This toolkit brings together Claudia Caballero’s complete approach to designing an intentional leadership transition: from the values exercise that gives you a sieve for every major decision, to the big-life questions she used to start imagining what comes next, to the practical tools for actually doing the handoff well.
From the Helia Library — based on the article Other Lives to Live: When It’s Time to Step Down, from our Coffee Chat with Claudia Caballero.
What’s Inside
01 — Claudia’s Core Values Exercise
A five-step exercise for finding the five values that will guide every big decision you make. Use this first — before you plan anything — to build the sieve you’ll run every option through.
02 — Claudia’s Next Chapter Questions
Four big, spacious questions for dreaming your next chapter before you have to decide anything. Use these when you need room to imagine before reality sets back in.
03 — Claudia’s Transition Timeline
Claudia’s actual month-by-month plan, from announcing her departure to walking the Camino. Use this as a model when you’re ready to stop thinking and start mapping.
04 — Claudia’s Stepping-Aside Email
The out-of-office message Claudia sent when she left Centro Hispano — warm, honest, practical, and completely unapologetic. Use this when it’s time to tell people, and you want it to sound like you.
When Resources and Templates Aren’t Enough
These tools will help you think through your transition, get clear on what you want next, and plan a handoff you can feel good about. What they can’t do is replace a real conversation with someone who’s actually been in it — someone who can sit with you in the uncertainty, tell you the truth, and help you figure out whether the voice getting louder is yours or someone else’s. If you’re somewhere between “existential crisis” and “existential revolution,” that’s usually when a thought partner makes the biggest difference.
If you want help with stepping aside
Claudia Caballero grew Centro Hispano from a $60K budget to a $3M organization and is now navigating her own intentional transition. She’s happy to connect with others in similar moments.
She’s a good fit if:
- You’re a nonprofit leader sitting with the question of whether it’s time to step back — and you want to talk to someone who’s actually in it
- You’re trying to design a gentle transition and don’t know where to start
- You’re somewhere between “existential crisis” and “existential revolution” and would really like to talk to someone who gets it
Note: Claudia will be traveling until December 2026. You can follow her journey on Instagram at @claudiacaminando.
