Cloud initiatives require a heavy dose of people and process investment.

How to do cloud the right way

Move to the cloud or die is a common headline in today’s tech journals. Such an alarming statement is not far from the truth. Any long-term technology roadmap worth executive consideration must have a significant cloud component. Unfortunately, research finds most multi-year IT transformations dominated by the technology prospects. All too often, leaders neglect to anticipate the people and mindset changes required to sustain a shift to a cloud centric universe. If you are sitting down to map out your long term cloud strategy, please make sure to anticipate the budgets and expertise required to address the cultural shift, skill gaps, learning capacity and leadership skill changes.

The reality is, migrating just one workload to the cloud will potentially impact your current IT operating model. Such a change will require a well-thought-out transformation plan, and an action list that scales to the volume of the workloads you anticipate migrating. This article highlights six key activities you must do well to ensure a sustainable and scalable cloud transformation program.

Cloud Transformation is More Than Just Change Management

Many managers don’t realize the difference between “change” and “transformation.” Understanding that difference is more than semantics. Change management consultants at Prosci define change management as: “the discipline that guides how we prepare, equip and support individuals to successfully adopt change in order to drive organizational success and outcomes.” So “change management” means implementing finite initiatives, which may or may not cut across an entire organization. The focus is on executing a well-defined shift in the way things work. It’s not easy, but the end results are predictable.

Typical change management initiatives are a process improvement or the implementation of a new tool. For example, when a global publishing company needed to extend a new CI/CD automation framework into its federated business units, there were shifts in roles, processes, tooling and teamwork. The change affected dozens of roles in the operations group. By applying well-known agile change management principles and techniques — such as building a coalition of leaders, getting early results, engaging stakeholders and managing execution — the CI/CD automation was adopted successfully, and significantly improved the company’s aggregated software development cycle times.

Transformation is a more encompassing problem domain. Unlike change management, it doesn’t focus on discrete, well-defined change outcomes, but rather on a portfolio of projects, which are interdependent, or often closely coupled. More importantly, the overall goal of transformation is not just to execute a defined change, but to recast the organization’s capabilities and to discover a new or revised operating model based on a future vision. Transformation is much more unpredictable, iterative, and requires a lot of experimentation, aka “learning fast from trial and error,” as the Lean Startup business book explain. Transformation also entails much higher risk. And, even if smaller successive change initiatives lead to certain accomplishments within the transformation portfolio, the overall success of the transformation is not guaranteed.

Reinventing oneself as an ISV to a SaaS provider is a transformation example. When an incumbent global software company realized that small startups potentially threatened their leadership position, they realized their current on-prem software solution was losing its competitive advantage and evolving too slowly. To respond to the emerging threat, the leadership team launched a cloud transformation strategy, with the goal of building a new SaaS-based product offering. This included a number of major “must-do” activities: implementing public cloud platforms, refactoring the core software architectures, introducing 23 new technologies, and rebuilding, from the ground up, a new customer support model. The transformation also required leadership to align all initiatives to a new DevOps and “Customer-First” mindset.

Understanding that you are dealing with more than change is the first step in scoping your cloud transformation. In essence, a true transformation requires a shift in people, mindset and culture. This is not just a new set of cloud technologies and some process changes.

Planning Your Sustainable Cloud Transformation Initiative

Key Activity 1: Keep your executive and sponsorship team actively involved in the cloud creation process

Your cloud initiative will fail without sustained executive and sponsorship alignment. The politics, resistance to change and focus on maintaining the status quo impact leadership and employees alike. The imperative presented with aligning leadership is that they control access to the resources and funding required to design, build and operate your cloud transformation. Funding is ephemeral: key sponsors can change their minds, especially in the rapidly changing technology space where there’s a new fangled distraction invented every day.

Here there are no easy solutions. One approach is to achieve consensus early, to continuously challenge the correctness of the cloud vision and to constantly renew consensus as to the transformation’s direction. Too often, big programs try to over-mitigate risk upfront, based on the thinking that a fixed plan leads to fixed outcomes. One lesson learned from the Agile world is you never know all the information upfront, so don’t waste energy building a plan that pretends you do.

A powerful technique to achieve continuous executive alignment is to build a “Cloud Change Canvas.” A change canvas is based on the business model canvas concept, a tool created in the lean startup universe. A change canvas provides a one-stop view of the business’ urgencies, success metrics, target conditions, visions, investments and desired wins/benefits driving its cloud journey. Canvas authoring is a group activity — very visual, with a powerful style to engage participation. It’s like a business case, but it’s lightweight to create and easy to evolve as the team builds and learns. In summary, the exercise forces your leadership team to take ownership and sustain involvement in the cloud transformation process.

Key Activity 2: Assess your current cloud maturity and set direction

Most likely you are not starting from scratch. Even if you are, the fact remains that you can leverage the learnings of others who have cloud transitioned before you. One common approach is to conduct a Cloud Maturity Assessment. If you are familiar with CMMI’s Service Capability Maturity Model, then you are familiar with the tactic.

In the cloud context, a Cloud Transformational Maturity Model (CTMM) yields an effective cloud adoption strategy. A CTMM defines the characteristics that determine the stage of maturity, transformation activities within each stage that must be completed to move to the next stage, and outcomes that are achieved across multiple stages of organizational maturity. CTP developed a CTMM to assess companies across three focus areas: service operations, technology and human capital. The process is a simple gap analysis. The initial step is to assess the current state. Then, based on the organization’s existing cloud capacity and readiness, a future state is identified and recommendations developed to achieve the “To-Be” state. A CTMM is a power tool to set your cloud journey in the right direction.

Key Activity 3: Conduct a stakeholder analysis

Assessing and profiling your key stakeholders is imperative. By definition, transformation means challenging shared beliefs, and potentially breaking organizational infrastructures designed not to change. A systematic and structured approach to managing your stakeholders’ interests helps to ensure understanding and commitment to the cloud project. Also, grouping individuals and groups into discrete buckets facilitates building support networks to anticipate and manage people resistance. The analysis can be broken into two steps:

Step 1: A common stakeholder assessment approach is to identify and prioritize groups of individuals who:

  • Are directly impacted by the new cloud initiative — including sponsors and change agents
  • Are Indirectly impacted by the new cloud initiative — including enablers
  • Influence or power the new cloud initiative — including those who are with you and those who are not

Step 2: Once you complete qualifying constituents into manageable segments, plot an analysis matrix into columns labeled “Level of Awareness of the Cloud”, “Commitment to the Cloud” and “Influenced and Impacted by the Cloud.”

The resulting single page data graphic provides a high-level road map of who you need to engage frequently, at mid-milestone and at major-milestone. For example, “I need your commitment and active roles in creating my cloud goals; this is the target you need to meet on a weekly, if not daily, basis.

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Key Activity 4: Design for effective communications and engagement

With a stakeholder map in hand, you are ready to establish an effective communications and engagement strategy to move leaders and teams to build sustained commitment to the new cloud vision. A cloud transformation plan needs to define and track engagement to address key content and timings. The tactical matters, such as engagement owners, mediums and measuring success metrics, all need definition.

Establish guiding principles to drive the change engagement. For example, the transformation adopters must own the cloud design, build and run phases. If they don’t, then you own the risk of building the wrong people, process and technology solution. To further help drive commitments, make certain that:

  • Success is measured in business outcomes, not just deliverables — business value must result from the cloud implementation, the sooner the better
  • Information flows two ways and is open and honest — a dialogue to provide feedback is established and acted on
  • Roles and responsibilities are clear — when people know what is expected of them, they can deliver results and respect accountability

Key Activity 5: Understand the re-skilling, education and training implications

One of the cloud’s dirty little secrets, often not discussed, is that the newfound automation in these hyperscale platforms can render as much a significant portion of the operational staff unnecessary. While certain job functions may be automated out of existence, the people in these functions still have great value to the enterprise. This is where the importance of re-skilling, education and training come into play.

Such efforts entail a range of formal and informal activities aimed at building cloud knowledge, skill and experience. You want your training program to construct a bridge from the traditional operating world to the new cloud centric world. Your investment demonstrates the company’s commitment to its employees. It also enables the evolution of valuable competencies and services.

A unified cloud learning plan augments existing in-house expertise and development capabilities with vendor provided materials. In addition, it creates learning communities and networks comprised of early adopters. A typical training program is a four phase life cycle:

  • Assess — Determine existing skill gaps, learning objectives and certification tracks
  • Communicate — Broadcast curriculum tracks, knowledge sharing opportunities and expert networks
  • Celebrate — Reward and recognise those that participate
  • Measure — Establish online portals and dashboards to report training participation and to track cloud specialists

Key Activity 6: Start building cloud and demonstrating value fast

This is the execution phase of the transformation, where you start to iterate and increment your demonstrable cloud solution. As opposed to a design-then-build “Big-Bang” technology project, the more successful path is to break the problem into small changes.

This is where you introduce the Minimal Viable Cloud (MVC) methodology. An MVC is derived from the lean startup community and their Minimal Viable Product (MVP) concept. The approach is to build a cloud implementation with just enough features to satisfy early customers, and to provide feedback for future development. Time box yourself to a six- to ten-week implementation window. This ensures you keep the requirements minimal, while turbo charging the learning and buy-in. Make sure to migrate a real-life workload, an application that tests the boundaries of acceptable business risk criteria.

Making it count motivates the organization to do it correctly. No pain, no gain, as the saying goes. Once you complete your initial MVC, continue to add workloads and capabilities to it to test additional controls and services. You will not always get it right the first time, so be ready to pivot if needed. Learn to tolerate failure and trust in yourself to always respond quickly.


The six key activities I’ve outlined above are intended to help you deliver a sustainable and scalable cloud transformation. At the end of the day, they propose to manage your three most common program risks:

  • Managing the people resistance to change
  • Building the right solution
  • Institutionalizing the change beyond the program timeline

Weaving in modern day lean and agile practices provides the change management method to break up a very large problem domain into manageable pieces. My goal in this article is to provide you with a practical reference guide to now sit down and plan a long range cloud transformation.