What Leaders Get Wrong Before They Touch the Technology
The hardest part of change is rarely the technology, and with artificial intelligence (AI), that is more true than ever.
I've spent three decades watching organizations approach transformation, and the pattern is surprisingly consistent regardless of industry or company size. The most common mistake I see has nothing to do with which platform a leader eventually chooses. It happens earlier than that.
The real challenge is that leaders are starting the conversation too far downstream. They begin with platforms, tools, and architectures, comparing vendors, before they have alignment on something far more foundational: what are we actually trying to become as a business, and how do we want to operate differently?
When that work gets skipped, the technology conversation starts standing in for strategy rather than enabling it. The tool gets chosen before anyone has defined the operating model it is supposed to serve.
What Would We Do If We Could Do Anything?
There's a single question I believe every leadership team should sit with before any technology conversation begins.
What would we do if we could do anything?
It sounds simple, but it gets to the heart of the issue very quickly. It forces leaders to separate the constraints they deal with day to day from the ambition they hold for the business. Most organizations walk into a transformation conversation already limited by their existing systems, processes, and habits.
The question shows you whether an organization is genuinely willing to rethink the work, the decisions, and the experience it provides to customers, or whether it is really just looking for better software to preserve the status quo. Most companies say they want to transform. What many of them want is a better version of what they currently have.
It also explains why so many implementations fall short, organizationally rather than technically. What is usually missing at the starting line is clarity: on the business outcomes, on how the work would change and who would own what across functions, and on the data and governance foundation that should have been settled first. A polished technology plan is not the same as an organization being ready to operate differently.
Unconstrained Reimagining
The phrase I use for the work that has to happen first is unconstrained reimagining. It is easy to mishear that as a brainstorming exercise detached from reality. It is the opposite: a disciplined conversation in which the leadership team steps back from their tools and asks a different set of questions. If we were redesigning this part of the business today, what decisions would happen differently? What work would disappear? What would move closer to the customer? Where does human judgment matter most?
These conversations tend to start cautiously because people are so conditioned by the environment they already operate in. But once they get going, what surfaces is rarely a list of system requirements. It is a clearer picture of how the business wants to operate.
The shift usually happens when you stop asking leaders what they want the system to do and start asking what they want the business to be able to do. Those are very different conversations. When a room gets stuck, what tends to break it open is outcome language like "How do we respond faster?" or "How do we serve customers better?" Once people start talking in those terms, the imagination follows.
What surprises leadership teams most is how often they have been building toward the wrong thing. They come in thinking they need a better planning platform, more automation, or a cleaner workflow. But what looks like a systems challenge usually turns out to be an operating model challenge.
Closing the Gap
There is a belief in this industry that the right platform will eventually close the gap between the commercial and operational sides of the business. I think that belief is dangerous, because it overstates what platforms can do and understates what leaders have to do.
A platform can improve visibility, bring process discipline, and streamline coordination. What it cannot do is align incentives across commercial and operational teams. It cannot clarify trade-offs, resolve fragmented ownership, or create shared accountability where none exists. When leaders lean on that belief, they are really just postponing the harder organizational work. Technology can patch the gap for a while, but closing it is still leadership work.
I've been around enough technology waves to recognize where implementations actually break down. It is the point where the technology stops being an IT program and starts requiring the business to behave differently. It calls for new decision rights and new workflows, surfaces exceptions no one planned for, demands skills the team may not have, and raises governance questions that were never fully resolved. Most organizations are prepared for implementation complexity. They are far less prepared for the organizational complexity that shows up once the business has to work in a new way.
Choose the Way You Want to Work
If a chief supply chain officer told me tomorrow that they were about to begin their AI transformation, the first thing I would ask is this: What decisions do you want to make differently, or faster, or better because of AI, and what operational outcomes would prove to you that it is working?
The answer tells you almost everything. If it comes back to outcomes, decision quality, and how work will change in live operations, you are talking to a leader who is thinking about transformation. If it starts with tools, pilots, and capabilities, they are already starting in the wrong place.
For any leader who recognizes themselves in this, the most important first move happens well before any technology decision. It is getting the leadership team aligned on the future operating model before the conversation gets deep into solutioning. That means agreeing on the outcomes, the decisions, the accountability, and how commercial and operational teams work together going forward. Without that alignment, technology becomes a very expensive way to automate what you already have. Before you choose the technology, choose the way you want the business to work.
Given the pace of AI adoption and the speed at which organizations can now get things done, the rules of the game have changed. Leaders are no longer bound to operate within the constraints of whatever software they happen to have. That only makes the questions I opened with more urgent. If we could do anything, what would we do differently? The leaders who ask those questions early will be far better positioned to use AI to create a different way of operating, not just layer new technology onto the old model.
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