Onboarding Guide for a Scout-based AI Executive Assistant

ℹ️ This article is a product education resource that reorganizes and summarizes the Scout EA package distributed by the Scout team (onboarding guide + skills + automations). Actual screens and features may change as the product is updated.

1. Overview — Hire Scout as “my assistant”

Scout Desktop is closer to a tireless chief of staff. Decisions are still made by a person, while Scout prepares options, writes drafts, and keeps the calendar tidy so important items are not missed. There are two main ways to work with Scout.

The point where these two methods come together into a single system is the folder system (Section 6).

2. Who this is for

The Scout EA package provides packs for three usage scenarios.

Standard vs CVP — The Standard pack fits any manager or assistant. The CVP pack additionally includes three executive-only skills needed for executive support: executive shuttle, executive travel booking, and executive support.

3. What you get — A toolkit for executive support

The Scout EA package provides a feature set optimized for executive support.

• ✉️ Inbox triage — Priority tiers, automatic classification, digests, and reply drafts written in your (or your principal’s) voice.
• 📅 Scheduling — Finds attendees (and their assistants), checks availability, and proposes candidate times in a courteous tone.
• 🏢 Room booking — Knows and books preferred rooms, including rooms that can only be booked by forwarding an invitation.
• ✅ Approvals — Batch-processes expenses, POs, access requests, and time off each day under risk gating.
• 🧾 Expense reports — Creates review-ready expense reports from receipts. A human submits them.
• ✈️ Travel & logistics — Travel, executive shuttles, restaurant reservations, and meeting materials.
• 🗓️ Daily briefings — Morning meeting briefings, weekly preparation resets, and 1:1 acceptance monitoring.
• 🧹 Calendar hygiene — Automatic event classification, focus-time protection, and cleanup of tentative holds.
• 📄 Doc reviews — Surfaces documents shared for review so they are not missed.

4. How it works — Skills when needed, automations on schedule

Scout operates on two axes: Skills and Automations.

5. Action folder system — Turning Outlook into Scout’s work queue

Create an assistant folder under your inbox (for example, Inbox / 🗂️ Assistant) and add the subfolders below. Drag any email into one of them, and Scout picks it up on the next run.

Draft-first example — Reply · Principal

1. Drag an email that needs a reply from the principal (first person, principal’s voice).
2. Scout creates a thread-preserving draft as if the principal wrote it directly — no assistant signature.
3. It tags the original with Scout: Drafted and leaves it in the folder until it is sent.
4. A human reviews and sends it in Outlook → Scout moves it to Done.

6. Drag-to-act loop

One simple habit runs the whole system.

1. The user classifies — Drag email into the folder that matches the desired task: reply, summarize, approve, or schedule.
2. Scout runs — On schedule (up to every 30 minutes), it opens each folder and runs the matching skill.
3. Scout drafts or processes — It creates drafts, books rooms, completes approvals, and tags status such as Scout: Drafted.
4. The user reviews and sends — Review the draft in Outlook and send it. When the loop closes, Scout moves the original to Done.

7. Email & replies — Classify, draft, and clean up in the right voice

In addition: priority tiers, automatic classification, deletion patterns, newsletter digests, thread-preserving drafts, and loop closure.

8. Meetings & rooms — From “finding a time” to “a scheduled meeting with a room”

• 📅 Schedule meetings — Resolves attendees to real addresses, finds their assistants when available, checks availability, and proposes 3–5 courteous candidate times.
• 🟢 Learn accept / 🔴 learn decline — Drag invitations into Learn · Accept or Learn · Decline to learn the principal’s patterns. It learns which invitations to process automatically, and keeps declines generic and private.
• 🏢 Book rooms — Knows and books preferred rooms, including rooms that open only when an invitation is forwarded. Selects based on attendee count.
• 🔁 Scheduling processing — Scans email and Teams for replies like “How about this time,” checks the calendar, and converts them into invitations or tentative holds.

9. Approvals & expenses — Handling administrative work with guardrails

Approve folder — Drag approval email (expenses, POs, access, time off, credential renewals) into Approve. Once a day, Scout batch-organizes completed items and processes up to five live approvals with risk gating. Standard low-risk items are approved automatically, while high-risk, ambiguous, or over-threshold items pause and ask for confirmation.

Expense reports — Point Scout to receipts, and it creates a complete, review-ready expense report (travel, recurring monthly subscriptions, hotel itemization, corporate card matching). It stops at a draft, and submission is always done by a human.

When Scout pauses

10. Automations — Ten scheduled runs

Start with read-only automations, then turn on the rest one by one as trust builds.

11. Installation — Let Scout handle it and answer a few questions

The easiest path is to hand the package to Scout and answer the interview. You do not need to edit anything by hand. Download the pack, open Scout Desktop, and paste the prompt below. Scout reads the built-in setup runbook, interviews you, and then performs the full installation: filling templates, creating Outlook folders, installing skills, and scheduling automations. It asks for confirmation before each change.

Prompt to give Scout (example)

I want to set up my Scout-based assistant using the Scout EA package. Open the package's setup runbook
(SCOUT-SETUP.md, inside the Scout EA package folder I received) and follow it from beginning to end.
Interview me for the required information a little at a time. Then execute the steps in order:
fill in the templates, create my Outlook action folders, install the skills, and create the automations
(enable only the read-only ones first). For any task that makes a change, such as creating folders,
installing files, or sending messages, ask me for confirmation before running it. Do not guess names,
email addresses, or meeting rooms; ask me. Keep email draft-first (either in the principal's name or
Scout's name). When you are done, give me a summary and one first test.

The interview works like this

1. Scout reads the runbook — It opens SCOUT-SETUP.md and CONFIG.md to understand what to ask and what to do.
2. Interview — It asks about the principal, assistant identity, leadership and organization, priority contacts, projects, rooms, and logistics in a few small groups of questions. Unused items are skipped.
3. Runbook execution — It fills every {{placeholder}}, creates Outlook folders, installs skills, and creates automations. It asks for user confirmation for each change.
4. Start operations — It turns on read-only briefings first, then provides a summary and the first test.

12. Package contents

The guide includes a fully templated package: 29 skills, 10 automations, and setup documents. All person-specific details are represented as {{PLACEHOLDER}} so Scout can fill them during installation.

• Standard pack — Suitable for all managers and assistants.
• CVP pack — Adds three executive-tier skills, including executive shuttle, executive travel, and executive support (for supporting CVPs/VPs).

Try it yourself — Download the general-purpose starter template

Included contents — Four documents (README, SETUP-GUIDE, CONFIG, CHANGELOG) · five skills (inbox-triage, reply-draft, schedule-meeting, book-room, daily-briefing) · three automation prompts (daily briefing, action folder processing, weekly focus time).

⬇️ Download the starter template (.zip)

After downloading it, you can say this to Scout Desktop: “Set up my assistant using this starter template. Open SETUP-GUIDE.md, interview me to fill in {{placeholder}}, then create the Outlook action folders, install the skills, and create the automations. Make sure you ask for confirmation before making any changes.”

⚠️ This starter template is an educational and demo example. Check your organization’s policies and data handling rules before using it.

13. Trust & safety

Scout is designed to protect the principal’s privacy and keep the user in control.

• 🖐️ Sending is approved by a human — Folder-based email is draft-only. Nothing goes out until you review it and click Send.
• 🔒 Private by default — Declines stay generic, and personal or travel information never leaks into messages that others see.
• ⏸️ Pauses on risk — Approvals stop on high-value, destructive, or ambiguous items and ask for user judgment.
• 🧭 Stays quiet — Automations notify you only when something actually needs attention — no “nothing to do” noise.

14. What’s new

The Scout EA package is continuously updated (latest example: v1.10.x, 2026‑07). Examples of recent changes:

• Persona selector revamped — Defaults to “I want my own assistant” (the general path).
• Folder naming cleanup — Onboarding folder explorer and mail cards now consistently use Reply · Principal / Reply · Assistant.
• Tiered installation packs (Standard vs CVP) — Skills now have tier: front matter so they can be separated by pack.
• why-did-i-get-this-email skill — Explains why the principal received a specific email.
• Pluggable personal calendar backend — Makes the personal calendar source replaceable.