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    May 19, 2021

    An Agile Strategy for Maximizing Business Value from Cloud Migrations

    As outlined in my earlier post (“Harnessing Cloud Services to Fuel Continuous Innovation”), many cloud migrations fall into the “ready, fire, aim” category. Based on executive edicts, teams are tasked with executing on a migration, while having little or no clarity into the business outcomes that are expected.

    Like any initiative, cloud migrations can provide significant potential benefits. However, these migrations need to be defined and managed effectively for that potential to be realized. In this post, I’ll outline an agile strategy that can help teams realize maximum business value from their cloud migrations.


    Once teams embark on their cloud migration efforts, they encounter new terrain and often hit stumbling blocks. While approaches to managing cloud migrations vary, many organizations are contending with similar challenges:

    Limited Visibility

    For managers to track status, they rely on cobbled-together spreadsheets and on teams doing manual updates. Often it falls to designated project managers to reach out to various teams; get subjective updates on whether projects are red, yellow, or green; and then manually generate reports. Beyond being extremely time consuming, these manual efforts lack currency and accuracy.

    In other cases, teams use separate task or project management tools, which are disconnected from investment planning approaches. Ultimately, at any given time, managers are not seeing the real execution status; they’re seeing a collection of team members’ subjective interpretations of where things stand. Because they’re not getting visibility into how execution is actually taking place, leaders are only finding out about delays and issues when it’s too late.

    Treating as Traditional Projects vs. Products

    In many organizations, cloud migrations are treated as projects. Staff are focused on specific deliverables and end dates, versus taking a more holistic, end-to-end product perspective. Fundamentally, these point-in-time projects are perceived as having a discrete end date, and they lack any clear definition of expected customer value. Plus, success is never tracked against whether value was delivered. (For more information on the distinction between projects and products and how to make this transition, see our blog post, “Becoming a Product-Focused Organization.”)

    Using Waterfall Approaches

    Rather than employing an agile strategy, teams often take a waterfall-based approach to their cloud migrations. Instead of managing migrations in an iterative fashion, teams take a “big bang” approach. Consequently, teams are not iterating, not getting regular feedback, and not assessing what kind of progress they’re making against plans and strategies. Ultimately, initiatives miss the mark, and it isn’t until the migration is over that leaders even realize that’s the case.


    To overcome these obstacles and set the stage for successful cloud migrations, teams need to focus on addressing the following requirements:

    Establish the Business Strategy

    Fundamentally, before any moves are made, it’s critical to establish clear top-level objectives. Simply put, it’s vital not to be migrating “because the CEO said to.”

    To start, migration initiatives have to be mapped to an overarching strategy. Teams need to start with a business strategy and a clear understanding of how a cloud migration will enable or complement that strategy. Ultimately, teams need to define in concrete terms the business value that will be delivered. (For more on this topic, see our blog post, “How to Establish Customer Value Definition—Before Funding Occurs.”)

    Establish a Plan to Execute Against Strategy

    Leveraging an advanced investment planning platform, teams need to define how they’ll execute on the strategy, including the investments that are required and the value streams that will be involved in advancing the strategy.

    Teams must define milestones that are linked to the top-level cloud transformation strategy. They must also iteratively define the steps and activities involved in pursuing the strategy. Some key considerations include determining how to design the architecture, provision cloud platforms, establish automation, allocate storage, and configure networks. Teams also need to weigh the pros and cons of various cloud approaches, for example, in the case of applications, determining whether to lift and shift, rewrite, or rearchitect code.

    It is vital to define all that work and ensure it’s linked to an investment planning solution, so, as teams initiate tasks and iterate, progress is visible.

    Gain True End-to-End Visibility

    On a continuous basis, it’s important for teams and leaders to centrally, uniformly manage strategy. This includes tracking progress, as well as managing funding and execution. As sprints and iterations progress and stories are completed, it is key to ensure status automatically rolls up into management dashboards and reports, so executives can track the percentage completed against plan. It’s vital that these rollups happen based on actual work completed, not on manually generated, subjective reporting. Ultimately, in this way, teams will be able to establish the visibility they need to tie execution back to strategy, and back to funding.

    Managing Investments

    It is vital for leaders to intelligently manage investments, and this is especially true for funding of cloud migrations. To start, leaders need to define big investment categories. In agile terminology, these are the “epic-level” activities that support top-level initiatives.

    Often, teams encounter sprawl and proliferating costs after migrating to the cloud. Consequently, cost management represents a vital effort. Leaders need investment management planning platforms that enable teams to track ongoing investments and ensure resources are provisioned and allocated optimally. It is essential to keep track of investments on a continuous basis to ensure costs don’t spin out of control.

    Managing Work

    As outlined earlier, teams should be employing an agile strategy and taking an iterative approach to their cloud migrations. As part of this, it’s vital to manage work effectively. Teams need to establish mechanisms for continuous iteration, feedback, and optimization.

    Toward that end, teams need to gain ongoing feedback on execution, and leaders need to be able to gain visibility into the progress being made toward the attainment of the agile strategy. They then need to manage continuous iteration and refinement to maximize the value ultimately realized. Teams need to constantly validate hypotheses around migrations. Plus, on an ongoing basis, it is vital to ensure that teams are focused on the highest value, lowest cost efforts.


    Like many key initiatives, cloud migrations represent strategic efforts for the business. Fundamentally, these are journeys, and they should only be started once there’s a clear picture of what the ultimate destination is. By starting with a clear view of business objectives, and seamlessly, uniformly managing work and funding throughout the process, teams can put their organizations in the best position to maximize the potential advantages of their cloud migrations.


    Dan Rice

    Dan Rice is an executive advisor with 25+ years experience in consultant, advisory and leadership roles in Web Services (AWS), Aviation, Telecommunications, Insurance, Automotive and Retail. Dan advises enterprises in the areas of cloud, business agility, value stream management and digital innovation.

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