This toolkit brings together Jess Skylar’s real-world playbook for reaching out. Real emails from her actual sent folder, plus Helia Collective member Jesse Noonan’s full series of job-search emails built with coach Eric Woodard. These are the tools Jess wishes she’d had every single time she stared at a blank email trying to figure out what to write.
From the Helia Library — based on the article The Magic In Reaching out to Others.
What’s Inside
Two resources, built to be pulled from in any order. If you’re job searching, fundraising, or doing any sustained outreach push, use both. If you’re trying to write a single email right now, start with Making the Ask.
01 — Making the Ask: Jess’s Sent Folder
A step-by-step exercise for tracking everything you do, rating it 1-10, and taking your below-7 list to AI to figure out what it can help with. Use this first — before you chase any tools — to identify exactly where AI should fit into your work.
02 — Jesse’s Job Search Series
Jesse Noonan’s complete seven-email series from her seven-month job search. Built with coach Eric Woodard of Win at Work. The clearest example we’ve seen of someone using a job search to actually deepen a network, not just activate it. Worth reading even if you’re not job searching. The principles apply to any sustained outreach effort.
When Would I Use This?
This toolkit is for anyone trying to reach out to another human and feeling a little stuck about how. You might reach for it when:
- You’ve been sitting on an email for two weeks, and the wording still isn’t coming
- You’re in a job search, a fundraising push, or any sustained outreach moment — and you want to do it really well over time
- You want to reconnect with someone you haven’t talked to in years and don’t know how to open up
- You’re doing a big life transition (new city, new role, new phase) and need to activate your network
- Someone just helped you, and you want to close the loop in a way that feels real, not performative
Each resource includes three ways to make it yours — including an AI-assisted option!
If You Want Help
Templates help you write the email. They don’t help you figure out:
- Who should I reach out to about this?
- What am I actually asking for, and is it the right question?
- Am I reaching out to avoid the real work, or is reaching out the real work?
- I’ve sent a bunch of these and gotten no responses. What’s going on?
That’s where a thought partner helps. Jess (Helia’s co-founder) works with a handful of leaders at a time on exactly this: figuring out the list, the ask, the next move. Between her network and the full Helia Collective, there’s almost always someone who’s been there on whatever you’re sitting with.
Connect with Jess!
About Jess
Jess Skylar has spent two decades learning — over and over and over — that the thing unsticking her was almost always a 15-minute conversation with a real human. She finally started Helia because she wanted the thing she kept needing to exist for other people, too.
She is trying very hard to reach out earlier these days. Still working on it.
This article comes from Jess’s own pattern of reaching out, over and over, and learning each time. These conversations, and the ones you’ll hopefully start having too, are the heart of the Helia Library. We don’t need to start from blank pages, or do everything alone.
As always, take what’s helpful, leave what’s not, and make it your own.
