Thanks for sharing lovely ideas. I've organized non-rationality meetups and similar social/intellectual gatherings. Much of what you write here is applicable to various extents to those events as well. I'm really glad you shared this.

a good manager would be good at optimizing against those utility curves

Yup! One of the best things a manager can do is to know their people, which allows them to tailor their communication, motivating words, and all other behaviors in a way that will be most effective for the target recipient. It is a beautiful thing to see in action, and it is a great aspiration to have in professional life.