Ready, Set, Roadmap—Getting Your Tech Transformation Moving in the Right Direction


Undertaking a big technology change for an organization is a lot like heading out on a road trip. The destination is exciting and you can’t wait to get there, but you need to give some thought to how you’re going to get from point A to point B to help the journey go off without a hitch.

With everything there is to do—exploring potential solutions, costing, implementation, integration, and training, while keeping your business up and running—it can be difficult to figure out where to start. That’s where strategic planning and building a roadmap come in. This process helps you make sense of a long list of mission-critical and interdependent things and put together a logical course of action.

The time to build a roadmap is immediately at the outset of a project. If you set out down the road without knowing your route—or how much it’s going to cost to get there—it could be a bumpy ride.

Let’s say your organization is looking to switch ecommerce platforms. This is typically a big project with a 1-3 year timeline. And just as if you were getting ready for a road trip, you need a plan, a budget, a process and achievable milestones to mark progress along the way. Roadmaps also align the technology change you are undertaking with your company’s short- and long-term goals.

What elements does this roadmap include?

  • A destination: The issue you are solving and the means you intend to use to do so, plus the criteria that mark completion
  • A carefully planned route: Establish milestones to assess, select and implement your new technology, and build timelines, budgets, and dependencies to consider during the change
  • A clear set of priorities: Set parameters around what is most vital at each stage of your project
  • Time to sightsee: Build leadership buy-in at the outset, and be sure to take the time to gather input and feedback from stakeholders along the way

Getting on the road

To get started on building your technology change roadmap, start with these four simple steps:

1. Choose your destination: What outcomes are you trying to achieve? Setting some strategic goals up front will help you prioritize your initiatives. Key performance indicators and milestones can come in a variety of forms, but you need a constant north star at all times. For example:

  • I need to increase conversion by X%
  • I need to decrease my total cost of ownership by $X dollars
  • I need to drive X% more traffic to the site

2. Plot the route: Build your plan, set your budget and milestones, and get the team moving towards the first goal. Track and measure your progress along the way and iterate as needed. Collaborate with your teams and make some lists: small tasks, critical needs, big ideas. Document everything in a central place, this way you’ll always have something to refer to in later discussions and evaluations.

3. Set your priorities: Answer the following questions to assign values to each milestone, goal, and requirement you’ve identified in the lists above to determine each one’s individual impact on you and your stakeholders while still driving towards your destination:

  • What is the level of effort required and the feasibility of what you’re trying to achieve?
  • What is the impact on your ultimate objective?
  • What are the quick and achievable wins along this journey? How do you group these together into thematic goals that map to your strategic goals?

4. Take time to sightsee: Ensure every voice is heard and consulted along the way by receiving and reinforcing buy-in from all key stakeholders, including executive sponsors, tech managers and end users. It’s the first step in alleviating the stress of worrying that every aspect is solely your responsibility, making everyone feel heard, and in making progress towards your goal.

Who gets a say?

Every successful roadmap should involve a process that considers input from all stakeholders. You need to create a dialog across your entire organization to quickly identify dependencies and potential conflicts well before they arise. However, strong leadership during big changes like these is also critically important and finding the right balance between that leadership and taking input from your stakeholders will ultimately impact how successful your transformation is.

Who should be involved in planning your roadmap? We recommend a cross-section of the following:

  • Executives and leadership—particularly with a project sponsor
  • IT stakeholders and technical or enterprise architects
  • Ecommerce representatives
  • Customer service, sales, marketing and brand strategy leads
  • Product owners
  • Distribution and fulfilment managers

By bringing representatives from each of these areas together, you get perspectives from all sides of your organization. When choosing participants, make sure you look for strategic thinkers who are willing to listen, learn and challenge the status quo. Also ensure that your roadmapping team is viewing the entire process through a customer-first lens.

At the end of the day, will every part of your plan go as expected? No. Will you immediately have the answer to every question that pops up along the way? Definitely not. But that’s the joy of the road trip. Always remember: progress over perfection. Learn as you go, enjoy the small wins, and know that with each step, you’re driving forward towards your destination.