Skippy in every place, in one shape.

One assistant, one interface, three ways of showing up: a full screen, a corner widget, and — on the desktop — a small window you park wherever you like. This is what it would take, what is genuinely possible, and the four things only you can decide.

The short version

Right now there are two different Skippys on screen: the app you just picked the look for, and a separate purple "Ask Skippy" pill inside the family app that was built earlier and looks nothing like it. They don't share code, a look, or a brain path.

The proposal is one component, built once, dropped in three places. It has exactly two states — a small pill you tap, and an expanded panel — plus the full screen you already have. Same thing everywhere; only the name and the personality change depending on who is signed in.

1 · Where it shows up

Place	What you see	Who it is
Skippy app (the one you use now)	The full screen — Talk, Dispatch, Status	Skippy
Family app every page	Corner pill → expands to the panel. Full screen on request.	Skippy for you, Gracie for Chantelle
Business hub	Same pill, same panel	Nico
Your desktop	A small window you drag anywhere	Skippy
Kids' app	Same pill	Wall-E / Eeva

The personality change is not cosmetic and it is not decided by the widget. Who you are is settled server-side before a single word is generated — that is what keeps Chantelle's private material away from you and yours away from her. The widget only asks; it never decides.

The two states, everywhere

Collapsed — a pill in the bottom-right. Carries a count when something needs you, so it doubles as the thing that stops dispatches going dark.
Expanded — a panel about the size of a phone screen, sitting over the page. Talk, Dispatch and Status all inside it. Tapping away closes it; it remembers where you were.
Full screen — one more tap. Identical content, more room.

2 · The desktop widget — what is actually possible

You asked whether you can have the app in one window and the widget floating somewhere else. Short answer: yes, and there are three levels of "yes" that cost very different amounts. One thing genuinely is not possible, and it is worth naming first.

Not possible

A widget sitting on the desktop wallpaper itself, among your icons. Nothing made of web pages can live there. Apple's own desktop widgets can, but they are read-only snapshots that refresh every few minutes — they cannot hold a conversation, run a microphone, or show a live list. So that specific picture is out, whatever we build.

Level 1 · works today, no new code

Install Skippy as an app, and it gets its own window with no browser bars. Resize it small, park it on a second monitor or off to one side, and leave it there. The full app can be open in another window at the same time — they're independent.

The catch: it does not stay on top. Click another window and Skippy goes behind it. For a second monitor that doesn't matter at all. On one screen it does.

Level 2 · small build · needs one check from you

A genuinely floating, always-on-top little window — draggable anywhere, resizable, sits above everything including full-screen apps. Chrome has a built-in feature for exactly this, and I confirmed the capability is present on your Mac.

What I could not confirm, and won't pretend otherwise: I tried to open one to prove it, and Claude's built-in browser refused — it can't create real windows. Your actual Chrome almost certainly can, but "almost certainly" is not "I checked". Ten seconds settles it — see the box at the bottom.

The catch: Chrome and Edge only. Safari does not have it. And it lives as long as the tab that opened it — close the tab, the widget goes.

Level 3 · about a day's work · guaranteed

A real little Mac app that is nothing but the widget. Always on top, drag it anywhere, remembers exactly where you left it, survives restarts, no browser involved, works regardless of what Apple or Google change. It loads the same web page inside, so there is no second version of Skippy to maintain — it is a frame around the thing that already exists.

The catch: it is a real app, so it needs building, signing and updating. It is the only option that is unconditionally yours.

My recommendation

Do Level 1 today — it costs nothing and you can be using it in a minute. Check Level 2 in ten seconds. If it works, that is very likely all you need and it's a couple of hours of work. Only go to Level 3 if you find yourself wanting the widget there permanently, across restarts, without a browser open. Don't build the app until the cheap version has annoyed you.

3 · What gets built, in order

Pull the interface out into one shared piece. Today it lives only in the Skippy app. It becomes one component that any of the apps can drop in.
Replace the family app's purple pill with it. This is where you'll feel it first — same Skippy on every page you already use, instead of the older one that looks different and answers differently.
Add the collapsed and expanded states. The full screen already exists.
Wire the count onto the pill so the corner tells you when something is waiting, from anywhere in any app.
Then the desktop widget, at whichever level you picked.
Business hub and the kids' apps last — same component, different name on it, no new work beyond dropping it in.

4 · How we know it's right

The same thing looks and behaves the same in all four apps — one piece of code, not four.
Chantelle opens the family app and gets Gracie, in the same shape, and proved in both directions: nothing of yours reaches her, nothing of hers reaches you.
The corner pill shows a waiting count from any page, and tapping it lands you in the right place.
Voice still interrupts properly when you talk over it. That is the thing most at risk when a working interface gets moved, so it gets checked every time.
It works one-handed, in sun, on your phone. Same test as before.

5 · What needs you

Decision 1 — the desktop widget

Which level? My recommendation: Level 1 now, then check Level 2, and leave Level 3 until the cheap one frustrates you.

Decision 2 — does the old "Ask Skippy" pill go away?

The family app's purple pill answers through a different route than the app you just picked. I'd replace it outright so there is only one Skippy. The alternative is running both for a while, which means two things to fix whenever something is wrong. My recommendation: replace it.

Decision 3 — does the widget carry Dispatch and Status, or just Talk?

The corner panel is small. It can hold all three, or it can hold Talk with a count that sends you to the full screen for the other two. My recommendation: all three — the whole point of Dispatch is that you see it without going looking.

Decision 4 — the kids' apps, now or later?

Wall-E and Eeva could get the same widget in the same pass, or wait. My recommendation: later — the kids barely opened the last two weeks of lessons, so more surface there isn't the shortage.

The ten-second check

This settles whether the free floating widget works on your Mac.

Open Chrome (not Safari, not the Claude browser).
Go to any YouTube video and start playing it.
Click into another window, or another tab.
If a small video window pops out and floats on top of everything — it works. That is the same feature the widget would use.

Tell me yes or no and I'll spec the widget against the answer instead of guessing.