The Quirky Rebel Guide to Easy Coaching Conversations
How to start and end your coaching conversations with clarity, ease, and genuine connection — no pressure, no push.
✨ A Gentle, Powerful Beginning
The start of a coaching conversation carries quiet tension — on both sides.
The client is often wondering, “Am I about to be sold to?”
The coach is quietly thinking, “How do I show the value of coaching without turning into a salesperson?”
The answer? Speak to it. Kindly. Honestly. Out loud.
This approach acknowledges the unspoken — and creates safety for both of you.
Here’s one way to begin, with presence and permission at the center:
You might say something like:
“Hi Emily. Before we get started, I want to check-in. I know you mentioned what you’d like to focus on today, but sometimes things shift. What would make this a meaningful conversation for you, right now?”
Let them speak. Actively listen — not to respond, but to understand.
Then gently offer the shape of the conversation:
“Thank you. We’ll begin by exploring that. At the end, I’ll check in with you about your insights and what next steps might feel helpful. I may also reflect on anything that comes to mind — ideas, resources, or if you’re interested, what ongoing coaching could look like. How does that sound?”
This isn’t a pitch. It’s a clear, caring structure. It gives them room to relax, and gives you a grounded place to lead from.
🌱 Add a Little Depth
You can take it one step further by setting an intentional tone:
“Everything we discuss is completely confidential. This is your space, and I hold it with care.”
(Pause here. Let it land. Let them respond.)
Then invite their participation in the way the session unfolds:
“One more thing — on a scale from 1 to 10, how direct would you like me to be today?
1 is soft and reflective, 10 is bold and challenging — the kind of honesty that helps shift things. There’s no right number. It’s about what feels supportive to you right now.”
This invites trust, collaboration, and choice — the very heart of coaching.
🪄 A Meaningful Completion
Rather than slipping into “sales mode” at the end, let your coaching speak for itself. Trust that a strong, honest session often does more than any pitch ever could.
As you begin to close the session, say:
“Before we finish, what’s one insight or takeaway that feels meaningful from today?”
Then ask:
“What’s one small action you feel ready to take after this conversation?”
Let there be a pause. Let the silence work its magic.
Two Directions the Conversation Might Go
💡 They say: “Tell me more about working with you…”
Beautiful. You’ve created connection, and now they’re ready to learn more.
“I’d be happy to share. There are a few ways I support people through coaching — would it feel helpful if I told you a little bit about what that could look like for us?”
Let it be light. Share with clarity, not pressure.
🙏 They say: “Thank you. That was helpful.”
This is just as meaningful. It may not be the right time. That’s okay.
“You’re so welcome. I’m really glad we had this time together. If you ever want to revisit this conversation or explore coaching down the line, I’m here.”
Holding space — even in a “no” — is a powerful act of generosity. People remember how you made them feel.
⚠️ A Note About Scripts
Use this as a guide, not a done-deal script. Read it out loud. Practice it until it sounds like you. Then let it go and just be present.
Your people don’t need perfection. They need honesty, warmth, and someone who will meet them where they are — and walk with them from there.