By Dan Feely, TSI President and Managing Partner

Digital transformation projects should be straightforward: select a system, implement it, and improve how the business operates. In reality, they often take longer than expected, cost more than planned, and leave leaders wondering, “Why was this so hard?”

After supporting more than 100 major ERP, CRM, and digital transformation initiatives, we’ve seen the same challenges surface again and again. And as organizations increasingly layer in analytics, automation, and AI, the cost of getting the fundamentals wrong only grows.

Specifically in this post, I’ll highlight the top 3 factors that arise that make digital transformation programs and initiatives more of a challenge than they should be.  Also, we’ve shared a few thoughts about what you can do to prevent or mitigate a less than positive situation related to the factors.

The 3 Biggest Blockers to Digital Transformation Success:

1. Lack of a Big Picture Perspective

Many organizations struggle to articulate how people, processes, and systems should work together in the future state.

As Chris Detloff, Director of Transformation at the Archdiocese of Chicago, puts it: “Transformation leaders must take a solution-based approach — people, process, and technology.”

When technology decisions lead the conversation, transformation efforts lose focus and momentum.

Here is a practical move:

• Create a high-level future-state process map before selecting tools
• Define a small set of business-critical outcomes that the transformation must achieve

As AI-enabled tools enter the picture, this clarity becomes even more important. AI should support clearly defined workflows and decisions, not introduce new complexity without purpose.

2. Unclear Process Details. How Will Work Actually Flow?

Having a vision is not enough. Organizations must understand how work is done today and how it needs to change. 

Process mapping clarifies who does what, where automation makes sense, and where inefficiencies exist. Without this foundation, advanced tools, including AI, often accelerate existing problems rather than solve them.

Practical move:

• Map current-state processes before designing future-state solutions
• Use customer or stakeholder experience to inform requirements

Applying automation to poorly understood processes rarely delivers meaningful improvement.

3. Weak Execution Discipline — The Project Doesn’t Run Itself

Transformation initiatives fail when accountability, ownership, and governance are unclear.

As Kerri S. Wagner, President & CEO of PharmChem, notes, complex implementations involve many actors, shifting priorities, and competing demands. Without disciplined project leadership, momentum stalls.

AI-driven initiatives raise the stakes even further, impacting roles, data ownership, and decision rights.

Practical move:

• Assign dedicated project leadership
• Establish clear governance and escalation paths
• Treat change management as a core workstream, not an afterthought

A Reality Check for 2026: Data and Decisions Matter More Than Tools

Most transformation failures are not software failures; they are data and decision failures.

Poor data quality, unclear ownership, and weak governance undermine even the most capable platforms. AI amplifies these weaknesses just as much as it amplifies opportunity.

Final Thought

Digital transformation succeeds when leaders treat it as a business redesign, not a software installation.

Organizations that align vision, process detail, disciplined execution, and data readiness are the ones that realize lasting value.

Want to pressure-test your organization’s readiness? Explore TSI’s free Change Readiness Survey and see where your transformation stands.

The post The Challenges of Digital Transformation appeared first on Transforming Solutions Inc..

By Dan Feely, TSI President and Managing Partner

Last month, I had an opportunity to go to the great city of Duluth, Minnesota to watch my favorite first daughter (not to be confused with my favorite 2nd or 3rd daughter) run her first marathon (shout out to Grandma’s Marathon). It was everything you would imagine a marathon to be – inspirational, motivational, emotional, and more.

After bouncing around to different marathon locations, the marathon app indicated our runner was nearing the last mile. So, we jockeyed for position in an area about 400 yards from the finish line hoping we could get a picture of and watch our favorite participant finish.

As we waited, we saw runners who were jubilant, fatigued and everywhere in between those extremes. Most, if not all runners, had their eyes fixed on the balloons marking the finish line that they’ve been dreaming about for the previous 26 miles. It was obvious that most, if not all, were using every bit of fuel they had left in their tank.

We spotted one runner, a guy who did not look well. I mean really unwell. His legs looked like they were made of rubber, and he was increasingly losing his balance with every step he took. Then he crashed. Literally, his legs gave out and he face planted on the pavement.

He did not look like he could get up, nor were any race volunteers in the area to attend to him.

Then, out of nowhere, two runners grabbed and lifted him up. One runner on each side, they grabbed his arms and lifted, dragged and pulled him along. They basically carried him the entire rest of the race.

I watched the entire thing. There were no introductions, no asking “do you need help”. Based on how quickly they jumped into action, I’m confident they didn’t talk about politics as a prerequisite to make sure they were aligned on volatile topics.

They simply helped a fellow human.

I have no idea whether these two competitors who helped this man were striving for a personal best, or simply striving to complete their first marathon. Regardless, I’m sure their stopping added several minutes to their time. With the finish line in sight, they very easily could have just run around him.

But they didn’t. They just did the right thing and sacrificed minutes on their time to do so.

Remarkable.

This event got me thinking about how divided so many of our communities, including our places of employment, are today.

But in a few easy steps, we can create a culture that rises above the rhetoric and divisiveness that it is so easy to get pulled in to.

1. Focus on what you have in common (i.e., common goals, perhaps a few shared values) with your team.
2. Pay no attention to the stuff that you don’t have in common.
3. Just help, add some value, bring something to the table, be a good team member.

The rest will take care of itself.

What perspectives can you add to this?  We’d love to hear from you and your digital transformation experiences.

Looking for more on culture? Go here and here

The post Culture Change 101 appeared first on Transforming Solutions Inc..

By Dan Feely, TSI President and Managing Partner

Maybe you are like I am and periodically embark on some home renovation project.  And, like most projects, they take longer, cost more, while leaving you with a feeling like “this should have been easier”, when you look back at the contributing factors for the delays and cost overruns.  There are a lot of similarities with a home renovation project and a major system implementation.  But since home renovation is not my business, I don’t profess to have all the answers there.  However, when it comes to digital transformation and ERP, CRM, and other major system implementations, I have a lot more expertise to draw from.  Here we will share some knowledge and experience we’ve gained while being involved with well over 100 major digital transformation and systems implementation projects collectively.

Specifically in this post, I’ll highlight the top 3 factors that arise that make digital transformation programs and initiatives more of a challenge than they should be.  Also, we’ve shared a few thoughts about what you can do to prevent or mitigate a less than positive situation related to the factors.

3 Top Blockers that Impede Digital Transformation Efforts:

1. Lack of a “Big Picture” Perspective
2. Not Having a Handle on Critical Details – How Will the Work Flow?
3. The Project Does NOT just Happen

First, let’s draw a distinction between the two typical approaches organizations take with systems implementations:

1. Focus simply on replacing an old system with a new one (also known as “lift and shift”).  This is a bare bones approach with most of the focus being put on the technology replacement and little to no attention to transforming the business, changing processes or roles.  While this may seem like the quick, easy, and cost-effective way to improve, we believe that there is no such thing as the easy button in digital transformation. There will always be data and setup challenges (just like our renovation example above) and preparing for them may be the difference between success and failure. TSI typically does not endorse this approach, but there are circumstances when this is warranted. The infographic at right highlights the most pervasive challenges that haunt lift and shift types of projects.
2. Digital transformation using the new system as a catalyst to change how the organization operates.  This approach will do a much better job in ensuring maximum value is extracted from the technology investment and has potential to significantly improve the organization. However, there is still complexity and risks to be aware of. Due to the number of “moving parts”, organizational change risks and other factors, this article is focused on this scenario and how to mitigate those risks. 

Below are some of the top reasons (in addition to those just listed) that make it challenging for a digital transformation project and pragmatic tips to address these challenges.

1. Lack of a “Big Picture” Perspective: Don’t have an understanding of how the systems, processes and people will work in the “new environment”. 

Chris Detloff, a very experienced veteran of many ERP implementations and the Director of Transformation for the Archdiocese of Chicago, has this to say, “In today’s historic era of accelerating market and technology disruptions that impact our lives in every way, transformation leaders must take a solution-based approach to transformation to be successful. Unfortunately, many transformation initiatives fail for the following reasons:

• Leading with technology instead of a solution-based approach (people, process, and technology)
• Lacking an agile, flexible, and collaborative operating model with well-established capabilities for their organization
• Partnering with professionals who lack proven transformation experience.”

Chris has been one of the most visionary leaders that TSI has worked with, and we echo his thoughts.  One way to put this into practice is by starting with a high-level context level process map that gives some clarity with respect to the project scope (see simple example below), the technology that is needed, even if the technology will get acquired and implemented a piece at a time.

In addition to this overview map, we also need to define the key “use cases” and supporting business case that articulates the stakeholder’s expected benefits associated with the transformation effort.  This perspective needs to be kept as a central theme during the project to help maintain focus and keep the project aimed toward a finite set of specific targets.

2. Not Having a Handle on Critical Details – How Will the Work Flow?

In addition to the “big picture” perspective mentioned above, an organization needs to have a solid understanding how the key processes (and key scenarios) will work.  Have you thought about your desired customer experience and used that perspective to inform your processes and key requirements?  If not, you have a little more work today. 

To start working toward an ideal future state operating model that leverages functional technology and makes you more efficient, it is imperative to start by mapping out the current state processes. Conducting business process mapping and improvement sessions help bring clarity to a process, including who is involved, whether activities are manual or automated, and necessary action to improve efficiencies. Business process mapping is a forward-thinking action aimed to understand what is happening now in a process, why it is happening, and what is desired to happen in the future. Below is a sample template of a business process map.

3. The Project Does NOT Just Happen

Kerri S. Wagner President & CEO, PharmChem, Inc. has this to say as she and her organization recently implemented a cloud-based ERP, “System implementations are harder than they should be because there are so many actors involved. Action items can get pushed back for weeks at a time due to employee shifting and job changes, and sometimes project knowledge isn’t transferred effectively, so the scoping must begin again. It can be frustrating when the system doesn’t end up doing what it was scoped to do without several months of specialized and costly development.  These frustrations can be eased if a company assigns a dedicated project manager to oversee all the moving parts. If one is not on staff, hiring an outside consultant will ease the pain and ensure the project gets over the finish line.”

According to John Bosshart, Chief Accounting Officer at OneSpan Inc. in Chicago, “Change management and upgrading systems are more difficult than people first realize.  Not only does your team have their day jobs but also need to carry out critical analysis, testing, and new sox controls with these new systems.  These are exciting projects but can also be extremely stressful on everyone in the project.”

Use These Factors to Direct Your Success

Just like that remodeling project I mentioned earlier, even if you are not a skilled worker that is transforming a facility or building out the new space, it takes time (usually more than you’d expect) to articulate what you want, what you think you need, design the solution, oversee how the development is coming along, keep your needs in line with what you originally asked for, provide timely feedback and finally, when the time is right, move into the new space.  

New systems and digital transformation projects are no different.  Being attentive, responsive, and present during a project like this, AND doing your day job well is extremely hard to do.

While there is a myriad of hurdles, with the right focus and assistance, please know that you can get over all of these.  Your project does not need to be another statistic on the log of failed or significantly underdelivered projects. Use this information as an input to your approach.  And if you are feeling extra resourceful, check out a tool that many of our clients have found to be useful.  The tool, beyond the insights above that may help, is TSI’s Change Readiness Survey (free for your use), to help assess whether your organizational change management factors are aligned.

Take this individually or share it with your team.  Take it, compare scores, and see if your organization is ready to embark on a major change effort, such as a digital transformation or even a “lift and shift” from an old to a new system.  

What perspectives can you add to this?  We’d love to hear from you and your digital transformation experiences.

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