Montréal CTO and Lead Developers Meetup

Difficult Conversations: Practice Lab (Live Rehearsal Session)
This session is focused on one thing: practicing real conversations before (or after) they happen.
If you have a conversation coming up that you’re unsure about (or one that didn’t go the way you wanted) this is a space to work through it in a structured, supportive environment.
What to expect:
This is a hands-on session with minimal theory.
1\. Quick Check\-In \(brief\)
We’ll start with a short reset and, if relevant, reflections from anyone who tried applying ideas from previous sessions.
2\. Real Situations \(focused\)
Participants can bring:
* an upcoming difficult conversation
* a recent interaction that didn’t go as expected
* something they’ve been avoiding
We’ll select a few situations to explore more deeply.
3\. Live Roleplay & Rehearsal \(core\)
We’ll actively practice conversations:
* try different approaches
* notice what changes
* repeat and refine
After each roleplay, we focus on:
* what was noticed
* where the interaction shifted
* what alternative responses might change the outcome
This is not about getting it “right.” It’s about experimenting and building awareness.
How this is different:
* This is a practice session, not a discussion group
* We work with real situations, not abstract advice
* We focus on patterns and responses, not critique
You don’t need to have attended any previous session to join.
If you’ve ever thought:
* “I need to have this conversation, but I don’t know how”
* “That didn’t go the way I expected”
* “I wish I could try that again differently”
This session is designed for exactly that.

Do you find it uncomfortable meeting new people? We've all been there.
This is a simple, structured space to practice one thing:
getting comfortable talking to someone you've never met before.
No pressure. No performance. No expectations.
Just real conversations with real people.
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What to expect
We'll keep things light and practical.
* You'll be paired with another participant in a breakout room
* Each conversation lasts about 10 minutes
* Then you'll switch and meet someone new
By the end of the session, you'll have spoken with several different people.
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How it works
The goal is not to impress or "get it right."
It's simply to:
* get words out of your mouth
* stay present in a conversation
* get more comfortable starting and continuing interactions
If the conversation stalls, you'll have a few simple prompts to help keep things moving - but feel free to let it flow naturally.
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A quick note on boundaries
This is a practice space for conversation skills, not a dating or networking event.
* Keep interactions respectful and low-pressure
* No need to share personal details or contact information
* If a question or topic doesn't feel right, simply steer the conversation elsewhere
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Who this is for
* If you sometimes feel unsure how to start a conversation
* If you find small talk awkward or draining
* If you just want a low-stakes way to meet new people
You're in the right place.
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Come as you are.
You don't need to prepare anything. Just show up and be willing to try.