How to Stay on Track with Your Digital Roadmap

A solid plan is essential for digital transformation. But that’s just the beginning. As you move from planning into execution mode, here are some practical pointers to help you achieve your vision for modernizing your business.

You’ve done the smart thing: rather than diving headfirst into technology changes, you’ve taken the time to create a detailed digital roadmap for your business. You’ve engineered a step-by-step plan, established KPIs so you can measure progress, and socialized the upcoming changes among your team.

All the key stakeholders in your company are onboard and ready to go. You have enthusiasm, commitment, and funding to fuel your journey. There’s just one problem: you’re not quite sure how to turn the key and ignite the engine of digital transformation.


No matter how thorough your plan, shifting from planning to execution can be challenging, especially when the path ahead involves unpredictable elements. As you well know, your digital roadmap gives you a flexible guide, but as you launch into the process of modernizing your business, you must be prepared to adapt and re-adapt.

Facing such uncertainty can make anyone a bit hesitant. But there’s no need to stall out before you’ve even started your digital transformation journey. By following a few simple practices, you can get your team moving and start reaping those quick wins you’re all so eager to achieve.

Foster the sense of shared ownership

Digital transformation means change, and change requires buy-in. Not just from leaders but from everyone across the organization, from customer service to production to the back office.

Keep those sparks of early enthusiasm alive by consistently reminding your team that the business is going through a metamorphosis.  Make the digital transformation journey an opportunity to engage leaders and employees in creative co-creation. The team that developed the roadmap together must stay together so they can build together.

Also extend the sense of ownership to stakeholders outside the company, including your customers. Share your excitement about the improvements ahead, emphasizing the value they’ll deliver for them. Relieve any anxiety about the future by referring to the digital roadmap, which provides a path forward through the uncertainty of change.   

Remember that slow and steady wins the race

Culturally, we’re programmed to believe that technology is magic, but digital transformation doesn’t happen with the swish of a wand. Digital transformation is a process, and it moves forward step by step. In many cases, it moves forward step by sidestep, or by two steps ahead and one step back.

Remind yourself and your team that you’re playing a long game. The roadmap you’ve created mitigates two common risks of digital transformation initiatives: overspending on poor-quality solutions and implementing flashy fixes that don’t make sense in terms of the big picture.

Remember too that a solid digital roadmap starts slow, with low-cost changes that result in quick wins. The first few steps along the path may feel perilous, but your planning should minimize the risk and optimize the return on investment.

Think like a scientist

A well-designed digital roadmap provides both clear guidance and flexibility. It gives directions for a series of experiments, allowing you opportunities to learn from each trial so you can continually adapt and keep moving forward with confidence.

When you adopt a scientific perspective on digital transformation, you come to realize that it’s not about getting things right the first time. It’s about exploring options, testing assumptions, investigating results, and refining solutions as you go. You don’t have to start the journey perfectly—you just need to begin.

Practice accountability

Your digital roadmap should establish timelines, budget guidelines, and team roles so you can keep everyone on track through the transformative process. Ideally, your roadmap also includes a strong set of KPIs so you can measure progress along your journey, not just at the end of it.

Focus your team on metrics that apply to both process and results. That way, when the going gets challenging and the ultimate vision seems far off, you can remind yourself of the progress you’ve achieved.

The KPIs you choose will largely determine the success of your digital transformation journey. Precise, realistic KPIs will motivate your team and spur them on whereas vague or overly ambitious KPIs will rub away at commitment and lead to frustration.

Find a partner for the journey

The most intrepid explorers take a guide with them as they travel into new territory. Sir Edmund Hillary didn’t reach the top of Mount Everest on his own; he had a Tibetan companion to show him the way.

As you embark on your trek to modernize your business, you may find it helpful to engage an experienced partner who can travel beside you. Not someone who will direct the journey but someone who will be there to answer questions and, more important, raise questions you might overlook.

At iTransform, we serve as sherpa to our clients throughout their digital transformation journey. Drawing on our experience working with many different industries, we:

  • Identify small issues before they become big issues.
  • Answer questions about “What if…?”
  • Recalibrate KPIs.
  • Source training solutions.
  • Liaise with providers of digital solutions (we speak their language).
  • Supervise certain implementation steps.
  • Hold the team accountable to timelines and budgets.
  • Coordinate team efforts.
  • Brainstorm ways to overcome challenges.
  • Recognize and measure successes.

With a thoughtful, committed partner by your side, the process of digital transformation doesn’t have to be intimidating. It becomes a shared adventure that enhances company performance and team confidence.

Curious about what it’s like to work with iTransform? To learn more, visit us at www.itransform.co.

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