Digital Transformation Isn’t Perfect—and That’s the Point
By Barbara Fischer, Associate Vice-President of IT and Data Analytics, The University of Toledo Foundation
Digital transformation initiatives often begin with detailed roadmaps, carefully selected tools, and ambitious timelines. It’s comforting to think that if we plan well enough, if we anticipate every risk, we’ll glide from vision to reality. At the University of Toledo foundation, we even had “acts of God” on our risk register, just in case.
We did not glide from vision to reality. But the things that truly tested us during our transformation weren’t lightning strikes or server meltdowns. They were the real-world disruptions that forced us to pause, pivot, and rethink our assumptions, sometimes on the fly and usually for the better.
The Illusion of the Perfect Plan
Transformation is inherently unpredictable. It challenges legacy systems, exposes outdated processes, and pushes people out of their comfort zones. No matter how thorough your plan, something will go off-script.
We experienced this midway through our Salesforce CRM implementation. Our email deployment system, something we hoped would limp along until we transitioned to Marketing Cloud, suddenly became unusable due to new bulk email regulations. Definitely not on our bingo card.
We paused the CRM rollout and quickly evaluated options: escalate Marketing Cloud or find an interim solution. We chose MailChimp on an interim basis, which allowed us to maintain donor communications without losing momentum.
Unexpectedly, this “workaround” became a win. It gave us a chance to refine our email strategy and address some long-standing issues in our processes. When we moved to Marketing Cloud, we were far more prepared than we would’ve been otherwise.
Sometimes the detours in a transformation journey end up taking you exactly where you need to go.
Transformation isn’t about preserving comfort. It’s about confronting what’s broken and making space for something better, even if the path there is messier than you expected.
Letting the Mess Surface
Before our CRM migration, we made the intentional decision not to do data cleanup. We knew our legacy system was riddled with workarounds and inconsistencies, many of them undocumented. Trying to clean up data we didn’t fully understand would’ve been like organizing a room in the dark.
Instead, we let the system migration surface the mess, and it did. We saw where processes broke down, where accountability was unclear, and where teams had relied on IT to answer questions rather than questioning the underlying processes.
It didn’t feel great at that moment. But it was exactly what we needed. By allowing failure to surface early, we could course-correct and build a better foundation for the future.
Lessons from the Field
At the University of Toledo Foundation, we didn’t just implement one new system, we implemented two. Alongside the CRM, we launched a new financial system. On paper, it was a bold modernization strategy. In reality, it was a high-speed crash course in navigating ambiguity and course correction.
When Automation Exposes Everything
For years, we manually moved data from our CRM into our finance system. It wasn’t efficient, but it got the job done. Part of our modernization effort was to automate that process.
But once we tried, we realized our chart of accounts, built to support years of manual work, wasn’t structured to handle automation. That discovery triggered a series of revisions. And then revisions of those revisions.
Those revisions delayed both projects. It created tension. But it also forced us to rebuild something with the intentionality that would serve us better in the long-term. It wasn’t failure, it was progress, dressed in discomfort.
The Hidden Value of Failure
Digital transformation shines a bright light on everything an organization has quietly worked around—inefficiencies, reliance on institutional knowledge, and missing documentation. It’s tempting to view these discoveries as failures. But they’re not. They’re insightful.
One of the biggest traps is replicating broken processes in a new system. There’s comfort in the familiar, and it’s easy to fall back on the old chant: “This is how we’ve always done it.”
But why invest time, energy, and budget only to recreate the same issues, with a shinier interface?
Transformation isn’t about preserving comfort. It’s about confronting what’s broken and making space for something better, even if the path there is messier than you expected.
Making Room for Imperfection
The goal of transformation isn’t to avoid failure, it’s to create a system where failure leads to learning.
Here’s how we’ve approached that:
- Normalize friction. Slow down and create space for honest conversations about what’s not working.
- Expect iteration. A go-live date isn’t a finish line. It’s a checkpoint.
- Redefine success. Wins often come after something breaks.
- Elevate functional voices. People closest to the work see the gaps first, listen to them.
- Stress test your design. If your process only works under ideal conditions, it won’t work in the real world.
When you plan for imperfection, you create the conditions for meaningful, lasting change.
Conclusion: Progress Over Perfection
Transformation is rarely flawless. But if you’re doing it right, it will be revealing. It will challenge assumptions, break old habits, and surface difficult truths.
The success of digital transformation doesn’t come from the original roadmap. It comes from how well your team adapts, learns, and rebuilds when the road map inevitably changes.
If you’re willing to embrace the friction, even the failures, you’ll come out with something far more valuable than perfection: a future-ready tool built on lessons that stick.