I’ve always loved words. The way they stir thought. The way they evoke emotion. The way a single word, depending on its context, can mean wildly different things.

Take the word wicked.

To some, it conjures excitement. To others, it is a complexity or a challenge. In organisational life, wicked problems are those deeply entrenched issues that defy easy solutions – problems we attempt to fix repeatedly, only to find them re-emerge in new forms.

Over the years, working with leaders, I’ve noticed that these persistently wicked problems often relate to people and culture:

These are complex, emotionally charged issues with multiple causes, competing perspectives, and no clear endpoint. They keep leaders up at night. They can feel overwhelming. And they can feel lonely.

But there is a powerful way forward: dialogue.

At its core, dialogue is about meaning-making. It allows us to think with others, not just talk at them. It shifts us from defending our positions to exploring possibilities.

The roots of the word “dialogue” come from the Greek dia (through) and logos (meaning)—literally, “through meaning.” In practice, this is where the magic happens: dialogue enables people to co-create understanding in ways that transform how problems are perceived, categorised, and solved.

This concept has strong roots in organisational psychology. Karl Weick’s sensemaking theory suggests that in ambiguous or complex environments, people must “make sense” of situations by sharing and interpreting cues with others. Dialogue is the vehicle for that shared sensemaking.

Wicked problems can’t be solved by logic alone. They’re messy, contextual, and emotionally laden. Dialogue offers a way to surface what is often hidden—mental models, assumptions, and unspoken tensions—so that they can be explored, rather than avoided.

From a systems psychology perspective, organisations are not machines—they’re dynamic human systems. Problems arise not in isolation but from patterns of interaction. Dialogue helps reveal those patterns and, more importantly, reshape them.

When done well—especially in a facilitated, psychologically safe setting—dialogue creates space for:

Dialogue doesn’t compete or analyse. It listens. It suspends judgment. It connects.

In my experience, the most impactful leaders are those who move beyond problem-solving as a solo act. They create the conditions for structured, inclusive, and generative dialogue—whether in one-on-one coaching, team offsites, or culture transformation work.

This doesn’t happen by accident. It requires humility, courage, and the willingness to both share vulnerably and listen deeply.

It also benefits from skilled facilitation. At Steople, we work with leaders to design and hold these spaces—places where wicked problems can be seen clearly, understood systemically, and responded to creatively.

If you’re facing a wicked people or culture challenge, know this: you’re not alone. And it’s not about having the right answer. It’s about engaging in the right kind of conversation.

Dialogue won’t solve wicked problems overnight—but it will begin to dissolve their power. It will bring clarity. Connection. And, over time, collective action.

Let’s talk. Book a conversation with a Steople consultant. Your wicked problem might just need a wise dialogue.