Digital Transformation Readiness Assessment

A digital transformation readiness assessment helps business leaders determine a starting point for building a DX roadmap.

Table of Content

    Digital Transformation Readiness Assessment

    Digital transformation is an org-wide effort involving many people, processes, and moving parts.

    All these different elements must come together in exactly the right way to deliver the results you’re looking for. Without a plan, it’s impossible to allocate resources, establish timelines, or measure progress toward big DX goals — and as a result, initiatives fail.

    But, even the planning process requires a good amount of preparation. You’ll want to ensure that your big-picture DX vision has purpose and direction. And, that your organization has what it takes to see things all the way through.

    A digital transformation readiness assessment helps business leaders do exactly that. It gives you a starting point for building a DX roadmap by identifying gaps in your strategy and the specific actions you need to take before moving forward.

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    In this article, we’ll go over some of the criteria included in a typical readiness assessment.

    What is a Digital Transformation Readiness Assessment?

    A digital transformation readiness assessment is a comprehensive analysis of your org’s current state to determine whether you’re ready to embark on a digital transformation journey.

    Done right, a readiness assessment identifies what specific actions you need to take to build a strong foundation for reaching critical transformation goals.

    Here, the aim is twofold. First, it’s identifying barriers and gaps that must be addressed before plans can move forward. And second, it’s establishing a baseline you can use to start building your DX roadmap.

    What’s Included in a Digital Transformation Readiness Assessment?

    The process typically centers on three core dimensions: people, processes, and technologies – looking at factors like available resources, operating models, data maturity, and culture, among other criteria.

    In these next few sections, we’ll go over some of the questions you might find on a typical readiness assessment.


    Businesspeople putting working together to complete a puzzle.

    One of the primary goals of a DX readiness assessment is understanding what it’s going to take to ensure that the transformation produces meaningful value for the business.

    So much of digital transformation is about people — culture, organizational structure, individual and team capabilities, cross-functional collaboration, and so on

    It demands a collective mindset shift that’s often harder to pull off than some of the more technical aspects of transformation.

    • Do you have a shared vision, clear goals for the proposed transformation?
    • What are your primary business objectives — both short and long-term? A year from now? Five, ten years down the line
    • How will these goals materially affect your overall business?
    • What has been the biggest company-wide change that has occurred within the past 1-3 years? What went well and what didn’t?
    • What is the status of your current initiatives? Are they on-track?
    • Is there clarity/alignment around priorities, objectives?
    • Is there buy-in from the top?
    • Are champions and leaders embedded across the entire organization?
    • Do you have a robust change management strategy in place?
    • How does your internal culture impact your ability to compete/innovate/adapt to change?
    • Does customer experience inform/influence everything you do?
    • How effectively does your org leverage data?
    • Does data maturity vary between teams? Individuals?
    • Do individual employees have the skills necessary for transformation?
    • Where are people running into trouble?
    • What are they hearing from customers?


    Understanding how core business processes are working is another key part of the readiness assessment.Two businesspeople sitting across from each other at a table in front of a checklist.

    Relying on analog, manual processes versus digitized, automated ones often determine whether your org is ready to transform or needs to deal with a few things first. Processes are also central when it comes to eliminating inefficiencies, mitigating risk, enforcing governance policies, and more.

    Not every transformation initiative requires you to reengineer every single business process. But, more often than not, you’ll need to adjust or replace existing processes and workflows – especially if you’ve been using them for years and/or your DX project involves replacing legacy solutions.

    That said, the main goal here is ensuring that you’re starting from a solid foundation — with well-designed processes, end-to-end visibility, and standardized system for measuring success.

    • Here, you’re trying to answer the following questions:
    • Have you mapped out all business processes, workflows, relationships, and dependencies?
    • Which processes deliver the desired results?
    • Are there any existing processes that hinder productivity?
    • Or prevent people from completing their work?
    • Where do redundancies/inefficiencies exist?
    • Do any current processes prevent individual contributors, business units, or the organization as a whole from reaching critical goals?
    • Where, specifically, are people running into barriers?
    • How do those barriers impact the organization, individual employees, and customers?
    • Do you have a clear picture of what needs to change – and why?
    • And – how, exactly, will you make that happen?
    • Do new solutions align with the current processes & workflows that are still working?
    • If not, what is your plan for adapting them to fit with the new system?
    • Do you currently offer a best-in-class digital experience?
    • Are products and services designed as digital-first experiences?
    • Are touchpoints connected across the entire digital ecosystem?
    • Can you effectively leverage data to optimize experiences in real-time?
    • Do your customers trust your systems/processes to deliver actions and recommendations with their best interests in mind?
    • How are you currently measuring customer experience?


    Businesspeople interacting with technology.The last piece of this puzzle is technology.

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    Once you’ve determined that your people and processes are ready to transform, it’s time to take a closer look at your tech.

    Technology is the enabler that makes it possible to automate processes, enforce governance, scale production, and so on. But readiness can only be defined in context with DX goals and tech maturity level.

    Past initiatives like ERP implementations or cloud migrations make it possible to reap the benefits of more advanced initiatives. For example, you can’t take advantage of digital twins or the IoT unless you’re already working with a unified system with tight integration across the entire enterprise.

    Broadly speaking, you’re trying to determine whether your existing technology can support your digital transformation plans. And, if the answer is “no,” then what needs to be retired, repaired, or replaced in order to move things forward?

    Organizations must also ensure that they have a system and standards for evaluating digital technologies and testing potential investments under a variety of conditions to determine whether they are capable of meeting new needs.

    • All that in mind, here are some questions you might ask yourself at this phase in the assessment:
    • What is the state of your existing infrastructure?
    • What resources are available?
    • Which resources need to be retired/replaced?
    • Does any of your current hardware/software/infrastructure put your business at risk?
    • Are you still using on-premises solutions?
    • If so, what are your plans for moving to the cloud?
    • Are you using physical infrastructure – will that be included in this initial transformation, or will you be replacing it?
    • What is the budget estimate for this project?
    • What tools/tech will you need to invest in to achieve DX goals?
    • What existing solutions are capable of supporting this initiative?

    Red Flags That Indicate You’re Not Ready to Transform

    We should also mention that there are some signs that may indicate you need to go back to the drawing board before your DX plans can move forward.

    In those instances, it’s not worth running through the assessment just yet. (In that case, you’ll want to evaluate your strategy and figure out how to address these issues before it even makes sense to start making serious DX plans.

    A few things to watch out for:

    • There’s no definitive vision.
    • Employees lack the mindset and/or tech skills needed to pull off the transformation.
    • You don’t have support or buy-in from internal experts.
    • The strategy is too narrowly focused on IT or doesn’t include the entire organization.
    • You don’t have a comprehensive change management strategy in place.
    • There’s no clear sponsor at every level of the organization.

    Final Thoughts

    Before embarking on any transformation journey, you need to be certain that you’re fully prepared to see this thing through.

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    A digital transformation readiness assessment can help your organization map out a path to success and avoid common pitfalls.

    While a digital readiness assessment can’t guarantee DX success by itself, it is, however, a powerful tool that can help you lay the groundwork for success.

    Working with a partner like Velosio can help you determine if you’re ready to take on this challenge and ensure that you focus on the right things and don’t overlook any important steps.

    But more importantly, we’ll help you figure out what happens next. Contact us today to book an initial consultation or chat with one of our digital transformation experts to learn more.

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