Jess’s Honest Transitions Toolkit
Everything you need to navigate the hardest people conversations — from the moment you know it's time to the email that tells your team.
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 bundle 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 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 bundle includes tips for adapting it to your specific situation, including AI prompts!
When resources and 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 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
Ready to talk? → Email ninarjacinto@gmail.com with "Helia Connection" in the subject line
Not sure Nina's the right fit? Book 30 minutes with Helia and we'll help you figure out who in our Collective might be.
Related Resources
Different Cultures Need Different Humans — Get honest about your culture BEFORE you build the questionnaire
Finding Your People Worksheet — Identify who actually thrives in your environment
The Right Role at the Right Level — Make sure you're hiring the right role before you start screening
Take what's helpful and make it your own.
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