Smb Onboard

SMB Onboard

Quick start

Four moves: connect two tools → run one recipe → capture business context → set a weekly rhythm. The whole arc takes 15–20 minutes and ends with Claude knowing enough about the business to be immediately useful.

User: "get me started"
→ Assess what's already connected; pick the best 2 tools to connect first
→ Guide connection of each tool (one at a time)
→ Run one recipe against live data to prove value
→ Ask 5 business questions one at a time; store answers to persistent memory
→ "Each Monday, say 'weekly check-in' — I'll pull your numbers and flag anything urgent."

Tone for connectors

Whenever a connector comes up — recommending one, naming what to try next, or clarifying mid-flow — describe what Claude will be able to do once it's connected, not what the platform itself is or sells. Owners already know what HubSpot, QuickBooks, Gmail, and Calendar do; they don't need a product pitch from us.

• Speak about capabilities we unlock ("draft follow-ups after every meeting", "pull your cash position anytime"), never feature lists.
• One short sentence per connector, max — unless the owner explicitly asks for more ("what does HubSpot actually do?"), in which case answer that directly.
• This rule applies to every step below.

Workflow

1. Welcome and assess. Greet the owner briefly. Check which connectors are already active. If a ## Business context block already exists in the owner's CLAUDE.md or memory, read it first — then skip to the return-session path: show the existing profile, ask what's changed, update only the fields that changed. Do not re-interview from scratch.

2. Pick two functions, then check what the owner uses. Ask: "What are your biggest day-to-day headaches — money, customers, scheduling, or getting organized?" Map the answer to the connector priority list in reference/onboard-checklist.md.

Name the two functions we want (e.g. "a place to track customers and deals" and "your inbox") — not the platform features. One short sentence each, max. Then ask whether the owner uses a supported tool for each.

For each function, branch:

• Owner uses a supported connector (e.g. they say "HubSpot"): say one sentence about what Claude will be able to do together with it, then guide the connection.
• Owner uses an unsupported tool or nothing yet: list 2–3 concrete things Claude will be able to do with the supported alternative, and 1–2 things that won't work without it. Then let the owner decide whether to switch or add it. Do not push.

Connect one tool at a time — never ask the owner to configure two simultaneously. See reference/gotchas.md for the failure pattern this replaces.

3. Run one recipe to prove value. Once the first tool connects — or if connectors are already active when the session starts — immediately run the matched recipe for the owner's primary headache (see connector-to-recipe table in reference/onboard-checklist.md). Narrate what Claude is doing and why — this is the "aha" moment. Do not skip it to get to the interview faster. For a worked example of the full arc, see reference/examples/happy-path.md.

4. Interview the owner. Ask the five questions from reference/onboard-checklist.md, one at a time, conversationally. Wait for the full answer before moving to the next. If the owner seems pressed for time, compress to three: industry, headaches, tools — but never fewer.

5. Store context. Show the owner the full profile before writing. Wait for explicit approval. Write the block to the Cowork session memory directory under the heading ## Business context using the exact format in reference/onboard-checklist.md. If a memory file already exists, update only the ## Business context section — do not touch other content. Confirm: "Saved. Every skill from here will know your business."

6. Set the weekly cadence. Propose: "Each Monday, just say 'weekly check-in' and I'll pull a snapshot of your numbers, flag anything urgent, and remind you what's due." If they prefer a different phrase or day, store it in the profile. If tools are connected, name one skill the owner can try right now. If the owner declined to connect tools, name two or three skills they can try once connected — include the exact trigger phrase for each.

Approval gates

• Show context before writing. Display the full owner profile draft before storing it. Wait for explicit approval.
• Never overwrite existing context silently. If a ## Business context block already exists, show current vs. proposed before writing any changes.
• Never connect a tool on the owner's behalf. Guide; do not act. Connector auth is always owner-initiated.

Reference

• reference/onboard-checklist.md — interview questions, connector priority matrix, recipe selection, context storage format
• reference/gotchas.md — Good / Bad patterns for pacing, tool selection, and context storage
• reference/examples/happy-path.md — worked example: retail shop owner, first session end-to-end

Happy path: Retail shop owner, first session

Setup

• Owner: Maria, sole operator of a hardware store with 3 part-time employees
• Session type: First session ("get me started")
• Connectors before start: None connected

---

Transcript

Claude: Welcome! I'm going to walk you through getting set up — takes about 15 minutes and ends with me knowing enough about your business to be immediately useful. Ready?

Maria: Sure.

Claude: What are your biggest day-to-day headaches — money stuff, keeping up with customers, scheduling, or something else?

Maria: Cash flow. I never know where I stand until the end of the month, and by then it's too late.

Claude: That's the most common one. Let's connect QuickBooks first — that lets me pull your cash position anytime you need it. Here's how to authorize the connection…

[Maria connects QuickBooks — ~3 minutes]

Claude: QuickBooks is live. Let me pull your last 30 days of cash flow right now.

[runs cash-flow-snapshot]

Claude: Here's your snapshot: $4,200 net cash in for the month, but $6,100 in outstanding invoices, mostly from two contractor accounts. Your biggest gap looks like Net-30 customers paying Net-45. Does that match what you're seeing?

Maria: Yes, exactly. I didn't know I could see that so fast.

Claude: That's available anytime. Second tool: let's connect Gmail so I can cross-reference those invoices with emails when you want to chase a payment.

[Maria connects Gmail — ~2 minutes]

Claude: Good. A few questions so I know your business — one at a time. What's the one-liner for what you do?

Maria: Hardware store. Retail and light contractor supply.

Claude: How many people work with you, including yourself?

Maria: Four total — me and three part-timers.

Claude: What are your top three headaches right now?

Maria: Cash flow, slow-paying contractors, and scheduling the part-timers around school.

Claude: Which tools do you already use day-to-day?

Maria: QuickBooks and Gmail, which we just connected. Also Square for in-store payments.

Claude: Got it. Last one: how often would you like me to check in — daily, weekly, or only when you ask?

Maria: Weekly's good. Monday mornings.

Claude: Here's what I'm about to save as your business profile — let me know if anything's off:

Business: Hardware store — retail and light contractor supply
Size: 4 people (including owner)
Top headaches: cash flow gaps · slow-paying contractors · scheduling part-timers
Connected tools: QuickBooks, Gmail
Weekly cadence: weekly check-in every Monday
Onboarded: 2026-04-23

Look right?

Maria: Yep, that's it.

Claude: Saved. Every skill from here will know your business. Each Monday, just say "weekly check-in" and I'll pull your cash snapshot, flag urgent invoices, and remind you what's due that week. Want to try the invoice reminder skill right now? Say "invoice chase."

---

Pass criteria

• [ ] Triggered on "get me started"
• [ ] Asked headache question before recommending connectors
• [ ] Recommended QuickBooks first (matched cash-flow headache)
• [ ] Ran cash-flow-snapshot immediately after QuickBooks connected, before interview
• [ ] Connected second tool (Gmail) before starting interview
• [ ] Asked all 5 interview questions one at a time
• [ ] Showed profile draft before writing
• [ ] Wrote context under ## Business context in ~/.claude/CLAUDE.md
• [ ] Named the weekly cadence trigger phrase explicitly
• [ ] Offered a next skill naturally at the end

---

Branch B: Owner uses an unsupported tool

Setup

• Owner: Dev, freelance design studio (2 people)
• Session type: First session
• Primary headache: Customer follow-up
• Current CRM: Pipedrive (no Cowork connector)

Transcript

Claude: What are your biggest day-to-day headaches — money stuff, keeping up with customers, scheduling, or something else?

Dev: Customer follow-up. Leads slip through.

Claude: For customer follow-up, the two pieces I'd want are a CRM and your inbox. Are you on HubSpot today, or something else?

Dev: Pipedrive.

Claude: Got it — we don't have a Pipedrive connector yet. If you stayed on Pipedrive, you'd still get cash-flow work and calendar work from Claude, but I wouldn't be able to score leads or draft follow-ups from inside the CRM. If you'd be open to trying HubSpot's free tier, here's what'd unlock: a top-5 call list every morning, drafted follow-ups after every meeting, and stale-deal alerts. Up to you — want to try it, or skip the CRM for now?

Dev: Skip for now. I'll stick with Pipedrive.

Claude: No problem. Then let's connect Gmail — that'll still let me surface customer threads waiting on a reply and draft replies for you. Sound good?

Dev: Yeah.

[Dev connects Gmail — ~2 minutes]

Claude: Gmail is live. Let me pull the three oldest unread customer threads…

Pass criteria

• [ ] Named the function ("a CRM and your inbox"), not the platform
• [ ] Asked what the owner uses before pitching anything
• [ ] On unsupported tool, listed gain/loss concretely without pushing
• [ ] Accepted the owner's decision and pivoted to the next supported tool
• [ ] No paragraph-long descriptions of HubSpot, Gmail, or Pipedrive

Gotchas

Gotcha: Skipping the prove-value step when a connection takes too long

Why it matters: If the owner connects a tool but Claude moves straight to the interview, the "aha" moment never lands. The prove-value step is what makes the owner trust the setup is worth completing — and what distinguishes this skill from a form-filling exercise.

✗ Bad

"Great, QuickBooks is connected! Now let me ask you a few questions about your business."

Skips the recipe entirely. Owner leaves not knowing what they just enabled.

✓ Good

"QuickBooks is live. Let me pull your last 30 days of cash flow — takes about 10 seconds."

[runs cash-flow-snapshot, shows results]

"That's what we can do anytime you want a number check. Now, a few questions about your business…"

The demo runs before the interview, every time, without exception.

---

Gotcha: Dumping all five interview questions at once

Why it matters: Five questions presented together feel like a form, not a conversation. Owners either skim-answer or drop off. Conversational pacing produces richer answers and higher completion.

✗ Bad

"To get you set up, I need: (1) What kind of business do you run? (2) How many employees? (3) What are your top headaches? (4) What tools do you use? (5) How often do you want check-ins?"

✓ Good

Ask each question, receive the full answer, then ask the next. Compress to three (industry, headaches, tools) if the owner signals they're in a hurry — never skip those three.

---

Gotcha: Writing context without showing the profile first

Why it matters: Silent writes feel intrusive and remove the owner's chance to correct misheard answers. Showing the draft profile is also a natural confirmation that Claude understood correctly — it often surfaces a correction the owner wouldn't have volunteered.

✗ Bad

"Got it, I've saved your business profile!"

No preview, no approval — owner doesn't know what was written.

✓ Good

"Here's what I'm about to save as your business profile — let me know if anything needs fixing:"

>

```

Business: Lakewood Hardware — retail hardware store

Size: 4 people (including owner)

Top headaches: cash flow gaps · slow-paying contractors · scheduling part-timers

Connected tools: QuickBooks, Gmail

Weekly cadence: weekly check-in every Monday

Onboarded: 2026-04-23

```

>

"Look right? I'll save it once you confirm."

Show the block, wait for approval, then write.

---

Gotcha: Pitching the platform instead of the capability

Why it matters: Owners already know what HubSpot, QuickBooks, Gmail, and Calendar do. When the recommendation reads like a product page ("HubSpot — One place for every lead, customer, deal, and conversation…"), it lands as an ad, not advice. The owner tunes out exactly when we need their attention.

✗ Bad

"1. HubSpot (CRM) — One place for every lead, customer, deal, and conversation. Once it's in, I can prioritize who to call today, draft follow-ups, log notes from your inbox, and spot deals going stale.

>

2. Gmail — Email is where most of the chaos lives: commitments buried in threads, customer questions waiting on a reply, things slipping through. Connecting your inbox lets me surface what actually needs an answer…"

Reads like marketing for HubSpot and Gmail. The owner is being sold to.

✓ Good

"For customer follow-up, the two pieces I'd want are a CRM and your inbox.

>

Are you on HubSpot today, or something else?"

>

(Owner: "Pipedrive.")

>

"Got it — we don't have a Pipedrive connector yet. If you stayed on Pipedrive, you'd still get cash-flow and calendar work, but I wouldn't be able to score leads or draft follow-ups from inside Claude. If you'd be open to trying HubSpot's free tier, here's what'd unlock: top-5 call list every morning, drafted follow-ups after every meeting, stale-deal alerts. Up to you — want to try it, or skip CRM for now?"

States the function, checks what the owner uses, gives a clear gain/loss in plain English, leaves the decision with the owner. If the owner asks "what does HubSpot actually do?" — that's an explicit invitation; answer it directly.

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.

1. Industry and business type. "What kind of business do you run? Give me the one-liner." 2. Team size. "How many people work with you, including yourself?" 3. Top three headaches. "What are your three biggest headaches right now — the things that eat your time or keep you up at night?" 4. Tools already in use. "Which tools do you already use day-to-day? Things like QuickBooks, Gmail, Slack, Square…" 5. 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.

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:

1. QuickBooks or Square → cash-flow-snapshot 2. HubSpot → crm-maintenance (log-a-note demo, read-only) 3. Gmail → search for unread invoice-related emails, surface top 3 4. Google Calendar → business-pulse 5. 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.