Difficult Workplace Conversations Toolkit: 10 Manager Scripts for Tricky Talks (Part 2)

Scripts for the conversations no one wants to have — but everyone needs to.

You know that look.
The “We need to talk” Slack message.
The awkward silence after a joke that didn’t land.
The side hustle that’s suddenly a direct competitor.

In startup life, uncomfortable conversations are everywhere.
And no, winging it isn’t working anymore.

Who it’s for:

Whether you’re a first-time manager, founder, HR lead, or just the person everyone comes to when things get weird — this toolkit’s got your back.

It’s built for real startup moments, where nuance matters and time is tight.

✅ 10+ Proven Scripts & Frameworks

From “How to say no without guilt” to “How to own your mistake without panic” — this pack covers the real conversations you wish you were better at.

• Say what you mean without sounding mean
• Manage up, down, and sideways like a natural
• Built by a startup operator who’s been through (and coached) it all

What’s Inside

From hygiene talks to AI layoffs, this volume covers the un-Googleable convos no one taught you how to handle — until now.

You'll get full scripts, teasers, and prep tools for talks like:

• “I Want to Work Abroad Permanently” – How to say no without crushing dreams (or violating tax law)
• “We’re Not Promoting You This Cycle” – Say it straight without killing motivation
• “Your Jokes Aren’t Funny Anymore” – Address microaggressions without sounding like the Fun Police
• “AI Took Your Job… Kinda” – Re-scope someone’s role without making them feel obsolete
• “We Need to Talk About Hygiene” – Yes, we really wrote this one — and made it bearable

…and 5 more uncomfortable but critical scripts for modern managers and startup teams.

💡 Every script includes:

• ✅ Step-by-step prep checklist
• 🌍 Regional legal & cultural watch-outs
• 📨 Full scripts for email, in-person, and async formats
• 📊 Bonus visuals (yes, there’s a Zoom fatigue chart)

📱 Mobile-friendly, perfect for a last-minute scan before your meeting

Talk less awkward. Lead more clearly.

📓 Built in Notion — duplicate with 1 click
🔁 Lifetime access
🧠 Use it before your next 1:1, Slack message, or all-hands

🎁 BONUS:
Includes 5 customizable message templates for Slack and Email.

Time to turn awkward moments into leadership wins.

👉 Click I want this and get the words, structure, and confidence to do it right.