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Don't Project Manage Your Digital Transformation: Try A Roadmap Mindset For Better Results

When I talk to clients and prospects about Digital Transformation and Project-to-Product Transformation, the first few questions I’m typically met with are “What’s the plan?” and “How long will it take?” At this point, I’ve learned to welcome these questions like old friends and use them as an opportunity to break the news nicely: These are absolutely the wrong questions to ask. 

Now, I don’t blame anyone for asking them, especially since most organizations have been operating with a Project Management mindset for a very long time. It’s a hard habit to break, but the reality is that you can’t project manage a Digital or Operating Model Transformation. 

Today we’ll explore the reasons why a Project Management approach falls short in the context of Digital Transformation, and why a Roadmap mindset is key to paving the way for success.

Why You Can’t Project Manage A Digital Transformation

No matter where you’re at in your Transformation endeavors, breaking from a Project Management mindset can be really difficult. 

At this point, it has probably become muscle memory at the onset of any endeavor to ask for an 18-24 month plan, or a detailed Gantt chart. But the reality is that there’s no one-size-fits-all approach to transformation. Sure, there are tried and true techniques and common, well-worn paths. But the way you navigate one is different from another because the people, problems, and contexts are all unique. For that reason, traditional Project Management methodologies simply don't align with the dynamic nature of Digital Transformation.

The Power of Roadmaps

Roadmaps, on the other hand, provide a more flexible framework for navigating the complexities of Digital Transformation. Unlike project plans that focus on tasks and timelines, roadmaps emphasize outcomes and continuous improvement. They’re also a powerful tool for painting a picture of what’s ahead and giving stakeholders a sense of what’s coming. 

No, it doesn’t promise dates – which I know can be uncomfortable for some in the C Suite – but it is a guide for the work and a rough order of operations with regard to now, next, and later. And it will get more specific over time because your team is going to learn things that impact the work and adjust accordingly. This is a critical piece for transforming companies because it helps ensure you’re not simply building something, but that you’re building the right thing.

By plotting the trajectory of change over time, Roadmaps enable organizations to align technology initiatives with overarching business objectives and, ultimately, provide the most value to the customer / user.

Crafting Your Roadmap

Embracing the roadmap mindset begins with envisioning the future state of your organization. 

First, define what success looks like in five years and talk in big-picture terms. What do you want it to feel like working for the company? How many teams do you see running in the operating model? What will the organizational culture need to look like to get you there?

Equally as important, be honest about your starting point. Do you have pockets within the org where a healthy model is already running? What does it look like? What’s working, what’s not, and why?

Next, start working backwards to define what would need to be true in three years, one year, next quarter, next month, etc., to achieve the big picture. These milestones become your roadmap. 

Be sure to cover various facets of organizational transformation, including talent acquisition, technology integration, funding allocation, learning and development initiatives, and cultural and change management. Basically, the major components of your Operating Model.

With a Roadmap mindset, the focus is on defining milestones and key objectives at different intervals along the journey rather than fixating on specific dates.

Socializing the Roadmap

Once your roadmap is established, the next step is to garner buy-in and alignment from stakeholders across the organization. Socializing the roadmap will also help cultivate a culture of collaboration and accountability, which is essential for driving meaningful change.

During these conversations, there may be pressure to put dates on the roadmap. RESIST THE TEMPTATION. Remember, the focus is not on deadlines or stagegates, but on building the best solutions for your users, and the path to get there is through a Roadmap mindset, not a Project Management approach.

In Conclusion

When it comes to Digital Transformation, traditional project plans simply fall short of addressing the dynamic nature of change. Embracing the roadmap mindset offers a more holistic and adaptable approach to aligning technology initiatives with business goals. Because true transformation is about plotting progress over time, thinking in terms of outcomes, and adapting as you go. It’s not about being done (if I had a dollar for every time I’ve said that, I’d be retired already).

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