One of the questions that pops up quite regularly and can be really nerve wracking is how to approach asking for initiation? How do you approach that leap of faith? As so often there is no one-size-fits-all rule and the specific “etiquette” will probably vary enormously depending on the tradition and group you have set your heart upon.
Speaking from personal experience, there is often a natural segway into having that conversation once training has progressed far enough. This was definitely the case when I was training with a coven myself. Having got to know my would-be-initiators thoroughly over the course of many months there were some strong hints that any such request would be met with a positive response and so I took my heart into my hands and popped the question.
Our own practice with our coven is similar and during the course of training both parties develop a good sense for whether this can be a happy fit or not and expectations can be managed accordingly. For us that’s actually the most important aspect of training: it’s not so much about imparting any specific knowledge - most people come to us fairly well read anyway - but it’s quality time spent together to allow a relationship of mutual trust to develop.
A good resource I can recommend in this general context is Thorn Mooney’s book “Traditional Wicca - A Seeker’s Guide”. It’s not a Wicca 101 book but instead gives practical tips how to approach to process of finding a group, asking for training and ultimately joining a coven.
Happy seeking!