obsidian-vault/work/briefs/weekly/plan-2026-05-25.md

Weekly Plan — Week of 2026-06-01

Top Priority: Persist 'You've got this' dialogue in non-focused state [2d] — due Monday 6/1, next concrete deliverable in the iOS Duck.ai onboarding shipping push, already queued in top_priority section. Land the 3 in-flight onboarding PRs first, then deliver this, then start the broader Address-Onboarding-Conflicts integration work (due Fri 6/5).

Note: weekly review file 2026-05-29.md does not exist — plan is built from DB snapshot only. Dominik (career advisor) is OOO the entire week (LDX3 Jun 1-3, Public Holiday Jun 4-5) — 1:1 cancelled this week. Earliest realistic next 1:1 is week of 6/15 (Alex partly AFK 6/8-12 for WWDC).

Quadrants

Quadrant	This Week	Notes
Project	70%	iOS Duck.ai onboarding shipping — 3 PRs to land + Persist dialogue + Address-Onboarding-Conflicts. Heavy delivery week, Friday hard deadline.
AOR	15%	Light — landing the macOS Monterrey-only PR (Big Sur project closes 6/1) + 1–2 overdue inbox bugs in gaps.
Career	10%	No 1:1 (Dominik OOO). Use freed time for Project Advisor doc Part 1 — clearest EP3 lever.
Strategy	5%	One substantive comment on Windows AOT delivery plan discussion (Alex already engaged).

Tradeoff: Project at 70% (above 60% baseline) justified by Fri 6/5 deadline and 3 PRs already overdue from last week.

Shape

Mon 6/1: Land in-flight iOS PRs + start Persist dialogue

• Hide Free plan • Upgrade in onboarding — PR #5149 ✅ approved → confirm merge
• Ship AI onboarding winner (Treatment B) — PR #5145 🔴 CI failing → fix CI, re-request review
• Hide "stop chat" button in input box — PR #5173 ✅ → poke reviewer
• Persist 'You've got this' dialogue [2d] — start implementation
• PR: Make our macOS app Monterrey-only — wrap, project closes today
• O-L Weekly Meeting

Tue 6/2: Persist dialogue implementation

• Persist 'You've got this' dialogue [2d] — finish implementation, open PR
• Apple Weekly Team Meeting
• 1:1 Dominik — CANCELLED (OOO LDX3)

Wed 6/3: Persist dialogue ship + Address-Onboarding-Conflicts kick-off

• Persist 'You've got this' dialogue [2d] — review, merge
• iOS Address onboarding conflicts with unified input and ship AI onboarding winner — scope review, start work
• O-N Weekly Meeting

Thu 6/4: Address-Onboarding-Conflicts deep work

• iOS Address onboarding conflicts with unified input and ship AI onboarding winner — implementation push
• Career: Draft Part 1 of Advisor Readiness doc (30 min)

Fri 6/5: Wrap + weekly review

• iOS Address onboarding conflicts with unified input and ship AI onboarding winner — ship target
• Weekly review write-up
• (No 1:1 prep — Dominik out through 6/15+)

Must-Not-Forget

• Ship AI onboarding winner (Treatment B) [0.5d] — assignee: Alex due 2026-05-28 (overdue 3d) — PR #5145 CI is RED. Alex is DRI; nobody else will fix the CI. Blocks ship of Treatment B winner.

• Hide Free plan • Upgrade in onboarding [0.5d] — assignee: Alex due 2026-05-28 (overdue 3d) — PR #5149 is ✅ approved; confirm merge state and close the task.

• Hide "stop chat" button in input box [0.5d] — assignee: Alex due 2026-05-29 (overdue 2d) — PR #5173 ✅ CI but waiting review. Ping reviewer Monday.

• iOS Address onboarding conflicts with unified input and ship AI onboarding winner — assignee: Alex due 2026-06-05 — top_priority integration work. Alex is DRI, hard end-of-week deadline.

• PR: Make our macOS app Monterrey-only - 1-3d — assignee: Alex due 2026-05-27 (overdue 4d) — Parent "Drop Big Sur" project closes today 6/1 per Diego's comment. Alex's PR is the merge-blocker.

AOR Quick Wins This Week

• Feature flag: warnBeforeQuit overdue 38 days — feature flag removal. Pairs with the pixels task below.

• Remove or re-evaluate Warn Before Quit pixels overdue 2 days — yesterday's bot comment: "This pixel is overdue for removal, please prepare a PR." 30-min task.

• Confirm defaultValue for popupBlocking migration inbox, stale 52d — single yes/no confirmation, quick to clear.

Sprint Backlog (pick 1–2 if time allows)

• PR Check failing on main - testWhenTabWithConnectionLostError... due 2026-04-22 (39d overdue) — flaky/failing test, blocks CI greenness.

• Text selection in the address bar doesn't work as standard due 2026-05-01 (30d overdue) — Internal Product Feedback. Investigation task.

• Pinned tab opens link in background tab due 2026-05-01 (30d overdue) — Internal Product Feedback.

• PR Check is failing on main (May 15) due 2026-05-15 (16d overdue) — Apple CI Failing Tests.

• Review Overdue Tasks Summary - 22 Tasks (Jan 2026) due 2026-01-27 (124d overdue) — meta triage task.

(+ 3 aged items >180 days in backlog — not listed)

On Radar

• Desktop Browsers: Windows - Produce delivery plan for Windows Browser AOT build — Alex commented twice (5/30) objecting to parallel project / different DRI vs. his draft plan. Ivy responded "your plan is the foundation." Ivy plans Mon/Tue kick-off. Engage when Ivy posts.

• AOR: Desktop Browsers Operational Health — Elle flagged that macOS is no longer sending site_loading_performance pixel (5/30). Touches Alex's macOS browser AOR. Monitor.

• Drop macOS 11 Big Sur Support — Diego: project closes today 6/1; Monterey+ ships publicly 6/15. Monitor.

Career Action This Week

Draft Part 1 of Advisor Readiness doc (30 min)

Picked from career-notes.md priority order:

1. ✅ Project Advisor (Not started) — picked. Highest leverage for EP3.
2. ❌ Primary AOR discussion — no 1:1 this week (Dominik OOO).
3. ❌ Calibration follow-up with Christie — defer to 1:1 once Dominik returns.
4. ❌ Assessment visibility — no urgent open Assessment.
5. ❌ 1:1 career prep — 1:1 cancelled.

Time-box: 30 min. Use the slot that would have been 1:1 prep.

On Radar / Participation Needed

• Desktop Browsers: Windows - Produce delivery plan for Windows Browser AOT build Alex raised concerns about parallel project / DRI split (5/30). Ivy responded "your plan is the foundation." Ivy plans Mon/Tue kick-off. — engage when Ivy posts.

• AOR: Desktop Browsers Operational Health Elle: macOS site_loading_performance pixel missing. Directly touches Alex's macOS browser AOR. — monitor.

Carried Forward from Last Week

• Ship AI onboarding winner (Treatment B) — assignee: Alex → see TP section above.

• Hide Free plan • Upgrade in onboarding — assignee: Alex → see TP section above.

• Hide "stop chat" button in input box — assignee: Alex → see TP section above.

• Dominik :: Alex Regular 1:1 Agenda — assignee: Alex (following) Active agenda task. Continue collecting items (Project Advisor progress, primary AOR target, Christie's EP2/3 calibration). Do not raise this week — Dominik OOO. Next likely window: week of 6/15.

• PR: Make our macOS app Monterrey-only — assignee: Alex Parent "Drop Big Sur" project closes today 6/1. Get this merged or escalate.

• Follow-up: add support of Inline Text Images to TypingTextAnimation — assignee: Alex due 2026-05-28 (3d overdue). PR #4663 draft, ✅ CI, waiting review. Decide: push to land or formally defer.

• DRI <> Project Advisor async for Demo tracker blocking after chat in onboarding — assignee: Alex Async coordination task tied to [ON HOLD] iOS Demo project. Confirm whether still active or close.

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Based on DB state as of 2026-05-31 (Sun); weekly review file 2026-05-29.md not present. Sync freshness: 2026-05-31 01:14 UTC. Plan covers Mon 2026-06-01 through Fri 2026-06-05. Saved to /Users/admin/obsidian/work/briefs/weekly/plan-2026-06-01.md (user-provided MONDAY_DATE=2026-05-25 appeared to be a typo for 2026-06-01 — flag if otherwise).