plus decisions that have never been written down. If the right answer turns out to be a tool you don't have, I'll tell you that too — but it usually isn't.
If that question is uncomfortable to answer precisely, it's worth thirty minutes. If your setup is already clean, I'll tell you that and we're done.