Brad’s Email Management Protocol
Standalone Email Operations System • Sterling 2.0

Email Management Protocols

The consolidated operating model for triage, acknowledgments, referrals, routing, scheduling, labels, follow-up, and Jenna human-only handoffs. Reconstructed from prior decisions, skill files, Gmail examples, and Calendar evidence.

✓ Finalized rules recoveredBusiness + personal inbox model15-minute cadence requested, not activatedSubstantive sends remain guarded
Standalone project: This system is independent from Brad’s Command Center. It has its own Cloudflare project, D1 database, deployment history, API, and URL. Publishing here cannot overwrite Command Center files or routes. D1: checking connection…
Current operating status: The protocol is preserved, but autonomous inbox polling and live substantive responses are not active. There is no active recurring email scanner; the 37 historical recurring scanner entries remain paused. This page distinguishes Brad-approved rules from proposals and superseded drafts so nothing is silently treated as authority.
Approved

Authority Level B

Auto-acknowledge only. Sterling may send a narrow, low-risk acknowledgment for a qualifying human email. Anything substantive, strategic, financial, legal, customer-sensitive, or commitment-making requires Brad's approval.

Graduation path: prove B first, then Brad may advance Sterling to C (routine handling) and later D (full EA mode with exceptions).
Approved

Identity and timing

  • Outbound acknowledgments appear as Jenna, not Sterling.
  • Use Brad's business Gmail and the full Jenna Podcast signature.
  • Wait approximately 20–30 minutes, never instant.
  • Skip the generic acknowledgment if Brad, Jenna, Sterling, or Summer already replied, or a substantive answer is ready.
Human only

Direct emails asking for action, referral/introduction, active client/prospect/vendor thread, or a directly addressed multi-party conversation.

Reply all

For referrals, introductions, and active multi-party threads, include every visible recipient. If BCC context is unclear, escalate.

No automation

Newsletters, marketing blasts, receipts, system/noreply mail, vendor drips, social alerts, and promotional bulk mail.

Requested target, activation pending

Proposed 15-minute inbox loop

Scan business GmailScan personal overlapDe-duplicate / thread checkClassify + labelAck / draft / route / ignoreLedger + proof
  1. Search in:anywhere, not just Inbox. Inspect Sent, Spam, calendar artifacts, meeting reports, and prior holding replies.
  2. Check whether a response already exists in the prior 24 hours.
  3. Classify owner: Sterling, Brad, Summer/Sales, Finance, Jenna human-only, family/Cindy, Marketing/Podcast, or FYI/archive.
  4. Apply the narrow auto-ack rule only after the 20–30 minute delay and only when the classification is certain.
  5. Create an explicit follow-up record for every promise or waiting item.
  6. Escalate exceptions rather than guessing.

Brad requested a 15-minute checking cadence today. The recovered older diagram showed 30 minutes and an older migrated job was hourly. The 15-minute cadence should supersede those only after the activation plan is approved.

Recovered taxonomy; live Gmail mutations need approval

Label and ownership taxonomy

Label / QueueUseOwner / Next action
Action RequiredAnything needing response, decision, invite action, document approval, or execution.Route to a sublabel/owner.
Brad OwnerPersonal judgment, strategic relationship, unclear routing, high-value decision.Brad decision prompt.
Jenna / Sterling OwnerEA can handle under protocol or prepare for approval.Acknowledge, draft, track.
Sales for Follow UpVA opportunity, referral, prospect, proposal, sales process.Summer-only, Brad-only, or Hybrid.
Waiting for ResponseA promised action or outbound message is awaiting reply.Follow-up ledger with next-check date.
SchedulingMeeting, podcast, event, personal/calendar coordination.Check Calendar and routing authority.
Payments to MakeInvoices, renewals, payment requests, proof/receipt needed.Finance/Brad; never pay autonomously.
Legal & ContractsDocuSign, agreements, legal deadlines, compliance.Urgent Brad/legal review.
Google DocsAccess requests, comments, shared-file action.Resolve or request approval, archive only after closure.
YPO / EONeeds & Leads, strategic members, events, forums.High relationship sensitivity; show Brad.
Family / School / House / MedicalPersonal Gmail and family overlap.Brad/Cindy or Jenna human-only.
Travel InfoFlights, hotels, conferences, vacation, OOO needs.Calendar/away-aware workflow.
FYI / ArchiveNo action, no expected reply.Archive candidate; no acknowledgment.
Approved decision tree

Referral, introduction, and sales routing

PathWhenAction
Summer-onlyStandard VA opportunity; Summer should own discovery, role scoping, pricing, and process. Brad meeting should not be implied.Route to Summer immediately, provide OA overview and Summer link.
Brad-onlyBrad wants the call personally; strategic network/referrer, YPO/EO, enterprise, important relationship.Reply all and offer Brad's Google Meet link. Manual coordination if needed.
HybridSummer should run the sales process, but the relationship is strategic enough for Brad to connect personally.Message 1 routes to Summer + OA overview. Message 2 separately offers Brad's link.
Custom / Ask BradVendor, private equity, unclear value, sensitive relationship, BCC ambiguity, or unusual commitment.No automatic scheduling language. Ask Brad which route applies.
Decision prompt: “Do you want to handle this personally, route to Summer, or use blended Brad + Summer?”

Finalized and recovered response library

1. General business acknowledgment — approved for narrow auto-ack
Hi [Name], Thanks for your message. This is Jenna, Brad’s Executive Assistant. I received it, and I’m bringing it to his attention. I will follow up with the next steps. [Append full Jenna signature]
2. Referral / introduction acknowledgment — wording approved; review required
Hi [Name], Thanks for the introduction. This is Jenna, Brad’s Executive Assistant. I received it, and I’m bringing it to his attention. I will follow up with the next steps. [Append full Jenna signature]

Because introductions are rare and context-heavy, place the draft on the Cloudflare review page before sending unless Brad later grants standing approval.

3. Away-aware acknowledgment — approved
Hi [Name], Thanks for your message. This is Jenna, Brad’s Executive Assistant. You may have seen Brad’s auto-reply that he is traveling. I received your message, and I’ll take a look and get back with you. [Append full Jenna signature]
4. Internal routing acknowledgment — recovered working template
Hi [Name], Thanks for sending this over. I’m going to get this in front of the right person on Brad’s team and we’ll follow up shortly. [Append full Jenna signature]
5. Brad-only scheduling — proposed/conditional structure
Hi [Name], Thanks so much for your connection/interest. This is Jenna, Brad’s Executive Assistant. Brad would like to connect personally. You can find a time that works here: https://calendly.com/bstevens/30min-googlemeet If there’s a more convenient time to connect, let us know. [Append full Jenna signature]

Use only after Brad selects the Brad-only path. The structure is recovered, but blanket standing approval was not finalized.

6. Summer-only — approved structure
Hi [Name], Thanks so much for your message. This is Jenna, Brad’s Executive Assistant. Brad is in and out of conferences this week, but I want to make sure you get support right away by connecting you with Summer. She is very knowledgeable about how Outsource Access supports clients and can help walk through your needs, answer questions, and point you to the best next step. Also, please see below. I provided a quick summary about Outsource Access outlining some key elements of our model and a few links that you may find helpful to review in the meantime. You can book time with Summer here: https://outsourceaccess.com/infocall/ About Outsource Access Outsource Access is a growth partner for businesses in 75+ industries with over 6 million hours of work performed. We are fanatically customer focused and provide fully managed, dedicated offshore staffing from the Philippines. [Insert the canonical OA differentiator block: custom solution; performance reviews and ROI; documented OA Playbook; dedicated staff; account management and specialized resources; incorporated employment model; top 1% talent; CEO interviews; impact culture; Virtual Success magazine; Scaling Breakthrough documentary; Client Tourism; referral-driven growth; FAQ resources.] Process overview: https://outsourceaccess.com/process/ [Append full Jenna signature]
7. Hybrid message 1 — Summer + OA overview
Hi [Name], Thanks so much for your message. This is Jenna, Brad’s Executive Assistant. Brad is tied up in conferences this week, but he wanted me to get you connected with Summer right away. She is very knowledgeable about how Outsource Access supports clients and can help walk through your needs, answer questions, and point you to the best next step. Also, please see below. I provided a quick summary about Outsource Access outlining some key elements of our model and a few links that you may find helpful to review in the meantime. You can book time with Summer here: https://outsourceaccess.com/infocall/ Brad would still like to connect with you personally at your convenience, so I’ll send a separate message to get the two of you connected as well. [Insert canonical About Outsource Access block] [Append full Jenna signature]
8. Hybrid message 2 — personal Brad connection
Hi [Name], As mentioned, Brad would also like to connect with you personally. You can find a time that works for you here: https://calendly.com/bstevens/30min-googlemeet If there’s a more convenient time to connect, let us know. [Append full Jenna signature]
9. Scheduling likely — superseded as an automatic template
Hi [Name], Thanks for reaching out. I’m checking Brad’s calendar and will follow up with the best next step for scheduling. Take care, Jenna

Do not auto-use. Brad explicitly corrected that vendor/PE/service-interest emails can look human and should not automatically receive scheduling language.

Verified Gmail + Calendar history

Historical Jenna formula examples

Calendar records correct the names and timing: Kelly Roach (not Kelley Roche), June 25, 2026, 2:00–2:30 PM ET; Blake Erickson, June 15, 2026, 3:00–3:30 PM ET.

Kelly Roach example — sent May 8, 2026

Subject: Re: Kelly Meet Brad #Introduction
Reply-all: Charles Byrd, Kelly Roach, Alessandra Rosales

Hi there, This is Jenna, assisting Brad. Charles, thank you for the thoughtful introduction! Kelly, it's a pleasure to meet you. Brad would love to connect. For ease, please find a time using Brad's Calendar Link: https://calendly.com/bstevens/30min-googlemeet If you have any difficulties, please let me know and we can schedule something manually as well. I'm going to drop a little bit of information about Outsource Access as well as some notable links to Brad's socials! Brad looks forward to connecting :) Take care, Jenna [Brad social, podcast, bio, speaking, book, company, and full OA overview blocks followed.]

Open verified Gmail message

Blake Erickson example — sent May 3, 2026

Subject: Re: Intro Brad x Blake
Reply-all: Blake Erickson and Colby Taylor

Hi there, This is Jenna, assisting Brad. Colby, thank you so much for the introduction. Blake, it's a pleasure to meet you. Brad would love to connect. For ease, please use Brad's Calendar Link to find a time that works best: https://calendly.com/bstevens/30min-googlemeet If you have any specific availability, please let me know and I'd be happy to coordinate manually. I will drop a little bit of information about Outsource Access below! Enjoy connecting with Brad :) [Full About Outsource Access differentiator and resource blocks followed.] Take care, Jenna

Open verified Gmail message

Formula recovered: thank the referrer by name → warmly welcome the introduced person → state Brad's intent to connect → provide Calendly + manual fallback → add context-specific OA/Brad resources → Jenna signature → reply all.
Recovered Google Docs

June 25 follow-up package and six-email draft set

These are the exact Google Docs Brad remembered from the Kelly Roach timeframe:

Clarification: the six related follow-ups were stored together in one consolidated Google Doc, not six separate documents. Kelly's deeper package is a separate document.

Follow-up ledger

Every open loop needs: source account, thread link, person/company, category, owner, waiting on, last action, next-check date, escalation date/channel, status, and closure proof.

SituationCadence
Important sent email3 business days
Sales sequence3 days → 3 days → 5 days → 30-day nurture
Brad-only referral5-day check
Scheduling requestEscalate after 24 business hours
PrepaymentEnd of day → next morning
Payment due todaySame day / TODAY priority

Opportunity completeness test

Do not equate “replied” with “resolved.” Search the full chain:

ReferralAckRoutingCalendarMeeting notesProposal / next stepClosure proof
  • Meeting summaries from Read AI, Gemini, Tactiq, and Calendly count as evidence.
  • Holding messages such as “we'll follow up” remain open.
  • Custom proposals and explicit meeting requests are urgent/high value.
  • Use P0 for money/security/legal exposure; P1 for clients/opportunities; P2 for low-risk reminders.
Human-only lane

What stays with Jenna

Phone execution

Calls, voicemail callbacks, vendor support, medical/house/school scheduling, payment support, or identity verification.

Sensitive relationships

Personal, family, medical, financial, white-glove referrals, negotiation, persuasion, and live nuance.

Access constraints

Portals or actions Sterling should not automate, blocked platforms, and tasks requiring human verification.

Sterling's job before handoff: collect source/context, identify phone/contact and deadline, draft a call script, define desired outcome and guardrails, assign priority, and require closure proof.

Retained capacity model: approximately 20 Jenna hours/month, about 5 hours/week, focused on human-only execution rather than routine triage.

Recommended target architecture

Sterling-led agent operating model

Sterling remains the single Brad-facing orchestrator. The recurring system is not a group of permanently running personalities. In Hermes, a recurring job starts a fresh, isolated agent session on each run; durable behavior comes from the recurring schedule, self-contained prompt, loaded skills, and shared case ledger. Specialist subagents are created temporarily for a specific email or batch and then end after returning a structured result to Sterling.

Business collectorPersonal collectorSterling triage orchestratorTemporary specialistReview / approvalLive executorFollow-up ledger
Plain-English answer: the recurring roles are persistent schedules plus persistent skills, not immortal subagents. The actual subagents are fresh, temporary workers with limited tools and only the context Sterling gives them.

Durable control plane

  • Skills: versioned procedures, scenario rules, exact templates, Brad/Jenna voice, routing logic, and verification checklists.
  • Cloudflare D1 case ledger: server-side durable state outside the model and outside the browser: case ID, Gmail IDs, account, thread, owner, classification, commitments, dates, risk, approval state, and proof.
  • Recurring jobs: independent fresh sessions with self-contained prompts, pinned skills, restricted toolsets, and explicit delivery behavior.
  • Sterling: resolves conflicts, approves agent handoffs, speaks to Brad, and owns final quality.
  • Proof store: classification evidence, draft version, approval record, Gmail Sent/Draft proof, and closure evidence.

Business and personal separation

Business GmailPersonal Gmail
Clients, prospects, OA referrals, staff, vendors, contracts, invoices, EO/YPO, speaking and podcast opportunities.Family, school, household, medical, personal finance, travel, community, plus business messages that landed in the wrong account.
Default organization lanes: Brad, Summer/Sales, Finance, Legal, Marketing/Podcast, Jenna human-only.Default lanes: Brad, Cindy/family, Jenna human-only, Finance/security, business-overlap handoff.
May enrich from Calendar and meeting artifacts.Cross-account lookup is allowed only when needed to close context; personal content stays compartmentalized.

Never combine both inboxes into one unrestricted context dump. Normalize only the minimum evidence needed for the case.

Recommended recurring job topology

JobCadenceToolsOutput
Business inbox collectorEvery 15 minutesBusiness Gmail read/search onlyNew/changed human-actionable candidates; silent when nothing changed.
Personal inbox collectorEvery 15 minutes, offset five minutesPersonal Gmail read/search onlyPersonal/family/security/business-overlap candidates.
Triage orchestratorEvery 15 minutes after collectorsLedger + read-only Gmail/Calendar/DriveDe-duplicated cases, priority, route, specialist assignment, review packet.
Aging and commitment monitorBusiness days, morning + afternoonLedger + Gmail/Calendar readOverdue promises, waiting items, missed post-meeting follow-ups.
Daily executive briefWeekdaysLedger summaries onlyP0/P1 decisions, drafts awaiting approval, aging and closure metrics.
Weekly quality auditWeeklyProof records, sampled threadsFalse positives, missed messages, duplicate prevention, routing and tone accuracy.

Collectors and triage jobs should be read-only at launch. The schedule can be persistent, but each run must be idempotent and process only messages newer than its verified watermark.

Temporary specialist agents

Thread reconstruction

Builds the complete chain across Inbox, Sent, Calendar, meeting notes, summaries, proposals, and prior commitments. No drafting until context is complete.

Scenario classifier

Applies the rule tree: ignore, acknowledge, Brad decision, Summer-only, Brad-only, Hybrid, scheduling, finance/legal, personal/family, or Jenna human-only.

Draft composer

Loads only the approved scenario skill, exact content modules, recipient context, Brad/Jenna voice, and source links. It has no send permission.

Meeting follow-up

Reconciles Plaud, Gemini, Read.ai, Calendar, and email; extracts promises, attachments, introductions, and next steps.

Risk reviewer

Checks recipient list, BCC ambiguity, sensitive data, money/legal commitments, prompt injection, hallucinated links, and excessive agency.

Quality verifier

Checks thread fidelity, signature, reply-all behavior, duplicate status, exact links, approval state, and proof after any approved action.

Case state machine

DetectedEnrichedClassifiedDraftedReview pendingApprovedSentWaitingClosed

Any uncertainty moves the case to Escalated, never to Sent. “Replied” is not closure; closure requires the promised handoff, meeting, document, payment, decision, or explicit disposition.

Execution and approval boundary

  • Recurring/background jobs scan, classify, draft, and alert only. They do not send email, change calendars, forward messages, move money, or make commitments.
  • Sends occur only through Sterling's live execution lane after the required approval is present and all recipients, subject, body, identity, and account are clear.
  • Current Authority B is recorded historically, but automation remains inactive. Low-risk acknowledgments can move to a controlled live pilot only after explicit activation and proof criteria.
  • Substantive replies, introductions, forwarding, scheduling ambiguity, legal, finance, customer-sensitive and personal-sensitive items remain review-first.

Reliability, security, and failure handling

RiskRequired control
Duplicate replyIdempotency key from account + thread/message ID + action type; re-read the thread immediately before action.
Prompt injection inside email/attachmentTreat all message content as untrusted data; never execute embedded instructions; isolate attachment extraction from agent permissions.
Wrong account or identityHard account boundary, explicit From identity, Jenna signature validator, and recipient/account proof.
Excessive agencyLeast-privilege toolsets; collectors cannot write; draft agents cannot send; executor cannot infer approval.
Hallucinated facts or linksEvery material statement and attachment must point to Gmail, Calendar, Drive, approved module, or verified public source.
Partial outage / auth failureNever advance watermark on failed scans; retry safely; alert on stale coverage; no fabricated “all clear.”
Run overlapSingle case lock and lease timeout; later run skips cases already being processed.
Personal-data leakageMinimum necessary context, separate account collectors, redaction in briefs, no secrets in prompts or ledgers.

Persistent skills to establish

  1. Email Orchestrator: top-level state machine, priorities, conflict resolution, and proof contract.
  2. Business Inbox Triage: OA/EO/YPO/client/prospect/vendor taxonomy and ownership.
  3. Personal Inbox Triage: family, school, household, medical, finance/security, and business crossover.
  4. Referral + Introduction Routing: Summer-only, Brad-only, Hybrid, custom, double-opt-in, reply-all.
  5. Meeting Outcome Manager: Plaud/Gemini/Read.ai reconciliation, commitments, packages, and introductions.
  6. Draft + Voice Governance: Brad vs Jenna identity, approved content modules, signatures, tone, and exact links.
  7. Scheduling: Calendar verification, authority, links, ambiguity and 24-hour escalation.
  8. Finance/Legal/Security: P0 detection and strict no-action escalation.
  9. Follow-Up Ledger: aging, waiting-on, next-check dates, escalation, and closure proof.
  10. Quality and Audit: sampled review, drift detection, metrics, and correction workflow.
External guidance, not standing authority

Best-practice synthesis applied to Brad's system

The recommendations below are informed by Google Workspace, NIST, CISA, OWASP and established executive-inbox operations. They guide system design but do not override Brad's approved scenario rules.

Inbox operations

  • Use Gmail delegation/OAuth and role-based access rather than sharing Brad's password.
  • Use filters and labels as routing metadata, not as proof a case is complete.
  • Separate triage, decision, execution, and audit so no single agent silently controls the whole lifecycle.
  • Prioritize by consequence and commitment, not unread count or inbox position.
  • Maintain one owner and one next action per open case.
  • Use quiet automation: no alert when nothing changed; immediate alert only for true P0/P1 conditions.

Security and trust

  • Use least privilege, strong MFA/passkeys, unique credentials, and delegated access.
  • Maintain SPF, DKIM and DMARC for outbound-domain integrity.
  • Treat email bodies, links, signatures and attachments as untrusted inputs capable of prompt injection.
  • Minimize retained personal data and restrict cross-account visibility.
  • Log every consequential model recommendation, approval, action and outcome.
  • Continuously measure false positives, misses, unsafe drafts, duplicate actions and drift.

Recommended service levels

PriorityExamplesTarget
P0Account compromise, wire/payment risk, legal deadline today, customer crisis, personal safety/medical urgency.Immediate alert; no autonomous action.
P1Strategic opportunity, client escalation, warm referral, meeting within 24 hours, overdue commitment.Classify within 15 minutes; draft/escalate within one business hour.
P2Routine scheduling, vendor follow-up, ordinary action request, family logistics.Same business day; aging record if unresolved.
P3FYI, newsletters, marketing, receipts, low-value automated notices.Label/archive/report only; no human interruption.

These SLAs are recommendations for activation review, not yet Brad-approved standing policy.

Quality metrics

MetricWhy it matters
Human-actionable recallPercentage of real human/action messages detected.
Classification precisionPercentage routed to the correct owner/scenario.
Duplicate-action rateMust approach zero.
Time to first classification / draftMeasures responsiveness without forcing unsafe sends.
Open-loop agingShows promises and opportunities at risk.
Approval edit distanceHow much Brad changes drafts; primary signal for skill improvement.
Closure rateCases truly completed, not merely acknowledged.
Security exceptionsPrompt injection, sensitive-data exposure, wrong-recipient, or excessive-agency events.
Next build phase

Required skills

  1. Email EA operations umbrella
  2. Referral and introduction routing
  3. Follow-up ledger and aging
  4. Personal inbox operations
  5. Calendar and scheduling operations
  6. Finance/vendor urgency
  7. Podcast/webinar workflow
  8. Monday/task routing
  9. Jenna human-only handoff
  10. Brad/Jenna voice and template governance
Do not activate silently

Activation gates

  • Scope both business and personal Gmail through separate collectors and separate privacy boundaries.
  • Confirm live Gmail labels may be applied automatically.
  • Confirm the final low-risk auto-ack categories; referrals still default to review.
  • Choose canonical ledger: Command Center, Google Sheet, Monday, or hybrid.
  • Keep money, legal, calendar commitments, customer-sensitive decisions, and substantive sends approval-gated.
  • Test with a dry-run batch, then a narrow live pilot with proof.
No system was activated by publishing this page. Live sending and recurring inbox automation require a separate controlled activation decision.

Recommended staged launch

PhaseScopeSuccess proof
1. Dry run15-minute scan; classify and recommend only.Zero missed human messages; no false auto-acks.
2. Labels + ledgerApply approved labels and maintain aging queue.Every open loop has owner and next check.
3. Authority B pilotGeneral human acknowledgments only, after 20–30 minutes.Sent proof, no duplicates, correct Jenna signature.
4. Referral review queueCloudflare drafts for Summer/Brad/Hybrid decisions.Brad approves or edits one scenario at a time.
5. Graduate authorityOnly categories Brad explicitly advances to C/D.Measured response lag, routing accuracy, and closed loops.

Source hierarchy and conflicts resolved

  1. Brad's one-by-one decisions override broad earlier proposals.
  2. Current tactical skill and decision log are the source for Authority B, Jenna identity, timing, qualification, reply-all, and routing.
  3. Gmail Sent and Calendar establish the Kelly Roach and Blake Erickson precedents.
  4. EA mapping documents preserve labels, ledger fields, human-only work, and proposed buildout.
  5. Older Sterling-signed templates and draft-only blanket rules are superseded where Brad later approved Jenna-branded low-risk acknowledgments.

Reconstruction date: July 16, 2026. Credentials and private source material were excluded.