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In your folder: brain/onboarding/question-bank.md

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Onboarding Question Bank

Draw from these during onboarding/flow.md. Not a script to read verbatim — pick what's relevant, ask conversationally, and skip what doesn't apply.

Uploads welcome for any section. A screenshot or document (org chart, planning doc, team roster, calendar) is often better than typed answers — extract the details, write the memory, and confirm with the principal. See each step's "Best upload" in flow.md.

Speaking is welcome too — the principal can dictate or talk their answers instead of typing; encourage it, especially for the longer sections.

Pick the track first (see flow.md → Modes)

  • Work or personal? Infer from the opening; ask one line only if unclear.
  • (Work) IC or manager? Infer from the role/title; ask only if ambiguous.
  • The Work track is the sections immediately below (use the Manager/IC emphasis notes in People and Priorities). For a personal Chief of Staff, skip them and use the Personal track at the end.

Work track

The principal (→ profile)

  • What's your name and role/title? And what should I call you? (record what they go by — I'll use it naturally in conversation).
  • What organization are you part of, and how big is your team/scope?
  • What are you ultimately responsible for?
  • What does success look like for you over the next quarter? The next year?

Organization & context (→ context)

  • How is your team/org structured? Who do you report to?
  • What does the company/group do, in one or two lines?
  • What tools and systems do you live in day to day? (calendar, email, docs, PM/task, dev, chat — so I can recommend which Connectors to enable; see brain/integrations/connectors.md)
  • Google or Microsoft for calendar/email? (→ Google Calendar/Gmail, or the Microsoft 365 connector)
  • Do you want scheduled briefs (daily / weekly retro / weekly preview) set up as routines?
  • Any acronyms, product names, or jargon I should know?

People (→ people, one file each — walk every circle)

Emphasis by role: manager — lean into direct reports, skip-down, and cross-org stakeholders (the team they run). IC — lean into their manager, skip-up, and the close peers/collaborators they depend on; don't dwell on a downward org they don't have.

  • Manager (up): Who do you report to?
  • Skip-level up: Who's your manager's manager — and how involved are they?
  • Peers: Who's at your level that you work with most — especially cross-functional peers you depend on?
  • Direct reports: Who's on your team?
  • Skip-level down: Beneath your directs, who are the key people you should know?
  • Cross-org: Who else across the company matters to you — other functions, exec sponsors, partner teams — even with no reporting line?
  • External: Who are your key external stakeholders — customers, partners, investors, board?
  • For each person: their role, your relationship, how often you meet, and anything about how to work with them (preferences, sensitivities, what they care about). Tag their relationship:.
  • Who are the stakeholders on your most important initiatives?

Priorities & projects (→ projects, one file each)

Emphasis by role: manager — the team's initiatives, OKRs, and the RAPID decisions they own. IC — their own deliverables and goals; OKRs optional, RAPID only if they actually drive decisions.

  • What are your top 3–5 priorities right now?
  • For each initiative: what's the goal, who owns it, what's the status, and what are the key dates?
  • What's at risk or blocked?
  • Do you run on OKRs? What are your objectives and key results this quarter/year? (→ okrs.md; I'll record them and can pressure-test the KRs — see brain/playbooks/okrs.md.)
  • What big decisions are you weighing right now? Who recommends, who has to agree, who decides? (→ decisions.md, tracked with RAPID roles — see brain/playbooks/decisions.md.)

Working preferences (→ preferences)

  • How do you like your answers — length, level of detail? (Don't ask how to reach you — I'm always here in the desktop app; just start a session in this folder and I load your context.)
  • How do you like to be briefed before meetings and decisions?
  • What are your standing rules or hard nos (calendar, interruptions, escalation)?
  • How proactive do you want me to be — draft-and-wait, or act-and-inform?

Routines & cadence

  • What are your recurring rhythms (weekly review, 1:1s, reporting)?
  • Which of my playbooks matter most to you (weekly review, meeting prep, decision briefs, inbox triage)?
  • Are there recurring commitments I should always track?

Personal track

Use this instead of the work sections when Context: personal. Same six steps; life, not org. No OKRs, no RAPID, no reporting lines.

You & household (→ profile)

  • What's your name, and what should I call you?
  • Who's in your household / immediate family I should know about?
  • What's the shape of your life right now — the big things on your plate?
  • What would a good few months look like for you personally?

Life context (→ context, one file per topic)

  • Home & household logistics (where you live, key routines, anything I should hold).
  • Finances at a high level (accounts/advisors to remember — not sensitive numbers unless you want).
  • Health & family logistics (appointments, care you coordinate).
  • Travel patterns and preferences.
  • Which of your tools should I lean on — calendar and email first (Google or Microsoft)?

Key people (→ people, one file each — natural relationship labels)

  • Family — partner, kids, parents, others you coordinate with (relationship: family).
  • Close friends you rely on or plan with (relationship: friend).
  • Advisors / providers — doctor, accountant, lawyer, contractor, agent (relationship: advisor or provider).
  • For each: how you're connected, how often you're in touch, anything useful about working with them.

Goals & plans (→ projects/, one file each)

  • What are you trying to get done — a move, a trip, a renovation, a health goal, a course, a side interest?
  • For each: what "done" looks like, key dates, who's involved, what's blocked.
  • Any recurring commitments I should always track (→ memory/commitments.md)?

Preferences (→ preferences)

  • How do you like your answers — length, tone?
  • Standing rules / hard nos (quiet hours, what to never surface, how proactive to be).

Routines & cadence

  • Recurring rhythms — a weekly review, bills/renewals, standing family or household commitments.
  • Want scheduled briefs (a daily look-ahead, a weekly review) set up as routines?