008. Questions are the answer
STOP making small talk, and ask something you really want to know the answer to.
Asking a good question is an underrated way to connect. It has the potential to remove a boundary, both for the asker and the askee. A good question can dissolve any real or imagined hierarchy that may exist. A bad question can make us want to turn invisible or go on autopilot due to a sense of insignificance.
If it’s a question you’ve heard in a hotel or a store, forget it. — David Sedaris
Questions are the frontier between what is known and what is not known. They provide an opportunity to turn inward and think. Like a tiny little key that unlocks parts of ourselves we don’t regularly visit, a good question can prove us wrong, open up what we know about ourselves, and what we are about to become.
It admits that you, as the asker, are someone who does not have all the answers, but are attempting to learn what you can, about yourself and those who share the journey. It’s earnest in that way. It makes you want to lean in and engage, shining with a sense of true curiosity like when you watch a baby.
You can bet that someone who asks a good question is paying extreme attention to themselves and the world around them. What a gift to be prompted with something so unique in a world of such generalities.
The world suffers from a scarcity of well-formulated questions from inquisitive people.
To ask a good question, think about what you really want to know. Ask weird questions, silly questions, questions that will surprise and delight people. Ask questions that have an uncommon attention to detail, or that just feel like you.
The worst that can happen is someone won’t respond the way you’re hoping, which is actually good information. It helps us reflect, learn, and iterate. It helps us understand who we are meant to connect deeper with and who we are just not.
No one wants their brain picked, or to jump on a call without knowing why, or to have more generic small talk they have to endure from the other 97% of their conversations. People want to get to know you. Be the 3% and be yourself, authenticity is in.
Here are 31 of my favorite questions I’ve asked in reach outs recently (with some little easter eggs thrown in, of course)