Avoiding Digital Transformation Pitfalls

Life and technology march on whether you’re ready or not. How you approach these transformative moments can mean the difference between true, successful change and finding yourself stuck.

As my youngest child prepares to head off to college this fall, my wife and I will begin a new chapter in our lives as empty nesters.  We find ourselves pondering a fundamental question: Where should we live?  Do we remain in our current home that has served us well for so long, or do we venture into a new home or even a new city?

In this moment of introspection, I realized that our situation mirrors that of many businesses today. Just as we contemplate our next steps, many organizations face a similar crossroads. The business landscape has shifted dramatically, demanding that they adapt and innovate. Digital transformation—once an option—is now a necessity for survival and growth.

However, this journey is fraught with pitfalls that can derail even the most well-intentioned efforts. The good news about pitfalls is that if you know they’re there, you can navigate them effectively. Here are some of the most common traps in a digital transformation, and how to pivot to avoid them.

Embracing Purpose

Failing to understand why you are modernizingClarify your “Why” and proceed with purpose

Deciding to embark on a digital transformation is the first step, but it must be guided by a clear understanding of the “why.”

Imagine embarking on a journey without knowing your destination. Similarly, transitioning without understanding the purpose can lead to misguided choices. By answering the “why,” you create a decision-making framework. It guides you throughout the process, ensuring alignment with your goals. Success becomes measurable against this purpose.

For example, if you’re driven by legacy systems that cannot be easily modified or adapted, ask yourself

What are the implications of staying put versus embracing change?

What new market opportunities will this transformation open for us?

If an application serves current needs but has high operational costs that are hindering growth, ask yourself

Do the benefits outweigh the expenses?

If so, when will we realize them?

In my personal example, my wife and I need to make our checklist for what will drive our decision. Why are we considering a change? What will we value in a new future home? Answering these questions will make our journey more efficient and more successful in the end. 

Armed with clarity, you can now go with purpose.

Recognizing the Change Opportunity

Replicating the PresentEmbracing the Change

Change is intimidating. In the face of a major upheaval like a platform modernization, it can be tempting to “minimize disruption” by replicating the past.

It’s comfortable, it’s familiar, but it’s a trap – don’t do it!

You’ve committed time and money to this digital journey, so stay true to your goals. Lean on your reasons why and truly transform. Those features that were once indispensable may not fit into your future.  In fact, they may be detrimental.

Be on high alert for your business experts who are consciously or unconsciously steering you back to today. Critically evaluate each feature and determine if it has merit. If it doesn’t pass muster or if you even question its value, leave it behind. Less will be more as you figure out the new future. 

As we figure out our future home, my wife and I will base our decisions on our future needs. Do we need all the bedrooms? Do we need a backyard? Not sure. But we definitely don’t need those unopened boxes we moved into the house 18 years ago.

Everything will face scrutiny. What doesn’t serve us now gets left behind. Approach your digital transformation with the same mindset.

Championing Business Rules

Assume the business rules are fully captured in the platformOwn the business rules …and refine them

This one is more nuanced, but I cannot emphasize it enough: What resides in the system today is the current implementation of the business rules – not the rules themselves.

You may hear from some of your business leads that the development team needs to tell you the rules – the system just produces the answer. The reality is that what’s implemented represents the total sum of all the business rules that have ever existed, whether or not they are still relevant. Some likely became business rules because it was fast to implement that way or the result of  a system limitation. 

To be successful, you will need to own the business rules and clearly define what is expected. You must be able to predict your outcomes. The existing system can be a valuable reference point, but not the sole source of truth. Treating it as such will doom you to failure. Once again, lean on the “why,” and define the outcome you want based on today’s business landscape.  As my wife and I work through our checklist, we need to own what is important to us now and make sensible decisions based on our current circumstances

Delivering Often

Delaying the launch until it is perfectIterating releases and acting on early feedback

The pursuit of perfection, coupled with the fear of change as people’s job functions evolve, can grind progress to a halt. Instead, the mantra should be progress over perfection. The key is to dive in. Don’t hesitate to start. Engage with the process head-on. Adopt an iterative approach, launching functionality early (and often) to gather feedback and demonstrate to your users what the future may look like. Early exposure can help mitigate concerns about change and pave the way for innovative solutions. Refine, add a few more features, and iterate again. This cycle is crucial for continuous improvement

The Big Takeaway

Digital transformation can instill anxiety and fear, but letting go of the past and embracing the future is very rewarding.  Just as exploring a new potential new home and/or location can be scary, we’ll only see the benefits once we start taking tangible steps!

Further Advisory helps companies strategize, plan, and deliver their most complex programs. From product launches to platform modernization to business transformation, we make strategy become a reality..

About the author


  • Jim Conzemius

    Jim has over two decades of experience building and delivering products and platforms. He primarily focuses on innovating and disrupting industries including the payroll services and healthcare industries. Jim has also championed the agile methodology and SDLC best practices helping companies become more disciplined and effective in delivering software for their customers.

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