The Leadership Paradox: Why the leadership skills we need can feel uncomfortable

In my work with leaders, I increasingly notice something interesting. The behaviours that enable us to lead well in complex systems: listening deeply, collaborating through tension, and navigating uncertainty, don’t always feel natural.

In fact, they can feel uncomfortable. Even risky.

This is because they are often counterintuitive (they go against how our brains are wired to keep us safe) and countercultural (they go against how we’ve been shaped to behave in systems like education).

My own understanding is this area has been drawn from my own grounding in anthropology. Despite my mum’s initial distaste at me choosing a degree that wouldn’t lead directly to a job, I can honestly say it was the most useful of subjects. And I studied both physical and cultural anthropology- how the human brain and body evolved over millions of years, effectively to survive, be safe (and reproduce) and also how humans collectively operate in complex cultural environments. So, for my work in education and now as a systemic leadership coach and trainer, this grounding has been invaluable.

What does this mean for how we lead?

From an evolutionary perspective, our brains developed to primarily help us survive immediate threats.

We are wired to:

• Avoid social risk

• Protect our status within a group

• Make quick judgments to stay safe

• Seek certainty

In early human environments, this made perfect sense. Belonging to the group was essential for survival. Being wrong, excluded, or seen as a threat could have fatal consequences.

Fast forward to today, and while the context has changed, the wiring remains and our brains still push us towards what feels safe.

Culture reinforces the same patterns

Alongside this biological wiring, culture plays a powerful role. In many of our systems, particularly education, we are shaped to:

• Value being right over being curious

• Avoid mistakes rather than learn from them

• Seek approval rather than challenge thinking

• Prioritise action over reflection

  
  

So we have both biology and culture reinforcing the same tendencies, which is why leading in a way counter to this can feel so hard.

Three relational capabilities that challenge this

Through my work (and a great deal of reading), I have identified three core relational capabilities needed to work well in complex high-pressure systems:

• Listening to seek understanding

• Radically collaborating

• Navigating with agility

  
  

Each of these, in some way or another, runs against both our instincts and our conditioning.

1. Listening to seek understanding

True listening is more than hearing words. It’s about seeking to understand both others and the wider system. But this can feel counterintuitive.

When we listen, our internal dialogue is often focused on:

• What we will say next

• How we are being perceived

• Whether we agree or disagree

  
  

This is our brain trying to protect us, maintaining status, avoiding looking foolish, staying in control. Culturally, we are also taught to value being correct. In education especially, success is often associated with having the answer. And the UK education system is particularly obsessed with this.

Our education system has also brought up leaders to make judgement. Again the UK seems to lead the way in this.  

So listening with curiosity, suspending judgment, and creating space for sense-making can feel unfamiliar, even uncomfortable. And yet, it is foundational to good decision-making and creating strong trusting relationships.

But the value of listening goes deeper than this. Listening to ourselves is often the hardest part. It takes time, can feel self-indulgent and requires a level of honesty that can be emotionally challenging. Yet without this, we risk leading on autopilot. When we make space to understand our own triggers, strengths, and values we build the self-trust needed to make sound decisions under pressure. Research by Dr Tasha Eurich and the work of Astrid Korin increasingly shows that self-awareness is a key indicator of both personal resilience and effective leadership. In this sense, listening inwardly is not a luxury, it is essential to leading well.

2. Radically collaborating

So to my second core attribute, Radical Collaboration. Why radical? The original meaning of radical is like a root (a radish) and more familiarly radical meaning different. So radical collaboration to me is about being rooted in shared purpose and a willingness to go beyond the status quo.

But again, this challenges our instincts.

We are naturally inclined to:

• Avoid conflict

• Protect relationships by not “rocking the boat”

• Seek agreement

  
  

This is about social safety. At the same time, many of us have been shaped by cultures that reward compliance and discourage challenge.

So working through tension, inviting different perspectives, and disagreeing well requires us to move beyond both instinct and conditioning. It asks us to hold two things at once: a strong sense of shared purpose (and root collaboration in this), and a willingness to sit in discomfort together. If we can learn both these things then we can work out how to move forward together, even when we are not fully aligned.

3. Navigating with agility

In complex systems, leadership is less about having the detailed plan laid out before us that needs to be implemented and bought into and more about collectively taking the next step.

This means embracing and making space for  sense-making, experimentation, learning from mis-steps.

But this runs directly against our need for certainty. Certainty feels safe. As leaders, we often feel pressure to provide it for ourselves and for others. Culturally, we have traditionally been rewarded for decisiveness and clarity. The archetypical strong leader has been decisive, a hero even.  

So saying “this is what we know, this is what we don’t know, and we will learn as we go” can feel exposing. And yet, the ability to navigate uncertainty with calmness, communicate openly, and take the next step is essential in today’s world.

Credible leadership now is more about confidently and coherently leading through uncertainty, when alignment isn’t always there.

Choosing differently

Acknowledging that these behaviours are both counterintuitive and countercultural provides an important starting point. We stop seeing the discomfort as a sign that something is wrong. Instead, we recognise it as part of the work.

Becoming aware of our human tendencies for safety can help us understand ourselves and others. We can also lean into our very human ability to connect well, something we most certainly need and are increasingly drawn away from in this digital age. And here is the hope. Not performative hope but realistic hope. As humans we have evolved the ability to connect well over millions of years, we’ve just forgotten how to do it. So now is the time to be more intentional about connecting well with others because this is where the light will shine brightest through the cracks.

So I ask you to notice:

Where are you and others you work with being drawn into behaviour that keeps us 'safer' than necessary?

And a question to ponder:

How can we collectively feel more comfortable with discomfort, in order to work well together?

My name is Tamara Zaple Rolfs. I help people work well together to drive positive change. Do get in touch if you'd like to find out more about how we can collaborate, connect or work together. www.my-delta.co.uk tamara@my-delta.co.uk