This bundle brings together Jess Skylar’s complete approach to employee transitions — from the opt-in conversation framework that replaces the ambush firing, to the severance philosophy that makes choice real, to the copy/paste emails you’ll need the day after. Jess has spent twenty years leading mission-driven organizations, and this is the process she wishes she’d had earlier in her career.
From the Helia Library — based on the article When It’s Time for Someone to Go.
What’s Inside
Three resources, meant to be used in sequence. Start with the Opt-In Conversation Guide — the other two pick up where that conversation ends.
01 — The Opt-In Conversation Guide
Scripts and a step-by-step framework for the conversation itself — including how to set the tone, name what’s not working, present a real choice, and close with care. Use this before, during, and after you sit down with the person.
02 — The Case for Generous Severance
A thinking tool for getting clear on your severance philosophy — and making the math-based case to your board or leadership team. Use this as you’re preparing for the conversation, so you know exactly what you can offer before you walk in the room.
03 — Transition Communications Templates
Copy/paste language for the three messages you’ll need after the decision is made: the confirmation to the departing team member, the announcement to your team, and the note to clients and external partners. Use this in the 24–48 hours after the conversation.
NOTE: Helia is not a law firm and this is not legal advice. Consult a lawyer if you have any legal concerns about the situation you’re facing.
When would I use this?
This toolkit is for leaders who know — or are starting to know — that someone on their team isn’t working out. You might reach for it when:
- You have a nagging feeling that it’s time for someone to go, but you keep finding reasons to wait
- You’ve been having the same performance conversation over and over, and nothing is changing
- You want to handle a transition with dignity and care, but you have no idea what to actually say
- You need to make the case to your board for a generous severance package, and you don’t know where to start
- Someone has made their decision to leave, and you’re staring at a blank email trying to figure out how to tell your team
Each resource in this toolkit includes tips for adapting it to your specific situation, including AI prompts!
When templates aren’t enough
These tools will help you prepare for and navigate a transition conversation. What they can’t do is tell you whether your instinct is right, help you see the politics around someone senior or long-tenured, or support you through the team dynamics that surface after the announcement. If there are potential legal concerns, a complicated relationship, or you’ve never done this before and you’re dreading it — that’s usually where having someone outside the situation makes a real difference.
If you want help with employee transitions
Nina Jacinto partners with leaders navigating org restructures, layoffs, and the human side of hard transitions — helping them think through the approach, navigate the politics, and make decisions that work for both the organization and the people involved.
She’s a good fit if:
- You need someone to gut-check your approach before you walk in the room
- You’re restructuring multiple roles and want to design the process thoughtfully
- You’re navigating a departure that involves someone senior, long-tenured, or well-liked
- You’ve been avoiding this conversation and need someone outside the dynamics to help you see it clearly
- You want to build a severance philosophy before you need one — not in the middle of a crisis
Connect with Nina!
This resource comes from a coffee chat with Leah Peters in November 2025 — and from my own years of watching teams struggle before I understood what I was doing to cause it.
Take what’s helpful, leave what’s not, and make it your own.
