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The strategist’s compass: Diagnose before you decide using Cynefin

When there’s an issue on the table, boards and leadership often jump to making decisions. What if the first move is to notice?

We’ve all been there. A room full of smart, experienced people – and instead of coming to greater clarity on a solution, we end up in circular conversations, experiencing decision fatigue, with a strategy that sounds fine, yet doesn’t actually land.

Here’s a moment I’ve seen many times in strategy workshops, especially with board. A tough issue is on the table – it’s unclear, tangled, politically charged. Yet before the group has even made sense of what they’re looking at, someone is calling for us to work out an action plan!

I get it. Leadership is often about  solving problems. The expectation is to be decisive, put our teams at ease, and take charge of the situation. Yet here’s the thing: we can’t reach for understanding unless we know what we’re really dealing with. If we skip the first step – slowing down (even briefly!) to diagnose – we risk wasting time, eroding trust, and missing what the moment is actually asking of us.

That’s why I find the Cynefin framework so helpful.

The question we too often skip: what kind of problem are we facing? 

How can you act decisively and design a way forward, when you don’t know what the problem is? Over the years, I’ve really seen the difference between those who stop and ask “What are we actually dealing with, here?” and those who don’t – reacting out of habit, pressure or panic.

Cynefin (pronounced “kuh-NEV-in”) is a decision-making framework that gives us insight into what’s really going on and the nature of the situation, before choosing a response. It helps us notice the pattern.

The Cynefin framework distinguishes between four types of challenges:
  • Clear: the cause and effect are obvious. Best practice applies.
  • Complicated: there’s a knowable solution. An answer already exists, though it might require expert analysis to find and apply.
  • Complex: patterns are emerging and the path forward isn’t predictable. You can’t analyse your way through – you need to sense, respond, and learn as you go. The answer will emerge over time. 
  • Chaotic: everything feels out of control and there’s no time to think. Immediate action is needed to stabilise things first. You can re-evaluate later.

Recently in a workshop, a team were wrestling with a challenge around partnerships and programs, and defining the right level of engagement. It was tricky – balancing empowerment of the partner with oversight by the board. There were also some other risk ‘red flags’. Yet – at least initially – there was no real discussion on what the problem was that they were trying to solve. Conversation focussed on solutions – the heads of agreement, who would speak to who, what the next ‘action’ would be. But something wasn’t sitting right.

I paused and asked:

“What’s really going on here? It feels like in some parts of this challenge we’re seeking a ‘simple’ solution to a complex challenge, and in others a complex solution to a simple challenge!”

That’s where the Cynefin framework is so powerful. That one shift of focus changed everything. The group started to explore more deeply – the layers, the dynamics and the shifting sands. From there, the group shifted to sense-making instead of solution-ing. Experiments were explored rather than solutions. Space for listening rather than speaking. All this led to greater clarity and buy-in.

Courtesy of my colleague and fellow coach, Kirsten Brown – who has a whole body of work around Cynefin that I draw from (thank you, Kirsten!) – here’s the simple guide I used to determine what kind of situation we were in, and what it was asking of us:

The power of Cynefin isn’t just in defining categories of problems and their responses. It’s in what they invite us to do: slow down our impulse to “get on with it” so we can get on with the right thing.

What happens when we forget to apply this lens?

When we don’t pause to consider what kind of problem we’re facing, we tend to default to what’s familiar. We reach for tools and responses that have worked before, even if the terrain is entirely different.

Clear issues get over-complicated. Complex challenges get oversimplified. Chaotic situations get ignored until they spiral. And the tricky stuff that sits between categories? That often gets avoided altogether.

I often say: If we can’t name what we’re in, we can’t lead through it.

The Cynefin framework helps us name it. It doesn’t give us the answer – it gives us a shared language and a map. And once we understand the landscape, we can choose the most appropriate next step. This small shift – diagnosing before deciding – changes the entire trajectory of a strategy conversation.

The 4 quadrants: lessons on from each domain

What are the patterns in how you and your board or team tend to respond?

Let’s take a look at some of my key learnings on each quadrant, based on what I’ve seen unfold across the organisations I work with.

As you move through each quadrant, I invite you to sit with your own experiences. Note whether you’ve made any assumptions, and that meant for your strategy.

In the Clear problem domain: clarity is enough.

We don’t need to reinvent the wheel. This is where good systems, checklists, and standard operating procedures shine. The risk here is overcomplicating things – spending precious energy solving problems that don’t need solving.

Imagine a People and Culture committee that keeps debating how to record leave balances when a simple policy refresh would’ve resolved it in minutes. I’ve seen hours lost to something that just needed a template. Have you?

Questions to ask here:

  • Are we making this harder than it needs to be?
  • Has someone solved this before – and can we borrow their method?
In the Complicated problem domain: seek the experts.

Expertise matters. There’s a right answer – it just might take effort to find it. Be careful here not to mistake the problem as clear and rush to a resolution, or assume it’s complex and becoming overly philosophical.

Years ago I joined a new board. When I saw their financial reports I was a little flummoxed – they didn’t resemble what I had seen on previous boards. Yet, there were some things in play with this organisation that made coming to the right answer more ‘complicated’ than ‘clear’. I could have jumped straight to demanding a profit and loss and balance sheet as I had always seen them.

Yet, taking the time to analyse what was happening was important in getting it right – working on an annual cycle rather than financial year; working on a big lot of revenue at the start of the year and then spending down. Only with this information could the right decision become clear.

Questions to ask here:

  • What kind of expertise do we need to inform this?
  • Are we asking the right questions – or just the most obvious ones?
In the Complex problem domain: let the path unfold.

This is the space of emergence. There is no obvious solution yet. It’s going to require a little experimentation, trial and error, and maybe encountering a few snakes before you find the ladder. Complex problems require leadership patience and collective noticing – not trying to tidy things up too soon.

An organisation I was working with recently was exploring future partnerships and mergers. What I loved about our discussion was that they started early – before any real options for merger were on the table. It gave time to navigate challenges before acting.  There were strong opinions and emotional dynamics, so they started by sharing, listening, trying small moves, and developing and adjusting the strategy and criteria based on what was learned.

Questions to ask here:

  • What safe-to-fail experiments might help us learn more?
  • What patterns are at play, underneath all the noise?

This is often where board conversations get stuck. Sitting in uncertainty is uncomfortable. I sometimes say: you don’t have to solve it in one go – aim to make progress. That alone can create a new kind of traction.)

In the Chaotic problem domain: stabilise first.

Think crisis, not committee. The fire alarm is going off. You need to act now, even if it’s not perfect. The goal here is to stabilise the system first so you can make sense of things later.

During a cyber breach, one board I observed wanted a full debrief and long discussion so they could make the best decision. Yet, the CTO had to act quickly to shut things down and preserve data. The board’s role became clear in hindsight, not in the moment.

Questions to ask here:

  • What’s the first action we can take to restore safety or order?
  • How will we regroup after the immediate chaos has passed?

(In board contexts, this is where some hesitate fearing it’s “too reactive.” Yet sometimes quick, decisive action is leadership. The key is knowing when it’s truly needed. And remember, this may not be a matter for the board.)

Final thought: you don’t need the answer; just to name what’s going on.

The power of this framework is in its honesty it helps us hold the ambiguity and urgency of leadership without collapsing into either inaction or overcontrol.

Next time you’re in a conversation that feels stuck, ask yourself, your board or your exec team: “What’s going on here? Which quadrant are we in? What are the appropriate next moves?”

And if you’d like some help bringing this thinking into your strategy sessions, let’s talk. I facilitate strategic conversations that help boards and leadership teams get clarity on what matters and where to next.

Strategy isn’t just about choosing what to do, and how best to do it. First and foremost, it’s about asking: what are we dealing with? Knowing what kind of problem you’re facing – so you can respond appropriately.

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Hello! I’m Helga.

I’m a facilitator, coach and strategy nerd who helps leaders and teams turn talk into action. Before talk can happen, there needs to be a kernel of an idea. This is what the Ideas to Action blog is for – providing inspiration, motivation and guided contemplation. Consider it your thinking space.

Whether you’re navigating complexity, shaping strategy, or stepping into board life, I’m here to support the next step of your journey. Get to know me better or explore my coaching and facilitation services to see how I can help you.