onboarding-flow-optimizer
Mission : Optimize the onboarding experience to reduce time-to-value, increase activation rates, and improve early retention (D1-D7). Design clear paths to the "aha moment" through checklists, product tours, educational content, and personalized onboarding flows.
STEP 0: Pre-Generation Verification
Before generating the HTML output, verify all required data is collected:
Header & Score Banner
Executive Summary
Funnel Analysis
Onboarding Checklist
Product Tour
Educational Content
Personalized Paths
Email Sequence
A/B Tests
Charts
Roadmap
STEP 1: Detect Previous Context
Ideal Context (All Present):
metrics-dashboard-designer → Activation metrics, D1/D7 retention, time-to-activate
customer-persona-builder → User segments, goals, pain points, skill levels
product-positioning-expert → Value proposition, key features, success indicators
retention-optimization-expert → Early churn data, D1-D7 retention by cohort
Partial Context (Some Present):
metrics-dashboard-designer → Activation metrics available
customer-persona-builder → User segmentation available
product-positioning-expert → Value proposition available
No Context:
None of the above skills were run
STEP 2: Context-Adaptive Introduction
If Ideal Context:
I found outputs from metrics-dashboard-designer , customer-persona-builder , product-positioning-expert , and retention-optimization-expert .
I can reuse:
Activation metrics (current activation rate: [X%], time-to-activate: [Y hours])
User segments (Segment A , Segment B with different onboarding needs)
Value proposition (core value: [X], key features: [Y, Z])
Early retention data (D1 retention: [X%], D7 retention: [Y%])
Proceed with this data? [Yes/Start Fresh]
If Partial Context:
I found outputs from some upstream skills: [list which ones].
I can reuse: [list specific data available]
Proceed with this data, or start fresh?
If No Context:
No previous context detected.
I'll guide you through optimizing your onboarding flow from the ground up.
STEP 3: Questions (One at a Time, Sequential)
Activation Definition & Current Performance
Question AD1: How do you define user activation?
Activation = "Aha Moment" (the moment a user experiences the core value of your product)
Examples :
Slack : "Send 2,000 team messages"
Dropbox : "Upload and share first file"
Facebook : "Add 7 friends in 10 days"
Canva : "Create and download first design"
Notion : "Create first page and add content"
Airbnb : "Complete first booking"
Your Activation Event : [e.g., "Create first project with 3+ tasks and invite 1 team member"]
Why this event? : [What value does the user experience at this moment?]
Alternative Metrics (if no single activation event):
☐ Feature Breadth : Used X out of Y core features
☐ Feature Depth : Used core feature X times
☐ Value Milestone : Achieved measurable result (e.g., "Sent first invoice", "Published first blog post")
Question AD2: What is your current activation performance?
Activation Metrics :
Activation Rate : [e.g., "42% of signups complete activation within 7 days"]
Time to Activate : [e.g., "Median time: 12 hours from signup"]
Activation by Cohort : [e.g., "January: 38%, February: 42%, March: 45%" — improving?]
Activation by Segment :
Activation Funnel (signup → onboarding steps → activation):
Step Users Conversion Drop-off 1. Signup completed 1,000 100% — 2. Email verified 850 85% 15% 3. Profile completed 680 68% 17% 4. First action taken 510 51% 17% 5. Activated (aha moment) 420 42% 9%
Where is the biggest drop-off? : [Which step?]
Industry Benchmarks (for context):
B2B SaaS : Activation rate 30-50%
Consumer Apps : Activation rate 20-40%
Productivity Tools : Activation rate 40-60%
Your Performance vs. Benchmark :
Current Activation Rate: [X%]
Benchmark: [Y%]
Gap: [Z percentage points]
Target Activation Rate : [e.g., "60% within 90 days"]
Onboarding Friction Analysis
Question FA1: Where do users get stuck during onboarding?
Drop-off Point Analysis (from funnel above):
Step Drop-off Why are users dropping off? How to fix? Signup → Email Verified 15% [e.g., "Didn't receive email, went to spam"] [e.g., "Improve email deliverability"] Email → Profile Complete 17% [e.g., "Too many fields, friction"] [e.g., "Reduce required fields to 3"] Profile → First Action 17% [e.g., "Don't know what to do next"] [e.g., "Add onboarding checklist"] First Action → Activated 9% [e.g., "Core feature too complicated"] [e.g., "Add interactive product tour"]
Top 3 Friction Points :
[Friction Point 1] — [Impact: X% drop-off] — [Solution]
[Friction Point 2] — [Impact: X% drop-off] — [Solution]
[Friction Point 3] — [Impact: X% drop-off] — [Solution]
Question FA2: How long does it take users to activate?
Time-to-Activate Distribution :
<1 hour : [X%] (fast activators — ideal)
1-24 hours : [X%] (same-day activators)
1-7 days : [X%] (slow activators)
7+ days : [X%] (very slow, likely won't activate)
Median Time-to-Activate : [e.g., "12 hours"]
Target Time-to-Activate : [e.g., "<1 hour for 50% of users"]
What delays activation? :
☐ Waiting for team members to join
☐ Waiting for data import to complete
☐ Learning curve (too complicated, need tutorials)
☐ Missing information (need to gather data before using product)
☐ Technical issues (bugs, slow load times)
☐ Other: [specify]
How to reduce time-to-activate :
[Action 1] — e.g., "Allow users to skip team invites and activate solo first"
[Action 2] — e.g., "Provide sample data so users can explore without importing"
[Action 3] — e.g., "Add quick-start video (2 minutes) to speed learning"
Onboarding Checklist Design
Question OC1: What is your onboarding checklist?
Onboarding Checklist = A clear, step-by-step guide to activation
Best Practices :
3-5 steps (not 10+)
Specific, actionable ("Create your first project", not "Explore features")
Trackable progress (show "2 of 4 completed")
Celebration on completion (confetti, badge, email)
Your Onboarding Checklist :
✅ Step 1 : [e.g., "Complete your profile (name, company, role)"]
Why it matters: [e.g., "Personalizes your experience"]
Time to complete: [e.g., "30 seconds"]
✅ Step 2 : [e.g., "Create your first project"]
Why it matters: [e.g., "This is where you'll organize your work"]
Time to complete: [e.g., "1 minute"]
✅ Step 3 : [e.g., "Add 3 tasks to your project"]
Why it matters: [e.g., "Experience how easy task management is"]
Time to complete: [e.g., "2 minutes"]
✅ Step 4 : [e.g., "Invite 1 team member" or "Connect your calendar"]
Why it matters: [e.g., "Collaborate with your team" or "Sync your workflow"]
Time to complete: [e.g., "1 minute"]
✅ Step 5 : [e.g., "Mark your first task as complete"]
Why it matters: [e.g., "Feel the satisfaction of progress"]
Time to complete: [e.g., "10 seconds"]
Total Time to Complete Checklist : [e.g., "5 minutes"]
Completion = Activation? : [Yes/No — does completing checklist = activation event?]
Question OC2: How do you incentivize checklist completion?
Incentive Strategies :
Progress Bar (visual progress indicator)
"You're 60% done! Just 2 more steps"
Visual: ▓▓▓▓▓▓░░░░ (6/10 complete)
Gamification (points, badges, streaks)
"Complete onboarding to unlock power features"
"Earn your 'Getting Started' badge"
Social Proof (show what others did)
"95% of successful teams complete all 5 steps"
"Top users completed onboarding in under 5 minutes"
Reward on Completion (unlock feature, give credits, send swag)
"Complete onboarding to get 100 free credits"
"Finish setup and we'll mail you a T-shirt"
Email Nudges (reminder emails for incomplete steps)
Day 1: "You're 2 steps away from full setup"
Day 3: "Just 1 step left! Finish now"
Your Incentive Strategy (choose 2-3):
[Incentive 1] — e.g., "Progress bar with % complete"
[Incentive 2] — e.g., "Unlock power feature after completing checklist"
[Incentive 3] — e.g., "Email nudge on Day 1 and Day 3"
Product Tour Design
Question PT1: Do you need a product tour?
Product Tour = Interactive walkthrough that guides users through key features
When to use product tours :
☐ Your product is complex (many features, steep learning curve)
☐ First-time users don't know where to start
☐ Activation requires using specific features in sequence
☐ You have multiple user personas with different use cases
When NOT to use product tours :
☐ Your product is self-explanatory (e.g., Google search)
☐ Users are experienced (e.g., developers, power users)
☐ Tour would interrupt critical workflows
Do you need a product tour? : [Yes/No]
If Yes : [Type of tour — full tour, feature-specific tour, or persona-based tour]
Question PT2: What does your product tour cover?
Product Tour Structure (3-7 steps):
Step 1 : Welcome & Goal
Message: [e.g., "Welcome to [Product]! Let's get you set up in 2 minutes"]
Goal: [e.g., "By the end, you'll have created your first project"]
Step 2 : Core Feature 1
Highlight: [e.g., "Project Dashboard — this is your command center"]
Action: [e.g., "Click 'New Project' to get started"]
Tooltip: [e.g., "All your projects will appear here"]
Step 3 : Core Feature 2
Highlight: [e.g., "Task List — add tasks to your project"]
Action: [e.g., "Click 'Add Task' and type your first task"]
Tooltip: [e.g., "Tasks can be assigned, prioritized, and tracked"]
Step 4 : Core Feature 3
Highlight: [e.g., "Collaboration — invite your team"]
Action: [e.g., "Click 'Invite' and add your teammates"]
Tooltip: [e.g., "Everyone can see updates in real-time"]
Step 5 : Power Feature (optional)
Highlight: [e.g., "Automation — save time with smart rules"]
Action: [e.g., "Try creating your first automation"]
Tooltip: [e.g., "Auto-assign tasks, send reminders, and more"]
Step 6 : Completion & Next Steps
Message: [e.g., "You're all set! Now go create something amazing"]
CTA: [e.g., "Explore on your own" or "Start your first project"]
Tour Format :
☐ Tooltip Tour (tooltips appear over UI elements, user clicks through)
☐ Modal Tour (modal dialogs guide user step-by-step)
☐ Video Tour (2-minute video walkthrough)
☐ Interactive Demo (sandbox environment to practice without consequences)
Your Tour Format : [Choose 1-2]
Can users skip the tour? : [Yes/No — forced tour or optional?]
Best practice: Always allow skipping, but track skip rate (high skip rate = tour isn't valuable)
Educational Content & Help Resources
Question EC1: What educational content do you provide during onboarding?
Educational Content Types :
Tooltips (contextual help, appears on hover or click)
Example: "💡 Tip: Assign tasks to team members to track accountability"
When to show: First time user sees a feature
Empty States (helpful messages when there's no data yet)
Example: "No projects yet. Let's create your first one!"
CTA: [e.g., "Create Project" button]
Help Docs (knowledge base, FAQs, tutorials)
Organized by: Getting Started, Core Features, Advanced Features, Troubleshooting
Format: Text + screenshots, or video tutorials
Quick-Start Video (2-3 minute overview)
Shows: Core workflow from start to finish
Hosted: Embedded in app (YouTube, Vimeo, Loom)
Webinars / Live Onboarding Calls (for high-touch customers)
Frequency: [e.g., "Weekly live onboarding session, or 1-on-1 call for enterprise"]
Who leads: CSM, Product Specialist, or Founder
In-App Messages (contextual nudges at key moments)
Example: "Try adding a due date to your task to set a deadline"
Trigger: User creates task without due date
Your Educational Content (choose 3-5):
[Content Type 1] — e.g., "Tooltips for all core features"
[Content Type 2] — e.g., "Quick-start video (2 minutes)"
[Content Type 3] — e.g., "Help docs with screenshots"
[Content Type 4] — e.g., "Empty states with CTAs"
[Content Type 5] — e.g., "In-app messages for key moments"
Question EC2: How do you measure content effectiveness?
Content Performance Metrics :
Content Type Metric Current Target Product Tour Completion rate (% who finish tour) X% >70% Tooltips Click-through rate (% who click "Learn more") X% >20% Quick-Start Video View rate (% of new users who watch) X% >40% Quick-Start Video Watch time (% of video watched) X% >60% Help Docs Search rate (% of users who search docs) X% >10% Help Docs Deflection rate (% who find answer) X% >70% Webinar Attendance rate (% who sign up and attend) X% >50%
Feedback Mechanisms :
☐ "Was this helpful?" (thumbs up/down) on help docs
☐ "Did this answer your question?" after tooltip
☐ CSAT survey after webinar
☐ NPS survey after completing onboarding
Personalized Onboarding Paths
Question PP1: Do different user segments need different onboarding experiences?
Personalization Triggers :
☐ By User Role : Marketer vs. Developer vs. Sales Rep
☐ By Company Size : Solo user vs. Small team vs. Enterprise
☐ By Use Case : Project Management vs. CRM vs. Content Planning
☐ By Experience Level : Beginner vs. Intermediate vs. Advanced
☐ By Acquisition Source : Organic vs. Paid vs. Referral
Do you need personalized onboarding? : [Yes/No]
If Yes : [How will you segment users? e.g., "Ask 'What's your role?' during signup"]
Question PP2: What are your personalized onboarding paths?
Onboarding Path 1 : [Segment Name — e.g., "Marketing Manager"]
Goal : [e.g., "Create first content calendar"]
Checklist :
[Step 1] — e.g., "Set up content pillars"
[Step 2] — e.g., "Add 5 content ideas"
[Step 3] — e.g., "Schedule first post"
Tour Focus : [e.g., "Content planning features, editorial calendar"]
Resources : [e.g., "Content Marketing 101 guide"]
Onboarding Path 2 : [Segment Name — e.g., "Software Developer"]
Goal : [e.g., "Integrate API and make first request"]
Checklist :
[Step 1] — e.g., "Generate API key"
[Step 2] — e.g., "Run sample code"
[Step 3] — e.g., "Make first API call"
Tour Focus : [e.g., "API docs, developer console"]
Resources : [e.g., "API reference docs, code samples"]
Onboarding Path 3 : [Segment Name — e.g., "Sales Rep"]
Goal : [e.g., "Add first contact and send outreach"]
Checklist :
[Step 1] — e.g., "Import contacts from CSV"
[Step 2] — e.g., "Create email template"
[Step 3] — e.g., "Send first outreach email"
Tour Focus : [e.g., "Contact management, email sequences"]
Resources : [e.g., "Sales email templates, best practices"]
How to personalize :
☐ Ask segmentation question during signup ("What's your role?")
☐ Auto-detect based on behavior (e.g., user clicks "Developer Docs" → developer path)
☐ Allow users to choose path ("I'm here to... [Manage Projects / Build Integrations / Track Sales]")
Email Onboarding Sequence
Question ES1: What is your email onboarding sequence?
Email Onboarding = Series of emails to guide users through activation
Email 1 (Day 0): Welcome + Quick Start
Subject : [e.g., "Welcome to [Product]! Let's get you started"]
Body :
Welcome message
Quick-start video (2 minutes)
Primary CTA: "Complete your setup" (link to onboarding checklist)
Support: "Reply to this email if you need help"
Email 2 (Day 1): Feature Highlight
Subject : [e.g., "How to [achieve goal] with [Product]"]
Body :
Highlight core feature (e.g., "Task management made easy")
Tutorial: Step-by-step guide with screenshots
Social proof: "10,000+ teams use this feature daily"
CTA: "Try it now"
Email 3 (Day 3): Success Story / Use Case
Subject : [e.g., "How [Customer Name] achieved [result] with [Product]"]
Body :
Customer success story (2-3 paragraphs)
Key takeaway: "You can achieve [result] too"
CTA: "Get started"
Email 4 (Day 5): Re-Engagement / Reminder
Subject : [e.g., "You're almost there! Just 2 steps left"]
Body :
Progress update: "You've completed 3 of 5 steps"
Reminder of incomplete steps
Incentive: "Finish setup to unlock [reward]"
CTA: "Complete setup"
Email 5 (Day 7): Support Offer
Subject : [e.g., "Need help getting started?"]
Body :
Offer help: "Our team is here to help you succeed"
Resources: Link to help docs, video tutorials, live chat
Optional: Book a 15-minute onboarding call
CTA: "Get help"
Email Cadence : [Day 0, Day 1, Day 3, Day 5, Day 7]
Trigger : [All users, or only users who haven't activated?]
A/B Testing Onboarding Variations
Question AB1: What will you A/B test in your onboarding?
A/B Test Ideas :
Checklist Length
Variant A : 3 steps (faster, but less guidance)
Variant B : 5 steps (more guidance, but longer)
Metric : Activation rate
Product Tour
Variant A : Forced tour (all users must complete)
Variant B : Optional tour (users can skip)
Metric : Activation rate, time-to-activate
Empty State CTAs
Variant A : "Create Project" button only
Variant B : "Create Project" + "Watch Tutorial" (two options)
Metric : CTA click-through rate, activation rate
Incentive
Variant A : No incentive
Variant B : "Complete setup to get 100 free credits"
Metric : Checklist completion rate, activation rate
Email Timing
Variant A : Email sequence (Day 0, 1, 3, 5, 7)
Variant B : Email sequence (Day 0, 2, 7)
Metric : Email open rate, activation rate
Your A/B Test Plan (choose 2-3 tests):
Test 1 : [What are you testing?] — Variant A vs. B — Metric: [X]
Test 2 : [What are you testing?] — Variant A vs. B — Metric: [X]
Test 3 : [What are you testing?] — Variant A vs. B — Metric: [X]
Testing Cadence : [How often will you run tests? e.g., "One test every 2 weeks"]
Implementation Roadmap
Question IR1: What is your 90-day onboarding optimization plan?
Phase 1: Foundation (Weeks 1-3)
Goal : Implement core onboarding elements
Deliverable : Onboarding checklist and email sequence live, activation tracking implemented
Phase 2: Educational Content (Weeks 4-6)
Goal : Add product tours, tooltips, and help resources
Deliverable : Product tour live, tooltips added, quick-start video published
Phase 3: Personalization & Optimization (Weeks 7-12)
Goal : Personalize onboarding paths and run A/B tests
Deliverable : Personalized onboarding live, 2 A/B tests completed, activation rate improved by [X%]
STEP 4: Generate Comprehensive Onboarding Optimization Strategy
You will now receive a comprehensive document covering :
Section 1: Executive Summary
Activation definition (aha moment: [X])
Current activation rate and target (X% → Y%)
Time-to-activate (current: [X], target: [Y])
Top 3 friction points and solutions
Section 2: Activation Funnel Analysis
Activation funnel (signup → email → profile → first action → activated)
Drop-off analysis (where users get stuck, why, how to fix)
Activation by segment (persona, acquisition source, cohort)
Industry benchmarks and performance gap
Section 3: Onboarding Checklist Design
3-5 step checklist with time estimates
Progress indicators and completion incentives
Gamification and social proof strategies
Email nudges for incomplete steps
Section 4: Product Tour Design
5-step product tour (welcome, core features, completion)
Tour format (tooltip, modal, video, interactive demo)
Skip option and tracking (completion rate, skip rate)
Section 5: Educational Content Strategy
Tooltips for core features
Empty states with CTAs
Quick-start video (2-3 minutes)
Help docs (Getting Started, FAQs, Troubleshooting)
In-app messages for key moments
Webinars / live onboarding (for high-touch customers)
Section 6: Personalized Onboarding Paths
Segmentation strategy (role, company size, use case, experience level)
2-3 persona-specific onboarding paths
Personalized checklists, tours, and resources
Section 7: Email Onboarding Sequence
5-email sequence (Day 0, 1, 3, 5, 7)
Email content (subject, body, CTA)
Triggers and segmentation (all users vs. non-activated users)
Section 8: A/B Testing Plan
3 A/B tests (checklist length, product tour, incentives)
Success metrics (activation rate, time-to-activate, completion rate)
Testing cadence (one test every 2 weeks)
Section 9: Implementation Roadmap
Phase 1 (Weeks 1-3) : Activation definition, onboarding checklist, email sequence
Phase 2 (Weeks 4-6) : Product tour, tooltips, help resources
Phase 3 (Weeks 7-12) : Personalization, A/B testing, continuous optimization
Section 10: Success Metrics
Activation Rate: [Baseline → Target — e.g., 42% → 60%]
Time-to-Activate: [Baseline → Target — e.g., 12 hours → <1 hour]
Checklist Completion Rate: [Target: >80%]
Product Tour Completion Rate: [Target: >70%]
D1 Retention: [Baseline → Target — e.g., 55% → 70%]
D7 Retention: [Baseline → Target — e.g., 40% → 55%]
Section 11: Next Steps
Launch onboarding checklist this week
Schedule weekly onboarding optimization meetings
Integrate with retention-optimization-expert (early retention data feeds churn analysis)
Integrate with customer-feedback-framework (gather onboarding feedback via surveys)
STEP 5: Quality Review & Iteration
After generating the strategy, I will ask:
Quality Check :
Is the activation definition clear and measurable?
Does the onboarding checklist reduce time-to-value?
Are drop-off points addressed with specific solutions?
Is the product tour helpful without being intrusive?
Are personalized onboarding paths feasible to build?
Are A/B tests designed to optimize activation rate?
Iterate? [Yes — refine X / No — finalize]
STEP 6: Save & Next Steps
Once finalized, I will:
Save the onboarding optimization strategy to your project folder
Suggest running customer-feedback-framework next (to gather feedback on onboarding)
Remind you to launch the onboarding checklist this week
8 Critical Guidelines for This Skill
Activation = Aha Moment : Define activation as the moment users experience core value, not arbitrary milestones (e.g., "Send 2,000 messages" > "Complete profile").
Reduce time-to-value : The faster users reach the aha moment, the better. Target <1 hour for 50% of users.
3-5 step checklist, not 10+ : Long checklists overwhelm users. Keep it short and actionable.
Product tours should be optional : Forced tours frustrate experienced users. Always allow skipping, but track skip rate.
Empty states are opportunities : Turn blank screens into onboarding moments (e.g., "No projects yet. Let's create your first one!").
Personalize for different segments : Marketers and developers need different onboarding experiences. Segment by role, use case, or experience level.
Measure everything : Track activation rate, time-to-activate, checklist completion rate, tour completion rate, drop-off points.
A/B test continuously : Run one test every 2 weeks to optimize activation rate. Small improvements compound.
Quality Checklist (Before Finalizing)
Activation definition is clear, measurable, and tied to core value
Current activation rate and target are defined (e.g., 42% → 60%)
Activation funnel shows drop-off points with solutions
Onboarding checklist is 3-5 steps with time estimates
Product tour is designed (5 steps, optional, tracked)
Educational content includes tooltips, empty states, quick-start video, help docs
Personalized onboarding paths are defined for 2-3 segments
Email onboarding sequence is 5 emails (Day 0, 1, 3, 5, 7)
A/B testing plan includes 3 tests with success metrics
Implementation roadmap is realistic (Weeks 1-3: Foundation, Weeks 4-6: Content, Weeks 7-12: Optimization)
Integration with Other Skills
Upstream Skills (reuse data from):
metrics-dashboard-designer → Activation metrics, D1/D7 retention, time-to-activate, activation funnel
customer-persona-builder → User segments, goals, pain points, skill levels (for personalized onboarding)
product-positioning-expert → Value proposition, key features, success indicators (for aha moment definition)
retention-optimization-expert → Early churn data, D1-D7 retention by cohort (to prioritize onboarding improvements)
Downstream Skills (use this data in):
retention-optimization-expert → Improved activation rates lead to better D1-D7 retention
customer-feedback-framework → Gather onboarding feedback via surveys (e.g., "How was your onboarding experience?")
metrics-dashboard-designer → Track activation metrics on product dashboard
email-marketing-architect → Email onboarding sequence integrates with lifecycle email campaigns
HTML Output Verification
After generating the HTML report, verify all elements render correctly:
Visual Verification Checklist
Data Quality Verification
Template Location
Skeleton template: html-templates/onboarding-flow-optimizer.html
Test output: skills/retention-metrics/onboarding-flow-optimizer/test-template-output.html
End of Skill