Asking questions when talking to someone is a great way to interact more with them because you may sometimes talk more or less with a person than them and the conversation can quickly end due to loss of interest. Asking questions encourages the other person to participate more, but the questions need to be varied and thoughtful. For example, alternating between yes or no questions, open questions, and fact questions is more exciting than staying on just one type. Additionally, asking questions that are very commonly said like "how are you?" or "how is the weather today?" will not keep the conversation going past the beginning stage.
If you feel like your ideas for questions aren't intriguing, consider saying something related to your question before or after it. For example, it could be about your personal life. "That hand writing looks like mine after I finished a tiring project. How did you get such neat hand writing skills?" is more engaging than just asking the question alone.
With that said, I will manually give out the role Question Asker to those who ask good questions to members in this server. You don't have to actively ask good questions to earn it, so your questions can be spread out.
Note: The requirement to obtain this role isn't difficult to complete if you do ask questions.