Self-Coaching in Complexity: Leadership as Sense-Making

Leadership situations rarely arrive labeled.

What feels obvious at first glance may turn out to be something else entirely.

Over the years, one framework has helped leaders make sense of this ambiguity: the Cynefin framework, developed by Dave Snowden.

It offers a way to distinguish between situations that are simple, complicated, complex, or chaotic and to respond accordingly.

I find this framework useful. And I also see where leaders struggle most with it.

Not in understanding the categories.

But in what complexity demands from them internally.

This piece is not a walkthrough of the Cynefin framework.

It’s an exploration of what it takes to self-coach when you’re leading in complexity — where outcomes can’t be predicted, certainty is unavailable, and the real work often happens beneath the surface.

And let's start from here:

Every leadership situation is ambiguous at first.

When leaders step into a situation, the most important question is not what should I do, but:

What kind of situation is this?

How we answer that question determines everything that follows.

Not All Situations Are the Same

Some situations are simple.

They are familiar.

There are clear procedures.

Cause and effect are obvious.

In these situations:

• There are established best practices.

• We rely on habits and experience.

• Mental and behavioural shortcuts work well.

This is efficient leadership.

When a situation is clear, common sense dictates that we do what we already know.

There is little value in overthinking, self-provocation, or extended reflection.

Execution matters more than inquiry.

The risk appears when we treat other situations as simple, just because we want speed or certainty.

When a Situation Is Complicated

Other situations are complicated.

They require thinking, not shortcuts.

Here, the answer is not immediately obvious, but it can be found through analysis, as in complicated situations:

• Variables are largely predictable.

• Expertise matters.

• Multiple perspectives improve understanding.

A leader may deliberately provoke their own thinking by looking at the situation through different lenses.

Not to doubt themselves — but to widen the field of view.

For example, they might ask:

• If I were the most experienced expert in this area, what would stand out as essential here?

• If I were new to this context, what would confuse me or feel unclear?

• From a managerial perspective, what trade-offs or constraints matter most right now?

• From the employee’s point of view, what impact would this decision have on daily work?

• Looking at the wider system, what ripple effects might this create beyond the immediate issue?

These questions are not about finding the “right” answer.

They are a way to stretch perspective, surface assumptions, and approach a complicated situation with greater range and judgment.

What emerges from this perspective work is not best practice, but good practice — shaped by judgment and context.

When a Situation Is Truly Complex

Complex situations are different.

This is the uncomfortable truth:

In complex situations, outcomes cannot be predicted, even with:

• expertise

• analysis

• multiple perspectives.

We can only form hypotheses.

Patterns become visible after action, not before it.

This is where many leaders struggle — not because they lack intelligence, but because complexity challenges our need for certainty.

Acting Without Knowing: Safe-to-Fail Experiments

In complexity, the task is not to find the right answer.

It is to design ways of responding that allow learning.

That means:

• small actions

• manageable risk

• clear first milestones

These are safe-to-fail experiments.

After acting, leaders pause and ask:

• What worked?

• What didn’t?

• What are we learning?

• What should we try next?

Progress emerges step by step.

The Hidden Work of Leading in Complexity

Ironically, the technical part of this process is not the hardest:

• designing experiments,

• taking action,

• reviewing outcomes.

That part is relatively straightforward.

The difficult work happens inside the leader.

Inner Barriers in Complex Situations

Complexity activates inner resistance:

• fear of mistakes

• fear of loss of control

• fear of being judged

• fear of not knowing

Often beneath these fears lie beliefs such as:

• “I should already know.”

• “Mistakes will cost me credibility.”

• “If this fails, it means I’m not capable.”

These beliefs quietly stop movement.

This is why resilience becomes central.

Not resilience as toughness.

But resilience as confidence in our capacity to:

• learn

• adapt

• recover

• respond again

Self-Coaching in Complexity

In complex situations, self-coaching is not a technique.

It is a direction of attention.

Here, the work shifts inward.

Leaders need to work with:

• beliefs

• emotional responses

• tolerance for uncertainty

• confidence in learning, not certainty

Without this inner work, even well-designed experiments stall.

To support themselves, leaders might ask:

• What is the fear here?

• What would help me feel just safe enough to take the next step?

• On a scale from 1 to 10, how much do I trust my ability to deal with the consequences — whatever they are?

• What story am I telling myself about failure here?

• If learning is the goal, what would “good enough” action look like right now?

These questions don’t remove uncertainty.

They increase capacity to stay present inside it.

That capacity — more than analysis or planning — is what allows movement in complex situations.

Crisis Situations: When Speed Matters

There is one more domain leaders must recognise: chaos.

In chaos:

• immediate action is required

• stabilisation comes first

• leaders rely on what they already know

• internal resources matter

• external expertise becomes critical

This is not the moment for self-coaching alone.

Support is essential.

Where Chaos Often Comes From

Here is a difficult insight.

Many crises emerge because leaders:

• treated complex situations as simple

• relied too quickly on shortcuts

• avoided uncertainty

• skipped exploration

What feels like a sudden breakdown is often the result of earlier misclassification.

Why This Matters

“Leading in a complex world” has become a popular phrase.

But complexity is not a slogan.

It requires:

• discernment

• humility

• experimentation

• resilience

• inner work

Self-coaching helps leaders stay present long enough to:

• recognise what kind of situation they’re in

• choose an appropriate response

• learn without collapsing into fear or over-control

A Closing Reflection

Before asking what should I do, try asking:

• Is this simple, complicated, complex, or crisis?

• What kind of response does this situation actually require?

• What inner reactions are shaping my behaviour right now?

• What would allow me to move forward with learning, not certainty?

Leading in complexity is less about having answers.

It is about having the capacity to stay in the question — and act anyway.