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Casper Studios client onboarding playbook for new engagements. Use this skill whenever a PM is onboarding a new client, ramping up on an existing engagement, setting up a new project in Linear, preparing for discovery sessions, drafting outreach to client stakeholders, or synthesizing post-discovery interview outputs back into project requirements. Triggers include: starting a new client, help me onboard to a client, set up Linear for a project, I have a new engagement, help me prep for discovery, I just got added to a client project, or any combination of reading client docs + setting up project infrastructure + reaching out to client contacts.
How this skill is triggered — by the user, by Claude, or both
Slash command
/brain:casper-client-onboardingThe summary Claude sees in its skill listing — used to decide when to auto-load this skill
This skill codifies how Casper PMs ramp up on a new client engagement and get the project infrastructure in place. It is built from the Cacique Foods onboarding (May 2026), refined from the Pendra onboarding (June 2026), and further refined from the Blueberry engagement (June 2026); update it after each new engagement to capture refinements.
This skill codifies how Casper PMs ramp up on a new client engagement and get the project infrastructure in place. It is built from the Cacique Foods onboarding (May 2026), refined from the Pendra onboarding (June 2026), and further refined from the Blueberry engagement (June 2026); update it after each new engagement to capture refinements.
The playbook has two phases:
This is a sequential, dependent flow — not a checklist. Pause for PM confirmation at every marked checkpoint before proceeding.
Codified from the Blueberry engagement — June 2026.
Before starting Phase 1, identify which type of engagement this is. The flow adapts to each.
DISCOVERY (default): Casper finds where the problems are, understands the current state, and recommends what to build. The client has not yet defined the solution. Pendra and Cacique are DISCOVERY examples. Run the full playbook as written.
BUILD: A working product already exists. Casper hardens it and adds features. The problem space is known; the work is prioritization and execution. Blueberry is the canonical BUILD example.
For BUILD engagements, adapt as follows:
Before pulling any source, detect what has already happened. Has a sponsor email already been sent? Is kickoff already booked? Has a weekly cadence been negotiated? Adapt to the actual state — augment what's in place, don't redo it. The playbook assumes a clean start; real engagements rarely are.
Pull and synthesize four sources before taking any action:
1. Google Drive — project folder Look for and read all of:
Key things to extract:
Drive folder scaffold
Locate the client's [NNN] Client folder. If the standard subfolders are missing, create exactly these four: Agreements & SOW, Data & Access, Meetings & Onboarding, Discovery & Research. Check whether folders already exist before creating anything — on Pendra (June 2026), we nearly duplicated an existing client folder. Consolidate strays — root-level docs and legacy subfolders — into the scaffold.
Tooling constraint: the Drive connector can copy but not move or delete. Shared or legal docs must be drag-moved manually by the PM to preserve links and comment history.
2. Slack — internal client channel
Look for channels named #internal-[client] or #emblem-[client]. Read for:
3. Fireflies — most recent internal call transcript Pull the most recent PM + engineer sync transcript. Look for:
Also pull the sales or pre-engagement call transcript if one exists. Read it before building any question list. Only ask what is genuinely still open after reading it. Do not re-discover what the client already walked you through during the sale or a product demo.
4. Gmail — client-facing threads Search for threads involving the client's domain. Look for:
On Pendra (June 2026), the Week 0 email thread was the highest-signal source — access status, kickoff scheduling, client philosophy, and the discovery attachments all lived there, none of it in Slack or Drive.
Tooling constraint: the Gmail connector cannot download attachments — the PM saves them to Data & Access by hand, then verify they arrived.
Data & Access dedupe pass
After saving email attachments, scan Data & Access for duplicates. Flag byte-identical files for the PM to delete. Flag near-identical files (e.g. two versions a few bytes apart) for a content diff or a question to the client — don't assume which is canonical.
Connector completeness Never assert a thread or channel was read "end to end" from connector data alone — confirm coverage with the PM. Known blind spot: emails in the sent folder may be invisible to the Gmail connector.
Do not take any action until all four sources are ingested.
Write a PM briefing before doing anything else. This is not a bullet-point summary of facts — it is a narrative briefing written the way a smart colleague who has already done all the reading would brief you before a meeting. It should read in under 2 minutes.
The briefing must cover:
The briefing must also include a FLAGS section. This is non-negotiable. Explicitly call out:
The briefing must also include a WHAT WE NEED TO DO NOW section — a short, prioritized list of the PM's immediate next moves. Not findings. Concrete actions, in order.
Quality bar: After reading this briefing, the PM should feel like they've been on the project for a week. Write in plain, direct sentences — avoid negation-heavy phrasing. Hard cap: readable well under 2 minutes. If it reads like a document summary, rewrite it.
⏸ CHECKPOINT — pause here. Show the briefing to the PM and wait for explicit confirmation before proceeding. The PM may have corrections, additional context, or want to resolve a flag before moving forward. Do not proceed to Step 2 until the PM says so.
Before outreach starts, review this checklist with the PM. Mark each item live — don't assume. The build clock doesn't start until these are resolved.
Surface any open item as a flag. If the PM is unsure, ask — don't skip.
Codified from the Pendra engagement — June 2026.
The output of this step is a single artifact: the Kickoff Prep Doc. It serves as the PM's prep document for the kickoff call and as the Phase 1 checkpoint deliverable. Draft it section by section with the PM in chat. Only save to Drive after the PM approves the assembled doc. Do not stack v1/v2/v3 files.
The doc has seven sections, in this order:
1. Title line
[Client] Kickoff Prep · [date]
2. Framing paragraph Two sentences, plain English: what we are actually building this engagement, and what is deliberately deferred. Written so a non-technical exec gets it in one read. Doubles as the anchor slide on the kickoff deck.
3. Attendees Name, role, one parenthetical of context each.
4. What We Already Know ~4 bullets max, one line each. Client business facts only: what the company does, who its customers are, what the pain is. Never engagement logistics (scope, timeline, deliverables). Those belong in the briefing, not here. Hard facts pulled from the SOW, proposal, client memos, and prior comms. These mark what not to re-ask on the call.
5. Session Objectives ~4 bullets. Learning goals and plan confirmations only. Never asks or document requests — those are "What We Need" items, not objectives. Test: an objective starts with understand / get specific / identify / confirm / build rapport.
6. Questions Split into two layers.
Kickoff-call questions (include in this doc): high-level questions about why, success, and prioritization. Sized for a 30-minute slot. Order by priority because you rarely finish. Mark lower-priority categories as deferred to deep-dive sessions so the PM knows what to skip if time runs short.
Deep-dive questions (draft after the kickoff, not now): detailed and technical, written after reviewing the data and the kickoff output. Do not write these at pre-kickoff stage.
Grouped under category headers. Adapt to the engagement (e.g. Success metrics and goals, Business context, Pain points, Workflows and systems, AI readiness and compliance). Draw from the Discovery Kickoff Playbook standard question set and adapt to the client. Offer the full relevant kickoff-call menu and let the PM prune to 8-12. Do not pre-cut for time without asking.
7. Hypotheses to Test 3-4 bullets. A hypothesis is a falsifiable pre-work guess where being right or wrong changes what we build. Facts the client already stated belong in What We Already Know, not here. Strongest form: claim plus consequence — "If true, X. If false, Y."
Style rules — non-negotiable. The PM has rejected drafts that violate these.
Sources — build in this order:
Data & Access before pulling from them. Treat them as primary methodology-capture evidence and book a walkthrough with whoever built them.Example: Pendra Kickoff Prep, June 2026
The gold-standard reference output. Use this to calibrate framing, bullet length, question depth, and hypothesis form.
Pendra Kickoff Prep · June 3, 2026
In the next 6 weeks we build the foundation: a shared filing system for the firm, the methodology written down in one place, naming conventions, one past engagement loaded in as a test, and the partners trained to use it. The analytical brains, the judgment layer, and the compounding memory come in later phases, but everything we build now is shaped so they can sit on top.
Attendees (Kickoff: Mon June 8, 1:30-2:00 PM ET) Brandon Heck, Partner (engagement sponsor, signed agreement) Chris Nichols, Partner (runs the Pendra and Blueberry relationships) Trendler and Danie, Partners (attendance TBD) Hirsch Keshav, Casper Studios PM Michael Slocum, Casper Studios AI Engineer Giorgio Barilla, Casper Studios AI Ops
What We Already Know Pendra is a 4-partner human capital diligence firm serving PE sponsors Three engagement types: full org diligence on new platform deals, standalone executive assessments, and modular reviews like AI readiness Each partner uses their own Claude instance their own way. Files sit across personal computers and cloud storage with no shared process Methodology splits two ways: the 7-dimension OQ Framework is Pendra owned, the individual assessment framework is licensed from Blueberry Core tools today: Claude, Hogan assessments, an org readiness survey, Fireflies for transcription, Word and PowerPoint deliverables Biggest stated pain: post-interview synthesis, and the fact that practitioner knowledge never accumulates across engagements
Session Objectives Understand where the partners lose the most time in a typical engagement, in their words Get specific on how the four workflows differ and how much is style vs methodology Identify 2-3 hypothesis areas for the partner working sessions to probe Confirm the discovery plan: one session per partner, pilot deal materials, methodology docs
Questions Success metrics and goals: What does success look like at the end of these six weeks? If Pendra OS solved one thing, what would make the investment worthwhile? What would each of you need to see to actually use this system on your next live engagement, rather than falling back to your own Claude setup? Are there specific metrics or KPIs you'd want to move? What would the team need to see to feel confident about adopting new tools? Business context: What are the key priorities for the business right now? Where is leadership focused? Are there any major initiatives, transitions, or milestones coming up that we should be aware of? How many engagements does the firm run per year, by type (full diligence, standalone assessment, modular)? How do you expect that mix to change? Any upcoming engagements, hires, or commitments in the next 8 weeks we should plan around, including live deals that could serve as the pilot? Pain points: In a typical engagement, where does the most manual time go? What feels like it should be easier than it is? When deal timeline pressure hits, what gets rushed or cut first? Workflows and systems: How does information flow between the four of you? Are there any handoff points that create friction? AI readiness and compliance: Where has AI output burned you or come closest to it: confident sounding errors, missed nuance, misattributed quotes? What do you double check every time? Any client side compliance, confidentiality, or bias concerns we must design around, given outputs inform hiring and investment decisions?
Hypotheses to Test The four partners differ in tools and prompts, but the underlying method is the same. If true, one shared system works. If false, Pendra OS needs flexibility per partner Post-interview synthesis takes the most time and is the first thing to suffer under deal pressure Migrating scattered historical materials into one system is the key delivery risk, and we need to scope it early
⏸ CHECKPOINT — pause here. Present the assembled Kickoff Prep Doc to the PM section by section. Wait for explicit approval before saving to Drive or proceeding to Step 3. Confirm: the framing is accurate, questions are specific to this engagement, hypotheses are falsifiable, and nothing in What We Already Know needs re-asking on the call. Do not proceed to Step 3 until the PM approves.
Applies to the Kickoff Prep Doc, kickoff decks, and any other document the client sees. Codified from the Blueberry engagement (June 2026).
This step is conditional. Skip it if the kickoff is already booked and the relevant client contacts are already engaged. Augment what exists rather than redoing it. On Blueberry (June 2026), this step was skipped entirely because access and the kickoff were already arranged.
When you do run this step: do not go directly to the SME. Go through the executive sponsor first.
The rule: the sponsor email must be specific enough that the SME could read it and immediately know what to prepare. If you can't write a specific email yet, the Kickoff Prep Doc isn't done.
Email structure:
Voice rules (Casper):
Every engagement will follow this flow: sponsor → SME intro → technical discovery session → business discovery session. The two discovery sessions may be with the same SME or different people depending on the client.
⏸ CHECKPOINT — pause here. Show the draft email to the PM and wait for explicit approval before any further action. The PM must review tone, specificity, and accuracy before this goes anywhere. Do not proceed to Step 4 until the PM approves.
Before building the board: if any flags from Step 1b remain unresolved — especially scope ambiguity or timeline uncertainty — surface them now and ask the PM how to proceed. Do not build a Linear board on a shaky foundation.
Project setup:
[Client] — [Project Name]Milestones:
Ticket principles:
Milestone assignment rules:
Ticket lifecycle rules:
Labels (Product & Delivery team):
Administrative — PM coordination, client-facing logisticsDiscovery — research, interviews, data collectionDelivery — build work, outputs, deliverablesDocument — documentation artifacts (data dictionary, ETL docs, business logic)Priorities:
Dependencies:
Assignees:
Reference: ITA Group project in Linear is the canonical Casper template for a short client engagement. Check it when in doubt.
⏸ CHECKPOINT — pause here. Show the PM the proposed board structure before creating anything in Linear. Confirm project name, milestones, and key tickets are correct. Do not create tickets until the PM approves.
Codified from the Cacique Foods engagement — May–June 2026.
Phase 2 turns raw discovery (interview transcripts, plus client data files on technical engagements) into a single authoritative findings export, then reconciles that export against the requirements and the Linear board. The findings export is the deliverable — everything downstream (engineer handoff, the Week-4 readout, requirement changes) is generated from it.
Discovery is rarely a clean two-interview set. The original plan assumed one technical + one business session. In practice it is a cluster of 3–5 sessions over a few days, often anchored on one SME (the analyst who owns the data), with the executive sponsor and others appearing in subsets. Do not hardcode a fixed session count. The first action of Phase 2 is to establish what the actual session set was.
Before synthesizing anything, list every discovery input that actually occurred:
Identify the anchor SME (usually the single person who owns the data and reporting) and the sponsor separately. They have different roles in the synthesis: the anchor gives you ground truth on data and workflow; the sponsor gives you success criteria and business questions.
⏸ CHECKPOINT — pause here. Confirm the session list with the PM before synthesizing. If a session the PM expected is missing from Fireflies, resolve that first — a missing transcript means a hole in the synthesis.
Run this branch only if the engagement involves building against client data files (a data pipeline, analytics agent, ETL, or anything where the client hands over raw exports). Skip entirely for pure advisory, design, or workflow engagements.
Profile every file the client shared, in isolated runs, and treat the output as discovery evidence on equal footing with the interviews. The goal is to confirm or invalidate what the interviews implied about the data.
For each file, establish:
Why this branch matters: on Cacique, data profiling drove roughly half the requirement changes and caught assumption inversions the interviews alone would have missed (e.g. a file naming convention that meant the opposite of what everyone assumed; four raw files that bypassed the transformation layer entirely). Profiling is not optional polish on these engagements — it is where the real spec comes from.
Capture the profiling output as an engineering spec document in the project (e.g. engineering_requirements.md). This becomes the definitive build reference handed to the engineer in Step 7.
📄 Reference: references/data-room-profiling.md — full per-file mechanics, triad reconstruction, join-key integrity checks, and inversion-hunting guide.
⏸ CHECKPOINT — pause here. Share the data-profiling findings with the PM. Specifically surface any finding that contradicts what an interview implied — those are the highest-value items and the most likely to change scope.
Synthesize all sessions (and, if applicable, the data profiling) into a single findings export — one self-contained document that someone with zero context could read and act on. This is the canonical Phase 2 artifact. Save it to the project folder and title it [Client] Discovery Export.
The export has six required sections, in this order:
Question-status table — every discovery question from the Phase 1 list, grouped by track, marked Answered, Partially answered, or Still open. The honesty of the "partial" and "open" marks is the point — do not round a partial up to answered.
Findings per question — for each answered/partial question, the actual answer, with the source session named (e.g. "Data Deep Dive Round 2"). Preserve specifics: real table names, field names, file paths, percentages, business-rule definitions. Do not summarize the detail away — the detail is what the engineer needs.
What surprised us — anything that contradicted a prior assumption or wasn't anticipated. Treat this as a required muscle, not a footnote: explicitly hunt for assumption inversions (things that turned out to mean the opposite of what was assumed). This section is where discovery earns its cost.
Still open / unresolved — questions not yet answered, PLUS new questions discovery created, PLUS who owes a response and on what (SME, sponsor, IT).
Requirement changes — for each change, state it as Before / Now / Why. Flag any scope nuance that wasn't in the original plan. This is the section the readout and the build both depend on.
Linear impact — the proposed board reconciliation (see Step 6b). List tickets to close, descriptions to update, tickets to create, and tickets to cancel — but do not execute yet.
📄 Reference: references/findings-export-template.md — copy this skeleton into the project folder as
[Client] Discovery Exportto start the export.
⏸ CHECKPOINT — pause here. Share the full export with the PM. Confirm the synthesis is accurate and complete before any Linear changes. The export can only contain what discovery actually surfaced — if a section looks thin, that is a real gap to fill, not a formatting problem.
After the PM confirms the export, apply the Linear changes directly — do not ask for per-ticket approval. Make all of the following changes, then present the full diff in one confirmation at the end.
Apply:
Then run two hygiene checks before presenting:
⏸ CHECKPOINT — pause here. Present the complete set of Linear changes as one diff — closed, updated, created, cancelled — and wait for the PM's confirmation. This is the single confirm gate for all board changes; the PM is reviewing the whole reconciliation at once, not approving tickets one by one.
Before the engineer starts building, prepare a clean handoff package:
What the engineer needs:
What goes in Linear ticket descriptions (engineer's perspective):
What goes in ticket comments (not descriptions):
⏸ CHECKPOINT — pause here. Confirm with the engineer that they have everything they need to start. Do not assume — ask explicitly.
Every step feeds the next:
It is a sequential, dependent flow — not a checklist. The checkpoints are not optional.
Guides collaborative design exploration before implementation: explores context, asks clarifying questions, proposes approaches, and writes a design doc for user approval.
Creates structured, bite-sized implementation plans from specs or requirements before writing code. Useful for breaking down multi-step tasks into testable steps with file structure and task boundaries.
Resolves in-progress git merge or rebase conflicts by analyzing history, understanding intent, and preserving both changes where possible. Runs automated checks after resolution.
npx claudepluginhub casper-studios/casper-marketplace --plugin brain