He sits between you and your inbox, your calendar, your SharePoint, and your Teams chats, and he does the work a real Chief of Staff would do.
Triaging. Summarizing. Drafting. Prepping. Tracking. Reminding. So you can spend your time on the work that actually requires you.
Named after Winston from John Wick, the man who ran the Continental. Refined, professional, knows everyone, pulls every string. Plays by the rules until the rules need breaking. That's the personality brief.
ChatGPT and Gemini are chatbots: you ask, they answer, they forget. Every conversation starts from zero. Winston is built on Claude Code , a full work environment that lives inside your tools and remembers what matters.
He lives inside your computer. Reads your files, opens your apps, uses your browser. Plugs into the tools you already work in: Outlook, Calendar, SharePoint, Teams, Drive, Slack.
A chatbot explains. Winston does. You tell him what you want. He finds a way and hands back finished work: drafted, summarized, scheduled. Not a list of instructions for you to follow.
He runs on a schedule, in the background, while you're in a meeting or with your family. The work doesn't stop when you stop. Morning briefing on your desk before you open your laptop.
ChatGPT talks to you. Winston works for you.
The job description of a real Chief of Staff, translated into software that actually does the work.
Sorts URGENT / IMPORTANT / FYI. Flags dollar amounts and deadlines.
Tells you what to prep, what conflicts, where the day is bending. One screen, one priority.
You approve. You send. He never sends without you. Ever.
Pulls history from Outlook, Teams, SharePoint. Hands you a one-pager. Walk in ready.
Every commitment you make goes into his log. He'll tell you what's overdue, before the other person has to ask.
The threads you dropped. The replies still waiting. The senders nobody answered for you.
Silent accounts. Stalled projects. Drifting deadlines. Before they become a fire.
What got done. What didn't. Tomorrow's #1. Sunday: a weekly report, wins, misses, patterns.
He gets smarter every day. Remembers what worked. Remembers when you corrected him.
A good Chief of Staff knows the boundaries of the role. So does Winston.
He's connected to your real tools, with memory that persists across days, weeks, quarters. ChatGPT forgets. Winston doesn't.
He drafts. You approve. He never auto-sends an email or auto-creates a calendar event. The keyboard stays yours.
Winston is work-only by design. Your weekend plans aren't his concern. Neither are your DoorDash orders.
He'll tell you when you're avoiding something. He'll surface what you'd rather ignore. You still have to act.
Every connector is read-first. Your CMI data never routes through third parties. Revoke any access in one click.
Core · Required
Optional · If your role uses them
Type a slash command. Winston goes to work. Phase 4 covers each skill, what it does, when to reach for it.
| # | Command | What it does |
|---|---|---|
| 01 | /morning-briefing | Outlook + calendar + open promises + your #1 priority for today |
| 02 | /evening-summary | End-of-day wrap: done, not done, tomorrow's plan |
| 03 | /draft-reply [name] | Draft an Outlook reply in your voice, you approve, you send |
| 04 | /prep-meeting [name] | Meeting brief pulling Outlook, Calendar, SharePoint, Teams |
| 05 | /tasks | View, create, update tasks, without leaving the conversation |
| 06 | /accountability | Tracks promises you've made; flags overdue commitments |
| 07 | /forgotten-emails | Surfaces emails you forgot + threads still waiting on a reply |
| 08 | /block-time [task] | Blocks Outlook calendar time for postponed work |
| 09 | /risks | Identifies business risks before they become problems |
| 10 | /weekly-report | Sunday wrap: wins, misses, numbers, priorities |
| 11 | /learn | Updates Winston's memory, captures patterns, gets smarter |
| 12 | /ask-jamie | Stuck? Winston checks the FAQ, then routes to Jamie or IT |
| 13 | /learn-me-work | Day-2 onboarding (work-scoped). Winston learns your role |
| 14 | /role-one-pager | Day-2 wow moment: role summary + voice-test email |
Self-paced. Each phase builds on the last. Stuck? Drop a question in the Teams support channel, someone will answer in minutes.
Get your environment ready, verify access, and meet Winston for the first time.
Install Claude Code locally, configure Winston's persona, run your first command.
Wire up Outlook, SharePoint, Teams. Optional: Google, Asana, Notion.
A walkthrough of every skill that ships in the box. What each one does, when to reach for it.
Power-user patterns. Future skills. How to give feedback that ships.
Winston connects to Microsoft 365 through the official Microsoft MCP, the same authenticated channel CMI already uses every day. Your existing MFA controls every login. Files and data flow through CMI's Barracuda email security layer and the CMI Share Drive cloud, the systems you're already protected by.
Nothing routes through third-party tools. No data leaves the CMI environment. No personal accounts. No outside vendors stitched into your inbox. What's already secure stays secure.
New skills. New connectors. New capabilities, shipped continuously. Today's version is the foundation. CMI's vision is for every employee to have the advantage of an LLM at work, with data security paramount. We're starting here.
Ready when you are. Use your @cmsales.com email to request access.