The number of articles and guides available on the topic of digital transformation is endless. People in organizations large and small generally have an idea of what digital transformation is, even if they haven’t yet gone through it themselves. Yet just because the concept of digital transformation is now widespread doesn't mean everyone understands how it works or that there is a one-size-fits-all approach.

We often see organizations go all-in on digital transformation efforts — taking up digital migration of their processes in all departments and for both customers and employees all at once. While some organizations succeed with this approach, there are potential pitfalls as well. Lack of adequate planning, testing and training, just to name a few, can derail any potential gains the digital moves would provide. Beyond the common pitfalls of going all-in, organizations also risk going over budget, which can result in reluctance to iterate on their changes down the line.

Digital Transformation Isn't a One-and-Done Deal

Digital transformation was never intended to be a one-time event. It can and should be a mindset and an ongoing process within your organization. Constant change, both in technology and stakeholder needs, is a given and it’s critical for organizations to be prepared to tackle digital transformation on a continuous iteration cycle.

One way to ensure this cycle of testing and shipping is part of your organization’s plan from the beginning is to strategically approach the entire process that way. Meaning, don’t go all-in right away. Start with specific areas of need, and then grow and iterate from there. This iterative process allows organizations to test the waters with their approach, tactics and software with a conservative risk when it comes to disrupting business activities and busting budgets.

One organization taking this approach to heart is Subway. It starts with the data and iterates from there.You need to have a system to analyze your data to take advantage of all the work you’ve done. If your analysis is not good, it’s all pointless. The most important part of successful testing is a scalable, repeatable process,” said Chad Sanderson, Subway’s digital optimization and experimentation lead.

Having the data to make objective decisions is what can also help your organization determine where to begin.

Related Article: 3 Decisions That Matter in Digital Transformation

Narrow Your Focus

Approaching digital transformation in smaller stages that build on one another is a solid way to execute digital transformation in theory, but how can organizations do this effectively? Rather than throw a dart blindfolded, hoping to find a process, area or department where they can roll out the changes, organizations must work collaboratively with internal and external stakeholders to identify where they can maximize the benefits of digital transformation while ensuring minimal disruption to regular business activities based on their existing data. The narrowed-down focus of the initial stages will define the following stages as well.

Starting with the area where you can have a big impact with little risk or possible downside is a great way to build your transformation roadmap. Once changes begin, it’s critical to take detailed notes to better understand what works and what doesn’t. And we aren’t just talking about software — this includes timing, management and transition plans.

Related Article: 5 Resolutions for a Digitally Excellent 2019

Learning Opportunities

Common Digital Transformation Roadblocks


Budget is always a top roadblock for digital transformation in organizations both big and small. However, when you begin with one business area and expand, it’s easier to budget by year or quarter to make change happen. You won’t have to worry about allocating a huge budget to the project just to get started — you can start with something more manageable while still seeing a direct impact.


Big projects often have long timelines that incur setbacks and delays. However, if you take digital transformation on in chunks, it can decrease the time it takes to see real results. Any results-driven organization knows the importance of seeing change quickly and those results can be used to drive the buy-in from other areas.


As I alluded to above, buy-in is critical for any project to get off the ground in an organization. Generally, buy-in comes from having clear support from case studies or smaller initiatives, which is what you gain from breaking your digital transformation efforts into smaller, more manageable stages.

Legacy software

An often overlooked roadblock to digital transformation is dealing with legacy software. Organizations that have spent heavily on existing software may be less apt to make changes. However, by starting small, organizations have the ability to evaluate how existing software can be used alone or with new software to maximize existing investments while still moving toward meaningful digital changes.

Related Article: Change Management: The Key to Successful Digital Transformation

Your Next Steps

If your organization hasn’t yet tackled digital transformation or if you have but it’s been a while, the best next step you can take is to identify areas in your business that would most greatly benefit from moving to digital. Decide which changes would have the most impact and refine your plan from there. Find the software you want or need to use, understand your timelines and interview stakeholders. By taking small steps and incorporating the lessons you learn along the way, your digital transformation efforts will have a positive, lasting and ongoing effect on your organization.

And remember, it’s all iterative. As Jeff Larche of Accenture says, your models should not be static. They should always be changing depending on results and desired outcomes.