The Year I Crashed: And Started Mapping the Mess

I moved into management thinking I could make it better.

I’d done the work. I knew the pain.

I thought that meant I could shield the team from it. Scope things properly. Push back harder. Protect them from the chaos.

But the system doesn’t want better. It wants certainty. Faster. Cheaper. Smoother. More.

The more uncertain things got, the more the system demanded predictability. But complexity doesn’t care what you want.

In-house teams are just as stretched as agencies. Only now the currency is different. No overtime. No safety net. Just pressure. Salaried employees aren’t clocking hours. They’re clocking loyalty. Working late to stay off the radar. Hoping this quarter’s sacrifice pays off next year.

That trade-off never sat right with me. Perform like you’re replaceable. Hope you’re not.

That was the year I crashed.

What I found when I started mapping

After the crash, I went back over everything. The friction points. The buried assumptions. The workflow illusions. This time, I wasn’t trying to fix anything. I was just trying to see the pattern.

I mapped it all out:

• •Where did decisions actually get made? (Not where the org chart said they should.)
• •Where did handoffs break down?
• •Where did trust erode, and why?
• •What constraints were shaping behaviour that nobody was naming?

What looked like chaos had structure. What felt personal was often systemic.

The problems weren’t about the people. They weren’t even about the processes. They were about the conditions those people were operating in.

And when the conditions shifted during a merger, a restructuring, a platform migration, or a leadership change, the old ways of working stopped functioning. Not because anyone chose dysfunction. But because the ground had moved.

The friction wasn’t a bug. It was a signal. A signal that the system was adapting to forces it had never encountered before. And until someone could make that adaptation visible, everyone would keep trying to fix symptoms while the real patterns stayed hidden.

That’s when I started asking a different question. Not “how do I fix this?” But “how do I help people see what’s actually happening?”

The turning point: learning to navigate unpredictable situations

I’d been bumping into Dave Snowden’s work with the Cynefin Company for a while. But I’d never really taken the time to sit with it. After the crash, I was ready to actually listen. And this was different.

Cynefin doesn’t tell you what to do. It helps you make sense of your situation. Not by categorising it into boxes, but by recognising patterns of constraint, allowing you to respond differently based on what’s actually emerging.

Most organisational transitions aren’t happening in one domain. They’re happening across all of them simultaneously.

The legal frameworks and IT systems integration? That’s complicated: analysable, predictable, and expertise-driven. The human dynamics, such as how trust forms, how meaning shifts, and how new patterns emerge under pressure, are complex.

And here’s the critical part: if you treat complex dynamics with complicated-domain tools, you’ll fail.

The critical first step: Sense-making

Before you do anything, before you plan, before you intervene, before you “fix,” you need to understand what kind of system you’re dealing with.

Because here’s what most leaders get wrong: they see a problem, they reach for the tools they know. And if those tools worked last time (in a different context, with different constraints), they assume they’ll work again. But a tool that works brilliantly in a complicated system will fail spectacularly in a complex one.

Complicated: Integrating two IT systems post-merger → Analyse dependencies, create detailed plan, execute with experts. This works because the system is knowable and predictable.

Complex: Integrating two organisational cultures post-merger → Analyse → Plan → Execute = failure. Why? Because culture doesn’t respond to engineering. It emerges through interaction.

The answer is: Sense first. Then respond appropriately. You’ll analyse for months while the terrain shifts beneath you. You’ll impose best-practice frameworks that don’t fit the context. Trying to impose a plan on a complex system can make things worse. The system adapts around your plan in ways you didn’t anticipate.

That’s why you need targeted experiments. They allow the organisation to respond, and you navigate based on what actually emerges.

What navigating complexity taught me

Over the next few years, I went deep. I enrolled in the Methods Marathons with The Cynefin Company. I studied the concepts: targeted experiments, organisational dynamics, the environment that shapes behaviour, narrative sense-making. But more importantly, I learned how to apply it. Not as theory. As practice.

1. Causality is coherent in retrospect, not predictable in advance

In complex systems, you can look back and construct a narrative about why something happened. But that doesn’t mean it was inevitable. The question isn’t “what’s the root cause?” The question is: “What patterns are emerging that we didn’t expect?”

2. Solutions don’t transfer cleanly

What worked in the last merger won’t necessarily work in this tech migration. Every system has its own history, its own constraints, its own emergent dynamics. Context matters. Always.

3. Multiple targeted experiments in parallel

In unpredictable situations, you don’t implement solutions. You run multiple small experiments, designed to be safe if they fail, so you can discover which ones amplify desirable patterns and which dampen them. You’re creating conditions for new patterns to emerge that you can then act on.

4. Gather stories from across the network, not just perspectives

You gather stories from across the organisation, not to synthesise them into “the truth,” but to understand how meaning, constraint, and pattern are distributed differently across the network. That’s where misalignment hides. That’s where the system is adapting in ways nobody planned for.

What this means for the work I do now

Navigating complexity isn’t a methodology I apply to organisations. It’s a lens that helps me see patterns I’ve watched repeat for 30 years, and help others see them before they get expensive.

We don’t start with solutions. We start with stories. Stories from across the organisation, especially from the edges where people see what’s coming before leadership does.

We map patterns, not problems. We make visible what the system is actually doing, through stories from across the network, so teams can see what they’re standing too close to see.

We design targeted experiments, not big-bang changes. Because in complexity, you learn by doing, not by planning.

We transfer capability, not dependency. The goal isn’t “Sherryl will tell you what’s wrong.” The goal is “your team can now see patterns, sense what’s emerging, and navigate the next wave of complexity on your own.”

If you’re standing in the middle of it

If you’re six months into a transition and you can feel the drag building but can’t point to where… or if you think you know what’s wrong, you’ve tried to fix it, but nothing’s working…

You might be treating complexity like it’s complicated. And that’s not a failure. It’s just a mismatch between the tools you’re using and the terrain you’re actually navigating.

You can’t analyse your way out of emergence. You can’t plan your way through adaptation. But you can learn to recognise what’s actually happening, through stories from across the network, and navigate forward based on the patterns that emerge.

That’s what I help teams do. Not because I have the answers. But because I’ve learned how to make the invisible visible, so you can make decisions about how to navigate it.

The journey continues

I’m still learning. Still refining my understanding of how to navigate unpredictable organisational transitions. Still seeing new patterns emerge in the work.

But here’s what I know for sure:

The crash taught me that you can’t fix systemic drag with individual heroics.

Learning to navigate complexity taught me how to see the organisation, and help others see it too.

And Unflocked exists because too many leaders are standing in the middle of organisational complexity with tools designed for something else entirely.

If that’s you, let’s talk. Not so I can tell you what to do. But so we can gather stories that make visible what you’re standing too close to see, and help you navigate based on the patterns that emerge. Then you decide how to respond.