Challenge 1: Plan

Challenge Snapshot

Field	Value
Duration	45 minutes
Type	Whiteboard Design Session
Points	25
Deliverable	Whiteboard assessment strategy and migration wave plan

Objective

Design a comprehensive assessment and migration planning strategy for Contoso Bakery using the Cloud Adoption Framework methodology.

The Business Challenge

Contoso Bakery has engaged your team to plan their migration from on-premises infrastructure to Azure. Before any migration can begin, you need to:

Understand the current environment — What workloads exist and how are they connected?
Assess readiness — Which workloads are ready for Azure?
Prioritize the migration — What moves first, and why?

Your simulated on-premises environment (ArcBox) contains:

Server	OS	Role	Notes
ArcBox-Win2K22	Windows Server 2022	Application Server	Hosts internal LOB app
ArcBox-Win2K25	Windows Server 2025	File Server	Department file shares
ArcBox-SQL	Windows + SQL Server	Database Server	Critical ERP database
ArcBox-Ubuntu-01	Ubuntu 22.04	Web Server	Customer-facing portal
ArcBox-Ubuntu-02	Ubuntu 22.04	Monitoring	Nagios/Grafana stack

Prerequisites

Before starting this challenge, ensure:

Azure 101 pre-work is complete
Team roles are assigned (facilitator, scribe, presenter, reviewer)
Whiteboard or flip chart is available

Your Tasks

Work with your team to design the assessment and wave planning strategy on your whiteboard.

Part A: Assessment Strategy (20 min)

Guiding Questions:

Discovery Approach
- How will you discover all workloads in the environment?
- What tools and methods will you use?
- What information do you need to collect?
Dependency Mapping
- How will you identify dependencies between servers?
- What happens if you miss a critical dependency?
- Agent-based vs. agentless analysis — which approach and why?
Assessment Criteria
- What factors determine if a workload is “ready” for Azure?
- How will you categorize workloads (ready, ready with conditions, not ready)?
- What blockers might you encounter?

Deliverable: Whiteboard diagram showing your assessment approach

Part B: Migration Wave Planning (25 min)

Use the Value vs. Complexity Matrix to prioritize workloads:

                    HIGH COMPLEXITY
                          │
    Strategic             │           Challenging
    Investments           │           (Plan Carefully)
                          │
    ──────────────────────┼──────────────────────
                          │
    Quick Wins            │           Fill-ins
    (Migrate First)       │           (Low Priority)
                          │
                    LOW COMPLEXITY
    LOW VALUE ────────────┼──────────────── HIGH VALUE

Guiding Questions:

Prioritization
- Which workloads are quick wins (high value, low complexity)?
- Which require more planning (high complexity)?
- What order makes the most sense?
Wave Design
- How will you group workloads into migration waves?
- What dependencies force workloads into the same wave?
- How long should each wave take?
Risk Mitigation
- What’s your approach for the SQL database (typically highest risk)?
- How do you handle the customer-facing web server?
- What if a wave fails — what’s your fallback?

Deliverable: Whiteboard showing migration waves with workload assignments

Part C: Success Criteria Definition (15 min)

Guiding Questions:

Migration Success
- How will you know the migration succeeded?
- What metrics will you track?
- Who signs off on completion?
Validation Approach
- How will you test workloads post-migration?
- What’s your rollback trigger?
- How long is the validation period?

Deliverable: List of success criteria for migration validation

Expected Deliverables

By the end of this challenge, your whiteboard should show:

✅ Assessment Approach Diagram
- Discovery method
- Dependency mapping approach
- Assessment criteria
✅ Migration Wave Plan
- Value/Complexity matrix with workloads placed
- Wave groupings with rationale
- Timeline estimate
✅ Success Criteria
- Validation checklist
- Rollback triggers
- Sign-off process

📸 Take a photo of your whiteboard — You’ll need it for your presentation!

📝 Fill-in-the-Blanks Template

Use this template to capture your team’s decisions:

### Team: ________________

### Assessment Strategy
- Discovery tool: _______________________________
- Dependency mapping approach: ☐ Agent-based  ☐ Agentless
- Data collection duration: ____________________

### Value vs. Complexity Matrix Placement

| Workload | Value (1-5) | Complexity (1-5) | Quadrant |
|----------|-------------|------------------|----------|
| ArcBox-Win2K22 | ___ | ___ | ________________ |
| ArcBox-Win2K25 | ___ | ___ | ________________ |
| ArcBox-SQL | ___ | ___ | ________________ |
| ArcBox-Ubuntu-01 | ___ | ___ | ________________ |
| ArcBox-Ubuntu-02 | ___ | ___ | ________________ |

### Migration Waves

| Wave | Workloads | Duration | Business Justification |
|------|-----------|----------|------------------------|
| 1 | ________________________ | _______ | ________________________ |
| 2 | ________________________ | _______ | ________________________ |
| 3 | ________________________ | _______ | ________________________ |

### Key Dependencies Identified
1. ________________________________________________
2. ________________________________________________
3. ________________________________________________

### Success Criteria
- ☐ ____________________________________________
- ☐ ____________________________________________
- ☐ ____________________________________________

### Rollback Triggers
- ________________________________________________
- ________________________________________________

Success Criteria (25 Points)

Criterion	Points	Description
Assessment approach defined	5	Clear discovery and assessment methodology
Dependencies identified	5	Method for mapping workload dependencies
Wave prioritization complete	10	Logical grouping with clear rationale
Rationale quality	5	Decisions are justified with business/technical reasons
Total	25

💡 Tip

💡 Start with business impact — Which workloads matter most to Contoso?

💡 Think about dependencies — The SQL database likely has apps that depend on it

💡 Non-production first — Consider migrating monitoring/dev environments before production

💡 Include one complex workload early — Learn lessons before migrating everything

Reference: CAF Migrate Phases

┌─────────┐   ┌─────────┐   ┌─────────┐   ┌──────────┐   ┌─────────────┐
│  PLAN   │ → │ PREPARE │ → │ EXECUTE │ → │ OPTIMIZE │ → │ DECOMMISSION│
└─────────┘   └─────────┘   └─────────┘   └──────────┘   └─────────────┘
     ↑
  YOU ARE HERE

⚠️ Watch out

Avoid over-optimising wave design without validating dependencies.
Keep migration rationale evidence-based, not assumption-only.

Reflection Questions

After completing this challenge, consider:

How did your team’s discussion reveal different perspectives?
What assumptions did you have to make due to limited information?
How would real dependency data from Azure Migrate change your plan?

Next Step

After your wave plan is complete and photographed, proceed to Challenge 2: Deploy Appliance to start discovering the actual environment.