What happens when a high schooler tells you your positivity feels fake — and it changes everything about how you lead? That’s just one of the moments that shaped Elysha Weissglass ’s path from school counsellor to leadership coach and people development partner.
In this episode, Fiorenza sits down with Elysha for a conversation that moves fluidly between boardrooms and kids’ dinners to career pivots and grief. They talk about what it really takes to support people through change — and why the messiest transitions are often the most important ones.
🔎 What we explore
In this episode, we explore:
From classrooms to corporate: why Elysha made the leap
The dual vantage point: working inside organizations building career tracks and coaching managers, while running a private coaching practice.
The sandwich generation struggle: aging parents, young kids, and how to find presence in the middle of it all
An exploration on how to allow joy and grief to co-exist
Belonging as a practice: what it looks like in moments of grief, identity shifts, and becoming
Fiorenza opens up about anticipatory grief, her grandmother, and the chair that was always set for anxiety at the dinner table
A thread running through it all: the in-between spaces — in a career, in a family, in yourself — are not obstacles to get through. They’re where the real growth happens.
"Things don't always fit into some perfect box. And there are ways to notice what really is here in the moment so that you can have connection and joy and feel what's really there.", says Elysha.
🎙️ Tune in for the full conversation!
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🔗 Links & resources
Explore Elysha Weissglass here on Substack.
Connect with Elysha on Linkedin.
