8 Questions to Ask When Developing a Cloud Strategy

Estimated Read Time: 7 minutes

CloudStrategyThis article was originally published on Unicon’s blog. You can learn more about Unicon here.

In just a few years, we have seen acceptance of public cloud shift fairly dramatically from concern and skepticism to eagerly embracing the opportunities afforded. Five years ago, many of our hosted clients wanted to know that Unicon (and indirectly, they) had physical control of the data, servers, and other infrastructure. Today, confidence in cloud providers to deliver the highest levels of security and reliability led us to migrate all of our remaining colo (colocation) customers into Amazon Web Services (AWS). In most cases, those conversations were generally an enthusiastic “It’s a no-brainer, let’s go!”

“Let’s go!” quickly turns to questions of what, when, who, how, and why. There are a myriad of valid approaches to adopting cloud, ranging from tactical reasons to full-on, strategic “all in” approaches. Giving consideration to strategic questions can help provide a framework for the decision-making that follows. Below are samples of topics for your team to consider as they start to develop a cloud strategy.

What is the Big Driver?

Are the primary motivations lowering cost (if so, capex, opex, or both)? Is it to improve service levels, improve agility, avoid a massive technology refresh (aging data center or other infrastructure)? Alternatively, is the goal more tactical – get your feet wet and learn? Really tease out the big “why” and keep that as a touchstone for the decision-making to follow.

Enterprise Architecture

How is the cloud environment going to fit into the overall enterprise’s technical architecture? What key processes or workflows may need to span the current infrastructure/solutions and the cloud? Also, how will that evolve or change over time? Does this change key data architectures that support critical missions such as compliance, accreditation, and financial controls?

“All in” or “What fits”

Do you just “lift and shift” and then evolve applications to become more “cloud native” over time?

This can actually cover a range of guiding principles. “All in” can mean fully moving all infrastructure to the cloud, but it can also refer to “all in” on a particular solution leveraging all of the chosen vendor’s services and solutions versus just deploying basic compute and “rolling your own” from there. The trade-offs here are fairly obvious: lower effort, possibly lower costs, and improved reliability at the expense of high switching costs. Also, do you just “lift and shift” and then evolve applications to become more “cloud native” over time? Giving some thought to these in advance, and involving the application architects/teams in developing the guiding principles here will also help clarify the approach.


Obviously, security is a big topic. Be sure to consider how the current security strategy can be implemented in the cloud or if it will need revision. Do the potential vendors support the security constructs, certifications, and features required for the workloads and data you will be moving? Your security team may need to conduct or update the enterprise risk analysis to identify new or different risks and engage in the appropriate discussions to address them. Your security team may need to become familiar with cloud-specific controls such as the Cloud Security Alliance Cloud Controls Matrix to help manage cloud risks.

What is my Vendor Strategy?

Some of your vendor strategies can be informed by your other strategy positions and whether best-of-breed and breadth of available services is the primary driver, or if cost (or even an existing relationship) is of overriding concern. If you have a vendor risk management framework already in place, this can help support your vendor selection as well as on-going relationship management.


What changes to operational support (incident and problem management) will the cloud effort require? How will you assess operational readiness? As you move into “shared responsibility” models, how will you partner with your cloud vendor to address these questions?

Budget and Finance

Factoring in your other constraints and strategies can help inform when these types of strategies can yield savings.

Having a clear cost picture will be almost certainly required, along with addressing shifts from capex to opex. Also, will you need to “self-fund” your efforts through cost offsets and savings? In some cases, there are cost trade-offs that can be made by reserving capacity through up-front payments to lower per-unit costs over the long haul. Factoring in your other constraints and strategies can help inform when these types of strategies can yield savings. Make sure that you partner strongly with your financial organization on these topics and have appropriate budget and cost accounting controls in place to avoid surprises.

How will my Organization Support this?

What new skills will we need to acquire and how are we going to create the learning/training time and budget to make that happen? Can we partner on those skill gaps, either in the short or long term? How will we retain the folks that may feel their job is threatened? Be sure to be able to tell the story of why, why now, and “what is in this for me?” to onboard the broader team that will be impacted.

As a final note, remember to onboard your stakeholders with the strategy that your team has identified. Ask for candid feedback – poke holes, gain contrary views, and use those to address gaps to strengthen your plans and thinking. Then, “We’re going!” can be met with much deeper support and fewer roadblocks to overcome on the journey.

Of course, this is just a sample of the strategic discussion topics that will emerge in any cloud initiative. There are a variety of resources available on developing a cloud strategy, including Gartner templates, whitepapers from the major cloud providers, and conference presentations and publications. You can also give us a shout on our contact page to start a discussion – we’d be happy to talk.

Unicon, Inc. is a leading provider of IT consulting, services, and support for education technology and works with institutions and organizations to find solutions to meet business challenges. Marquess Lewis fills numerous roles at Unicon, with involvement in learning systems architecture for various clients, operations, architecture, and IT Security for Unicon’s hosted offerings and as a member of the Unicon executive team. Mr. Lewis has over 20 years of experience in complex systems development and operations, delivering SaaS platforms and services supporting millions of customers. A majority of this experience is in Education, both Higher Ed and K12 in the US and in global markets as well.
What other questions would you ask while developing a cloud strategy? Let us know in the comments.
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