Nonprofit Resilience and AI Newsletter #19

May 28, 2025

Jordan Gill, in her Systems Saved Me newsletter, suggested a prompt that will blow your mind. It's not for the faint of heart, but if you use ChatGPT regularly and you use this prompt, you will likely get more unvarnished truth than you usually hear from people you know. So here it is, modified slightly. Put this in ChatGPT and prepare to listen.

1. What are some patterns you've recognized in me? The good & the bad (growth edges).
2. What are some other data or insight you can give me about myself?
3. Be ruthless. I need to hear what most people are afraid to tell me.
4. This is spot on. Help me come up with a plan to unpack all of this. What does this look like in execution?
5. What are other ways you can support me as my coach? What else could you help me with that might take this chat to the next level? How am I still thinking small here and not asking you the deep, needle moving questions?

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