Challenges you face working with designers
I think the main challenge is that can be a disconnect between what one can design and what one can (efficiently) build. It’s easy to add a button that does X in a design, but actually implementing it might either be impossible or very expensive.
What works well, what doesn’t work well
Doing designs together, going over pages and discussing them. And the converse doesn’t work nearly as well: sending a designer the “specs” and then getting a design back (unless you then iterate on it together).
When projects have/haven’t gone well
I think Exercism v3 is a project that went really well. Lots of discussions were had and it really felt like a collaborative effort with a great result.
What you have/have not enjoyed
It is absolutely fantastic seeing something come to life before your eyes, often in ways that you didn’t even think possible. I couldn’t design something to save my life, so I always make sure to really appreciate any design efforts.