Yes. Its possible. Take this example. Put a single clownfish into a 20 gallon tank - with nothing except water and a filter (without bacteria). Depending on how much you feed you may never see an ammonia 'spike'. Same example - add bottled bacteria - you may never see any ammonia spike.
Part of the issue 'what is the definition of cycled' - there are 30 of them. Is it when one clownfish can live in a tank - is it when 10 fish can live in a tank. Is it when a tank can process x ppm ammonia in 24 hours. Is it when nitrite is 0, ammonia is 0 and nitrate is rising? etc etc.
So - to answer your question - how do you know how much ammonia to add - if you are using Dr. Tim's method - it's when the tank can process x ppm in 24 hours, its "safe" to add a bio load of fish according to their directions. If you are adding fish with bottled bacteria - the thought is go slowly - and watch total ammonia. Ie. Do not add 5-6 fish at once

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Having said that - I have never 'cycled' a tank for weeks - measuring ammonia, nitrite and nitrate. Since it has been available - I have merely added fish and bacteria on day 1 - If I have a lot of fish - I may add a little more bacteria than the recommended amount. So - also in answer to your question - part of it is experience.
I believe
@Lasse also has a protocol of adding fish slowly. I know he also focuses on nitrite measures as well - whereas others do not.
PS - I do not like the comment 'cycled' as one definition. I did an experiment (which is in the experiment section) - whereby live rock that had been in a sump/tank for years (so should be well colonized) could not process 2 ppm ammonia on week 0 (within 24 hours) However as ammonia was added sequentially, within a period of time - the same amount of rock could easily process 2 ppm ammonia in 24 hours. Suggesting (in part) - that as fish (ammonia) is added, there is a lag time in which the bacteria needs to 'catch up'. The good news is, when you add fish (as compared to ammonia directly) - you are not reaching 2 ppm quickly.
Hope this helps - sorry so long