Over the past 20 years, I’ve been asked to rescue quite a few ‘failed’ implementations—projects that were supposed to revolutionize pricing, operations, and finance (sales-to-cash). As you may have guessed if you read my first article in this trilogy: the problem never was the tool.
In fact, a lot of companies don’t need a new tool. What they do need to do is stop blaming their existing tool for their own failures.
It’s all about Adoption with a capital A.
One of the biggest misconceptions about digital transformation is that people resist change. Of course some do, especially fraudsters who prefer things “off-screen”, or the older generation who cling to familiar inefficiencies. But for the most part, people don’t resist change — they resist solutions that are going to make their lives harder.
It’s never about features. It’s about value. No matter how hard the software provider tries to convince you otherwise.
Making a tool succeed means making it an attractive alternative — something that makes life easier, faster, and less frustrating. And not just for management, who are always pushing new systems because they promise to cut costs or increase revenue, but for the people in the trenches who actually have to use it every day.
When companies decide on a new tool, there’s always a room full of decision-makers: executives, project managers, IT, finance, and sometimes legal or procurement. But the actual user? The one who knows exactly what’s broken and what would practically help? They’re almost never part of the discussions.
Even when companies claim to capture user requirements, it’s usually indirect through IT teams, who translate those needs into large lists of features and system specs — the ‘what’ and the ‘how,’ but rarely the ‘why’ or the ‘what if.’ That’s why small, critical gaps — like a missing backdate field or a complex dropdown — can quietly derail the most expensive implementations. (I’ve seen it happen more than once.) The tool becomes more of a hassle than the workaround users have spent years perfecting and it was supposed to replace.
When a system fails, companies rarely ask if they even needed a new tool in the first place. Is the problem the software… or the fact that no one ever addressed why people aren’t using it?
The Real Reasons Projects Fail
Digital transformation doesn’t collapse because of bad tech — it collapses because organizations haven’t aligned the real system: decision rights, incentives, priorities, and people. That’s a change management problem, not an IT one.
Here’s what that misalignment looks like:
1. No shared definition of success
I once led a pricing system rollout that should have been straightforward — except every department had a different idea of what the tool was for. Finance wanted tighter controls. Sales wanted maximum flexibility. When account managers realized the system limited their ability to play with discounts, they resisted. Understandably so. But the irony? The tool actually helped them — it gave access to pricing benchmarks from global deals, a huge asset in negotiations. No one had framed it that way.
Lesson: Change fails when people lose autonomy without understanding what they’re gaining in return. If you don’t align the ‘why,’ the ‘how’ will always get blocked.
2. Fixable problems get mistaken for systemic failure
At another company, leadership was preparing to scrap an underused system. “It’s outdated,” they said. “Nobody’s using it.” But once we spoke to the frontline teams, we found something else: a few small issues had snowballed into workarounds and frustration. Step by step, we cleaned it up — and usage rebounded without a single new license.
Lesson: If no one is listening to users, even minor frictions start to look like system failure. And change management that skips listening isn’t change management — it’s simply superficial.
3. Buying new tools instead of asking better questions
In yet another case I managed, the company was ready to invest millions in a new data warehouse — just to get dashboards. But the reporting functionality already existed in their current set-up. The real issue? No one had asked which teams needed what data, in what format, or for what purpose. If they had bought the new tool, they’d still have had to answer all the same questions, but at a fee of US$ 1-2M.
Lesson: You can’t automate something you don’t have. Tools don’t clarify — they just execute.
✨✨✨
A successful digital transformation doesn’t begin with a tool. It begins with the truth:
👉🏽 Do you really need new software, or do you need to make the current one usable again?
👉🏽 Are you solving real user pain points, or just ticking off features to make a business case lookmore attractive?
👉🏽 Are your teams aligned on why this matters, or is each department optimizing for its own reality?
Until you solve those questions, any new system will just speed up what’s already not working. Tech won’t fix a broken process — it’ll just make the break faster, more expensive, and harder to undo.
Up Next: What Real Change Looks Like
If tech isn’t the problem, then what is?
And more importantly — how do you actually get it right?
The next article maps a different approach: one that starts with users, builds from real value, and only introduces technology as the final step — not the first.
Because if your transformation doesn’t work for the people doing the work… it doesn’t work at all.