The team has an executive-approved brief, reply queue and scheduling plan, with source evidence and an explicit approval before any external action. Track time spent triaging the executive inbox against a baseline; do not assume automation improves it.
What you build
A connected workflow that uses authorized inbox folders, calendar, approved contact list and explicit executive preferences to summarize priorities, draft replies and propose meeting times without sending messages or committing the calendar. It produces an executive-approved brief, reply queue and scheduling plan.
Where AI helps, and where a person decides.
AI does
AI can summarize priorities, draft replies and propose meeting times without sending messages or committing the calendar. It drafts and organizes; it does not authorize spending, commitments, clinical decisions or customer communication. The executive or delegated chief of staff verifies the source facts and approves the final action.
A person approves
Executive or delegated chief of staff is accountable. People approve customer-facing, sensitive, financial, and legally binding actions.
Executive or delegated chief of staff: Capture the source and scope
Executive or delegated chief of staff: Review the proposed outcome
Executive or delegated chief of staff: Release only the approved version
Executive or delegated chief of staff: Check the result and exceptions
A named person approves customer-facing messages, spending, record changes and binding commitments before release. Pre-approved scripts are versioned; exceptions stop for review.
02 · The handoffs
How the work moves.
Every handoff has an owner. Select a step to open or close its detail.
Start when: An executive requests a briefing or a consented inbox item needs attention. Connect only authorized inbox folders, calendar, approved contact list and explicit executive preferences. The executive or delegated chief of staff confirms the request is authorized and in scope.
Ready when: The source reference, permissions and accountable owner are recorded.
Use the authorized records to summarize priorities, draft replies and propose meeting times without sending messages or committing the calendar. Preserve the original language alongside the draft and label uncertain fields.
Ready when: Each proposed fact links back to a source, and missing information is visible.
Check an executive-approved brief, reply queue and scheduling plan against the original records and current policy. Correct errors and escalate exceptions to the qualified specialist; do not auto-approve.
Ready when: Executive or delegated chief of staff has recorded approval or a reason to hold the item.
After explicit approval, save an executive-approved brief, reply queue and scheduling plan in the system of record. Send only approved messages to verified recipients. Record the version and prevent duplicate delivery.
Ready when: The approved record is saved; any delivery is confirmed or placed in the retry queue.
Review time spent triaging the executive inbox each week, sample completed records for quality, and resolve held items. Change the rules only after reviewing actual errors and staff feedback.
Ready when: Exceptions have owners, the metric has a baseline, and corrective actions are assigned.
Sample record.
$ david run --workflow=imessage-executive-assistant
ILLUSTRATIVE RECORD / NOT LIVE CUSTOMER DATA
Example
Illustrative only — not a real client record
Reference
IMESSAGE-EXECUTIVE-ASSIS-DEMO-001
Trigger
An executive requests a briefing or a consented inbox item needs attention.
Owner
Executive or delegated chief of staff
Prepared output
an executive-approved brief, reply queue and scheduling plan
Review status
Awaiting human approval — no external action taken
Missing information
Owner to verify source completeness
Measure
Time spent triaging the executive inbox
Start with your tools.
Connect CRM, Google Workspace, Slack through approved APIs or controlled exports. Map record identifiers first; test permissions and field updates in a sandbox. Vendor names describe possible connections, not a guarantee of an available integration or license.
iMessageGoogle CalendarGmailMicrosoft 365
When things go wrong.
A named person approves customer-facing messages, spending, record changes and binding commitments before release. Pre-approved scripts are versioned; exceptions stop for review.
Use only authorized sources and role-based access. Keep an audit trail of source records, drafts, approvals and delivery status; deduplicate retries.
If an integration fails, a source is missing or confidence is low, pause the action and assign the original request to the accountable owner.
For healthcare uses, validate HIPAA applicability, execute required BAAs, restrict PHI to the minimum necessary, and use approved secure systems. Clinicians handle symptoms, urgent care and clinical decisions.
For legal work, preserve privilege and confidentiality, check conflicts before substantive intake, and require a licensed attorney to approve legal advice, filings and engagement terms.
For financial or insurance work, a properly licensed professional approves recommendations, coverage, suitability and binding actions. Apply the firm's supervision, retention and advertising rules.
An iMessage experience requires a supported, authorized messaging bridge and explicit device/account permissions. Validate feasibility during the Fitting, our 2–3 week AI audit; use a secure alternative when the bridge cannot satisfy access, retention or security requirements.
Try this week / no DAVID required
A useful first step.
This week, have your executive or delegated chief of staff time five examples of this work. Use redacted copies of authorized inbox folders, calendar, approved contact list and explicit executive preferences to make an executive-approved brief, reply queue and scheduling plan manually, then list which fields required judgment.
What to measure.
01Time spent triaging the executive inbox
02Minutes of human handling per completed item
03Drafts needing substantive correction
04Exceptions unresolved beyond the agreed review window
Estimate your time back.
A baseline, not a promise
Estimated hrs / month20.8
Estimated value / year$11,232
Estimate assumes all entered task time is recovered, over 52 weeks. Human review, setup costs, and overlapping work reduce actual savings. Annual value is time valued at your rate, not guaranteed cash savings.