Client Kickoff — a Microsoft 365 Copilot Cowork custom skill

Agent Academy Hackathon 2026 · Track: 🤝 Cowork Collective

Turn a signed proposal or engagement deck into a ready-to-run client kickoff meeting, agenda, Word document, and a finance intake email in one approval-gated Copilot Cowork conversation.

You hand Cowork the proposal. It analyzes it, extracts the deliverables, tasks, and the team, resolves those people against your tenant, then (after you confirm) schedules the kickoff, builds a ime-boxed agenda into the invite and a Word doc, and sends a structured intake email to Finance. Nothing is sent or created without your explicit per-item approval, and nothing is fabricated.

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The problem

At a consultancy, every signed proposal kicks off the same manual scramble before any billable work can begin. Someone has to re-read the proposal, pull out the deliverables, tasks, and the team, find a kickoff slot that works for everyone, write an agenda, and hand the project details to Finance so the engagement can be created in the finance system. It's repetitive, spread across Outlook, Teams, Word, and email, and easy to delay or get wrong yet the kickoff is the client's first impression right after they sign. Days can slip between "deal closed" and the project actually being set up and on the calendar.

Who benefits. Consultants, project leads, and delivery managers stop doing the post-signature admin scramble — kickoff prep is assembled for them, with a human approval at every step. The client gets a fast, professional kickoff with a clear agenda within days of signing. Finance and operations receive a complete, structured intake email and can create the project without chasing anyone for missing details. The consultancy as a whole gets a shorter, more reliable path from signature to a running project.

What success looks like. A signed proposal goes from a PowerPoint to a scheduled kickoff, an agenda, a Word doc, and a finance intake email in minutes instead of days. Every person, date, and deliverable is extracted from the deck or resolved against the directory — unknowns are flagged, never invented. The kickoff lands on the calendar within the next five business days with the right attendees, Finance can stand up the project straight from the intake email, and the whole flow runs identically for the next engagement.

How it works

The skill runs in two gated phases. Phase 2 only starts after you confirm the attendees.

Phase 1 — Analyze (read-only)

1. Locates and reads the attached proposal deck (PPTX / PDF / DOCX).
2. Extracts and shows three blocks: project summary (client, goal, scope), deliverables & tasks, and an attendee list with each person resolved against your directory (unresolved people listed separately).
3. If the deck names no people, it asks who the attendees should be; for anyone unresolved, it asks you to confirm their email.
4. Stops. It schedules, drafts, and sends nothing in this phase.

Phase 2 — Execute (after you confirm attendees)

Four outputs, shown together in one approval batch, each executed only on explicit per-item approval:

1. Kickoff meeting — soonest 50-minute slot in the next 5 business days where all confirmed attendees are free, created as a Teams online meeting.
2. Agenda — built from the extracted deliverables/tasks, time-boxed to 50 minutes (welcome & intros → goals & scope → deliverables → ways of working → timeline & milestones → risks/dependencies → next steps & owners).
3. Word document — the agenda saved to OneDrive.
4. Intake email — sent to the Finance intake address with a structured new-assignment table, so the project can be created in the finance system.

Guardrails

• Never fabricates people, dates, deliverables, rates, or emails extracts from the deck or resolves with tools; unknowns get a clear placeholder.
• Hard stop between phases; per-item approval gates in Phase 2 (no silent sends).
• All dates resolved to explicit calendar dates in the user's local time zone.

Technologies

The solution itself

• A custom Cowork skill (client-kickoff, defined in SKILL.md) a reusable, two-phase, approval-gated workflow invoked by name.

Microsoft 365 tools the skill orchestrates

• Document readers (PPTX / PDF / DOCX) — to read the proposal deck.
• People / directory resolution (SearchPeople → GetUserDetails, via Microsoft Graph / Entra ID) — to match named people to real accounts.
• Outlook Calendar (FindMeetingTimes, CreateEvent with is_online_meeting=true) — soonest common slot, created as a Teams meeting.
• Microsoft Word + OneDrive — the agenda document.
• Outlook mail — the structured Finance intake email.
• AskUserQuestion — the gated questions (confirm attendees, approvals).

Architecture / data flow

Proposal deck (PPTX/PDF/DOCX)
        │  attach in Cowork
        ▼
[ Cowork + ]  ── loads ──>  client-kickoff/SKILL.md
        │
   Phase 1  ── document readers ──> project summary + deliverables/tasks
            ── SearchPeople/GetUserDetails ──> attendee list (resolved/unresolved)
            ── AskUserQuestion ──> confirm attendees / emails
        │  (gate: user confirms)
   Phase 2  ── FindMeetingTimes + CreateEvent ──> Teams kickoff meeting
            ── agenda generation ──> invite body + Word doc (OneDrive)
            ── Outlook mail ──> Finance intake email
        │  (per-item approval on each)
        ▼
   Scheduled kickoff · agenda · Word doc · intake email

Getting started

Prerequisites

• Microsoft 365 Copilot license with Copilot Cowork enabled
• Frontier enrollment for both your user account and your tenant
• Anthropic models enabled on the tenant (Microsoft 365 admin center)
• Clone the repo

Step 1 — Edit the skill before uploading

Open SKILL.md and change the Finance intake address to your own.

In Phase 2, step 4 you'll find:

Send the intake email to **info@contoso.com** ...

Replace info@contoso.com with the address that should receive new-assignment intakes at your organization (e.g. your finance/PMO mailbox). This is the only value you must change. Everything else (project name, attendees, dates) is read from the deck or asked for at runtime.

Step 2 — Upload the skill to OneDrive

Cowork discovers custom skills stored in your OneDrive. Create this folder structure and place the (edited) SKILL.md inside it (or move the client-kickoff from this repo to OneDrive/Documents/Cowork/skills/):

OneDrive
└── Documents
    └── Cowork
        └── skills
            └── client-kickoff
                └── SKILL.md

Each skill lives in its own subfolder; Cowork auto-discovers it at the start of your next conversation. (You can have up to 20 custom skills; each SKILL.md can be up to 1 MB.)

Step 3 — Run it

1. Open Microsoft 365 Copilot and select Cowork (Frontier).
2. Attach your proposal deck before sending your first message.
3. Ask Cowork to run the client kickoff skill, for example:

   Run the client kickoff skill on the attached proposal.

4. Review the Phase 1 analysis, confirm/adjust the attendees, then approve each Phase 2 output (meeting, agenda, Word doc, intake email) in turn.

Demo tip: attendees must be real people in your tenant or the invites will bounce — use yourself and a couple of colleagues when recording the demo.

Demo

A walkthrough video (≤ 5 min) is included with the submission. It shows the skill being invoked in Cowork, the Phase 1 analysis (including a client contact that isn't in the tenant being flagged and excluded), and Phase 2 producing the invite, agenda, Word doc, and intake email as approved tabs.

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Screenshots

1. Invoking the skill with the proposal attached

2. Phase 1 — analysis (summary, deliverables, attendee list) and first validation question

4. Phase 2 — approval batch (invite, agenda, Word doc, intake email)

4. Phase 2 — approval email)

5. Outputs created (kickoff meeting, agenda doc, intake email)

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What worked well using the Agent Academy curriculum

• Badge Check taught us the custom-skill mechanics — the SKILL.md structure (YAML name/description plus markdown instructions) and OneDrive auto-discovery — which is exactly how this skill is built.
• The Compliance Packet showed us grounded multi-document generation and the "only source of truth, don't fabricate" pattern, which became our extract-only-from-the-deck rule and approval-gated outputs.
• Out of Office Vacation Handoff gave us the discovery-first pattern and recurring scheduled automation, which shaped our Phase 1 / Phase 2 split and the optional weekly follow-up.

The three Cowork Collective missions doubled as our build plan, each contributing a piece we reused directly. Together they covered how to author a skill, how to generate grounded documents safely, and how to structure discovery and automation. The through-line across all three was Cowork's approve-before-acting model, which is the safety backbone of this skill too.