How to have hard conversations without losing yourself
(Or: what happens when you stop bracing and start listening)
Dear Substack Reader, Happy Friday!
If you’ve ever delayed a conversation because it felt “too loaded” — this is for you. In this post, I share a coaching moment with a leader preparing for a high-stakes conversation with her CEO. Together, we unpacked how to stay grounded, intentional, and clear — even when emotions are high. Coaching gave her the space to pause, reflect, and lead forward from a place of strength.
Main takeaway from this newsletter
High-stakes conversations aren’t just about what you say — they’re about how you show up. Coaching can help you clarify your intention, sort through the noise, and step into the room with both confidence and care. When you pause long enough to reflect, you often find the conversation you were dreading is the one that sets you free.
High-Stakes Conversations: How to Lead Without Losing Yourself
There’s a moment that happens just before a big conversation — the kind that sits heavy in your chest.
You know the one.
You’ve played it out in your head a dozen different ways.
You want to be calm, clear, and constructive…
But underneath, there’s tension. Emotion. Maybe even fear.
A client of mine — a strong, emotionally intelligent leader — came to our session recently preparing for one of those conversations. She was about to speak with her CEO. Not a performance review. Not a formal 1:1. A real, open conversation about how they work together. About what wasn’t working. About what needed to change.
It was personal. And it was strategic.
She didn’t want to “go in guns blazing.” She didn’t want to fall apart emotionally either. What she wanted was far more nuanced:
→ A respectful, adult-to-adult conversation
→ One where both people could feel heard
→ A moment to re-align, not accuse
That kind of conversation is harder than it sounds.
Because when something’s not working — when meetings get cancelled, communication is spotty, and expectations are left vague — it’s easy to slip into frustration or silence. Either you push too hard… or say nothing at all.
What we worked on in coaching was this: how to hold the middle.
How to show up with clear expectations and care.
How to lead with honesty without becoming defensive or avoidant.
How to ask for what you need, and still make space for the other person’s perspective.
Here’s the line she crafted to open the conversation:
“I’d love to have a quick check-in on how we’re working together—especially around expectations and communication. My goal is that we both feel heard and aligned.”
Simple. Grounded. No blame. No flattery. Just clear intent.
We also talked through what to do if the tone shifted — if defensiveness crept in, or if the conversation became more heated than expected. And this was a breakthrough moment for her: she realized that walking away isn’t failure. It’s actually a boundary. A signal of self-respect. Staying grounded sometimes means knowing when to pause.
This conversation hadn’t happened yet, but the leadership shift already had.
Because what she was really doing was re-claiming her own agency. She was no longer waiting to be given permission, clarity, or recognition. She was choosing to create the conditions for it.
And that’s the invitation of any high-stakes conversation:
Not to win. Not to prove.
But to show up fully, and to lead from a place that’s calm, honest, and deeply self-respecting.
Coaching creates the space you often didn’t know you needed:
A pause.
A breath.
A question that doesn’t rush to fix, but invites you to see.
That’s where the real shift happens — not just in what you say, but in how you say it, and who you are when you do.
If you’re sitting with a hard conversation, I see you.
You don’t have to do it alone.
🛠️Resources / Prompts to Reflect On
Journaling prompts if you’re sitting on a hard conversation:
What am I hoping will change by having this conversation?
What would “success” look like — even if it’s not perfect?
What am I afraid of, and is that fear protecting something useful or outdated?
How do I want to feel about myself when the conversation is over?
📚 If this resonates, here are a few resources:
Susan Scott – Fierce Conversations: practical, human, and direct
Kim Scott – Radical Candor: especially helpful if you struggle to balance care with clarity
The Coaching Habit by Michael Bungay Stanier: a simple intro to building reflective conversations
📣 Connect With Me
If you have any thoughts, questions, or insights you’d like to share, please feel free to reach out to me on LinkedIn or reply directly to this email. I’d love to hear from you! Feel free to go check my website if you are interested for us to partner together.
🙏 Thank you for spending part of your week with us. Stay strong, keep leading, keep inspiring, and fully embrace the roller coaster of leadership.
Warm regards,
Vanessa