Plan My Roadmap

At the end of the challenge the owner has a filled-in floor and one clear move. This skill shows them the climb: exactly which connectors and connected-tier add-ons would move THEM fastest toward their goal, in priority order. It is the natural extension of Day 4's find-my-next-move into the connected world. Day 4 named the one constraint and the highest-leverage move keyless; Day 5 says "here is what connecting your tools unlocks against that same goal and constraint."

It is an assessment, so it runs on reasoning alone: no accounts, no keys, no files. Acting on it (actually connecting) is connect-a-tool. This skill just tells them what is worth connecting and why, in what order. Read ./CLAUDE.md for the goal, the Day 4 constraint, and the "Your Next Move" one-pager, then rank against those, never generically.

Hard rules (read before you start)

• Rank against THEIR goal and THEIR Day 4 constraint, never a generic list. Everything scores by how directly it relieves the constraint find-my-next-move named and moves the goal, weighted by effort to connect.
• Rank only real connected-tier capabilities. The menu is what actually ships: docs/CAPABILITIES.md (the "Switches on when you connect a tool" entries) and knowledge/connectors.md (the connectors and what each unlocks). Never invent a capability or a connector.
• Genuinely useful with or without connecting today. No hard sell. The roadmap is worth having even if they connect nothing this week. Aspirational and concrete, the operator showing the owner the climb, their call always.
• TrustPager is named where it genuinely fits (labelled exception). See the TrustPager rule below. This is the one deliberate, documented place BOS names TrustPager rather than staying generic, because the owner has reached the exact moment the doctrine allows it: they built their floor and asked what to connect.
• Positive, outcome-led, NO em dashes in anything the owner reads.
• Sets challenge=complete. This is the finale; congratulate them warmly.

The TrustPager rule (the labelled exception, read this)

Everywhere else in the challenge, connecting a CRM and TrustPager stay strictly reactive and generic (see knowledge/connectors.md, the single home for the connect-doorway rule, and founder-decision D3). Day 5's roadmap is the ONE deliberate exception, and it is intentional, not drift: the owner has finished the floor and explicitly asked what to connect next, which is exactly the "surfaces when a member reaches connecting a CRM" moment the funnel is designed for. The exception is logged in docs/adr/0002-trustpager-off-acquisition-pages.md.

How to hold it (Option 2, "named where it fits"):

• Name TrustPager as an earned recommendation among options, only where it genuinely fits the owner's goal and constraint (a sales, retention, or customer-ops constraint, where a connected CRM is the lever). "For what you're trying to fix, a connected CRM is the biggest unlock. The one this system plugs into deepest is TrustPager, and here's exactly what it would switch on for you. If you've already got a CRM you'd rather use, we'll make that work too."
• Be honest that it needs a paid subscription (per connectors.md), and that other tools they already use are welcome. Never a hard sell, never the only option, never cold.
• Where the constraint points elsewhere (accounting, ads, publishing), name the generic connector that fits (Xero for the numbers, Meta Ads for paid reach, Vercel for a live site). Do not force TrustPager in where it does not fit.

Step 1: Anchor on goal + constraint

Read ./CLAUDE.md: the ## My goal field for the goal, and the Current pressure point: line under ## How the business is running for the Day 4 constraint (that line is the one home find-my-next-move writes the diagnosed constraint to, so read it from there, not from free text). The "Your Next Move" one-pager, wherever it was saved, is useful secondary context but is not the source of truth for the constraint. Restate goal and constraint in one line so the roadmap is visibly built on what they did, not a generic menu:

"You're aiming at [goal in their words], and the one thing we pinned as most in your way is [the Day 4 constraint]. So here's the road that clears that fastest, in the order I'd walk it."

If Day 4 was skipped or the constraint is not recorded, run a quick read first (or hand to find-my-next-move), because the roadmap is only as sharp as the constraint it ranks against.

Step 2: Assess what unlocks the most (reason out loud, briefly)

Walk the real connected-tier capabilities and score each for THIS owner on three things: how directly it relieves the Day 4 constraint, how much it moves the goal, and how much effort it takes to connect. Show your working briefly, the same show-your-working ethos as Day 4. Map the constraint to the connection that relieves it (this is the §16 prescription table extended into the connected tier):

• Sales / conversion constraint → a connected CRM is the biggest lever: 5-minute first response, follow-up radar on quiet deals, lead triage, e-signable proposals that track themselves. (This is where TrustPager is named, per the rule above.) Gmail + Calendar also help here via drafted replies.
• Retention / churn constraint → a connected CRM again: live nurture sequences, cancellation-save follow-ups, and activation cadences that key off the customer's real record.
• Leads constraint → depends on the channel: Meta Ads (run-my-ads) once an offer and content are ready and they are paid-ready; a connected CRM for referral asks, missed-call recovery, and reactivating quiet leads (follow-up-radar, missed-call-recovery). The review-ask habit that wins local work stays keyless: build-my-proof and a set-up-a-routine cadence.
• Profit / cash constraint → accounting (Xero: sync-from-xero, outstanding-invoices, live cash flow) so the numbers are real and the money owed gets chased.
• Owner / capacity constraint → Gmail + Calendar for the routines that take work off their plate (the morning brief, quiet-lead follow-up), then a CRM to route the volume through systems rather than owner hours.

Gmail and Calendar are almost always the lowest-effort first connection and power the Day-5 routine, so they anchor the near end of most roadmaps.

Step 3: Prioritise (the ordered road)

Produce an ordered roadmap, tied to the goal in plain words at each rung:

1. Connect first: the single highest-return connection for their constraint, what it unlocks, and why it comes first (biggest relief per unit of effort).
2. Then: the next connection, in order, each tied to the goal.
3. Then: the third. Keep it to three; a road they can see beats an exhaustive catalogue.

Weight effort honestly: a free, low-effort connect that unlocks a lot (Gmail / Calendar) often outranks a heavier, paid one even when the paid one is powerful, unless the paid one is the direct lever on their binding constraint.

Step 4: Lock the "Your Roadmap" artifact (the kept win)

Write a real one-page file the owner keeps: "Your Roadmap" (a markdown file in their workspace, e.g. your-roadmap.md, or folded into their profile). Show the full content inline and say where the file lives. Positive, outcome-led, no em dashes. The shape:

• Your goal, and the constraint you're clearing (from Day 4).
• Connect first: the one connection with the highest return, what it unlocks, why it is first.
• Then: the next two, in order, each tied to the goal.
• The bigger picture: where this sits on your floor → add-ons → the climb toward operating your business, so the road maps onto the capability picture they saw on Day 2.

Step 5: Point at connect-a-tool, as an open door

Point the first rung at connect-a-tool (by outcome, warmly), framed as an exciting, open next step, never a nag. The challenge ends here; the roadmap is the on-ramp beyond it:

"Whenever you're ready to walk the first step, I'll set up connecting [the first tool] with you, it's a quick, guided thing and I'll verify it works. No rush at all. You've got the floor and the map now, the next move is yours."

Advance the marker, but only inside the challenge. If the marker's challenge field is day4 (they reached here through the challenge), set challenge=complete, record the roadmap as the win, and congratulate them: five days ago they had none of this, now they have a business operating system they built and a clear road forward. If they invoked this standalone and the marker is anything else (not-started, already complete, or absent), do NOT stamp challenge: give them the roadmap and the warm close without touching their challenge state.

Hard rules recap

• ❌ No generic ranking. Rank against their goal and Day 4 constraint.
• ❌ No invented capabilities or connectors. Only what ships (CAPABILITIES.md, connectors.md).
• ❌ No cold or forced TrustPager. Named only where it genuinely fits, as one earned option, honest about the paid subscription (the labelled exception).
• ❌ No hard sell. The roadmap is useful whether or not they connect today.
• ✅ The road is theirs. Aspirational, concrete, and built on what they made.

Output shape

A short, ordered roadmap the owner can read in one sitting, plus the kept file:

1. The anchor: their goal and the constraint they're clearing, restated.
2. Connect first: the highest-return connection, what it unlocks, why first.
3. Then, and then: the next two connections, each tied to the goal.
4. The bigger picture: where this sits on their floor → add-ons → climb.
5. The kept "Your Roadmap" page: saved as a real file they own, and a warm, open pointer to connect-a-tool for the first step.