Delegation Conversation Scripts
Language for handoffs, check-ins, and the moments when things go sideways.
The template structures what you delegate. These scripts help you navigate the conversations that come after — from the initial handoff to checking in when you're worried to handling it
when the work comes back wrong.
From the Helia Library — based on our Coffee Chat with Laila Plamondon
When would I use this?
You've handed something off and you're not sure how to check in without micromanaging
The work came back and it's not what you wanted — you need language that doesn't shut them down
You're tempted to take something back and need to figure out if that's the right call
Someone's ready for more responsibility and you want to have that conversation well
The Scripts
When you're handing off
Opening the conversation:
"I want to walk you through something I'm delegating to you — not just the what, but the why and the how. I've thought through the details, but I want to make sure you have everything you need and that we're aligned before you start."
After walking through the template:
"On a scale of 1-10, how confident are you that you can deliver this by [date]? ... What would get you closer to a 10?"
When you're checking in (and it's going well)
"I wanted to check in on [project]. From what I can see, you're [specific observation of what's working]. Anything you need from me, or are you good to keep running?"
When you're checking in (and you're worried)
"I want to check in on [project]. I've noticed [specific observation — deadline slipping, quality concern, stakeholder feedback]. Help me understand what's happening and what you need."
If they need help: "Okay, let's figure this out together. What's the biggest blocker right now?"
If they need more direction:"Let me be clearer about what I'm looking for. [Restate expectations.] Does that help?"
When the work comes back and it's not right
If it's fixable: "Thanks for this. I want to walk through a few things that need to shift before this is ready. [Specific feedback.] Can you take another pass with these in mind?"
If you need to understand what happened: "This isn't quite what I was expecting. Help me understand your thinking here — I want to make sure we were aligned on what success looked like."
If you realize YOU weren't clear enough: "Looking at this, I think I wasn't clear enough about [X]. That's on me. Let me clarify what I need, and let's figure out the path forward."
When you're tempted to take it back
Pause and ask yourself:
Is this actually broken, or just different from how I'd do it?
What would they learn if I let them struggle through this?
What am I teaching them if I take it back?
If you decide to take it back (sometimes that's right): "I'm going to take this back — not because you did anything wrong, but because [honest reason: timeline shifted, stakes changed, I realized I need to be closer to this]. Let's debrief so this doesn't feel like it came out of nowhere."
When they've grown and you're expanding their scope
"You've been doing great work on [X]. I want to talk about expanding your ownership to include [Y]. This is a stretch — here's why I think you're ready, and here's what support will look like."
How to Make These Yours
Quick version
Pick the script closest to your situation, adapt the bracketed parts, and practice saying it out loud before the actual conversation.
Deeper version (recommended for high-stakes conversations)
What to upload:
This scripts document
Context about the specific situation (what you delegated, what happened, what you're worried about)
Anything you know about the person's style, past reactions, or what motivates them
The prompt: "I need to have a difficult delegation conversation. Here's the situation: [describe]. The person I'm talking to tends to [their style — gets defensive, shuts down, needs a lot of reassurance, etc.]. Help me:
Adapt the most relevant script to this specific situation
Anticipate how they might react and suggest responses
Give me an opening line that sets the right tone"
Pro tip: If you're nervous about the conversation, ask the AI to role-play it with you. "Play the role of [person] and respond the way they might. I'll practice what I want to say."
Take what’s helpful and make this your own!
When Scripts Aren’t Enough
These give you the words. They don't give you:
The judgment call on whether this is a "let them struggle" moment or a "step in now" moment
How to repair trust if you've taken things back too many times
What to do when the person is struggling but won't admit it
How to delegate when you're not sure you trust the person yet
If you find yourself avoiding delegation conversations — or having them and watching things fall apart anyway — the issue might be what's happening underneath the words.
→ Email Nancy to work through the specific dynamic that's tripping you up.
Related Resources
Delegation Template — The full framework for structuring handoffs
Delegation Self-Assessment — Figure out where your delegation is breaking down
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