Hi Reader,

I hope this email finds you well! I want to get straight to this week’s excerpt because I think it covers one of the most underutilized tools in the DX leader’s toolkit — and one that almost every organization I’ve worked with has gotten wrong in some way.

But first, a quick update on the manuscript.

I’m in the middle of a focused revision pass on Part 2, which covers all of the preparatory steps before a project kicks off. This is the section that I believe matters most, because as I argue throughout the book, we don’t have an execution problem in digital transformation — we have a preparation problem. I’m making sure every chapter in this section gives you something specific and actionable, not just general principles.

This week’s excerpt is from Chapter 5, which covers building your Technology Roadmap. If you’ve ever been part of an initiative that felt chaotic or disconnected from the company’s actual goals, this section explains why — and what to do about it.

Excerpt from The Digital Transformation Guidebook

Chapter 5: Building Your Itinerary

The GPS Your Digital Transformation Is Missing

Not too long ago, embarking on a road trip involved either wrestling with a paper map that never quite folded up the same way, or relying on multiple pages in an Atlas. Today we are fortunate to have GPS effortlessly guiding us from point A to B and suggesting detours based on road construction or traffic updates. Regardless of the navigation method, planning your route and referencing it along the way are crucial in ensuring you reach your destination.

When it comes to your DX journey, a technology roadmap is that essential navigation tool. When used effectively, the technology roadmap will allow you to manage resources, unite team members toward one goal, and facilitate an effective change management strategy. It lays out all planned initiatives and is a critical tool for annual planning and budgeting, as well as risk mitigation and communication strategies.

What a Technology Roadmap Actually Does

A technology roadmap is an artifact that outlines an organization’s technology adoption plan, detailing budget, milestones, risks, and more. It covers specific details for initial project phases and general outlines for future ones. An effective roadmap not only documents the list of planned implementations and what is needed to complete them, but more importantly it describes how each of these projects supports the overarching organizational goals, enabling future planning and effective portfolio management.

The biggest reason why a technology roadmap is so critical is that it ensures each department, team, and team member is aligning their individual and collective efforts around the organizational priorities. With a clear, prioritized roadmap, leaders are able to effectively communicate not just the overarching strategy of the company, but how each individual fits into that strategy.

This organizational change management piece is often overlooked when building a technology roadmap, but it is no less critical for its efficacy. The roadmap needs to communicate how your people will be equipped to handle these changes with technology, based on the results from the organizational maturity and risk assessments. This broad overview will be the bedrock upon which your OCM strategy will be built, empowering your team to take ownership of the changes and propel your organization to greater maturity, resilience, and success.

The benefits extend far beyond just aligning with organizational goals and priorities. A well-maintained roadmap promotes effective communication channels, helps manage interdependencies between different teams and departments, breaks down silos that hinder collaboration, reduces the level of risk associated with technological changes, and fosters stronger interpersonal trust within your team while also boosting morale and productivity levels. In short, putting in the work to outline a technology roadmap, communicate it to your team, and ensure it is well-maintained significantly reduces your chances of making costly, detrimental mistakes.

What Happens When You Don’t Have One

Neglecting to build or follow a technology roadmap results in the direct opposite of all those benefits. But arguably the biggest danger lies in the damage it causes to your teams.

If deadlines are continually pushed out or new initiatives and milestones added, it erodes people’s trust in the leadership, the organization, and each other. It increases frustration and causes a sense of stagnation. It is incredibly important to maintain motivation and morale, and that is done by setting accurate goals, milestones, and deadlines and then meeting them consistently — all of which cannot be accomplished without an effective technology roadmap.

Not following the roadmap results in misalignment between projects and organizational priorities, leading to wasted resources and ultimately, project failure. Without a well-maintained roadmap, you risk losing sight of the bigger picture, getting bogged down in unnecessary details or side projects that do not contribute to the overall goals, and losing your team’s trust and respect, which will crumble your organization’s culture.

The Six Critical Elements of a Technology Roadmap

Under each initiative listed in the roadmap, you should include six critical elements. While these can be included with varying degrees of detail, it is important to ensure all six are present for every opportunity on the roadmap.

1. Milestones & Releases
   Listing all relevant milestones or applicable releases for each project assists in providing a rough timeline. This timeline will be reevaluated and updated as new information comes to light. Don’t worry about being specific with projects further down the road if you don’t have that information yet. Focus on being as specific as you can with projects closer to the front of the roadmap and be prepared to adapt.
2. Resource Planning​
   When considering the resources needed to fulfill a project, include a variety of resources, not just financial. Consider including team members responsible for the project and any external resources needed such as consultants or contractors. By clearly outlining resource needs at the beginning, you can better manage your budget and ensure the right people are available when needed. ​
3. Budget​
   Include an overview of the budget considerations for all expenses including people resources, equipment, software purchases, external consultants, travel, and any other expenses that the implementation may incur. Don’t worry about fleshing out an entire project budget at this time — we will cover that step in more detail in a later chapter.
4. Training & Organizational Change Management​
   Change management is a critical component of a successful technology roadmap. Make sure to outline your organizational change management strategy in the roadmap including training plans and communication strategies. Without this step, user adoption will suffer, and your initiative will fail.
5. Assumptions​
   As it is impossible to obtain all the necessary data at this time, you will need to make assumptions about things such as design and scope. It is important to recognize, label, and document these assumptions so that they can be challenged and revisited throughout the journey.
6. Risk Factors​
   Call out any risk factors and known mitigation with as much specificity as possible. Risks may be general or specific in nature, with some having more obvious or immediate mitigation steps.

The Roadmap Is a Living Document

The technology roadmap is your tool to ensure that every project and person is supporting the overarching objectives. However, a tool is only useful as long as it is being used. For a technology roadmap to be effective, it must be managed properly and updated consistently.

Regularly review the roadmap with stakeholders to verify its accuracy and adherence. While it is good to try and make the roadmap as accurate and specific as possible, you should expect to make changes. The technology roadmap is a living, breathing document that should continuously evolve as the organization itself evolves.

Similar to a GPS rerouting you after taking a detour or a wrong turn, your technology roadmap should also adapt and shift to accommodate the changes and challenges that arise. When something is identified as being outside of the technology roadmap, it is important to get back on track — either by integrating the new information into the roadmap, or by terminating any project or initiative that falls outside of it.

I’d love to know — does your organization have a technology roadmap? And if so, is it actually being used as a living document or is it sitting in a folder somewhere? Hit reply and let me know. These are exactly the kinds of real-world stories that are shaping how I write the book.

I hope you found this email useful. I'd love to hear your feedback. You can send me an email with your thoughts or if you would like to talk to me you can use the button below to schedule a time on my calendar.

Kind regards,

Tory Bjorklund