The Courage to Stay With: What Empathy Really Requires of Us

Melissa
Jul 22, 2025
4 min read

Empathy is at the heart of courageous coaching, but let’s be honest, it’s not always easy to practice.

It sounds so simple: to sit with someone in their pain, their uncertainty, their stuckness. To let them know: “I’m here. I get it. You’re not alone.”

But most of us, even as trained, committed coaches, miss the mark sometimes. Because empathy asks something vulnerable of us: to connect with our own discomfort and stay present without fixing, avoiding, or taking over.

Empathy isn’t about getting it right every time. It’s about recognising when we miss, and being willing to come back. And the truth is, we all miss the mark sometimes — even (and maybe especially) those of us who coach for a living.

And here’s something important to name:

As coaches, we might not say these empathy misses out loud — we’re trained not to. But that doesn’t mean they’re not happening.

We might think:

“I wouldn’t have handled it like that.”
“This really isn’t that big a deal…”
“I hope we move on from this soon.”

And whether we realise it or not, those thoughts can leak out, in our facial expressions, our posture, our energy. Our clients feel that disconnection, even if they can’t name it.

Empathy isn’t just what we say. It’s how we are in the room.

With that in mind, Brené Brown’s research on empathy misses gives us a powerful lens to notice when and how we unintentionally disconnect, not just in coaching, but in everyday relationships too.

The Empathy Misses: How We Get It Wrong (Even When We Mean Well)

Here are some of the most common ways we can move away from connection — often without even realising it:

Sympathy Instead of Empathy

“Oh no, that’s awful.”
“You poor thing.”
“I don’t know how you’re coping.”

These comments sound caring, but they create distance. The subtext is: “That would never happen to me.” It separates us instead of standing alongside.

Reflection: When someone shares something vulnerable, do I try to soothe with sympathy… or do I stay alongside with empathy?

Judgment or Disappointment

“Oh wow, I can’t believe you did that.”
“I thought you were stronger than this.”

Judgment is often a cover for our own discomfort. Sometimes we feel the shame for the other person and project it back. Sometimes we’re too attached to a polished version of them to hold space for their humanity.

Reflection: Can I allow someone to be messy, imperfect, or emotional — without needing to resolve it or distance myself?

Discharging Discomfort With Blame

“What were you thinking?”
“Who let this happen?”

Blame helps us feel in control, as if assigning fault will make the pain more manageable. But it can leave the other person feeling alone or even shamed.

Reflection: When I feel discomfort in a conversation, do I look for someone to blame — including the person speaking?

Minimising or Avoiding

“It’s not that bad.”
“You’re amazing, don’t be so hard on yourself.”
“Let’s not dwell on it.”

We do this when we feel uncomfortable — not them. It may be well-meaning, but it can leave the other person feeling unseen or dismissed.

Reflection: What feelings do I struggle to sit with — in others and in myself?

Comparing or Competing

“That’s nothing. One time I…”
“Oh yes, something similar happened to me…”

Relating can be powerful — but not if we use it to take the spotlight or shortcut connection. It’s not about you right now.

Reflection: Am I truly listening to understand, or preparing to share?

Speaking Truth to Power — and Not Being Believed

“You said that to your boss?”
“You can’t talk about that stuff at work!”

When someone shows courage, especially in standing up for themselves or others, they don’t need to be managed. They need to be seen and supported.

Reflection: When someone challenges the status quo, do I meet their bravery… or try to shrink it?

Advice-Giving and Fixing

“Have you tried…?”
“What about…”

This is a classic — especially for coaches and helpers. We want to help. But rushing into problem-solving often bypasses the deeper need: to feel understood.

Reflection: What part of me wants to jump in and fix? Can I trust that presence is enough?

This Isn’t Just About Coaching

These empathy misses don’t just show up in our coaching work. They show up in every part of life.

With friends, we try to cheer them up when they’re grieving. With colleagues, we rush past their feelings in favour of getting things done. With partners, we try to ‘logic’ them out of their pain. With kids, we dismiss what feels big to them because it seems small to us.

But empathy, real, grounded, courageous empathy, invites us to stay with someone, just a little longer.

To resist the urge to move things along. To notice when we’re uncomfortable. To come back to presence.

The Courage to Stay With

Empathy takes courage. It asks us to sit beside someone in a place we might not want to visit, and not turn away.

It’s not about saying the perfect thing. It’s not about having the right tool or intervention. It’s about being with, not doing to.

That’s not just courageous coaching. That’s courageous living.

Final Reflection

What would change if you brought just 10% more empathy into your next conversation, with a client, a friend, or your partner? What would it mean to stay with someone’s experience a little longer, without fixing, comparing, or rushing in? And what kind of courage might they catch from you, just by feeling truly seen?

If you like recognise some of those misses in yourself and you like some help developing your empathy, you know where I am.

About Me

I'm a coach, supervisor, and courage cultivator, supporting coaches to lean into vulnerability, embrace their humanity, and show up with courage in their coaching practice and businesses.

Through my work, including The Courageous Coach Programme launching in November 2025, I help coaches move beyond collecting tools and techniques, and instead build the inner foundations needed for transformational coaching.

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