Working session · Mario Testa & Romansas · 24 September 2026

An assistant that knows how you work.

Not an email tool. A business assistant that helps with information, priorities, communication and decisions across the company, built one safe step at a time.

Demos run on Jason's own data. No Milano Bro data is connected. No decision needed today

The opportunity

A chatbot answers. An agent works for you.

An agent has two things a chatbot does not: context about you and your work, and tools such as mail and calendar, used only with your approval. Context is the important part. Thin context gives generic answers. Deep, trusted context gives judgment that feels like someone who lives inside the company.

Click a graphic to open it.

The proposal

A secure context layer for Mario, with an assistant on top.

A private memory of Mario's priorities, people, decisions and know-how, held in a cloud account Milano Bro controls, with narrow Microsoft 365 access that IT grants and can revoke. On top of it, a chief-of-staff assistant that briefs what matters, thinks through decisions with company context, drafts the work, and acts only with clear approval.

Phase 1

Email

Morning brief, triage, drafted replies.

IT review before start
Phase 2

Calendar & meetings

Meeting prep, actions from transcripts, follow-ups tracked.

IT review before start
Phase 3

Teams

A full picture of what's moving across the company.

IT review before start
Later

Voice & more

Talk to it anywhere. Deeper operating know-how.

IT review before start
Scope, as Mario set it. No other employees' mailboxes. No SharePoint, OneDrive or broad document stores for now. Microsoft 365 access limited to what the pilot needs. Which cloud hosts the memory is IT's decision.

Where we are

A clear view of what exists today.

So each item can be checked on its own. "Working" is used only where it runs today.

Working

Jason's assistant

Runs daily on Jason's own data. Chat, voice, meeting → actions, approval gate, memory with sources.

Needs setup

Daily operations

Scheduled briefs, monitoring, backups. Built, needs configuring for a new user.

Not built yet

Milano Bro version

Private memory in a company-controlled cloud, with narrow Microsoft 365 access. Not built, connected, or security-reviewed.

Future phases

Mario's full assistant

Calendar, meetings, Teams and voice, added one phase at a time.

Proven today

Jason runs his own businesses this way, every day.

The same pattern is already working on Jason's own data and machines: two ways in (chat and voice), a chief of staff that routes work and holds the approval gate, six live desks, and one shared memory. This is what you'll see in the demos.

The live agent org chart

Hermes (chat) and Grok Bot (voice) are equal front doors into one context layer: an Obsidian vault as the human-readable truth, GBrain as the search over it. Agents read there; none keeps a second brain.

Open the org chartThe context layer ↗
Jasonasks · approves · decides
Hermeschat
Grok Botvoice
Chief of staffroutes work · approval gate
Mimi's Market
MG Consulting
Work Different AI
Ledger
Health coach
Homeopathy
Context layerObsidian vault + GBrain
Executive awareness
"What should I focus on today?"

A short brief on what deserves attention, and why.

For Mario: one morning brief across email, calendar and Teams.
Strategic support
"Help me think this through."

Weighs a real decision using what it already knows, plus research, with sources.

For Mario: a thinking partner who knows the company's history.
Execution with control
"Take care of this for me."

Does the work, then stops at the approval gate before anything is sent.

For Mario: replies, meeting prep and follow-ups, ready to approve.

Built for IT control

Power for Mario. Control for IT.

IT decides how far and how fast it goes. Every step can be reviewed and reversed.

1

Mario's data only

No other mailboxes. No SharePoint or OneDrive for now.

2

Access inside your tenant

A single app registered in Milano Bro's Microsoft 365. IT grants, audits and revokes it.

3

Each phase approved

Nothing new is connected until Romansas has reviewed it.

4

Company-controlled home

The memory lives where IT chooses. Which cloud is IT's decision.

5

Nothing acts on its own

Sending, booking and changes all wait for Mario's approval.

6

Support during the pilot

Jason supports the pilot. Long-term support is agreed together afterwards.

Copilot, looked at together. Copilot is a reasonable default: mail, calendar, Teams and meetings already live there. The narrower question is whether it covers this one personal pilot: multilingual work at the level Mario works in day to day, the degree of personalisation Mario has described, and where a separate, evolving context layer adds something Copilot does not. To follow in writing: a data map (what is stored, what is only looked up, how it is deleted) and a side-by-side comparison with Copilot.

Next steps

What we'd like to leave with today.

From Mario

  • Does this match the assistant you have in mind?
  • The top three tasks you'd most like help with

From Romansas

  • The evidence and controls IT needs to see
  • The order to work through them

From Jason

  • Written data map
  • Copilot comparison
  • A follow-up date