Asking right question is approximately ~ 50% achievement towards right answer. Asking a wrong question, even though if you find any genuine answer to it, will take you in wrong direction. As there is only one underlying reality and truth, asking one wrong question is enough to permanently deviate the trajectory of your searchlight of thought away from the truth, no matter how many right questions you will ask after one wrong question. This is the real meaning of the expression of "the path to the truth is very narrow and straight". 

It is very critical to find what is really important and what is the right question out of the superrreal postmodern world. Original truth was encoded with sings and symbols which have now lost their meanings and replaced with similar but not identical imitations. Now the "garden variety" of reality is based on those false imitations, signs and symbols which is totally disconnected with original reality and replaced by more sensational superrrealty. To ask right question on right issues out of these garbage "truths", it needs some intense thought training. Good news is, this part you can cultivate. Do your homework on that, mostly by self-learning and observations. 

Once you have decided what are the things that really matters, then it is time to ask questions about those. Be careful before you ask. You have to treat each questions as important as if your life depends on each questions. Asking 10 consecutive right question, for example, will bring you 99% towards the truth but even then, it will never take you to the truth itself. At the end, you need the gift of intuition. How can you make or train your intuition? Unfortunately, you cannot and fortunately, it's already there. In order to find it and use it, you have open up all options on the table. You have to travel the unknown abyss of yourself and you have to let go. Its like Heisenberg's uncertainty principle. If you try to catch it, it will only recede. You have to be submissive and humble, not by empty words, but by your whole self, which will be expressed in your acts and deeds. Then it will come to you, if you are sincere and honest enough for knowing. This is the rationale behind disciple, asceticism, sacrifice, chastity and meditation. It gives you the better chance of finding the deep intuition. Then the ultimate powerful intuition will come to you and you will find the answer of everything you ever asked.