YOUR AI CHIEF OF STAFF
A useful inbox brief. Every day. At your time.
https://clearroadlabs.com/prompts

Today we will build a useful daily brief, set the time it runs, and check how the update reaches you. The website is the map; ChatGPT does the work. I will project fictional Clear Road Labs emails. Your task uses your own real inbox privately; my fictional projection only demonstrates the steps. If you are stuck for one minute, watch and rejoin at my step. I will keep moving so we all reach scheduling.

STEP 1 / Open ChatGPT & connect / 5–15 min
chatgpt.com → Work → left-rail Plugins icon → Customize → Plugins
1. Open chatgpt.com and sign in. Select Work at the top; look for Work with ChatGPT in the message box. Click the loop-shaped Plugins icon in the far-left rail. The Customize sidebar opens; choose Plugins there. Keep this guide in a second tab.
2. Search Gmail, then choose Gmail by OpenAI. For Microsoft mail, search Outlook Email by OpenAI. Open its details.
3. Choose Install or Connect if offered. If already installed, use Manage to inspect the connected account; Try in chat opens a conversation.
4. In the provider window, check the account address and read the requested permissions before you approve. Only connect an account your business permits. Return to ChatGPT.
DONE WHEN: You can identify the connected account. A plugin being installed alone does not prove inbox access.
IF BLOCKED: No Work toggle or Plugins entry? Confirm your signed-in account and workspace. If unavailable, watch the presenter and save the prompt; your setup is pending. Do not spend more than a minute troubleshooting during the session.

STEP 2 / Prove it can read the right inbox / 15–20 min
Work conversation → select Gmail in Plugins → verify one known email
1. In ChatGPT, select Work and your email plugin. On clearroadlabs.com/prompts, open Step 2 and copy Verify one known message. Replace the account, subject, sender and date before sending in your Work chat.
2. If a consent or tool-approval screen appears, check the account and requested read action. Continue only when correct. Already authorized? You may go directly to the result.
3. Privately compare the returned sender, subject, date and source with your inbox. If you cannot recall an exact subject, use the three-recent-emails alternative, then independently check one.
4. Wrong account or unavailable source? Correct the connection before continuing. Never treat the fictional projection as verification of your own inbox.
DONE WHEN: The returned email matches a message you independently recognize, from the intended account.
IF BLOCKED: If the known email cannot be verified, watch the demo and record the blocker. Resume here later; a fictional result does not verify your mailbox.

STEP 3 / Make one brief worth receiving / 20–30 min
Clear Road Labs website → Step 3 → Copy prompt → same ChatGPT Work chat
1. Switch to clearroadlabs.com/prompts#step-3. Keep Your inbox selected. Choose Full brief, or Short starter if you want a simpler first result. Click Copy prompt.
2. Switch back to the same ChatGPT Work chat. Paste, replace BUSINESS, email tool, ACCOUNT EMAIL and TIME ZONE. For Full brief, also edit or remove the priorities line. Then send.
3. Expect a dated brief with up to three priorities, source links or IDs, and a reply draft when needed. Open two source messages privately: check the newest update and actual deadlines.
4. Save the complete edited instructions that produced your good result. Step 4 must use that exact version, including any corrections. The website does not automatically receive your ChatGPT edits.
DONE WHEN: You have a dated brief, traceable priorities, visible unknowns and a useful draft—and a saved copy of the instructions that produced it.
IF BLOCKED: No relevant mail today is a valid result if access and the searched window are verified. If access fails, save your edited prompt and finish later; do not schedule an unverified inbox.

STEP 4 / Schedule your tested brief / 30–40 min
Website Step 4 → paste tested instructions → copy request → same Work chat
1. Save your complete edited Step 3 instructions. On the website, go to Step 4 and paste those instructions into the box. Choose no new inbox or prompt version here.
2. Copy Schedule my tested brief. Return to the SAME Work chat and paste. Before sending, change the task name, 8:00 AM time and America/Chicago zone if needed. Send once.
3. Wait for a saved task card. Open it and verify the instructions contain your exact account. Check Daily, time, Advanced → Time zone and Same chat for every run.
4. Find that task under Scheduled → Active. Check the next run and that Pause is available. If any time disagrees, reopen Edit and resolve it. Keep only one intended daily job.
DONE WHEN: A saved active task appears in Scheduled with the intended daily time and time zone. A copied prompt or screenshot does not count.
IF BLOCKED: If Scheduled is unavailable for your plan/workspace, watch the demonstration and save the full prompt. Mark your status “not scheduled”; use the manual brief until access is available.

STEP 5 / Choose how you hear about it / 40–45 min
Profile menu → Settings → Notifications → Tasks
1. Open your profile menu, Settings, Notifications. Find Tasks and open its channel menu. Choose Push, Email, or both if available.
2. For app notifications, sign into the same ChatGPT account on your phone and allow ChatGPT notifications in the phone’s system settings.
3. Task emails can include generated content plus a View message link. Check the first delivered email to see how much is included; do not assume every account or long brief has the same format.
4. The connected inbox supplies the source messages; notification delivery belongs to your ChatGPT account. Check the actual destination on the first notification.
DONE WHEN: The intended task notification channels are selected. Delivery is still unverified until a real task update arrives and opens the right result.
IF BLOCKED: No push? Check the same account, OS permission and Focus/Do Not Disturb. No email? Check Tasks → Email and spam. You can always open Scheduled to inspect the run.

STEP 6 / Test it, then leave it running / 45–50 min
Scheduled → task’s ••• menu → Run now → inspect Work result
1. In Scheduled, find your saved Work task. Open its ••• menu and choose Run now. Wait for the final response, then confirm your exact account and time window, then open two real source messages to verify the facts. Presenter-only demos should retain their fictional label.
2. Confirm the task is still active and the next daily time is correct. Do not make a second schedule just because the first run is taking time.
3. Check your selected app/email notification and open it. A manual test may not exercise every delivery path: check again after the first timed run before calling delivery verified.
4. For a practice-only job, pause it or set an end date after the workshop. For a real brief, review the first few mornings and refine its saved instructions.
DONE WHEN: Record four results: real inbox verified; schedule saved; run completed against that inbox; notification received. If any is missing, write exactly what remains unverified.
IF BLOCKED: If the final response cannot load, confirm that the task was created from a Work chat. Pause a failing duplicate before replacing it. At 50 minutes, stop individual troubleshooting; save the remaining issue and use the prepared example.

Ask attendees to record: exact inbox account, known message verified yes/no, daily time, time zone, task link, schedule saved yes/no, real inbox run completed yes/no, notification received yes/no. If anything is unverified, write the next action. Pause or end fictional practice jobs. Keep real jobs active and review the first few mornings. Never describe a blocked or unsaved job as automated.

Clear Road Labs workshop simulation. Clear Road Labs and Damon are real; all email text, counterparties, dates, amounts and project history below are invented for teaching. These are not messages retrieved from a mailbox. Fictional amounts are not Clear Road Labs pricing.

PERMISSION SCREENS
Connection consent: you may see Connect Gmail, then Google or Microsoft account selection and requested access. Check the exact account and permissions before continuing.
First-use approval: after sending the verification prompt, ChatGPT may ask to use the email tool. Review the named account and requested read action. Approve only if these match your intent; cancel if they do not.
No prompt? An existing connection or permission may already cover the read. Continue by checking the returned source; absence of a popup is not evidence of failure.
An unattended brief needs permitted reads when you are away. If it waits for approval, review Plugins → Manage → Permissions within your workspace policy. Read-only access is sufficient for this exercise; do not enable all actions just to get past a blocker.

SAVED TASK CHECKS
WHAT: the complete instructions you tested, with your exact account; sources refreshed on every run. Damon's example instead repeats labeled fictional emails.
WHEN: Repeat = Daily, your chosen time, Advanced → Time zone. The example is 8:00 AM, America/Chicago (Central Time). Check the next run as well; resolve conflicting times before calling it saved.
WHERE: same tested Work chat for every run. The result lives in ChatGPT; Tasks notifications choose how you hear about it.
STATUS: active, with Pause available. One intended daily task. A screenshot or a sentence promising to schedule is not a saved job.

NEXT PROJECTS (OPTIONAL)
Meeting prep — Email + Calendar: Tomorrow's meetings, relevant email context, and questions to prepare.
Client follow-up — Email + Drive: Compare a client thread with the agreed project document; draft the next reply.
Weekly review — Calendar + Drive: Compare the week's meetings with your priorities document and propose next steps.
