There’s No Such Thing as a Difficult Conversation
The illusion of certainty and the power of curiosity
“Every difficult conversation contains a gap between where we are and where we need to be. The question is whether we enter that gap with the certainty of knowing or curiosity as a way of being.”
THE SHIFT | 60 second CONTEXT
“How do I have a difficult conversation?” is a question many leaders carry. Someone isn’t performing. Behaviour is impacting the team. Two people are in conflict. Someone wants a promotion or pay you can’t give them. Expectations aren't aligned.
Different situations. Same response: It’s difficult. You’re concerned, “What if they get angry, defensive or upset?” “What if it makes things worse? What if I damage the relationship? What if it hurts morale?”
If we shift the context, we shift the question:
Same situation. Different context. It’s purposeful. You’re curious, “What’s going on? What don’t I understand? What’s their intention? What assumptions am I making?
The shift: “How do I have a difficult conversation?” to “How do I have a purposeful one?”
What makes a conversation difficult?
It happens all the time, and it’s not just leaders who experience it. It’s part of being human.
A decision gets made you don’t agree with. Someone says something you don’t like. Someone offers you advice you didn’t ask for or they don’t like the way you’re doing something.
Someone’s not pulling their weight, they cut you off in traffic, they take forever in a queue, or they speak in a way you find rude and disrespectful. It doesn’t take much for a reaction.
Seriously? What are they doing? Why are they taking so long? Who do they think they are? Why would they say that?
Without realising it, our brain is firing off thoughts in all directions.
Just like a pinball machine, one thought triggers another, and another, and another. Assumptions. Predictions. Replays. Rumination. Strategising. Rehearsing what to say. Before long, our brain has built an entire story about what’s happening and what it means, with concerns about:
Others:“They’re rude. They don’t listen. They need to change. They’ll disagree. They’ll get defensive. They’ll get angry or upset.”
Ourselves:“What do I say? What if I get it wrong? What if I can’t handle their response?”
The impact:“What if I damage the relationship? What if it hurts morale? What if it makes things worse?”
Our concerns then shape the decisions we make, and how we respond.
If we think they’re wrong, we might correct them. If we think they won’t listen, we might stop talking. If we’re worried they’ll get angry, we might avoid them. If we’re afraid of upsetting them, we might soften what we really want to say.
BE AUTHENTIC ABOUT YOUR OWN EXPERIENCE
As a leader, I’ve found it far more effective to be authentic about your own experience than to tell someone what you think they should do. Share where you’ve struggled with the same thing yourself.
While we might not like to admit it, most of us don't like being told what to do. Yet so much of leadership is spent doing exactly that: giving advice, offering feedback, pointing out what someone could have done better, or differently.
There is another way. A more effective way to influence change.
Tell a story of where you got it wrong, what you struggled with and what you discovered. Let people see themselves in your experience. Stories have a powerful way of holding up a mirror without pointing a finger. They allow people to feel seen, heard, to listen, reflect and discover something for themselves.
There’s one experience I’ll never forget.
What started as a disaster became one of the most powerful opportunities to step up and be a leader: a lesson in what becomes possible when we shift our own context from certain to curious.
The relationship that started like any other, good. Then one interaction changed everything. I went from “this person is great” to “I need to stay away from them.”
I’m not going to sugar-coat it. In a meeting and someone says something that, quite frankly, pisses me off. I go quiet, muttering to myself about how self-centred and disrespectful they are. My chest tightens. My body tenses. I take a long, deep breath.
One of my colleagues notices, “Reading the tea leaves, is there something you want to say?”
All eyes are on me. My brain goes into overdrive, “Do I speak up? Do I keep quiet? Do I tell them what I really think? What if they get angry? What if I make things worse?”
I know what to say, but I don’t say it. I feel like I’ve been thrown under a bus. I diminish my experience and dilute what I say. Anything to “keep the peace”, while frustrated, annoyed and resentful. I avoid him.
Speaking up gets harder and my confidence spirals, “It’s not safe. It’s not worth it.”
There’s one problem. I’m stuck on the question: How do I have a difficult conversation?”
THE TRANSFORMATION: Get Curious
What if there’s something I haven’t seen?
I’ve come to understand that what creates the foundation for great leadership, great organisations and a great personal life doesn’t simply live in what we know or what we know to do. It lives in who we are being.
Simply put, who we’re being describes how we experience ourselves and the impact we have on others — how our thoughts, emotions, beliefs and values shape the way we interact with others and the world around us.
Embracing the wisdom of Indigenous ways of knowing, doing and being, Being invites us beneath the surface, to become more aware of ourselves, to explore the values and beliefs shaping how we see the world, and to be authentic in how we express ourselves.
Being authentic, that is, being consistent with who I hold myself out to be for myself and others — is one of my core values. It’s what people know me for and what people count on me for.
I wasn't being authentic. I was holding back, diminishing my experience and saying what I thought would “keep the peace.” While there are many things I’ve learnt as a leader, and a human, when all is said and done, without integrity, nothing works.
Integrity:
Doing what you know to do, when you know to do it; doing what you say you’ll do, when you say you’ll do it; and honouring your word to yourself and others.
I wasn’t doing what I knew to do. Despite knowing ‘certainty is an illusion, my attention was stuck in the certainty of what I thought I knew. I wasn't curious. I was reacting, making assumptions and filtering what I was seeing through my own beliefs, and past experience — a very normal human response.
Getting curious shifted my attention from what I thought I knew to what really mattered: to be authentic, to listen and lead with purpose. “What is my intention? What really matters here?”
The shift: certainty to curiosity.
“We don’t see things as they really are, we see them as we are”
listen deeply: LISTENING for purpose
Our reactions don't only tell us something about others or what’s happening around us. They can reveal something about us: what matters to us, what we believe and the assumptions we bring.
Think of it like a pair of glasses. We each look at the world through our own lens, shaped by our experiences, beliefs, expectations and assumptions. Most of the time, we don't notice the lens. We assume what we're seeing is real.
If I'm wearing rose-coloured glasses, everything I see has a rose-coloured tint. The colour isn't what I'm looking at. It's in the lens I'm looking through. Like a fish swimming in water: The fish doesn't see the water. It simply experiences the world through it.
This isn't just a metaphor. It's what the brains does.
It doesn’t just observe what’s happening. It filters information, draws on past experiences, beliefs and expectations, interprets what things mean and predicts what might happen next. Much of it happens automatically. A comment becomes disrespect. A disagreement becomes rejection. Speaking up becomes humiliation, exclusion and getting it wrong.
Before consciously examining what’s happening, our brain’s formed an interpretation of what it means and our instinct is to respond to what it means: Stay quiet. Keep the peace.
When faced with uncertainty, our brain naturally looks for answers.
Getting curious asks us to pause before assuming we've found one. It creates space to listen deeply, connect with our values, collaborate with purpose and shift our attention from certainty to curiosity. It’s where a difficult conversation becomes a purposeful one — an intentional practice of creating space between what’s happening and how we respond.
“Between stimulus and response there is a space. In that space is our power to choose or response”.
A principle often attributed to Viktor Frankl, Holocaust survivor, psychiatrist and author of Man’s Search for Meaning, who devoted much of his life’s work to our capacity to choose our response, even in the most difficult circumstances.
We may not choose every thought. But we can choose what we do with it. Perhaps the most important reminder when it comes to a difficult conversation is this:
“There is no such thing as a difficult conversation, only a difficult way of listening”
a reflective PRACTICE: ATTENTION
Next time you find yourself reacting to something someone says or does, and you go to fire off your advice, an email, or prepare for a “difficult conversation,” do the following:
PAUSE: Perhaps Another Unseen Solution Exists
Get Curious, by asking yourself: Where is my attention?
Are you stuck on the content of what they’re saying, or is it on the context? Are you listening for what you already know, or are you listening for purpose?
What is your intention? Why are you here? Are you listening for the fulfilment of your organisations purpose and getting curious about what will help your people connect? OR Are you stuck reacting to what you think we already know?
When you get out of certainty and into curiosity, you create space to discover something new. This is where connection deepens, engagement lifts, and our collective potential is realised, purpose strengthens and growth accelerates.
ABOUT THE AUTHOR
Kylee Stone is an award-winning leadership expert, executive leader and keynote speaker with more than 25 years’ experience leading people, teams and transformation.
An Aboriginal woman with ancestral connections to the Kullili and Waka Waka First Peoples, Kylee’s work in Purposeful Leadership brings together Indigenous wisdom, modern neuroscience and lived leadership experience to challenge conventional thinking about how we listen, lead and succeed with purpose.
She is the Founder & CEO of The Performance Code, presenter of the Growth Faculty’s Emerging Leaders Program: The Foundations of Purposeful Leadership and host of The Uncharted Leader Podcast.
Her philosophy is simple: leadership is a not a position, it’s a practice. It begins with listening.
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