Does any sutta talk about the right conditions for teaching the Dhamma?

I've read in other posts (such as [this one](https://buddhism.stackexchange.com/questions/18799/right-way-to-teaching-dhamma)) about the right way to teach the Dhamma. But is there a way to know about the "when", i.e. when to reach out someone else to teach the Dhamma? In specific, I'd like to know if one should teach only when asked for it, or if one should make assumptions about the other's needs or degree of knowledge when trying to help him/her (regardless if that person asked for that helped or not). If you could provide information about suttas where this is talked about, I'd really appreaciate it. I'd even be grateful if personal experiences are given. Thanks for your time and patience!