Rethink Your Understanding

Transforming Software Delivery

Beyond Frameworks: The Real Weight of Leading Transformation at Scale

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9 min read

A leadership case study for those carrying the weight of transformation—when the change is working, but the friction won’t quit.

This isn’t about criticizing an organization—it’s about honoring the complexity of leading through change, even in highly successful environments.

Transformation fatigue: Is there light at the end of the tunnel? Yes, but just as things begin to brighten, change strikes again, and the path might grow dim once more.

This article was sparked by a quiet but revealing moment: a leader hesitated to define expected outcomes in Jira1. It reminded me that transformation fatigue doesn’t come from stalled progress—it comes from something slower and more dangerous: the erosion of alignment when leadership philosophies diverge over time.

This article connects with thoughts shared by Willem-Jan Ageling, whose work I came across shortly after drafting this piece. Ageling highlights that team autonomy can only succeed when leadership supports it with genuine trust—demonstrated through actions, not just words. Building on that, I want to ask: What happens when the right frameworks are in place, the transformation is progressing, yet trust begins to erode? Not because of outright failure, but due to ongoing, subtle friction at scale.

You may know the feeling if you’re a senior leader navigating Agile, DevOps, or product transformation. The structures shift. The frameworks are adopted. But the mindset? That’s where the real work lives.

I’m incredibly proud of our organization’s transformation over the past decade. It’s not just a success story—it’s one I consider industry-leading in many respects. We’ve gone from legacy delivery models to empowered, product-focused teams aligned around value. We’ve modernized our technology stack, redefined our operating model, and adopted practices many organizations still strive to implement.

But let me be clear: I didn’t say perfect.

Transformation is not a box you check. It’s a system you nurture. And it’s a mindset you must defend—especially as leadership shifts, ownership changes, and misalignment creeps in.

One of the hardest lessons I’ve learned is that not everyone on the journey is aligned on the destination—or how to get there. Some leaders have been at my side for years, yet comments or decisions occasionally reveal a superficial sense of agreement rather than true shared understanding. And those moments? They’re not setbacks. They’re opportunities to rethink, reconnect, and improve how we deliver work together.

This article isn’t a playbook. It’s a reflection. A case study. My own.

Willem-Jan Ageling recently wrote about the importance of trust in team autonomy. His article, Team autonomy only works when leadership shows trust 2, highlighted how quickly things can go off track when a leader reverts to control or bypasses key Agile roles. I see this all the time—not just in isolated teams, but in entire systems. In fact, one of the hardest parts of leading transformation is defending that trust across layers of leadership, especially when new leaders join the organization carrying different philosophies. Trust doesn’t scale automatically. Alignment doesn’t hold itself. And fatigue? It rarely comes from a lack of progress. It comes from the constant effort of holding it all together.

It’s what happens when the transformation is fundamental, yet the friction remains.

If you’ve felt that weight, you’re not alone.

Transformation doesn’t end. It evolves.

As organizations grow, so does the complexity of sustaining alignment. When you’re small—maybe a startup or a few hundred people—it’s easier to rally around shared goals, maintain tight communication loops, and stay close to your delivery model. But as headcount scales, layers are added, and teams diversify, the fatigue risk rises.

We aim for growth, but it’s a mixed blessing—it magnifies both your strengths and your cracks.

Fatigue is no longer isolated to individuals or pockets of teams. It becomes systemic when leadership philosophies diverge, alignment fades, or superficial agreement masks deeper disconnects.

Over the past decade, I’ve helped lead our organization from waterfall delivery to modern, empowered, product-focused teams. We’ve adopted Agile, DevOps, Lean, and Value Stream Management. We’ve moved from outputs to outcomes. We’ve rearchitected our application and modernized our platform.

And we’ve made real progress.

But no framework prepares you for the repetition, the re-explaining, and the relitigation of decisions you thought were long settled.

New executives arrive. Stakeholders change. Strategic direction pivots.

Fatigue doesn’t come from the frameworks—it comes from the effort required to protect them when leadership philosophies keep shifting.

When done correctly, the effort doesn’t end. Transformation is not a one-time project—it’s a continuous journey and a mindset of leadership.

Even years in, the friction returns

By 2020–2021, we were six years into our transformation and hitting our stride. Then leadership changed. A new technology leader arrived with a more hierarchical approach to Agile—one rooted in functional oversight and centralized control. It wasn’t wrong—it was simply misaligned with the autonomous, cross-functional team structure we had built, grounded in Team Topologies 3, Team of Teams 4, and Turn the Ship Around! 5.

Where we embedded all roles necessary to deliver value in one team, this leader expected delivery to be driven by an Engineering Manager-led model—one where the EM managed both delivery and people. Both models are valid. But they are fundamentally different philosophies.

Around the same time, our private equity firm introduced the idea of tracking individual productivity units—a shift back toward legacy thinking like lines of code and activity-based metrics.

Fortunately, I had already introduced Value Stream Management and Flow Metrics, which emphasize outcomes, not output—and especially not at the individual level.

We educated. We realigned. We defended the system.

We succeeded. But it was exhausting.

I’ve been that legacy leader

Earlier in my career, I led the traditional way: resource plans, Gantt charts, and command and control. Even as I started reading Agile literature and implementing new ceremonies, I hadn’t changed my thinking. I was doing Agile—but not leading through it.

My real shift came during a quiet moment of clarity when I realized that I was the one in the way. That moment was the precursor to Rethink Your Understanding—not just a phrase, but a mindset I committed to living and leading through. It’s been my compass ever since.

Resistance doesn’t always yell—it nods

The hardest resistance I’ve faced hasn’t been loud. It’s been polite. Strategic. Sometimes even supportive—on the surface.

One of the longest-running tensions came from a senior product leader I respect for product decisions. He believed in strong direction and centralized control. I believe in empowerment and team ownership.

He would express agreement in executive sessions, but the structures remained top-down. Product managers were not empowered. Roadmaps were handed out rather than co-created. And teams, even years into our transformation, still hadn’t been trained in Agile principles.

Not wrong—just not aligned.

And the cost? Quiet drag. Misunderstood roles. Fatigue.

A moment that made it clear

After our acquisition and the departure of our former CEO, I asked that same colleague for his thoughts on how our division’s executive team might change—a team I’ve been part of for the past few years.

“We’ll be focused on operations. We’ll bring in some senior managers from the business. I’m not sure this is the best use of your time.”

That moment hit hard—but it wasn’t personal. It was clarifying.

He still didn’t see engineering as strategic, and he still didn’t view my technology leadership as part of operational decision-making.

That’s when I realized that fatigue doesn’t come from open disagreement—it comes from the illusion of alignment.

I’ve been writing this story for years

Many of my articles have tried to name this tension:

These weren’t rants. They were reflections—a way to process what it means to lead inside a transforming organization—even when not everyone is transforming with it.

Post-acquisition, two paths emerge

Today, I report to a senior leadership team that believes in transformation through a different model. They emphasize Engineering Managers embedded within teams, hands-on principal-level leadership, and individually oriented career frameworks built quickly based on experience.

It’s not a bad model. It’s simply different from ours, focusing on cross-functional autonomy, long-term capability building, and outcome orientation over individual output.

Neither approach is wrong. But this team operates from very different assumptions.

And reconciling them—that’s where the fatigue returns.

Industry conversations keep me grounded

Outside the walls of my org, I don’t need to explain why value streams matter or why DevOps is more than automation.

When I connect with other leaders at conferences or through advisory boards, I am reminded that I am not alone.

These conversations bring clarity, encouragement, and strength when the internal friction gets heavy.

And yes—sometimes I want to be right

Inside my team, we joke about “Phil Fridays”—that’s when my conviction tends to spike after a week of hard conversations…

It’s not about ego. It’s about care.

I want to build the best teams on the field.

I want to give people purpose, clarity, and ownership.

I want to lead in a way that leaves systems better than I found them.

Others feel the same. And that’s why this isn’t about who’s right or wrong.

It’s about alignment—and the emotional toll when it’s missing.

Agile isn’t failing. Leadership is

You’ve heard it: “Agile is failing.” “DevOps didn’t deliver.”

But it’s not the frameworks that fail—it’s how they’re implemented and, more specifically, how they’re led.

When Agile is used to mask command and control, or DevOps becomes just a reporting layer—don’t blame the model. In most cases, blame leadership, blame the mindset.

Leading transformation means choosing clarity—again and again

Top 5 Triggers of Leadership Friction

  1. Leadership turnover or strategic pivots that deprioritize transformation values.
  2. Conflicting ownership philosophies (e.g., empowerment vs. control).
  3. Introduction of metrics or standards that contradict autonomy.
  4. Rhetorical alignment masking structural or behavioral misalignment.
  5. Organizational scaling that stretches philosophical consistency.

As organizations scale, the stakes grow higher. Alignment becomes harder and systems become more complex. And that means transformation fatigue doesn’t just linger—it compounds. What once felt like a collaborative push for change at a smaller scale can start to feel like a grind as your influence spans more teams, departments, and philosophies.

Growth is a sign of success, but it also magnifies misalignment if we’re not actively checking for it. It’s not just the number of people that changes—it’s the number of assumptions.

Here’s what I’ve learned:

  • You’re not signing up for a framework when you sign up to lead transformation. You’re signing up for a lifetime of rethinking your beliefs and inviting others to do the same.
  • You’re signing up for fatigue—not because you’re weak, but because the work is real.
  • You’re signing up for friction—not because people are bad, but because philosophies differ.
  • You’re signing up for progress—not perfection.

And if you’re still showing up, holding the line, listening, and learning while advocating for your path—you’re leading.

And that’s the work.

Let’s be transparent and honest and stop pretending we’re aligned when we’re not. For those leading transformation: Don’t confuse alignment with agreement. Keep asking. Keep listening. Keep showing up.

References

  1. Clark, Phil (April 12, 2025). From Feature Factory to Purpose-Driven Development: Why Anticipated Outcomes Are Non-Negotiable. rethinkyourunderstanding.com.
  2. Ageling, Willem-Jan (April 06, 2025). Team autonomy only works when leadership shows trust. https://medium.com/@WJAgeling/team-autonomy-only-works-when-leadership-shows-trust-2ab59182f350.
  3. Skelton, M & Pais, M. (2019). Team Topologies: Organizing Business and Technology Teams for Fast Flow. IT Revolution Press.
  4. McChristal, S. (General) & Collins, T. & Silverman, D. & Fussell, C. (2015). Team of Teams: New Rules of Engagement for a Complex World. Portfolio.
  5. Marquet, David L. (2015). Turn the Ship Around! Penguin publishing.

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