My mentor at work recently taught me a great lesson about asking question. Garbage-in-garbage-out: when questions are asked poorly, you don't get the information you want; if asked appropriately, however, valuable information can be extracted.
Here are a few things I've learnt about asking "good" questions.
Be precise: be precise about the specific information you are asking for.
Bad question: "please provide historical financials of the borrower"
Good question: "please provide past 3 years consolidated financials for abc company".
Demonstrate your knowledge: when asking questions, it is also important to demonstrate that you are not completely clueless about the situation.
Bad question: "please describe the company's growth strategy"
Good question: "please describe the growth strategy of company's financial business (include divestment of trading firm), industry business, and consumer business (include potential joint venture with xyz company)
This way, you are also asking about the company's growth strategy - but you demonstrate that you are aware of the company's situation, you just want to know more precise details.
Ask for information iso presenting a view: asking questions is an opportunity to get valuable information, not to present a view or to state an opinion.
Bad question: "the value of the company's land seems small; what other assets can be pledged to the bank as security?"
Good question: "please provide the market value of abc company's land as of today. What is the expected value of abc company's land in development? Is there any data from past transaction to support such expected valuation?"
This way, you avoid potential argument about whether the value of the land is big or small; instead, you are asking for precise / useful information about the market value and expected future value of the company's assets.

It is interesting topics for me to know more on I-banker and CFA ! Thanks.
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