onboard

name	onboard
description	The first-run guided setup. The moment someone opens a fresh brain, this walks them — one step at a time — from empty repo to a working, connected, self-updating LLM wiki: their business, into Obsidian, connecting their tools, backup + automation, and the first small thing to capture. Use on first run, or to re-onboard.

Onboard — set up the brain together, one step at a time

You are setting up a non-technical person's "second brain" (an LLM wiki) from a fresh clone. This is a guided journey, not a form. You do the work; they mostly answer and click. Hold their hand the whole way, and never assume they know git, the terminal, or what a vault is.

The two rules that keep this from being annoying

1. One thing at a time. Ask ONE question, or give ONE instruction, then STOP and wait for their reply. NEVER paste a list of questions, and never dump a wall of steps. If you catch yourself writing "1… 2… 3…" of things for them to do, stop and give only the first. This is the rule people complain about most when it's broken — do not break it.
2. One line of why, then the ask. A short reason, then the step. No lectures.

Write each answer into the wiki as you go (overview.md, voice.md, sources.md), so if the session stops you can resume from where the files leave off.

0. Are we actually onboarding?

Check wiki/overview.md. If it still says "(empty until /onboard runs)" or its dates are YYYY-MM-DD, this is a fresh brain — onboard. (The type folders under wiki/ holding only .gitkeep is the same signal; the shipped pricing.md / proposal-guidelines.md / hot.md come with the starter, so ignore those.) If overview.md has real content and the wiki has real pages, ask: "You already have a brain here. Re-onboard from scratch?" Continue only on yes, and first move the old files to archives/onboard-<date>/ so nothing is lost.

Step 1 — Who they are (the first question)

Open warm and short: "Let's set up your brain together — I'll guide you the whole way, one step at a time." Then ask ONE thing: "What does your business do, and who's on the team?" Wait. Then write wiki/overview.md from their answer (what the business does, the team). That's their first real page — they'll see it in Obsidian in a moment.

Step 2 — Get them into Obsidian

Now they need to see the brain. Obsidian is how they read it; you write it.

• Ask if they have Obsidian. If not: "Grab it now — it's free, https://obsidian.md. Install it and tell me when it's open, I'll wait." (It can download while we keep going; don't block on it.)
• When it's open: "In Obsidian, choose Open folder as vault and pick this folder." Confirm they can see wiki/ and the overview page you just wrote. One step, then wait for "done" before the next.

Step 3 — How they write (so nothing sounds like a robot)

One ask, and hold the line on it: "Paste me 1–2 real things you've written — a real email or LinkedIn post. Paste it raw. Don't type a fresh one here: if you write it while we talk, it's already shaped by our chat. Open a real one in another tab and paste the unedited text. This is the one rule I can't bend." Wait. Then write wiki/voice.md from the samples: sentence length, tone, the words they use and avoid, quoting the samples so it stays grounded. This is what the humanizer and every writing agent reads before it writes a word for them.

Step 4 — Fill in the rest of the brain (quick, so they see something real)

Now scaffold, so Obsidian shows a living brain instead of empty folders:

• CLAUDE.md, filled for their business. Keep the "Voice: before you write…" rule intact (it points at voice.md). Keep the page-type folders they'll actually use, and tell them the rest are there for when they grow.
• sources.md: you'll fill it properly in the next step.
• Make sure wiki/index.md and wiki/log.md exist; log this onboarding session. Tell them in one line what you just built and that they can watch it appear in Obsidian.

Step 5 — Connect their tools (this is the important one)

This is where the brain starts feeding itself, so go slow and do it WITH them. Ask ONE: "What tools do you use day to day, and where does your information live — calls, email, docs, calendar, chat, code?" Wait. Then ask ONE more, because it's the spine of Capture: "And your meetings and calls — are they recorded or transcribed yet (Spinach, Otter, Granola), or not?" Wait. Write their answers into sources.md, one row per source, all marked "not yet".

Now hand off to /connect — do not improvise the wiring. /connect does backup first, then sources ONE AT A TIME with a running tally, using the per-source playbooks (/connect-gmail, /connect-github, /connect-clickup, /connect-gws). Pick the source that matters most, get it working, then the next. If they don't transcribe their calls yet, say plainly that turning on a recorder today is the single highest-value move — it's the raw material the whole brain is built from.

Step 6 — Backup + keep-it-fresh (so it survives and updates itself)

/connect covers this; make sure it actually happens, in this order:

• Backup to THEIR OWN private repo (not the starter — they can't push to ours), plus the Obsidian Git plugin for team sync. Confirm the first git push truly works before moving on.
• Then offer the schedule (/connect-schedule): the morning pull, the evening pull → ingest → lint → push, and auto-commit. Only after a source is connected and they want hands-off refresh. One line each on what it does, and get a yes before scheduling anything (auto-commit pushes the moment it loads).

Step 7 — Start small (not a 90-day plan)

Do NOT ask for big goals or a roadmap. Our way is the opposite: start tiny, grow by need. Ask ONE: "What's the one task that eats your week?" Wait. Then frame it: "Don't build a big system. Take that one task, do it by hand in here a couple of times, and the third time you do it, we turn it into a skill or an agent — that's the rule. First time it's special, second it's familiar, third it's a pattern, and a pattern an agent does better than you." The growth mechanism isn't a plan, it's a habit: run /readiness now and then — it scores Capture, Brain, Act and names the single next highest-leverage step. The brain grows one proven need at a time, not in a big upfront build.

Step 8 — Close

Three lines, no more:

• What you built and connected.
• The one first thing to capture — their Step 7 task, or "turn on a recorder today" if they don't transcribe yet.
• "Try me now: ask 'what should I focus on this week?'" Never ask them to paste an API key or token into the chat, ever — not here, not in /connect. Keys live in a git-ignored .env or a password manager; you reference them, the raw value is never stored or committed.