Cloud Readiness Score
Cloud Readiness Assessment Checklist
Evaluate your organization's preparedness for migrating to the cloud with our comprehensive, step-by-step guide
Cloud Readiness Assessment Checklist
Migrating to the cloud is a strategic milestone for many small and mid-sized enterprises (SMEs).
Industry trends show that cloud adoption is accelerating – Gartner predicts over 85% of organizations will embrace a cloud-first strategy by 2025. However, moving to the cloud isn't a simple flip of a switch. Not every IT asset is cloud-compatible, and not all workloads benefit equally from cloud hosting.
This comprehensive checklist is organized around key readiness pillars – Infrastructure, Applications, Security & Compliance, Cost & ROI, and Organizational Preparedness – with an emphasis on Microsoft Azure. Use this as an interactive guide to methodically evaluate your cloud readiness.
85%
Cloud-First Strategy by 2025
40%
TCO Reduction Potential
94%
Report Security Improvements
Cloud Insight
Organizations with proper cloud readiness assessments have 35% more successful migrations.
Cloud Migration Challenges
Current IT Infrastructure Assessment
Evaluate your existing infrastructure to ensure it can integrate with Azure cloud services
Preparing Your Foundation for the Cloud
Before moving any workload to Azure or another cloud, take stock of your current IT environment. This involves examining your hardware, network, and virtualization platforms to ensure they can integrate with the cloud.
Network Readiness Is Critical
Microsoft's Azure Cloud Adoption Framework emphasizes that network topology and connectivity are critical foundations for cloud design. Overlooked infrastructure elements (like network bandwidth or legacy hardware) can derail a migration.
Some companies find that a small pilot runs fine, but scaling up exposes network bottlenecks: moving large data and voice traffic to the cloud can turn into a "major network program with unexpected cost implications" if the WAN is not prepared.
Infrastructure Assessment Checklist
Use the interactive checklist below to evaluate your infrastructure readiness for cloud migration. Check off items as you review them to track your progress.
Azure Migration Benefits
Reduced Infrastructure Costs
Eliminate capital expenditures on hardware replacement cycles
Increased Scalability
Scale resources up or down based on actual demand
Enhanced Business Continuity
Built-in disaster recovery and high availability options
Modern Security Features
Access enterprise-grade security technology and compliance
Infrastructure Readiness Interactive Checklist
Track your infrastructure assessment progress by checking off completed items. This checklist covers the essential aspects of infrastructure readiness for Azure migration.
Servers & Hardware Inventory
Virtualization Platforms
Network Assessment
Storage and Database Assessment
Legacy and Specialty Systems
Environmental Documentation
Application Assessment
Evaluate your existing applications to ensure they are ready for cloud migration
Application Readiness Assessment
Before migrating applications to the cloud, it's important to assess their readiness. This involves evaluating the application's architecture, dependencies, and potential for migration.
Application Migration Strategy
A well-defined migration strategy can make the application migration process smoother.
Some applications may require significant changes to be cloud-compatible. For example, applications that rely on specific on-premises hardware or software may need to be rearchitected for cloud hosting.
Application Assessment Checklist
Use the interactive checklist below to evaluate your application readiness for cloud migration. Check off items as you review them to track your progress.
Application Migration Benefits
Reduced Application Costs
Eliminate capital expenditures on hardware replacement cycles
Increased Scalability
Scale resources up or down based on actual demand
Enhanced Business Continuity
Built-in disaster recovery and high availability options
Modern Security Features
Access enterprise-grade security technology and compliance
Application Readiness Interactive Checklist
Track your application assessment progress by checking off completed items. This checklist covers the essential aspects of application readiness for cloud migration.
Application Architecture
Application Dependencies
Application Security
Application Performance
Security and Compliance Requirements
Ensure your cloud environment meets your security standards and regulatory obligations
Securing Your Cloud Environment
Moving to the cloud introduces a shared responsibility model for security: Azure provides a secure foundation, but it's up to you to secure your applications, data, and identities in the cloud. For SMEs in regulated industries or handling sensitive data, compliance considerations are equally important.
The good news is that leading cloud platforms like Azure invest heavily in security – 94% of businesses noted improvements in their security after moving to the cloud – and offer a broad range of compliance certifications (Azure has over 90 compliance offerings covering global standards and regulations).
Avoiding Security Misconfiguration
The challenge is configuring and managing the cloud securely: a misconfigured cloud resource can create vulnerabilities. Gartner estimates that through 2025, 99% of cloud security failures will be the customer's fault – not the cloud provider's, mainly due to misconfiguration or inadequate oversight.
Security and Compliance Assessment Checklist
Use the interactive checklist below to evaluate your security and compliance readiness for cloud migration. Ensure you've addressed all key security aspects before moving workloads to Azure.
Shared Responsibility Model
In the cloud, security responsibilities are shared between you and Microsoft Azure:
Microsoft's Responsibility:
- Physical security of data centers
- Network infrastructure security
- Hypervisor security and isolation
- Cloud service security and patching
Your Responsibility:
- Identity and access management
- Data classification and protection
- Operating system security (for IaaS)
- Application security and configurations
- Network controls within your environment
Security & Compliance Interactive Checklist
Track your security assessment progress by checking off completed items. This checklist covers the essential aspects of security and compliance readiness for Azure migration.
Compliance Standards and Requirements
Cloud Security Architecture
Identity and Access Management
Data Protection and Recovery
Security Operations and Monitoring
Cost and ROI Considerations
Understand the financial impact of your cloud migration and maximize return on investment
Understanding Cloud Economics
One of the biggest questions for any SME considering a cloud move is: What will it cost, and will it save us money in the long run? Cloud economics work differently from traditional IT. Instead of large upfront capital expenditures on hardware, you have ongoing operational expenditures for cloud services.
This can lead to cost savings and improved cash flow – you pay only for what you use – but it can also lead to surprises if not monitored. In fact, managing cloud spend has become the #1 challenge for organizations, cited by 82% of cloud decision-makers.
Potential for Significant ROI
When done right, cloud adoption can drive significant ROI: an Accenture study found you can reduce total cost of ownership by up to 40% by migrating to public cloud, and a Deloitte survey noted that SMBs using cloud achieved 21% higher profit and 26% faster revenue growth than their peers.
Cost and ROI Assessment Checklist
Use the interactive checklist below to evaluate your financial readiness for cloud migration. Create a clear business case and establish cost governance for your cloud environment.
Cloud vs. On-Premises Costs
Cloud migration shifts your IT spending model from capital expenditure (CapEx) to operational expenditure (OpEx):
Traditional On-Premises Costs:
- Server hardware (every 3-5 years)
- Storage systems
- Network equipment
- Data center space/power/cooling
- IT maintenance staff
- Software licenses
Azure Cloud Costs:
- VM compute (per hour/month)
- Storage (per GB/month)
- Network traffic (per GB)
- PaaS services (databases, etc.)
- Support plans
- Azure Reserved Instances (optional)
Cost & ROI Interactive Checklist
Track your financial assessment progress by checking off completed items. This checklist covers the essential aspects of understanding and optimizing cloud costs.
Current IT Cost Baseline
Cloud Cost Estimation
Pricing Model Optimization
Migration Investment Planning
Cost Management and Governance
Organizational Readiness
Prepare your team and organization for the cultural and operational shift to the cloud
People and Process Transformation
Cloud migration is as much about people and processes as it is about technology. Organizations that focus exclusively on technical aspects without preparing their teams often struggle with adoption, creating resistance and reducing the ROI of cloud investments.
Skills Gap Challenge
According to IDC, 70% of organizations have reported a significant cloud skills gap, making training and organizational readiness critical success factors for cloud adoption.
For SMEs, this often means developing new skills within existing IT teams, creating cloud governance frameworks, and establishing new operational processes for managing cloud resources (often called Cloud Center of Excellence or Cloud Operations teams).
Organizational Readiness Checklist
Use the interactive checklist below to evaluate your organizational readiness for cloud migration. This covers critical aspects like skills readiness, change management, and operational processes.
Cloud Operating Model
Moving to the cloud requires new approaches to IT operations:
Traditional IT Operations:
- Infrastructure-focused teams
- Manual provisioning workflows
- Fixed capacity planning
- Periodic hardware refreshes
- Asset-based management
Cloud Operations Model:
- Service-oriented teams
- Self-service and automation
- Dynamic capacity optimization
- Continuous innovation cycles
- Consumption-based management
Organizational Readiness Interactive Checklist
Track your organizational readiness by checking off completed items. This checklist covers the essential aspects of preparing your team and processes for cloud adoption.
Skills and Training
Cloud Operations Model
Change Management
Cloud Governance
Multi-Cloud Considerations
Evaluate whether a multi-cloud approach is right for your organization
Managing Multiple Cloud Environments
While our checklist focuses on Azure readiness, many organizations ultimately adopt a multi-cloud approach. Gartner reports that over 81% of public cloud users work with two or more providers. For SMEs, this decision introduces both benefits and complexity.
Strategic Benefits vs. Operational Complexity
Multi-cloud strategies can reduce vendor lock-in and allow you to leverage each provider's strengths, but they also increase management complexity, require broader skill sets, and may reduce volume-based discounts from a single provider.
For most SMEs starting their cloud journey, focusing on a single cloud provider offers the simplest path to success. However, you should still evaluate whether specific workloads might benefit from alternative platforms—for example, specialized AI/ML capabilities or unique services offered by specific cloud providers.
Multi-Cloud Strategy Checklist
Use the interactive checklist below to evaluate whether a multi-cloud approach makes sense for your organization, and if so, how to prepare for it effectively.
Multi-Cloud Drivers
Best-of-Breed Services
Leverage specialized services unique to each cloud provider
Reduced Vendor Lock-in
Lower dependency on a single cloud provider
Geographic Coverage
Access to data centers in regions not served by your primary provider
Business Continuity
Redundancy across providers for critical systems
Multi-Cloud Strategy Interactive Checklist
Track your multi-cloud assessment by checking off completed items. This checklist helps you determine if multi-cloud is right for your organization and how to prepare.
Multi-Cloud Evaluation
Multi-Cloud Management
Technical Standardization
Operational Readiness
Conclusion and Next Steps
Prepare for a successful cloud migration with confidence
Your Cloud Journey Awaits
Embarking on a cloud migration is a significant undertaking, but with this comprehensive readiness checklist, you can proceed with confidence rather than encountering surprises along the way.
The cloud can make your business remarkably agile and resilient – if you prepare properly.
Benefits of a Well-Planned Cloud Migration
What's Next in Your Cloud Journey?
With your cloud readiness assessment in hand, the next phase is to create a detailed migration plan (which workload moves first, timelines, who is responsible for each task) and to design your cloud architecture ("landing zone") according to the requirements you've gathered.
Detailed Migration Plan
Develop a phased migration strategy with clear timeline and responsibilities
Azure Landing Zone
Design and implement your secure, scalable cloud foundation
Migration Execution
Execute migration with proper testing and validation
You don't have to do it alone – our team is here to help translate this checklist into action. As a trusted cloud migration partner, we bring deep expertise in Azure and other clouds, ensuring each pillar – from network design to application refactoring to user training – is handled with best practices.
Ready to Take the Next Step?
Download your completed checklist or schedule a consultation with our cloud migration experts.
