Onboarding Checklist

Onboarding Checklist Generator

Generate a comprehensive, customized client onboarding checklist saved as onboarding-checklist.md in the current working directory. The checklist is actionable, phase-structured, and tailored to the specific engagement type.

Contents

• references/output-template.md -- Full output structure: header block, four phases, handoff criteria, formatting rules.
• references/engagement-types.md -- How to classify Consulting vs SaaS vs Agency, and per-type adaptation guidelines.
• references/task-banks.md -- Reference task pools per engagement type and phase.
• references/email-templates.md -- The five required email templates, their structure, and content guidelines.
• references/scaling-and-pitfalls.md -- Timeline and team-size scaling rules, common pitfalls, and the final quality checklist.

Required Inputs

Gather these before generating. If any are missing, ask for them explicitly:

1. Client Type: Industry, company size, maturity (e.g., "Series B fintech startup"). 2. Services Purchased: Exact scope of work or product tiers. 3. Team Size: Number of people on both provider and client sides. 4. Tech Stack: Relevant technologies, platforms, tools, integrations. 5. Timeline: Total onboarding duration and any hard deadlines.

Workflow

1. Collect all five required inputs from the user. 2. Classify the engagement type (Consulting, SaaS, or Agency) using references/engagement-types.md. This classification drives the structure and tone of the entire checklist. 3. Select and customize tasks from references/task-banks.md, adapting language, deadlines, and owners to the specific engagement. Reflect tech-stack items in relevant tasks. 4. Apply timeline scaling rules from references/scaling-and-pitfalls.md based on the specified duration. 5. Apply team-size scaling rules from references/scaling-and-pitfalls.md based on team composition. 6. Generate all five email templates with full body content per references/email-templates.md. 7. Compile the complete onboarding-checklist.md following references/output-template.md. Apply the per-type adaptations in references/engagement-types.md. 8. Verify the result against the quality checklist and common pitfalls in references/scaling-and-pitfalls.md. 9. Write the file to the current working directory using the Write tool. 10. Confirm completion and summarize key stats (total tasks, timeline, engagement type, file location).

Email Templates

Generate 5 email templates, one for each milestone. Each must include subject line, recipient guidance, and full body text with placeholders in square brackets. The tone should be professional but warm, never stiff or robotic.

Required Email Templates

1. Welcome Email (sent at contract signing, before kickoff)

• Purpose: Introduce the team, set expectations, share next steps
• Tone: Enthusiastic, confident, organized

2. Kickoff Recap Email (sent after the kickoff meeting)

• Purpose: Summarize decisions, confirm action items, attach relevant docs
• Tone: Clear, action-oriented, collaborative

3. Week 1 Status Report (sent end of Week 1)

• Purpose: Report progress, flag blockers, confirm Week 2 plan
• Tone: Transparent, structured, forward-looking

4. Mid-Onboarding Check-In (sent at Week 2-3 midpoint)

• Purpose: Gauge client satisfaction, surface concerns early, celebrate progress
• Tone: Empathetic, proactive, solution-oriented

5. Onboarding Complete / Handoff Email (sent when all handoff criteria are met)

• Purpose: Confirm completion, introduce steady-state contacts, share final docs
• Tone: Celebratory (without being over the top), professional, thorough

Template Structure

Each email template must follow this exact structure:

### Email [number]: [Template Name]

**When to Send**: [Trigger event]
**From**: [Role]
**To**: [Role(s)]
**CC**: [Role(s) or "None"]

**Subject Line**: [Subject with placeholders in brackets]

**Body**:

[Full email body text with placeholders in square brackets. Minimum 8-10 sentences per email. Include a greeting, context-setting paragraph, body content organized with bullet points or numbered lists where appropriate, a clear call to action, and a professional sign-off.]

Email Content Guidelines

Welcome Email specifics:

• Open with genuine enthusiasm about the partnership
• Introduce each team member by name placeholder and role with a one-line description of their responsibility
• List the 3-5 immediate next steps with owners and dates
• Attach or link to the onboarding guide, team contact sheet, and project timeline
• Close with an invitation to reach out with any questions before the kickoff

Kickoff Recap Email specifics:

• Reference specific decisions made during the meeting
• List every action item with owner and due date in a numbered list
• Note any open questions that need follow-up
• Attach the kickoff deck, meeting notes, and updated project plan
• Confirm the next scheduled meeting date and time

Week 1 Status Report specifics:

• Use a structured format: Accomplishments, In Progress, Blockers, Next Week Plan
• Quantify progress where possible (e.g., "3 of 5 integrations configured")
• Flag any risks or timeline concerns with proposed mitigations
• Include a brief "Team Spotlight" noting strong collaboration moments
• End with a confirmation of the Week 2 priorities

Mid-Onboarding Check-In specifics:

• Open by acknowledging the progress made so far with specific examples
• Ask 2-3 targeted questions about the client's experience
• Proactively surface any concerns the provider team has identified
• Share a brief preview of what the remaining onboarding period will cover
• Offer to schedule a call if the client prefers a verbal discussion

Handoff Email specifics:

• Confirm that all handoff criteria have been met (reference the checklist)
• Introduce the steady-state support team with contact details
• Summarize what was delivered, configured, or accomplished during onboarding
• Provide links to all documentation, training recordings, and support resources
• Include the process for submitting support requests or feature requests going forward
• Express appreciation for the client's partnership during onboarding

Engagement Types and Adaptation

Engagement Type Detection

Based on the services purchased and context clues, classify the engagement as one of three types. This classification drives the structure and tone of the entire checklist.

Consulting Engagement

• Characteristics: Advisory work, strategy deliverables, workshops, assessments, recommendations
• Emphasis: Discovery depth, stakeholder alignment, knowledge transfer, deliverable review cycles
• Typical phases: Discovery, Analysis, Recommendation, Implementation Support, Handoff
• Owner balance: Heavier on consultant ownership early, transitioning to client ownership

SaaS Engagement

• Characteristics: Software platform onboarding, configuration, data migration, user training
• Emphasis: Technical setup, data integrity, user adoption, integration testing, go-live readiness
• Typical phases: Account Setup, Configuration, Data Migration, Testing, Training, Go-Live
• Owner balance: Shared ownership with CSM/onboarding specialist leading, client IT supporting

Agency Engagement

• Characteristics: Creative deliverables, campaigns, website builds, brand work, ongoing retainers
• Emphasis: Creative briefs, approval workflows, asset collection, revision cycles, launch coordination
• Typical phases: Kickoff, Creative Development, Review Cycles, Production, Launch, Transition to BAU
• Owner balance: Agency-heavy execution with client approval gates

Adaptation Guidelines

For Consulting Engagements

• Add a "Discovery Workshop Agenda" section within Week 1
• Include a "Findings Presentation" task in Weeks 2-4
• Add "Knowledge Transfer Sessions" to handoff criteria
• Email templates should reference strategic recommendations and stakeholder alignment
• Heavier emphasis on documentation and deliverable review cycles

For SaaS Engagements

• Add a "Technical Configuration Checklist" section within Week 1
• Include "Data Migration Validation" tasks in Weeks 2-4
• Add "User Adoption Metrics Baseline" to handoff criteria
• Email templates should reference product features, training resources, and support channels
• Include system health checks and integration verification tasks

For Agency Engagements

• Add a "Creative Brief Approval" task in Pre-Kickoff or Week 1
• Include "Asset Review Cycle" tasks with explicit revision limits in Weeks 2-4
• Add "Brand Asset Handoff" to handoff criteria
• Email templates should reference creative direction, approval workflows, and launch timelines
• Include approval gate tasks that block downstream work until sign-off

Output Template

Generate onboarding-checklist.md with the structure below. Every section is mandatory. The final document must exceed 300 lines.

Header Block

# Client Onboarding Checklist

**Client**: [Client name/type]
**Engagement Type**: [Consulting | SaaS | Agency]
**Services**: [Services purchased]
**Timeline**: [Start date/duration]
**Generated**: [Current date]

---

## Team Roster

| Role | Name (TBD) | Organization | Email |
|------|-----------|--------------|-------|
| [Role] | [Placeholder] | [Provider/Client] | [Placeholder] |

---

Phase 1: Pre-Kickoff (Before Day 1)

Generate 8-12 tasks that must be completed before the kickoff meeting. Each task follows this format:

### Task [number]: [Task title]
- **Owner**: [Role responsible]
- **Deadline**: [Relative date, e.g., "Day -5", "Day -3"]
- **Dependencies**: [What must be done first, or "None"]
- **Acceptance Criteria**: [Specific, measurable completion standard]
- **Notes**: [Context or tips for execution]

Pre-kickoff tasks must include (adapt to engagement type):

• Internal team briefing and role assignment
• Client background research and account review
• Access provisioning and tool setup
• Contract and SOW confirmation
• Kickoff meeting agenda preparation and calendar invites
• Welcome packet or onboarding guide preparation
• Stakeholder mapping on the client side
• Risk and dependency identification

Phase 2: Week 1 (Days 1-5)

Generate 10-15 tasks covering the first week. This is the highest-intensity phase. Must include:

• Kickoff meeting execution
• Discovery sessions or requirements gathering
• Technical environment setup or platform walkthrough
• Communication cadence establishment (standups, Slack channels, status reports)
• Initial deliverable or milestone planning
• Access verification and permissions testing
• Document sharing and knowledge base setup
• Quick wins identification and execution
• Escalation path and point-of-contact confirmation
• First status report or check-in

Phase 3: Weeks 2-4 (Days 6-20)

Generate 12-18 tasks covering the remaining onboarding period. Organize by week where appropriate. Must include:

• Core deliverable production or configuration work
• Review and feedback cycles
• Training sessions (if applicable)
• Integration testing or QA
• Stakeholder demos or progress presentations
• Documentation and runbook creation
• Process optimization based on Week 1 learnings
• Client satisfaction check-in
• Risk mitigation actions
• Preparation for handoff or steady-state transition

Phase 4: Handoff Criteria

Generate a clear, binary checklist of conditions that must ALL be true before onboarding is considered complete:

## Handoff Criteria

All of the following must be verified before transitioning to steady-state:

- [ ] [Criterion 1]
- [ ] [Criterion 2]
...

Include 10-15 handoff criteria covering:

• All deliverables accepted and signed off
• Access and permissions verified for all users
• Documentation complete and accessible
• Training completed with attendance confirmed
• Communication channels transitioned to BAU (business-as-usual)
• Escalation paths documented and tested
• Outstanding issues logged and assigned
• Client satisfaction survey sent and baseline recorded
• Internal retrospective completed
• Billing and invoicing confirmed

Formatting Rules

• Use Markdown throughout
• No emojis anywhere in the document
• Use tables for structured data (team roster, timeline summaries)
• Use checkboxes - [ ] for actionable items in handoff criteria
• Use ### for individual tasks, ## for phase headers, # for document title
• Include horizontal rules --- between major sections
• Every task must have all five fields: Owner, Deadline, Dependencies, Acceptance Criteria, Notes
• Deadlines use relative format: "Day -5", "Day 1", "Day 3", "Day 10", etc.
• Owner fields use role titles, not names (e.g., "Project Manager", "Client IT Lead", "Account Executive")
• The final document must be self-contained and immediately usable without further editing beyond filling in names and dates

Scaling Rules, Pitfalls, and Quality Standards

Timeline Scaling Rules

Adapt the checklist timeline based on the user's specified duration:

• 2-week onboarding: Compress Weeks 2-4 into Week 2. Reduce tasks per phase by 30%. Combine related tasks. Pre-kickoff period is 3 days maximum.
• 4-week onboarding (standard): Use the default structure.
• 6-week onboarding: Expand Weeks 2-4 into Weeks 2-6. Add a dedicated "Optimization and Fine-Tuning" phase in Weeks 5-6. Increase tasks per phase by 20%.
• 8+ week onboarding: Add monthly milestone reviews. Include a formal "Phase Gate" review at the midpoint. Add change management tasks. Include a "Lessons Learned" session at Week 4 before continuing.

Team Size Scaling Rules

Adapt the checklist based on the number of people involved:

• Small team (1-3 per side): Individual task assignments. Fewer handoff points. Combined roles (e.g., PM doubles as account lead). Shorter meetings.
• Medium team (4-8 per side): Dedicated roles for each major function. Sub-team leads for client and provider. Weekly all-hands plus daily standups for active workstreams.
• Large team (9+ per side): Workstream-specific onboarding tracks. RACI matrix required. Executive sponsor check-ins. Dedicated change management tasks. Communication plan as a standalone deliverable.

Common Pitfalls to Avoid

Actively guard against these common onboarding failures:

1. Front-loading all work onto the client: Ensure the provider team owns the majority of early tasks. Clients are busy -- reduce their burden in Week 1. 2. Vague acceptance criteria: "Set up the platform" is not an acceptance criterion. "All 5 integrations return 200 status on test API calls" is. 3. Missing dependencies: If Task 12 requires Task 8's output, that dependency must be explicit. Never assume the reader will infer the order. 4. No escalation path: Every checklist must include at least one task for defining and documenting the escalation process. 5. Ignoring the client's internal approvals: Enterprise clients often need internal sign-offs that add 2-5 days. Build buffer into deadlines. 6. Training as an afterthought: Training tasks should appear in Week 2 at the latest, not crammed into the final days. 7. No success metrics: The handoff criteria must include at least one quantitative measure (e.g., "90% of users have logged in at least once"). 8. Forgetting the internal retrospective: The provider team needs a post-onboarding debrief to improve the process for future clients.

Quality Standards

Before finalizing output, verify: 1. The document exceeds 300 lines 2. Every task has all five required fields populated 3. Dependencies form a logical chain (no circular dependencies, no references to nonexistent tasks) 4. Deadlines progress chronologically within each phase 5. Owners are balanced across provider and client roles 6. All five email templates are present with complete body text 7. Handoff criteria are specific and binary (pass/fail, not subjective) 8. The engagement type classification is reflected throughout the document structure 9. Tech stack items from the input appear in relevant tasks (e.g., "Configure Slack channel" if Slack is in the stack) 10. No emojis appear anywhere in the output

Engagement-Specific Task Banks

Use these as reference when generating tasks. Select and customize based on the user's inputs. Do not copy verbatim -- adapt language, deadlines, and owners to match the specific engagement.

Consulting Task Bank

Pre-Kickoff:

• Conduct preliminary industry research and prepare a one-page client landscape brief
• Review prior engagements with the client (if any) and extract lessons learned
• Identify key decision-makers and map their influence and priorities
• Prepare a draft project charter with objectives, scope boundaries, and success metrics
• Distribute pre-read materials to the consulting team (SOW, org chart, relevant reports)
• Schedule discovery interviews with 3-5 client stakeholders
• Confirm travel logistics if any on-site work is planned
• Set up a shared document repository with folder structure aligned to deliverables

Week 1:

• Conduct a 90-minute kickoff workshop covering goals, constraints, and working norms
• Execute stakeholder interviews (minimum 3 in the first week)
• Synthesize interview findings into a preliminary themes document
• Establish a weekly steering committee meeting cadence
• Deliver a "What We Heard" summary to the client sponsor for validation
• Set up a project tracker with milestones mapped to the SOW
• Identify and log initial risks to the project risk register
• Define the deliverable review and approval process (number of rounds, turnaround times)

Weeks 2-4:

• Conduct deep-dive analysis sessions on priority workstreams
• Prepare a mid-engagement progress report for the steering committee
• Draft preliminary recommendations and pressure-test with internal team
• Present findings to client stakeholders and gather feedback
• Iterate on recommendations based on client input
• Prepare the final deliverable package (report, presentation, executive summary)
• Conduct a formal knowledge transfer session with the client team
• Deliver a transition plan outlining post-engagement next steps and ownership

SaaS Task Bank

Pre-Kickoff:

• Provision the client's account and configure organization-level settings
• Generate API keys or integration tokens required for third-party connections
• Prepare a data migration plan with field mapping and validation rules
• Send a technical requirements questionnaire to the client IT team
• Configure SSO/SAML if included in the subscription tier
• Set up a sandbox or staging environment for client testing
• Prepare user role definitions and permission matrix for client review
• Create a training curriculum outline tailored to the client's user segments

Week 1:

• Walk the client admin through the platform dashboard and core settings
• Import a test data set and validate field mapping accuracy
• Configure notification preferences, email templates, and workflow automations
• Set up integrations with the client's existing tools (CRM, email, analytics)
• Conduct a permissions walkthrough ensuring each role has correct access levels
• Deploy a "Day 1 Quick Start Guide" customized with the client's branding and terminology
• Execute a platform health check (page load times, API response times, error rates)
• Schedule end-user training sessions for Week 2

Weeks 2-4:

• Execute full production data migration and run validation scripts
• Conduct end-user training sessions (split by role: admin, power user, standard user)
• Run user acceptance testing (UAT) with a defined test script and sign-off sheet
• Monitor early usage metrics (login frequency, feature adoption, support ticket volume)
• Troubleshoot and resolve integration issues surfaced during testing
• Conduct a security review of the configured environment (access logs, permission audit)
• Prepare go-live readiness checklist and obtain sign-off from client IT
• Execute go-live cutover and monitor for 48 hours post-launch
• Deliver a "Getting the Most Out of [Platform]" resource pack to end users

Agency Task Bank

Pre-Kickoff:

• Conduct a competitive audit of 3-5 competitors in the client's space
• Prepare a creative brief template and send to client for completion
• Collect existing brand assets (logos, fonts, color codes, photography, tone of voice guide)
• Set up a project management board with milestones, deliverables, and approval gates
• Define the revision policy (number of included rounds, cost of additional revisions)
• Assign creative leads for each workstream (design, copy, development, strategy)
• Prepare mood boards or style references based on initial client conversations
• Schedule a brand immersion session with the client's marketing team

Week 1:

• Conduct a 2-hour brand immersion workshop (positioning, voice, visual identity, audiences)
• Review and finalize the creative brief with client sign-off
• Present initial creative direction options (2-3 concepts) for client reaction
• Establish the content calendar or campaign timeline
• Set up the proofing and approval tool (e.g., Figma comments, markup tool, review link)
• Begin asset production on approved direction
• Deliver a written summary of brand guidelines as understood by the agency team
• Confirm the technical requirements for any digital deliverables (CMS, hosting, tracking)

Weeks 2-4:

• Deliver first round of creative assets for client review
• Incorporate Round 1 feedback and deliver revised assets
• Conduct a midpoint creative review with all stakeholders
• Produce final assets in all required formats and sizes
• Execute QA on all digital deliverables (cross-browser, responsive, accessibility)
• Prepare a launch plan with go-live checklist and rollback procedure
• Coordinate launch timing with client's marketing calendar and PR schedule
• Deliver a complete asset library with naming conventions and usage guidelines
• Conduct a post-launch performance review (first 48-72 hours of metrics)
• Transition ongoing work to the retainer team with documented processes