If you’re querying for the very first time and aren’t super confident about your query so you choose to start with tier two, the sign you’re looking for to query your tier one agents is that you start to get requests. If you don’t get any requests on your first round of queries, reach out to trusted friends or writers in your circle to get feedback on your query letter (which hopefully you already did before you started!) to see if it needs to be fine-tuned.
If you are getting requests, after three or so requests, go ahead and query your top-tier list. Because once agents start requesting your material, the only other type of feedback you’re likely to get will be on the book itself, and it’s not likely to be super helpful (but if it is and you end up rewriting significantly, it doesn’t hurt to query people again and let them know that).
We’re talking feedback like, “I’m not feeling as immersed in the world, and gripped by the story, as I had hoped” or “this is a really great premise, but unfortunately, after careful consideration, I've decided I'm not the best agent to represent this book” or “It's with a lot of regret I'm going to pass on offering representation. I just didn't get that ‘must have’ feeling when reading” or “ I’m sorry to say, though, that I just wasn’t as completely drawn in by the material as much as I had hoped.” (Yes, these are from my actual rejections while querying).
So when should you start querying new people? I like to query someone new every time I get a rejection. Essentially I treat it as a one in, one out sort of thing. If I’m really bummed out by the rejection, then I might send two queries to feel like I have more control of my life. It’s an illusion, but it feels better than doing nothing.
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