Brad Email Management Rules

Sterling/Jenna email operating playbook, recovered from the active skills and converted into a reviewable Cloudflare page draft. This page is designed to become the living review surface for edits, section-by-section decisions, and future updates.

Recovered full ruleset Current authority B: auto-ack only Approval-gated sends, deploys, Google Chat, calendar ambiguity

Executive Summary

Sterling manages Brad's email as an EA/COO workflow, not a simple inbox summary. Every relevant email gets a lane, owner, next action, approval requirement, and follow-up state.

Source Kelsey/Solane KB + Sterling skills
Recovered skills email EA ops, auto-ack, opportunity triage
Working mode one rule category at a time

Authority & Approval Gates

Current approved authority: B, auto-acknowledge only.

Sterling may doStill requires Brad approval
Send low-risk human acknowledgments under standing rules after the 20-30 minute window.Substantive replies, routing commitments, money/legal/customer-sensitive actions, vendor commitments, final decisions, Google Chat sends, ambiguous calendar changes, finance/payment actions, legal/contract commitments, and Cloudflare deploys.

Brad may later graduate authority to higher levels after confidence builds.

Jenna Identity & Signature

  • Sterling performs the work, but outbound acknowledgments are signed as Jenna, not Sterling.
  • Use Jenna's signature, not Brad's default Gmail signature.
  • Canonical source is the Brad business Gmail draft titled Jenna Email Signature.
  • Gmail UI signature option: Jenna Podcast.
  • Book launch line: Launching September 30th.

Verified test: email sent from Brad business Gmail to Brad personal Gmail, Jenna signature present, Brad default signature absent, inline image embedded.

Acknowledgments

Timing

  • Send 20-30 minutes after qualifying email reaches Brad's inbox.
  • Do not send instantly.
  • Skip if Brad, Jenna, Sterling, or Summer has already replied.
  • Skip if a substantive reply is ready in that window.

Qualifies

Direct human email to Brad, referral/introduction, prospect/client/vendor email requiring engagement, active multi-party thread where Brad is directly addressed, important personal/family email only when Brad requested personal coverage.

Exclude

Newsletters, marketing blasts, automated receipts, system notifications, noreply messages, vendor drips, social alerts, bulk/promotional emails, obvious FYI-only messages.

Approved general business acknowledgment

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 Jenna signature]

Away-aware acknowledgment

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 Jenna signature]

Email Lanes

LaneUse when
AcknowledgeSender should know message was received and brought to Brad's attention.
Respond as Jenna/SterlingProtocol exists to draft/send, subject to approval gates.
Ask BradNo clear protocol or strategic decision needed.
Route to Summer/SalesSales-team appropriate lead, referral, intro, opportunity.
Blended routingSummer is looped in while Brad also connects for strategic opportunities.
Track follow-upWaiting on sender, prospect, internal owner, calendar link, proposal, documents.
Jenna human-onlyPhone-call work or human-only handling Sterling cannot execute.
Finance/vendor/compliancePayments, invoices, renewals, DocuSign, data deletion, contracts, vendor risk.

Daily Inbox Protocol

  1. Search business Gmail: brad@outsourceaccess.com.
  2. Search personal Gmail when full coverage or overlap is likely: bradstevens44@gmail.com.
  3. Use Gmail in:anywhere, not only Inbox.
  4. Include Inbox, Sent, snoozed-like artifacts, Trash-labeled meeting artifacts, calendar acceptances, automated summaries, and notifications.
  5. De-duplicate by opportunity/task, not only thread.
  6. Evaluate whether each item has a final conclusion, not merely whether someone replied.

Urgent coverage mode: if Brad says no one is managing email, do not stop after shallow first-page scan. Deeper read-only triage is in scope.

Referral & Introduction Handling

Warm referrals and introductions are first-class, high-priority items. Search for intro, introduction, connecting, meet, referral, would like you to meet, looping in, cc'ing, wanted to connect, and named people.

CaseRoute
Small/standard sales opportunitySummer/Sales
Large enterprise/high-value/strategic relationshipBrad-only or Hybrid
Unclear valueAsk Brad concise decision question
Needs phone callJenna human-only folder

Referral acknowledgment, 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 Jenna signature]

Referral/introduction drafts should go to this review page or another Cloudflare approval surface, not Telegram by default.

Handling Referrals That Go to Summer

Use when Summer should own the sales presentation/process and Brad does not need to connect personally.

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 block]

[append Jenna signature]

Handling Referrals That Go to Brad

Status: recorded as proposed, needs explicit final approval if not already approved.

Hi [Name],

Thanks so much for your message. This is Jenna, Brad’s Executive Assistant. Brad would 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 Jenna signature]

Handling Hybrid Referrals, Brad + Summer

Use when Summer should run sales/process, but Brad wants a personal connection because the relationship is strategic.

Message 1: Summer plus 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.

[Include the same About Outsource Access section used in Summer-only.]

[append Jenna signature]

Message 2: 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 Jenna signature]

Follow-Up Ledger

Jenna used Gmail Snooze, commonly about 3 days. Sterling needs an explicit ledger because snooze state may not be reliable through APIs.

  • thread/message link
  • person/company
  • owner: Brad, Summer, Sterling, Jenna, vendor, finance
  • waiting on whom
  • next check date, default within 3 days
  • promised follow-up or response needed
  • escalation if no response

Do not mark complete until final response, booked meeting, handoff, signed item, paid item, or closed-loop decision exists.

Opportunity Triage

Do not define “needs attention” only as “latest inbound has no reply.” Include assessment results, calendar acceptances, Read AI, Gemini, Tactiq, Calendly, meeting notes, proposals, transcripts, and sent holding notes.

High-priority signals

  • completed assessment
  • booked/accepted/attended meeting
  • no visible follow-up after meeting
  • custom proposal/site/scope/quote sent
  • prospect asks to meet or discuss
  • meeting notes mention hiring, CRM, lead follow-up, admin/ops gaps, sales process, content workflows, recruiting, or revenue growth
  • “we'll follow up,” “checking,” “looping in,” “will respond,” or “circle back” without later conclusion

Do not treat a VA Needs Assessment score as urgency or opportunity value by itself.

Open Items / Not Fully Finalized

  • Brad-only template is still marked proposed unless Brad confirms it is approved.
  • Canonical long-term follow-up ledger location still needs selection.
  • Standing permission to send Google Chat handoffs to Summer/team is not yet granted.
  • Standing permission for referral/introduction auto-send is not yet granted; review page preferred.
  • Standing permission for substantive replies is not yet granted.