Leading with Humanity: Exploring Shadows at Work
By Helen Wada with Steven D’Souza
Leadership with Humanity. Are we embracing its full potential?
In the latest episode of the Human Wise podcast, I had the privilege of speaking with Steven D’Souza, author, educator and leadership expert, whose work has inspired leaders worldwide to bring more reflection and humanity into their practice. Steven’s exploration of “the light and shadow of leadership” challenges the idea that leadership is about perfection — instead, it’s about wholeness, courage, and the willingness to lead with both strength and humility.
Steven: “I would know my shadow and my light. Then at last I shall be whole. So for me, being human at work means being conscious of our shadow and our light.”
That phrase set the tone for our conversation — an invitation for leaders to look inward, to reflect, and to recognise that the parts we often hide are the very things that make us most human.
The Shadow Side of Leadership
The notion of “shadow” is one many leaders resist. Yet, as Steven described, acknowledging our shadow can be transformative. It’s not about avoiding discomfort but seeing darkness as a place of growth and change.
Steven: “I see the dark as offering the space of transformation and change... the darkness is actually the space of transformation... it’s the place that we can lead from.”
He reminded us that leadership and culture are inseparable. When organisations value only speed and profit, ignoring the shadow side, the cost can be devastating.
Steven: “Leadership drives culture and culture drives behaviour… we’ve seen the cost when speed and profit were valued over safety… 346 lives lost.”
Helen: “That’s such a powerful reminder that leadership isn’t about image or projection; it’s about responsibility — the human impact of every decision we make.”
The Power of Reflection
In a world obsessed with constant motion, reflection can feel countercultural. Yet Steven spoke passionately about its role in sustainable, conscious leadership.
Steven: “Think about the game of basketball... the coach calls a timeout. It may just be a few seconds, but the whole direction of the play could change. That’s the power of a strategic pause.”
Taking time to reflect creates space for perspective — to see beyond immediate challenges and lead with clarity.
Helen: “We often treat reflection as optional, but it’s fundamental. Those pauses — those quiet, uncomfortable moments — are where real growth begins.”
Embracing Uncertainty and the “Negative Capability” of Leadership
One of Steven’s most compelling ideas was drawn from poet John Keats: negative capability — the ability to stay present with mystery, uncertainty, and doubt without rushing for easy answers.
Steven: “Negative capability... is the ability to live with mystery, uncertainty and doubt without irritable reaching after fact and reason.”
In leadership, this capability builds resilience and creativity. When we resist the urge to control outcomes, we allow space for collaboration, innovation, and unexpected insight.
Helen: “That’s the essence of human-centred leadership — holding the tension between knowing and not knowing, and trusting that stillness can be productive.”
Curiosity as a Catalyst for Connection
Curiosity, Steven noted, is a defining trait of great leaders — yet often undervalued.
Steven: “A child at school, if they ask more than a couple of questions, they’re thought to have a deficit disorder… yet the ability to ask questions is the mark of a great leader.”
Curiosity fuels connection and empathy. By asking questions — not to perform, but to understand — leaders move from command to collaboration.
Helen: “Curiosity is the bridge between perspective and compassion. When leaders stay curious, they create cultures that listen before they act.”
The Invitation to Explore Our Shadow
Perhaps the most transformative moment in our discussion came when Steven encouraged leaders to turn inward with compassion.
Steven: “Use that as an invitation to become curious, to move from defence to curiosity… in noticing our shadow we can bring more compassion, not judgment.”
Helen: “My reflection... is taking time, making time to do this work... to explore our shadows to see the light, to take time, to dive deeper.”
That reflection captures what Human Wise stands for — choosing to pause, reflect, and explore what it means to lead from the heart as much as from the head.
Practical Steps for Leading with Humanity
Pause with Purpose: Create moments of reflection in your day — short timeouts can shift the whole direction of your work.
Acknowledge the Shadow: Notice what you avoid or criticise; it may reveal where growth lies.
Embrace Uncertainty: Resist the rush to know; sit with ambiguity to find deeper insight.
Stay Curious: Ask questions that open dialogue, not close it.
Lead with Compassion: See yourself and others as human first, professionals second.
Final Thoughts
Steven’s words remind us that leadership is not about being flawless but about being whole. It’s about holding our light and shadow together, leading with courage, reflection, and compassion.
At Human Wise, we believe that leading with humanity is not a soft skill — it’s the cornerstone of sustainable growth and authentic connection.
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Listen to the full episode with Steven D’Souza on the Human Wise podcast, available on all major platforms.
Connect with Steven D’Souza on LinkedIn to explore his work on reflective practice and the power of the shadow in leadership.