Navigating Complexity with Context and Culture

I often talk about the complexity levels and the Cynefin framework, and I know it can sometimes seem a little intangible how it applies to real life. I’d like to share a potent example that came to mind from my time in South Africa.

My background is in manufacturing, where everything is processed and rule based. The perennial dilemma for organisations is what to do about the unexpected. Insist on strict rule-following, and you get obedience at the cost of adaptability and initiative. Have unclear or absent rules, and you risk unpredictable, often detrimental, outcomes. One established fix is to cultivate a strong vision and values, giving staff a compass to act accordingly when faced with the unknown.

I also believe context itself is a guide, and I’ll give you an example.

Lessons from the road

I used to drive on a road in South Africa that had a busy intersection. The road I was on had priority, and the two side roads had a stop sign. The highway code (the rule-based system) is simple: those on the main road have priority, and those with a stop sign must yield. This worked fine every time I went past. Once, however, I arrived at rush hour. The traffic on the main road was a continuous, unbroken flow of cars, making it utterly impossible for anyone at a stop sign to cross.

As I reached the intersection, I saw something totally improbable unfolding. Drivers had unofficially changed the rules and began treating the intersection as a four-way stop. The first car to arrive, no matter where it came from, was the first to leave. This meant that whether you were on the main road or not, you stopped and yielded to whoever was before you. And whilst the traffic was dense, there was no gridlock; it just flowed.

Coming from France, where this likely would have descended into a every-driver-for-themselves stalemate, this was a complete surprise. The local culture had enabled something different: an unwritten rule, known to and applied by all, that was entirely contextual and the best possible solution for the situation at hand.

As I drove away, I pondered how to apply this to a business context and culture. And as I rolled up to the next traffic light, or “robot,” as they call them there, I was reminded of another layer to this lesson.

Lessons from the Contextual Robot

When you drive up to an intersection with a robot in South Africa, your first task is to ascertain whether it is working or not. There are multiple options:

• It’s working: You follow the lights (although, in practice, there are many local accommodations, from anticipating the green, to rolling forward on red, to going through on red because they know the sequence, etc.).
• It’s switched off: There are no lights, or they are flashing. Then the rule is simple: it becomes a four-way stop. This is simple to apply on single-lane roads, more complicated on dual carriages, and gets very complex on some intersections with three lanes and two turning lanes in every direction. In the latter case, it becomes an art form of mastering sequence and flow.
• It’s partially working: There is a great variety of weird and wonderful cases. I encountered one where the lights cycled from red to orange only. It took every driver one cycle to understand the system, and then we all learned to proceed on orange.

What I learned from this is that an intersection is never a given; it’s always to be managed on a case-by-case basis. Local knowledge helps, but just because you drove by in the morning and it was working doesn’t mean it will be in the afternoon. It’s a dynamic environment, ever-changing and impacted by circumstance. You can imagine what it’s like at night.

So, the first business lesson is to treat every major intersection, every choice point, as unique. We must spend time evaluating the context: Is this a no-brainer (a working traffic light) where we just follow our normal processes? Or are we facing a complicated or complex situation (a varying level of dysfunctional robot) that we need to assess individually, in this moment in time?

But I don’t believe that mechanistic assessment is enough. The cultural aspect plays a huge part.

As a foreigner, I’ve made my share of mistakes and misjudgements. Until now, luckily with no serious consequences. Whilst I have been honked at for not going through on red, I have never been honked for making a genuine mistake! I have sensed a surprising amount of tolerance for my failings. I’m not saying everything is perfect or that there isn’t any road rage, there is. However, I have seen more evidence of a culture favouring resilience and flow than of people getting upset simply because a rule has been broken.

How do we bring those aspects, contextual awareness and cultural tolerance, into our organisations to better navigate the complexities of our modern working world? This is where frameworks like Cynefin become essential.

A Brief on Cynefin

Cynefin is a sense-making framework that helps you decide how to act based on the nature of the situation you’re in. My driving stories are perfect illustrations of its domains:

• Clear (The working robot): The domain of best practice. The situation is stable, cause-and-effect are obvious to all. Response: Sense – Categorise – Respond. Follow the established rule or process.
• Complicated (The partially working robot): The domain of experts. The right answer exists, but it is not self-evident; it requires analysis and expertise. Response: Sense – Analyse – Respond. Bring in experts to diagnose and decide on the best approach. In this case, do your best to see who was there before you.
• Complex (The switched-off robot at rush hour): The domain of emergence. The situation is unpredictable; there is no one right answer, the only way forward is to experiment and see what works. Response: Probe – Sense – Respond. This is what the drivers did by creating a new, emergent rule (the four-way stop). You run safe-to-fail experiments, learn from the results, and adapt.
• Chaotic (A major accident at the intersection): The domain of rapid response. The immediate priority is to stop the bleeding and stabilise the situation. Response: Act – Sense – Respond. Act decisively to establish order, then look for patterns to move into the Complex domain.

Understanding which domain you are in prevents you from applying a simple, rule-based solution to a complex, emergent problem, a critical skill for modern leadership.

Ready to Build a More Adaptive Organisation?

The challenges of today’s world can’t be solved with yesterday’s rulebooks. They require a new approach: one that blends nuanced understanding with practical action and replaces rigid control with guided adaptability.

This is the work I do. I help leaders and teams navigate complexity and build cultures that are resilient, adaptive, and human-centric. We move beyond one-size-fits-all models to develop the contextual awareness and practices that work for your unique environment.

We achieve this through:

• Sensemaking Workshops: Using tools like Cynefin to understand your true context and identify which domains your challenges fall into.
• Cultural Diagnostics: Mapping the unwritten rules and rituals that truly guide behaviour, much like the emergent four-way stop.
• Leadership Development: Cultivating the awareness, empathy, and skills to lead through uncertainty, fostering tolerance for experimentation and learning.
• Designing for Adaptability: Co-creating processes and structures that learn and evolve, turning your organisation into one that knows how to handle a broken robot.

This approach is deeply informed by the perspectives in my book, How Might We?.

How Might We? offers a groundbreaking perspective on organisational transformation, rooted in neurodivergent ways of seeing, sensing, and solving complex problems. Drawing from lived experience and systems thinking, it takes leaders on a journey through what truly makes transformation succeed.

Ready to lead real change? Get my 292-page eBook How Might We? + a free 5-day email course on leading transformation from a fresh perspective.

Let’s connect and discuss how we can build a culture that knows when to follow the lights, and when to create a better way forward together.