Originally aired April 9, 2026 on Extropy On AIr.
Digital transformation is usually treated as a technology project, but technology is often the least important part. New platforms amplify whatever system they sit on, for better or worse. In this episode, Kevin Zirkle and Mike Jasper of Extropy Advisors explain why structure and system design have to come first, and how to tell when technology is driving your process instead of supporting it.
Listen to the full episode on the Extropy On AIr podcast page or on Spotify.
Key takeaways
- Technology doesn’t fix a broken system. It makes existing problems more visible and lets you do the wrong things faster.
- Tech-first transformations often create visible progress with invisible stagnation: green dashboards on top of the same workarounds.
- Structure decides who owns what, the system decides how work flows, and technology should come last to enable and scale both.
- Three common failure patterns are tool-first thinking, fragmentation through success, and assuming integration will create alignment.
- Coherence isn’t a one-time achievement. It has to be designed and then reinforced as the business changes.
Why is technology the least important part of transformation?
Because it’s the final layer, not the foundation. Technology should sit on top of decisions that have already been made about how the organization and its processes should work. If those decisions are unclear or inconsistent, the technology will scale that confusion.
Mike said that whenever he makes this point to a leadership team, there’s a pause in the room, especially when they’ve invested heavily in platforms, AI tools, automation and analytics. But the same story keeps coming up: the systems are live, and things still feel harder than they should. That’s usually the first sign the issue isn’t technology, it’s structure. As Kevin put it, technology lets you do the wrong things faster than you ever could before.
Mike added a second reason. Technology is finite, with defined capabilities. Organizational behavior is dynamic: it adapts and creates workarounds. If the system isn’t designed for real behavior, the technology will always lag behind reality.
Why did technology become the center of transformation?
Because it’s concrete. You can budget it, put a timeline on it and assign an owner. It feels controllable.
It also lets organizations avoid harder conversations. Who actually owns this process end to end? Why are there three definitions of the same metric? Why did two teams make the same decision differently? Most organizations don’t have clean answers, so they focus on what they can control: buying platforms, building workflows and launching dashboards. That creates a feeling of progress.
What is “visible progress with invisible stagnation”?
It’s when the transformation looks successful on the surface while nothing fundamental changes underneath. The system is live, dashboards are active and reports look cleaner, but decisions are still slow and people still rely on spreadsheets, tribal knowledge and workarounds.
Executive reporting often reinforces the illusion by tracking implementation metrics like adoption rates, transaction counts and cycle times. As Mike put it, the question shifts from “Did this reduce friction across the system?” to “How well are we using the tool?” Those are very different questions.
Kevin shared an example from a finance team that had fully implemented an AP automation platform. On paper it was a success, with high automation rates and strong throughput. But the team had built an entire shadow process to manage exceptions. The dashboards were green, yet nobody was saving time, the team was still working overtime and they were still asking for more headcount. The complexity had simply moved somewhere else.
What is the structure, system and technology framework?
It’s the order transformation should follow:
- Structure defines how decisions are made and who owns each piece.
- System defines how work and information flow.
- Technology enables and scales that system.
Most organizations invert it. They start with technology, then try to retrofit their structure and system around it. Kevin compared it to building a house starting with the roof. Everything underneath becomes reactive, and teams end up adjusting processes to fit the tool instead of designing the tool around the process.
You can hear it when it happens: “The system won’t let me do that” or “We have to work around this step.” Those are signs technology is dictating behavior instead of enabling it, and over time those workarounds accumulate into entropy.
Where do tech-first transformations go wrong?
- Tool-first thinking. Starting with a solution and looking for problems it can solve, instead of starting with the system you want to design.
- Fragmentation through success. Different teams successfully implement different tools, but nobody owns how they work together. Each group looks fine, but the company does extra work between departments.
- Treating integration as the fix. Connecting systems connects data. It doesn’t align decisions, and teams using the same data for different purposes recreate the complexity.
What should be at the center of transformation?
Coherence and purpose. Transformation should be centered on how decisions are made, how information flows and how accountability is structured, with everything else supporting that. Mike noted that Extropy frames it as people, process and purpose, rather than the familiar people, process and technology.
That shifts transformation from something you implement to something you design and maintain. Businesses change, regulations change and acquisitions happen, so coherence has to be reinforced continuously. When it is, each improvement makes the next one easier.
What should leaders do differently next week?
- Pause before the next technology decision. Ask what system you’re actually trying to create.
- Find where you’re compensating for weak structure. Look for band-aids and places where you expect technology to fix what is really a process problem.
- Map decision friction. Where do decisions slow down, get escalated unnecessarily or produce inconsistent outcomes?
- Redefine success metrics. Measure clarity, alignment and coherence, both quantitatively and qualitatively, not just tool adoption.
In their words
“Good technology rarely makes things harder, but it does make existing problems way more visible.”
Mike Jasper, VP of Finance Transformation, Extropy Advisors
“Technology is not the driver. It’s really just the amplifier.”
Kevin Zirkle, Director of Business Development, Extropy Advisors
About the speakers
Kevin Zirkle is Director of Business Development at Extropy Advisors, where he works across Extropy’s partner ecosystem, matching organizations with the right technology and the right people to move transformation from the whiteboard into production. He also hosts Extropy On AIr’s series on corporate entropy. Mike Jasper is VP of Finance Transformation at Extropy Advisors, where he leads digital transformation and client success, working hands-on with clients to set success criteria, optimize their people, process and technology, and measure the results. He is also a regular voice on the show.
Frequently asked questions
Why do digital transformations fail to deliver value?
Usually because technology is put at the center instead of the system it supports. New platforms get implemented on top of unclear ownership, inconsistent decisions and broken processes, so they automate existing problems and make them faster instead of fixing them.
What is more important than technology in transformation?
Structure and system design. Structure defines how decisions are made and who owns them. The system defines how work and information flow. Technology should come last, enabling and scaling a design that has already been decided.
How can you tell if technology is dictating behavior?
Listen for phrases like “the system won’t let me do that” or “we have to work around this step.” Workarounds, shadow processes and spreadsheets that sit beside a new platform are signs the tool is driving the process instead of supporting it.
Keep exploring
- More episodes of Extropy On AIr
- Previous in the entropy series: Entropy vs. Extropy: Why Digital Transformations Fail
- Previous in the series: AI in Finance Transformation: What SSON Revealed and the Dexcom Win
- Next in the series: 5 Signs Your System Is Breaking Down
- Related: AP Is Not an Afterthought: Why ERP Transformations Keep Leaving Accounts Payable Behind
- How we approach transformation: Why Extropy
Invested in technology but still feel like something is off? Book a discovery call to talk through where your transformation might be breaking down at the structure or system level.
