In this study, we explore the proactive ability of LLMs to seek user support, using text-to-SQL generation as a case study. We propose metrics to evaluate the trade-off between performance improvements and user burden, and investigate whether LLMs can determine when to request help and examine their performance with varying levels of information availability. Our experiments reveal that without external feedback, many LLMs struggle to recognize their need for additional support. Our findings highlight the importance of external signals and provide insights for future research on improving support-seeking strategies.