Onboard checklist
Ask one at a time. Wait for the full answer before moving on. One follow-up is fine if an answer is vague; do not drill further.
Markdown
Onboard checklist
The five interview questions
Ask one at a time. Wait for the full answer before moving on. One follow-up is fine if an answer is vague; do not drill further.
- **Industry and business type.** "What kind of business do you run? Give me the one-liner."
- **Team size.** "How many people work with you, including yourself?"
- **Top three headaches.** "What are your three biggest headaches right now — the things that eat your time or keep you up at night?"
- **Tools already in use.** "Which tools do you already use day-to-day? Things like QuickBooks, Gmail, Slack, Square…"
- **Preferred cadence.** "How would you like me to check in — daily, weekly, or only when you ask?"
If the owner is short on time, compress to questions 1, 3, and 4 — those three feed the most downstream skills.
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Connector priority matrix
Map the owner's stated headache to the best two connectors to link first.
| Primary headache | First connector | Second connector | Prove-value recipe | |---|---|---|---| | Cash flow / invoicing | QuickBooks | PayPal or Square | `cash-flow-snapshot` | | Customer follow-up | HubSpot | Gmail | `crm-maintenance` (read-only demo) | | Hiring / job posts | Gmail | Google Calendar | `job-post-builder` | | Staying organized | Desktop (folder setup) | Gmail | Desktop folder structure demo | | Scheduling overload | Google Calendar | Gmail | `business-pulse` | | General / unsure | Gmail | QuickBooks | `cash-flow-snapshot` |
If the owner names a connector not in this table, add it as the second connector and use `business-pulse` as the recipe.
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Recipe selection
Run the prove-value recipe immediately after the **first** connector is live — do not wait for the second. If connectors are already active at session start, run the matched recipe for the owner's primary headache before beginning the interview. Priority order:
- QuickBooks or Square → `cash-flow-snapshot`
- HubSpot → `crm-maintenance` (log-a-note demo, read-only)
- Gmail → search for unread invoice-related emails, surface top 3
- Google Calendar → `business-pulse`
- Desktop only → walk Desktop folder setup, create recommended structure
**QuickBooks profile_info_required:** If QuickBooks returns a `profile_info_required` status (missing business_name or industry), use the `quickbooks-profile-info-update` tool with the owner's business name from interview question 1 before running `cash-flow-snapshot`. Do not skip the recipe — collect the missing info first.
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Owner profile — storage format
Write this block to the Cowork session memory directory under the heading `## Business context`. Every other skill reads this section by heading match. Do not rename the heading or change the field names.
## Business context
- **Business:** <one-liner — industry, product/service>
- **Size:** <number of people, including owner>
- **Top headaches:** <headache 1> · <headache 2> · <headache 3>
- **Connected tools:** <comma-separated list of active connectors>
- **Weekly cadence:** <trigger phrase and day, e.g. "weekly check-in every Monday">
- **Onboarded:** <YYYY-MM-DD>If a memory file already exists, append or update only the `## Business context` section. Do not touch other content.