Late one evening in the tiny village of Cong in the west of Ireland I was enjoying a glass of Green Spot with Damian Costello. He said something I haven’t stopped thinking about.
We were talking about why so many technology projects fail – and why the failures are so predictable. Damian has spent thirty years consulting in complex systems. He’s seen every pattern.
His point was simple: you cannot, for any sustained period, defy the reality of the system you’re operating in.
Human nature, economics, politics, organisational inertia – these forces don’t care how clever your solution is.
I live in a small surfing village on the Atlantic coast, and Damian used a metaphor I loved: leadership is like surfing.
You cannot impose your will on the ocean.
You have to read the currents and move with them.
The currents he meant weren’t just technological (although they’re some pretty strong riptides right now).
They were social, political, economic. They included what people actually believe, what they’re afraid of, what they’re motivated by.
And if you try to push against all of that because you think your solution is clever enough to override reality – you might get lucky for a while. But eventually, the system wins.
The Three Circles
Damian drew a Venn diagram on a napkin with 3 overlapping circles:
Leadership. People. Technology.
Most technology work happens in the non-overlapping part of the technology circle. People try to solve problems by looking only at the tech.
They’re really good at what they do – but they can’t affect real change because they’re ignoring the other two circles entirely.
If you really want to influence a system, you need to own all three.
- Authentic engagement with leadership – what the business could and should be aiming for.
- Understanding people – their motivations, their resistance, what they’re actually afraid of.
- Only then does the technology piece fall into place.
When you get all three right, the solution almost falls out on its own.
Solutions are rarely the problem. The problem is the politics, the misaligned motivations, the conditions that were never set up properly in the first place.
The Fragility Nobody Mentions
This is where I pushed back a little.
These systems are inherently fragile. And that fragility is built in by default.
Here’s what I mean. You can build a proof of concept that looks amazing. It does exactly what you want. Everyone’s excited. And then you try to take it to production – and suddenly it’s 100x more complex than anyone expected.
Credentials expire. Authorisations don’t transfer. The person who set up the integration leaves. The API changes. One system thinks the user has access; another system disagrees. What worked perfectly in the demo environment falls apart the moment it touches reality.
This is the gap that kills projects. And it’s almost impossible to explain to the people who control the budgets.
Damian agreed, but his point was that the people who formulate budgets don’t see that level of granularity.
It’s filtered through their vendors. And their own internal people have been taught to think the same way.
You can’t rely on your own team to be objective – because they’ve been trained by the same system that’s selling to you.
This explains something I’ve seen repeatedly: organisations where the internal technology team genuinely can’t see the problem, because they’ve been conditioned to see through vendor-shaped lenses.
The “Dentist Rule”
Damian told me his number one lesson from thirty years of consulting: never answer a question you haven’t been asked.
The key is figuring out how to get them to ask the right question in the first place.
He used this analogy: you’re the best dentist in town, walking down the street. A parent is coming toward you with their child, and you can see the child’s teeth are a disaster. If you walk up and say so – unsolicited – you’re the one who’s going to have the problem.
Then we take the same dentist. Same knowledge. Same teeth.
But if that parent walks into your clinic and says, “We’re worried about her teeth – what can we do?” – now you’re trusted. Now you can help.
The difference isn’t politeness vs. impoliteness.
It’s their awareness of and readiness to discuss the issue.
Until someone can see the problem clearly, even the right answer sounds wrong.
What This Looks Like in Practice
A few months before that conversation, I’d been working with a blood testing lab.
They have highly trained scientists running critical diagnostic tests. Their expertise mattered. Their time was expensive.
And they were spending hours every day typing handwritten data into spreadsheets.
When I asked why, the answer was familiar: “That’s how the system works.”
The changes I suggested we make were very narrow and surgical. Smart data capture with a tiny custom solution. Automated validation with another. Nothing revolutionary – just removing the friction that had become invisible.
Processing time dropped by 92% per sample. The lab unlocked 12x more capacity without hiring anyone. And more importantly, the highly trained scientists were able to spend more time on science, not spreadsheets.
The investment for that initial build was miniscule – only €2,500, and their first-year savings exceeded €250,000.
But here’s the thing: those numbers only made sense after the inefficiency became visible. Before that, everyone assumed complexity was inevitable.
They’d been told – by vendors, by their own systems, by years of accumulated habit – that this was just how it worked.
They weren’t wrong about reality. They were wrong about which parts of reality were fixed and which parts were just… never questioned.
That project was on my mind when Damian and I talked.
What’s the Point?
If you’re leading a team through AI adoption, you’re probably feeling two things at once.
- First: pressure to move fast. Everyone’s talking about AI. Competitors are making claims. Your board wants a strategy.
- Second: suspicion that something’s off. The pilots don’t scale. The integrations break. The ROI projections feel optimistic. Your own team seems confident, but you’re not sure they’re seeing the full picture.
Both instincts can be correct.
The currents are real. The fragility is real. And the conditioning – the vendor-shaped thinking that makes it hard for anyone inside the system to see clearly – that’s real too.
The way through is to step back and see all three circles: what leadership is actually trying to achieve, what people are actually motivated by, and only then – what the technology can actually do.
Often the solution falls out on its own once you’ve done that work.
As Damian put it in Cong: “Someone needs to stand with the client and say, ‘We’re on your side. We’re going to add value. And we’re going to be honest about what’s actually happening.'”
That’s the work.
If this resonates, I’d be glad to hear from you. I’m at [email protected]
