How To Ask Tough Questions

There are many situations in life that could be defined succinctly as “tough”. One of these would involve asking tough questions, or questions that may be hard to both ask and answer. Generally, however, the tougher a question is, the more important it is that you get to know the answer. So if you’re looking for some pointers on how to ask tough questions, here are some that would help you out:

  1. Make some preliminary research to know enough details. To be able to ask intelligent questions, you’d have to know enough about the subject. This will enable you to use proper terminology to ask effectively, to probe, and to know which details aren’t essential and which are. Otherwise you might just get stuck with the non-essentials, or you may just get to know the superficial answers that don’t really have the information that you’re looking for.
  2. Be sure of whatever you do know. For tough questions, in particular, you’d have to know enough material to be absolutely sure of the background of the situation that you are asking about. Otherwise, the other person might just claim that you are only “imagining it” or “making it all up”. Stand by what you do know, and it’s better if you are able to supply strong material evidence for your claims.
  3. Keep your temper. Your main goal is to find out the answer to your question, and not to irk out the other person. Try to keep your calm while asking, and phrase your question in a respectful manner. As much as possible, don’t ask in a confrontational manner. It’s also a great idea to ask in as low-key and mild a manner as possible, so that the other person won’t be guarded and it’d be more likely that you’d get the answer that you need.
  4. Know of some asking and probing strategies. As mentioned earlier, asking tough questions doesn’t mean that you’d have to ask it in a tough, confrontational way. Sometimes, you’d best get the answer if you’re not obviously desperate in getting it. Some options you may consider include asking conversationally in an intimate or non-threatening setting; asking the tough question after the other person has sufficiently warmed up to you;  and asking the question as if it were just a follow-up question to a statement that he said. It’s also highly important that you listen very carefully to the other person and watch out for some hidden meanings and insinuations that could reveal the answer that you need, or which could lead you to ask the actual question that you were planning to ask all along.
  5. Make sure you have the right purposes and intentions for asking. When asking tough questions, ask yourself these questions first: Would it be beneficial for you in any way? Is it really your business, or are you just meddling or interested in it as gossip? If you’ve assessed that you’d need to know your answer for your own personal benefit (or for the greater good of many), then it’s highly likely that the other person would know that you are in the right, and he would likely be more inclined to give you the answer.
  6. Be prepared to hear the answer. What if you do get the answer to your tough question? Are you sure you’d be prepared for it? What if you’re better off not knowing? Take the time to psychologically prepare yourself for the worst scenario possible. Remember, knowing how to ask the tough question is nothing compared to knowing how deal with a tough answer.

There you have it! These are just some tips that would help you ask tough questions, whatever situation it may be. Good luck!


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