From the threads: Digital transformation challenges no one talks about
Reddit threads reveal the harsh reality behind digital transformation failures
Digital transformation is often looked at as the golden path to innovation, efficiency, and market leadership. But in certain Reddit threads, particularly this one on r/consulting and another on r/ExperiencedDevs, professional consultants, engineers, and insiders tell a very different story.
These raw, unfiltered conversations expose truths many in the enterprise world prefer to ignore:
- Fancy tools don’t fix broken processes
- Data is usually a mess
- Leadership buy-in is often performative
- Culture change is the toughest transformation
So why do digital transformations really fail? And more importantly, how can enterprises do it right?
Let’s look at key challenges uncovered in these threads and how Fortude helps businesses overcome them.
1. The hidden iceberg: Bad data quality
Many digital transformation and AI projects fail not because the technology is flawed, but because they are built on poor data foundations. The top of the iceberg, shiny AI tools like Large Language Models (LLMs), chatbots, and RAG systems, gets the attention. But beneath the surface, the foundation of the iceberg, is the unstructured, outdated, or siloed data.
In a popular comment on the thread, one user laments:
Fortude’s approach:
Fortude understands the important role data plays in digital innovation. Through our Data & AI Services we conduct a comprehensive data maturity assessment and ensure data is clean, structured, and business-ready, long before deploying any analytics, automation, or AI.
2. Leadership misalignment: Buying tools without vision
Multiple Reddit users vent their frustrations about executive teams that treat digital transformation like a tech shopping spree, purchasing Workday, Salesforce, or Microsoft Copilot, without a cohesive plan.
There may be multiple reasons for this, such as lack of experience, internal politics, or different leadership models. This is where employing a company like Fortude could help.
Fortude’s approach:
Fortude’s Digital Transformation Advisory practice helps organizations avoid this trap by bridging the gap between C-suite vision and operational execution. We work directly with leadership teams to define goals, map priorities, and build a transformation roadmap that aligns technology investments with measurable business results.
In organizations where internal capacity or expertise is a challenge, we often advise bringing in a Fractional CIO to provide strategic oversight and drive cross-functional alignment. When positioned effectively, this role can ensure decisions are made through the lens of long-term digital value rather than short-term convenience or the latest hype.
3. The culture wall: Change resistance & legacy thinking
One of the threads on r/ExperiencedDevs is titled: “Where are the examples of successful digital transformations?” The underlying theme? Change is hard, especially when legacy employees and management styles are deeply entrenched.
A Microsoft employee offered one solution:
“What got us here won’t get us there. Leadership needs to embrace new styles of management.”
Fortude’s approach:
We don’t just implement new systems, we guide cultural transformation. Our methodology ensures people adopt, not resist, digital change. With Fortude, you receive a holistic approach to digital transformation.
4. Unrealistic expectations & rushed timelines
Another common frustration is timeline pressure. Businesses expect results in weeks for initiatives that require months of alignment, process design, and upskilling.
Fortude’s approach:
With Fortude, transformation roadmaps are grounded in reality. We create phased implementation plans, build internal capability, and measure ROI with precision, ensuring transformation is effective.
5. Transformation as a buzzword (not a strategy)
This raw honesty highlights a broader issue: “digital transformation” is often used as corporate theater, not an authentic strategy.
Some execs see it as a line item, not as long-term commitment. Others use it to mask reorganization or layoffs. As a result, transformation efforts stall or fade.
Fortude’s approach:
We help companies move beyond buzzwords. Every engagement starts by clarifying the “why” behind transformation, whether it’s operational efficiency, customer experience, or compliance. From there, we build a change model that sticks.
Reddit was right, but here’s the fix
These Reddit threads, while humorous and sometimes cynical, offer powerful truths:
- Tools won’t transform your business, alignment will.
- Data chaos kills AI initiatives before they start.
- Culture kills transformation early on.
But these challenges are not unsolvable. With the right partner, one who knows how to translate strategy into action, and tech into results, transformation is not only possible, but scalable.
How Fortude helps enterprises win at digital transformation
Fortude has led digital transformation initiatives across fashion, food & beverage, manufacturing, and distribution sectors. We combine strategy, systems, and cultural alignment to ensure our clients avoid the pitfalls exposed in these Reddit threads.
From Infor ERP implementations to automation services, our transformation playbooks are built on decades of global expertise instead of the latest trends.
Ready to transform with clarity and confidence?
Digital transformation isn’t about jumping on a tech trend, it’s about aligning people, processes, and platforms around a shared vision. Reddit shows us what not to do. Fortude shows you how to get it right.
Let’s transform the right way.
Get in touch with Fortude’s Digital Transformation team
FAQs
The biggest reason is organizational misalignment, a disconnect between leadership vision, technical capability, and operational readiness. Leadership often sets ambitious goals without ensuring teams have the skills, infrastructure, and processes to support them. At the same time, IT and operations may be focused on maintaining legacy systems instead of enabling new capabilities. This makes transformation a series of disconnected projects rather than a coordinated strategy, leading to slow adoption, budget overruns, and ultimately failure.
No, AI cannot fix what is fundamentally broken, it only amplifies what already exists. If processes are inconsistent, undocumented, or full of manual workarounds, AI will simply automate those flaws or produce unreliable outputs. AI works best when layered on top of standardized, repeatable, well-governed processes. Before implementing an LLM, organizations often need to streamline workflows, modernize systems, and clean or structure their data.
It depends on complexity and scope, but a meaningful transformation usually takes 12–24 months, progressing through defined phases such as discovery, design, pilot, scale, and optimization. Successful transformations include quarterly ROI checkpoints, allowing teams to validate impact, adjust plans, and maintain executive support instead of waiting years for results.
Employee buy-in is earned through participation, transparency, and upskilling. Organizations should involve frontline teams early so they understand the problems being solved, not just the technology being deployed. Clear communication about the “why” reduces fear and resistance, especially when changes affect roles or workflows. Investing in training, coaching, and hands-on experimentation empowers employees to feel ownership of the transformation. When people see how the change benefits both the business and their daily work, adoption increases dramatically.
Jumping into AI without a clear plan often leads to wasted investments and failed projects. The right approach starts with understanding three critical questions:
- Do we have the foundation to succeed with AI?
- Is this the right AI initiative for our business?
- What measurable value will this AI project deliver?
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