Maurice Adam Weber is a Dutch tech entrepreneur, author, tech pioneer, and CEO at HenriPay Holding N.V.
For readers of a certain age—say, Gen-Xers and Millennials—partying like it’s 1999 will never go out of style; however, operating your company like it’s 1999 is an entirely different matter.
Many older business leaders today are running their companies as they always have—that is, grounded in decades-old operational logic. And indeed, there may be value in keeping certain systems or processes consistent, or in maintaining certain philosophies or values. But in the past 30 years, bluntly, everything has changed—particularly where digital technology is concerned. Now we’re working in an era of AI, automation and data, which aren’t merely “nice things to have”; they’re necessary for maintaining a competitive advantage. This is the case in virtually every industry.
Despite this reality, many business leaders are still stuck in the past. They don’t understand the capabilities of the technology and, because they lack that knowledge, they treat digital transformation the wrong way.
A Technology Commitment Problem
A lot of company leaders approach technology implementation like a gym membership: They sign up in January, post about it once … and then never go again. But they still expect results. Their approach to tech stacks is the same; they purchase XaaS, roll it out, never use it and then remain mystified why they haven’t gained any value from it. Statistically, more than 70% of digital transformation projects fail. Is the issue technical capabilities? Not really. The core problem is culture—how people treat technology.
Lack of knowledge is one major component of the problem. When we talk to many experienced leaders, we see a huge difference between those who have even a baseline understanding (What is AI? What is data? Why do we use these tools?) and those who don’t. Companies may have hundreds of SaaS tools, but leaders often have no idea why or how they’re being used.
But there’s another issue as well. Returning to the gym analogy for a moment: People assume they’ll get fit without knowing how to work out or what maintaining consistency actually looks like. Many business leaders treat technology the same way. They view it as a cost center as opposed to a growth driver.
Defining The Cost Center Fallacy
The biggest issue, for many of these business leaders, is that they still see investment in technology, particularly IT, as the price of doing business, as opposed to the engine that drives growth. They think about uptime and cost before they think about output or value creation. If they deploy new tools, they don’t measure the business impact, the employee experience impact or the productivity gains. They measure only cost, not benefits.
Don’t get me wrong: Leaders already want to grow their businesses. But for whatever reason, they have trouble seeing how technology figures into that plan. They see IT in particular as a bottleneck or as the “handyman” who fixes laptops. That’s not IT; that’s tech support.
I remember when I first began working in technology. Suddenly, all my friends and family started asking me to fix their computers. But that’s not what tech expertise is. This mindset—treating tech as a repair service rather than a strategic lever—is exactly why companies get stuck.
Business leaders must change the cultural mindset around technology. Many of them are still operating with a 1999, pre-digital-bubble mentality. But technology is no longer optional. With the acceleration of AI, companies that don’t adopt a growth-driven view of technology are losing ground.
Look at newer companies that run billion-dollar operations with only 10 full-time employees. How is that possible? Because they don’t see technology as a cost center—rather, they see it as the core engine of the business.
Giving IT A Seat At The Table
If you’re a business leader reading this article and thinking, “Oh no, this is my company he’s describing!”, don’t hit the panic button.
Instead, start by having an open conversation with your IT department. It sounds simple, but for many organizations, that conversation just never happens. IT is viewed as something that “just needs to be handled,” and leadership never prioritizes it.
So go to your IT department or your CTO and say: “I’ve changed my mindset. I no longer see what you do as a cost center. How can we grow the business with the work you’re doing?” Then listen. Truly listen.
One of the best lessons I’ve learned is that when encountering an expert in any field, the first thing you should say is “Have a seat.” Then listen. If leaders had regular, open conversations with their CTO or IT team—without preconceived notions—they’d gain enormous insight into their organization: where they’re strong, where they’re weak and how they can grow using AI, automation, digital transformation and data. IT teams sit at the heart of the organization. They see all the systems, all the data, all the workflows. They know exactly what’s happening. Even in a single meeting, leaders would probably learn more about the real state of their business and its growth potential than in most other meetings they attend.
We’ve had countless conversations with companies—small, large, everything in between—and the biggest problem with the “1999 mindset” organizations is that they don’t have a technology leader involved at the board level. IT sits a layer below, and everything has to trickle up and back down. So, decisions get made at the C-suite level without the technical voice in the room.
Solving For System Fragmentation
When we talk to company leaders trying to shift to a more modern framework, I often ask, “What metrics are you tracking to determine whether your IT department is performing well?” If the only metrics you have are uptime or cost, then you’re looking at it completely wrong.
You should be measuring things like automation rates across the organization, employee output with automation and AI and other indicators that help you understand the bottom-line impact on operations. Across most companies, roughly 40% to 50% of work consists of manual, repeatable tasks. Once leaders become aware of how much time is wasted on those tasks, they can start making meaningful changes.
So, a major step for any company is identifying those inefficiencies and understanding whether they already have the right capabilities—or whether their system landscape is fragmented.
And who can actually solve that fragmented landscape? IT. They can connect departments, tools and systems and give you a single source of truth, whether through dashboards, data, communications systems or workflow tools.
Right now, calls, meeting notes and conversations may all be scattered across different systems. If you want to break down silos, only IT can really do that. Many growth barriers in organizations can be fixed by IT … but only if leaders stop viewing it as a cost and start viewing it as a growth driver.
Look at something as simple as deploying an AI note-taking tool. The time savings alone create enormous value. But companies fixate on the subscription cost instead of the output and efficiency gain. It’s all about shifting the question from “What does this cost?” to “What value does this create?”
Speaking Different Languages
Finally, it’s important as a business leader to invest your own time in understanding AI and automation rather than relying 100% on your IT team. You don’t need deep technical knowledge, but you do need a baseline understanding of AI, automation and data so you can communicate your business objectives to IT effectively.
Having someone (yourself or a trusted associate) who can serve in the “translator” role—the bridge between business and technology—is vital. If you’re hiring, bring in people who can speak both languages. Business and tech often feel like different languages entirely. Having someone who can translate, even at a basic level, makes a huge difference.
With this mindset shift, we hope company leaders can go from 1999 to, if not the year 2525, at least sometime closer to today … with a successful and thriving tech stack that allows them to innovate, create and deliver transformative services and solutions.
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