20 Questions

Cloud Questions to Ask

Essential questions to ask about cloud computing, helping you understand cloud services, evaluate vendors, and make informed decisions about cloud adoption and strategy.

1

What are your specific business needs and goals for moving to the cloud?

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Why this works

Establishes clear objectives and ensures cloud migration aligns with business priorities and delivers measurable value.

2

What is your total cost of ownership (TCO) for current infrastructure versus cloud solutions?

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Why this works

Provides realistic cost comparison including hidden costs, helping you understand the true financial impact of cloud adoption.

3

What security measures and compliance certifications does the cloud provider offer?

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Why this works

Ensures the provider meets your security requirements and regulatory compliance needs for your industry and data.

4

What is the provider's uptime guarantee and SLA (Service Level Agreement)?

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Why this works

Clarifies reliability expectations and what compensation you'll receive if the service doesn't meet promised availability.

5

What data residency and sovereignty requirements do you have, and can the provider meet them?

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Why this works

Ensures data is stored in appropriate locations to meet legal, regulatory, and business requirements.

6

What is the cloud provider's disaster recovery and backup strategy?

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Why this works

Reveals how your data and applications will be protected and restored in case of disasters or failures.

7

What migration strategy and timeline makes sense for your applications and data?

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Why this works

Helps you plan a realistic migration approach that minimizes disruption and risk to business operations.

8

What are the exit costs and procedures if you need to change providers or move back on-premises?

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Why this works

Ensures you understand vendor lock-in risks and have options if the cloud solution doesn't work out.

9

What support and service levels are included, and what additional costs apply?

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Why this works

Clarifies the support you'll receive and identifies any additional costs for premium support or services.

10

What cloud computing models (IaaS, PaaS, SaaS) best fit your needs?

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Why this works

Helps you understand different service models and choose the right level of management and control for your organization.

11

What scalability and performance capabilities does the provider offer?

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Why this works

Ensures the cloud solution can grow with your business and handle peak loads and changing demands.

12

What integration capabilities exist with your current systems and tools?

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Why this works

Reveals how easily the cloud solution will work with your existing technology stack and workflows.

13

What monitoring, logging, and visibility tools are available for your cloud resources?

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Why this works

Ensures you can track performance, costs, and security across your cloud environment effectively.

14

What training and change management will be needed for your team?

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Why this works

Helps you plan for the human side of cloud adoption and ensure your team has the skills needed.

15

What are the bandwidth and network requirements, and what are the associated costs?

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Why this works

Identifies network infrastructure needs and costs that are often overlooked in cloud planning.

16

What automation and DevOps capabilities does the provider support?

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Why this works

Reveals opportunities for improving efficiency through automation and modern development practices.

17

What governance and cost management tools are available to control cloud spending?

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Why this works

Ensures you can monitor and control costs to prevent unexpected bills and optimize spending.

18

What is the provider's track record for security incidents and how were they handled?

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Why this works

Reveals the provider's security history and their transparency and response to security issues.

19

What environmental and sustainability commitments does the provider have?

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Why this works

Shows their commitment to sustainability and helps you meet your organization's environmental goals.

20

What questions should I be asking that I haven't considered yet?

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Why this works

Shows openness to guidance and potentially reveals important considerations you may have missed.

Best Practices for Cloud Evaluation Conversations

Expert tips and techniques for getting the most out of these questions.

Best Practices

Start with Business Needs

Begin with your business objectives rather than technology features, ensuring cloud adoption serves your strategic goals.

Compare Multiple Providers

Evaluate at least 2-3 cloud providers to understand different approaches, pricing, and capabilities.

Plan for Total Cost

Consider all costs including migration, training, data transfer, and ongoing management, not just cloud services.

Question Sequences

The Business Assessment

1
What are your business needs for moving to the cloud?
2
What is your total cost of ownership?
3
What migration strategy makes sense?
4
What training will be needed?

The Provider Evaluation

1
What security measures does the provider offer?
2
What is the provider's uptime guarantee?
3
What support levels are included?
4
What are the exit costs and procedures?

Common Pitfalls

Don't Underestimate Migration Complexity

Cloud migration often takes longer and costs more than expected. Plan for challenges and allow extra time.

Don't Ignore Hidden Costs

Data transfer, support, training, and network costs can add up quickly. Factor in all expenses for accurate TCO.

Don't Skip Security Planning

Cloud security is a shared responsibility. Understand what the provider secures and what you must secure yourself.

Conversation Templates

The Cloud Strategy Discussion

1
Step 1: Start with: "We're exploring cloud options. What are our specific business needs and goals for the cloud?"
2
Step 2: Follow with: "What is our total cost of ownership comparison?"
3
Step 3: Deepen with: "What security measures and compliance certifications do we need?"

Further Reading

"Cloud Computing" by Thomas Erl
"The Cloud Adoption Playbook" by Moe Abdula
"Cloud Strategy" by Gregor Hohpe

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