Imagine you’ve finally decided to renovate your entire house. You’re talking about the kitchen, three bathrooms, a new roof, and finishing the basement. Now, imagine trying to do all of it in a single weekend while you, your spouse, three kids, and a confused golden retriever are still living there. You’d have contractors tripping over toys, no working toilets, and a 100% chance of a breakdown by Sunday brunch. Yet, for some reason, when it comes to Digital Transformation, many corporate leaders think this “Big Bang” approach is the only way to fly.
Why do we do this to ourselves? We see “Digital Transformation” as this monolithic, once-in-a-decade event that everyone must finish at the exact same time. It’s like trying to swallow a watermelon whole instead of enjoying it slice by slice. The reality is that the “all-at-once” mindset is exactly why a staggering 70% to 88% of these massive projects end up as expensive paperweights.
The smarter way? Thinking in Agile. It’s about breaking up the big, scary ideas into bite-sized workflows and automation. It’s about iterating, improving as you go, and realizing that a “Digital Transformation” isn’t a destination you reach, it’s a muscle you build.
The “Monolith Myth” is the belief that if you just plan hard enough, you can launch a massive change perfectly on Day One. It’s the “Giant Jenga Tower” of business strategy. You spend months building this perfectly rigid structure of requirements and code, but the second you try to pull out a legacy system or slide in a new automation, the whole thing starts to wobble.
In 2025, research shows that global spending on these transformations is hitting $3.4 trillion. But here’s the kicker: only about 35% of these initiatives actually reach their goals. When leaders treat transformation as a tech upgrade rather than a living business process, they aren’t just wasting money; they’re wasting the most precious resource of all: time.
If you want a front-row seat to what happens when even a giant moves a little too slowly, look at the Siri saga. For years, Siri was the digital assistant that mostly just set timers and told you it couldn’t find your “Play Jazz” playlist. While competitors were sprinting ahead with generative AI, Apple was stuck in a “build-it-internally” loop that felt like watching a prestige drama on a 1990s dial-up connection.
By 2024 and 2025, Apple had to make a pragmatic and very expensive pivot. They realized they couldn’t just “monolith” their way into being an AI leader overnight. Instead, they started a multi-layered partnership ecosystem, reportedly finalizing a $1 billion annual deal to license Google’s Gemini model to give Siri a much-needed brain transplant. They even brought in OpenAI’s ChatGPT to handle the complex stuff Siri still can’t touch.
There’s a lot of “what if” floating around watercoolers lately. Should Apple have simply bought an AI powerhouse like Perplexity or Claude back when they were just rising stars? While they reportedly considered it with rumors of a potential $30 billion price tag for Perplexity, they ultimately chose a hybrid approach: building their own “Apple Intelligence” for privacy and on-device tasks while borrowing the “heavy lifting” power from rivals. It’s a classic Agile move: admitting you don’t have all the answers and partnering to get to market faster.
I once sat in a boardroom where the plan was to “reclaim our destiny” by firing a vendor and bringing a complex service entirely in-house. It sounded great on a PowerPoint slide. We’d save money! We’d own the code! We’d be the masters of our own digital universe! Fast forward one year: the project was a ghost town. We had spent twelve months on “integrations” that didn’t integrate and “code creation” that didn’t actually do anything for the customer. We had a large team, a mountain of lost time, and zero progress to show leadership. The project was eventually put on “indefinite hold,” which is corporate-speak for “we’re burying this in the backyard and never speaking of it again.”
This is the “In-House Trap.” When you try to transform everything internally all at once, you often end up building a bridge to nowhere. An Agile approach would have asked: “What’s the smallest piece of this we can bring in-house in the next two weeks to see if it actually works?”
So, how do we stop the madness? We start treating Agile as a business strategy, not just something the people in the basement do with Jira tickets. Agile is basically just a fancy word for “learning from your mistakes quickly.”
Instead of a three-year plan that is guaranteed to be obsolete by month six, think of “Sprints.” Imagine you’re a marketing manager. Don’t try to automate your entire lead-gen funnel on Monday. Start by automating one repetitive email. See if it breaks. If it doesn’t, do another one next week. This iterative process reduces your risk of failure because you’re testing and refining in stages rather than betting the farm on a single “Go-Live” date.
The goal is to move from a “Project” mindset where there’s a start and an end to a “Product” mindset, where you are constantly tweaking and improving. Think of it like a smartphone update. You don’t wait five years for a “Perfect OS”; you get small updates every few months that make your phone slightly less annoying.
Ultimately, the smartest companies in 2026 aren’t the ones with the biggest budgets or the most “in-house” developers. They’re the ones that know how to pivot. They’re the ones who, like Apple, realize when they need to partner to stay in the race. And they’re the ones who understand that 70% of software implementations fail because of human behavior, not just bad code.
Digital Transformation isn’t a monster to be conquered; it’s a path to be walked. If you break up your ideas, workflows, and automation into manageable pieces, you’ll find that the “scary” change actually feels a lot more like progress.
I’d love to hear your thoughts! Have you ever been part of a “Big Bang” project that went bust, or have you seen the magic of small, agile wins? Share your stories and tag @iamcezarmoreno on social media!
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