54 Questions To Ask About Your Next Cloud Project

Cloud services make sense for many business IT projects, but shifting to the cloud requires careful planning. This list of questions to consider when moving to the cloud can make that process much easier and more effective.

We compiled this list through crowdsourcing. One of the activities during our recent Lifehacker Meetups involved attendees hearing about a Windows Azure project that had been implemented in that city and then listing the questions they would have asked to ensure that project was a success. We’ve gathered together all that reader wisdom into a collection of issues that are worth considering for any cloud project.

Some of these questions might seem obvious, but overlooking the obvious is a common failing in many IT projects. We’ve deliberately avoided highly specific technology questions here, since those will vary depending on the chosen platform and scope of your undertaking.

The big picture

• What is the budget for this project?
• What’s the deadline for deployment?
• What happens if we don’t meet the deadline?
• How will this system integrate with existing IT infrastructure?
• How important is scalability?
• Who are the key stakeholders providing support and direction to the project?
• Who ultimately makes the decision that the project has been a success/failure?
• Could you halve the cost?
• Could you deliver it tomorrow?

Selling the project

• What are the expectations for the business owner?
• What are the expectations for the end user?
• What are the day-to-day processes actually used with our current systems (not those we theoretically should follow)? Can these be replicated?
• What bespoke solutions have been built by users to work around existing limitations? Can these be replicated? Should they?
• What research into end user requirements has been undertaken to ensure we’re building something they need/want?
• How do you plan to attract a user base or convert existing users into the system?
• What type of service level agreement are you offering users?
• How much interface retraining will be needed?
• What’s the biggest problem with your current implementation?
• What are the essentials, the nice-to-haves and the unnecessary elements?
• Are your staff prepared to give up day-to-day management tasks?

System concerns

• What are the uptime requirements for the project?
• How many concurrent users do you want to support?
• What are the security requirements for this project?
• What are the supported platforms/languages?
• Do you have access to relevant development skills for those platforms/languages?
• Will your choice lock you in to a particular vendor for database, development tools, delivery browser or any other relevant technology?
• What is the risk management plan for your project?
• If one element in the system breaks, what happens?
• Where is the data centre located?
• Are there legal restrictions on where your data can be stored?
• Is usage of a specific data centre guaranteed?
• What are the benefits of your chosen cloud platform over competitors?
• How will we deliver support?
• Are there redundancy options covering both power availability and natural disasters?
• Does this need to integrate with a broader project methodology?
• How will you deal with concerns over speed of access?
• How can you effectively allocate resources so you don’t overpay?
• Will latency be an issue? If so, when?

Deployment concerns

• How easily can you transfer existing databases and resources into the system?
• Can you merge data sources and work effectively in a multi-tenant environment?
• Is a sandbox server available for app testing prior to deployment?
• How is support delivered from your cloud provider? Can you get a dedicated support person if needed?
• Is the browser interface standards compliant?
• Does the software cater for leap years, the year 2038 and the impending Mayan apocalypse?
• How can I automatically scale instances?
• Is one-click deployment of new services enabled?
• Are there datasets available for integration and analysis?
• Will all data be stored in the cloud or will data be replicated offline as well?
• If there is local storage, how are conflicts resolved?
• What level of granularity is required for reports?
• How will we measure improvements?
• What happens when everything dies at 7am on a Sunday morning?
• What is the air speed velocity of an unladen African swallow?
• Have you paid attention to every question?

Got additional suggestions for questions on this list? Tell us in the comments. And thanks to everyone who came to one of our meetups and contributed!