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Today’s businesses need a defined strategy for the ongoing adoption of evergreen cloud technologies like Microsoft 365.

Help Employees Thrive

ThreeWill’s core focus is helping employees thrive in the Microsoft cloud and is based on the parallel concepts of flourish and prosper in the definition of thrive. However, there is a third definition of thrive, meaning to progress toward or realize a goal despite or because of circumstances.

It is this third definition that is the basis for this blog since a DEX (Digital Employee Experience) roadmap helps organizations progress towards the goal of an improved DEX. For purposes of this blog, the DEX roadmap guides the journey of adopting digital technologies in an organization to support a prioritized set of initiatives that improve the digital employee experience and overall employee experience.

Many of my colleagues at ThreeWill have written excellent blogs covering the definition and importance of the DEX and overall EX (Employee Experience). They’ve also provided some specific examples of particular focus areas for technology initiatives to enhance the DEX. While those blogs focused on the “why” and “what” aspects of the DEX, I’ll focus on the “how”.

The DEX Journey

Like any roadmap, a DEX roadmap communicates a high-level plan to achieve the desired outcome as well as major steps or milestones needed to reach it. Although it does not capture all the details of the plan, it is an invaluable tool for leadership teams to maintain the long view as they guide their organization through the DEX journey.

Author Gino Wickman calls this “climbing the tree”. He compares guiding long-term strategic efforts to a team of people cutting a road through a jungle. They might be a highly productive team at road building, but without a leader to periodically climb a tree and tell them if they’re headed in the right direction, they might very well be zigzagging or running in circles1.

You might think of this roadmap as a single visual, but there are actually many ways to visually depict organizational initiative roadmaps.

The Employee Experience Organization Initiative Roadmap

In practical terms, the DEX roadmap may consist of multiple documents covering starting vs. ending business scenarios, key objectives, timelines, success measurement, technologies leveraged, and adoption strategy.

Regardless of the document formats leveraged for the DEX roadmap, “technology enablers” will usually be identified for specific steps in the roadmap “journey”. These enablers will usually be related to deployments of Microsoft 365 applications or features within those applications.

We have seen a few common patterns for deploying M365 applications as part of this journey in our client projects. Probably the most common pattern is what I’ll call the “Organize – Collaborate – Communicate – Empower” pattern indicated below.

The Digital Employee Experience Journey

Organize: Initially, we may have an organization that contacts ThreeWill to say, “we have a document storage organization problem”. This could be based on a merger/acquisition situation or general disorganization evolving over time. The solution may involve content rationalization (getting the right content) and migration (moved to the correct location) in the M365 cloud.

Collaborate: However, most of these documents aren’t static and require an ongoing development and management process that involves the collaboration of groups of people. This motivates consideration of new ways of working using Microsoft Teams for groups of people collaborating on documents and communicating and collaborating in general. Helping employees understand best practices for using Microsoft Teams and OneDrive for document collaboration is a key focus here.

Communicate: Effective collaboration generally results in creating authoritative content that needs to be efficiently shared with the overall organization, not just within work groups. In fact, helping employees effectively locate and consume authoritative content (both documents and general corporate news & communications) come to the forefront in this phase. Consequently, we see Modern SharePoint-based Intranets and Microsoft Viva connections as key enablers in this phase of the journey.

Empower: The later phase of this journey typically focuses on more targeted improvements to the DEX. This could take the form of modernizing the line of business applications or automating repetitive yet business-critical tasks, using Power Apps or Power Automate as technology enablers.

Community Management: It’s important to note that this journey is constantly evolving with the advent of “evergreen”, i.e., continually changing, cloud technology platforms like Microsoft 365. So, this journey should not be viewed as a set of few specific “sprints” but rather a marathon involving a constantly evolving roadmap based on business and technology environments. ThreeWill provides a service specifically to align changing business scenarios with Microsoft’s constantly evolving M365 roadmap, called “Community Management”. Note – In this context, “Community” refers to the general community of employees/technology users.

Please note that the above journey is just one pattern we see with customers. Some customers have a different starting point or may have a completely different roadmap that leverages different M365 technology enablers.

The bottom line is that, once this journey starts, we’ve seen that it promotes the ability of the whole organization to re-think how they collaborate, communicate, and connect with people and information.

Technology is Not “the” Solution

Admittedly, the title of this section was chosen to grab attention, and, perhaps, it is a bit shocking considering that the above sections focused mainly on technology. However, it is based on a core fact that organizations will no longer invest in technology for technology’s sake. Technology must be seen as an enabler to solve real business problems. (Notice the term “enabler” in the previous section!). So, no discussion of a DEX Roadmap should be solely based on technology.

Microsoft shares this perspective in a white paper published in 2020 entitled “Accelerating Modern Workplace Productivity Adoption. This paper asserts that the effective adoption of M365 technology requires a shared journey between business and technology. Specifically, they state that any effective solution to leverage M365 technology must consider business process changes, behavioral changes, and cultural changes.

In the context of the DEX roadmap, this means that roadmap target objectives/milestones should be chosen based on a 5-step process:

*Diagram from Accelerating Modern Workplace Productivity Adoption

Overcoming Obstacles

You don’t get the benefits of developing and following a DEX roadmap without overcoming some obstacles. I’ve included a few common obstacles below.

Cost & Complexity – Overlaying all the applications and services available in Microsoft 365 on top of the business process and change management considerations mentioned above can be an ongoing headache that, if not managed, could result in negative cost impacts. To help sort out some of the complexity, Microsoft has developed the “Modern Collaboration Architecture (MOCA)” (for details, see the Accelerating Modern Workplace Productivity Adoption). While MOCA provides an excellent framework for developing a DEX roadmap, it does not make the process simple. Need convincing? Check out this overview diagram of the MOCA architecture:

*Diagram from Accelerating Modern Workplace Productivity Adoption

Misguided IT Decisions – Funding and support for a DEX Roadmap may evaporate if IT purchasing decisions are based on reasons that have nothing to do with corporate priorities. The result is that IT decisions will not be seen as contributing to corporate objectives in the same way that decisions in other business areas do.

Historically-based Employee Perspectives – Legacy approaches to technology deployments may result in a culture where employees view technology change as an imposition rather than something positive. This results in a history of failed IT initiatives as people ignore invites to training sessions, proposed IT changes are never truly adopted by users, and problems remain unsolved. Conversely, a DEX Roadmap is an excellent tool for promoting employee buy-in and avoiding getting sidetracked as new DEX ideas surface. Without a roadmap, there’s not a lot of confidence or comfort when you say, “We’ll get to it.” But when you have a DEX Roadmap, you can add it to the roadmap as evidence that it will be considered in the future.

One size may not fit all – If you are a small or medium-sized business, some of Microsoft’s MOCA mainstream recommendations and related M365 applications may not be a perfect fit for your organization. You may need to decide on alternative ways to accomplish similar outcomes for some of the benefits offered by the full suite of M365 applications. ThreeWill can help in evaluating alternatives based on our experience in guiding other small or medium-sized businesses.

It doesn’t happen overnight – A DEX Roadmap defines an ongoing program of effort to review, implement, and refine the roadmap. Depending upon your organization size/budget, this could include one or more of the following: full-time staffing (job listings for full-time “Director of Digital Employee Experience” are now common), assembling a center of excellence that includes representatives from business & technology areas of the organization, or leveraging a Microsoft partner (like ThreeWill) for assistance.

Despite the obstacles, opportunities for businesses offered by the M365 cloud platform are more exciting than ever and a DEX Roadmap helps keep organizations from being overwhelmed with all the possible technologies that exist in the Microsoft cloud.



Wickman, Gino. (2011). Traction – Get a Grip On Your Business (expanded ed). Benbella.

Other Digital Employee Experience blogs by ThreeWill:

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