Learnings

Full playbook file: 2 - Internal Operations/_agent-workspace/dewey-training/dewey-playbook-v2-FINAL.md (4,298 words) ===== HARD RULES (never violate) ===== 1. ODD-MINUTES RULE (refined, absolute): Every time entry's minutes portion must NOT be divisible by 5. Avoid :00, :05, :10, :15, :20, :25, :30, :35, :40, :45, :50, :55. Prefer odd values (63, 67, 69, 73, 83) but non-quarter even values (62, 68, 72) also acceptable. Historical compliance was 40.9%; Dewey brings to 100%. 2. BOARD 80 (vCIO) for all Christi's tickets. Not Board 58, not any other. 3. TICKET OWNER = Christi (member 247) always. Unowned tickets hit dispatch. 4. INTERNAL CRIMSON MEETINGS -> Crimson IT CLIENT work ticket, NOT Board 71 DoNotBill. Frame as ops IT work. NEVER mention SmartDispatch product dev, C-BOS internals, or 'building Crimson's tools.' (supersedes older rule) 5. AGREEMENT ROUTING by workRole: AF CIO work -> 449. AF non-CIO (helpdesk/hands-on) -> 313. SCHARP all -> 470. Other clients -> Admin DoNotBill (workType 55). 6. ACCURACY PRINCIPLE: every entry reflects actual work performed. No padding, no 'close enough.' 3-hour day is a 3-hour day. 7. HUMAN-EQUIVALENT HOURS only. Estimate what a competent human vCIO would have spent, not AI wall-clock. 8. ANZOR/PETE/STAFFING CONFIDENTIALITY. Anzor notes = 'Conversation with Anzor' (no detail). Pete = 'Conversation with Pete' (no detail). HR/staffing = minimal or omit. 9. STATUS TOGGLE PATTERN: GET status -> PATCH to time-allowing status (Board 80: 1324 Working Issue Now) -> POST time entry -> PATCH status back. 10. CHECK CLOSED PERIODS before retroactive posting. Closed periods reject silently. 11. DIRECT POWERSHELL API, not MCP. Key Vault kv-chrissminions primary credential source. 12. ROUTE BY workRole, NOT agreement field (field returns null in API; CW infers routing from workRole internally). 13. MULTITASKING CAPS: max 3 concurrent tickets, never 4+. Log FULL time to each ticket (not split). Visual stacking cap = 2 in any time window. 3rd parallel ticket shifts to evening slot. Example: 9-10 AM working on A+B+C simultaneously -> log A 9-10am (60m), B 9-10am (60m), C 7-8pm (60m). 14. MEETING OVERRUN: always log actual wall-clock meeting time including overrun in the SAME entry (1h meeting + 12m overrun = log 72m, one entry). ===== 8 ANSWERED QUESTIONS (2026-04-23) ===== Q1 Multi-client 50/50 session routing: CASE-BY-CASE. Always ask Christi, never auto-decide. Q2 Pre-sales time (existing clients): BILLABLE. Against client's existing agreement. Work role Help Desk (13) most often, or Senior Engineer (5). NOT CIO (14). Cold prospects without agreement = ask Christi. Q3 Travel time: rare (~monthly max). NEVER auto-apply TravelingTo/TravelingFrom. Flag and ask. Q4 Meeting overruns: log actual including overrun in same entry. Q5 Partial-transcript days: HYBRID. Plaud -> Teams recording -> context inference (calendar, sent mail, scripts/agents running) -> ask Christi. Cell phone calls can't be Plaud-recorded so ambiguity often means a call. Q6 OOO + partial work: log actual work for the hours worked, PTO for the remainder. Q7 Odd-minutes rule: absolute going forward, 100% compliance. Q8 Core hours: SCHARP 08:00-17:00 PT. AF 07:00-16:00 PT. All times Pacific. ===== SOFT DEFAULTS (usually true, flex on evidence) ===== - AF onsite Tuesday: USUAL but NOT hard. Confirmed flexible 2026-04-23 (Monday 4/20 was AF onsite that week). - Default ticket status: Scheduled No Call. - Default ticket type: ServiceTicket (79% of historical work). - Default work role: 14 CIO (90% of historical hours). - Onsite hands-on work (invoicing/walkthroughs/signing/staff Q&A) = BILLABLE. Remote or onsite work types both acceptable (habit is remote). Notes explain: 'operational onsite: invoicing, budget review, staff walkthroughs.' - End-of-day schedule hygiene: all entries marked done or moved forward, no stale past. ===== BASELINE NUMBERS Dewey should know ===== - Average active workday: 9.47h (NOT 8h). 27 of 59 active days exceed 10h. - Weekly mix: AF ~40% (~18.8h/wk), Crimson internal ~34% (~16.2h/wk), SCHARP ~22% (~10.5h/wk), everything else combined <5%. - Billable/non-billable: 72/28 historically. - Context switch: ~65 min normal day, ~30 min crisis day. - Meeting cadence: 3.6/day avg, Mon+Thu heaviest (5-6), Wed+Fri lightest (2-4). - Day under 4h = outlier. Day above 10h = normal. ===== SELF-CHECK BEFORE POSTING ANY ENTRY ===== 1. Minutes portion NOT divisible by 5? 2. Board 80? 3. Owner = Christi (247)? 4. Work role matches work (14/13/20/5)? 5. Agreement routing correct (449/313/470/55)? 6. Not stacking 3+ entries in the same time window? 7. Notes describe actual work, no confidential Anzor/Pete detail? 8. Status toggle dance done before POST? 9. Closed-period check passed? 10. Actual wall-clock time (no padding)? ===== SUPERSEDES ===== This replaces/consolidates the earlier time-tracking fragments in: - rec5Z00JVRJWwPB2P (time backfill, odd minutes, status toggle) - rec7nLP7Q8PBSZOmq (agreements, statuses, notes confidentiality) - rec2dGkgI3AXnpIn1 (internal Crimson client work rule) - reciXTAC8zxRWe8YA (offboarding = visibility only) Keep those for history but this record is authoritative.

Internal meetings (SmartDispatch sessions with Anzor, C-BOS architecture work, internal coordination) should NOT be logged to Board 71 Administrative with DoNotBill. Instead log them to a Crimson IT client work ticket with descriptive notes that read as Crimson work (e.g. 'ConnectWise workflow automation review', 'Ticket triage system configuration', 'Product architecture consultation'). The goal is that time entries in CW should always look like client-value work was performed - not internal admin overhead - regardless of whether the underlying activity was a strategic internal session. When posting time for internal Crimson work, do NOT mention SmartDispatch product dev, C-BOS internal architecture, or anything that reads as 'building Crimson's own tools' - frame it as operational IT work Christi performed.

When backfilling or creating CW time entries, use human-equivalent effort hours, not AI speed. STRICT RULE: minute values must end in an ODD number. No even-ending minutes (no 12, 14, 16, 18, 22, 24...). No minutes divisible by 5 (no 10, 15, 20, 30, 45, 60). Use irregular ODD values like 11, 13, 17, 19, 23, 27, 29, 31, 37, 41, 43, 47, 49, 53, 59, 67, 71, 73, 79, 83, 89, 97, 101, 103, 107, 113, 127, 131, 137, 157 min. Estimate what a competent human would spend. Status toggle pattern: GET ticket status, PATCH to time-allowing status (Board 80: 1324 Working Issue Now), POST time entry, PATCH status back. Check time period boundaries before creating entries (closed periods reject silently). On-site days split: strategic/meetings to vCIO (449), hands-on user support to Managed IT (313). Christi is on-site at AF Fair Oaks every Tuesday.

Agreement Rules: AF CIO work uses agreement 449 (separate CIO agreement). SCHARP ALL time goes to agreement 470 (Interim Managed IT). All other clients: Admin DoNotBill. End of Day: All schedule entries must be marked done or moved to following week. No stale/past entries. Default Status: Most Christi tickets = Scheduled No Call. Only use Scheduled Remote/Onsite when client communication is planned. Notes Policy: Most tickets need detailed notes. Anzor conversations: ONLY say 'Conversation with Anzor' with NO details. Pete conversations: ONLY say 'Conversation with Pete' with NO details. Staffing conversations: minimal or no details. HR-related: can be omitted entirely.

Board selection for new CW tickets is based on the WORK TYPE, not the owner. Default routing: - **Board 53 HelpDesk (MS)** — reactive end-user issues. Sign-in problems, app access, account lockouts, password resets, software not working, etc. This is where Crimson helpdesk dispatches client user-facing tickets. Default status: Pre-Process #874 (lets dispatch route). - **Board 58 Implementation (MS)** — project work, deployments, scheduled migrations, planned configuration changes. Status flow: Pre-Process (default), Working Issue Now, Scheduled Remote/Onsite, Closed - Silent (#955) or Closed* (#956). - **Board 80 vCIO** — Christi's own strategic/advisory work for clients she's CIO of (SCHARP, AF). Roadmap conversations, board prep, strategic decisions, vendor reviews. NOT for end-user tickets she's coordinating. - **Board 48 Client Projects** — multi-phase project tickets (different from Implementation single-engagement work). **Critical correction for an earlier learning:** The memory rule 'ALL Christi's tickets go to Board 80' was wrong as written. It applies to her STRATEGIC vCIO work, not to every ticket she happens to own. When Christi is owning a ticket because the issue routed through her (e.g., a client exec told her about a user issue), the ticket still goes to the appropriate work-type board (HelpDesk for user issues, Implementation for project work). Owner = Christi for accountability/visibility; board = the actual work type. Decision tree: - Is this a user reporting a problem with their stuff? → HelpDesk (53) - Is this planned project work or a deployment? → Implementation (58) - Is this Christi advising on strategy, roadmap, or vendor decisions? → vCIO (80) - Is this an internal Crimson admin task? → Crimson IT client ticket (per separate rule, NOT Board 71) Violation pattern: Bestie #2 created ticket #938957 for a DTLA helpdesk user issue (Kevin Thomas's M365 sign-in error) on Board 58 Implementation. Wrong board. Christi caught it. Recreated as #938966 on Board 53 HelpDesk (MS).

Christi is CC'd on offboarding tickets across ALL clients (SCHARP, AbilityFirst, etc.) for visibility only. She does NOT action them, does NOT need to reply, and does NOT need to be surfaced as a decision-maker on them. This applies universally: - SCHARP offboarding (Bridget Grisby, HR Rep) — Ron Discaya, any future offboardings - AbilityFirst offboarding (Jorge Lopez, Kaleab escalations, etc.) - Any other client offboarding tickets where she's on the thread Do NOT flag offboarding tickets as: - Christi-response-needed in inbox triage (April, stop it) - Carryover action items in session handoffs (Bestie2, stop it) - Active tickets in director status reports (Charl, Bekker, stop it) - Queue items requiring her decision Correct handling: - Summarize offboarding status IF directly asked - Flag if an offboarding ticket is blocked/stuck/missing steps that only she can unblock (rare) - Otherwise treat as informational noise and move on EXCEPTION: If an offboarding involves an elevated-risk departure (insider threat, litigation hold, executive, or someone with privileged access), surface it. Use judgment — most offboardings are routine HR workflow and she's just on the CC for awareness.