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I would strongly advise you have some thought out, engaging, semi-personal (in the professional arena) questions thought up. Things like..

  1. Why did you decide to enter this field/firm/role etc.
  2. What was the biggest success (or even challenge) you experienced
  3. I'm doing XYZ (something about you), what advice would you give?
  4. What do you think about XYZ (some topic of interest to you/them)?

The key is to be a bit provocative and interesting, get them talking and even bragging. The more positive the vibe, the more you get associated with it.

You can ask the standard what do think about X investment or other stuff about the firm. But if it is a boring question (or god forbid one that Google could answer.....), they will be bored and thus you miss the real opportunity to have an engaging conversation.

 

this is your chance to show what you have learned about the firm and to differentiate yourself. if you don’t ask a question about a firms recent deal, you won’t be competitive. Do a quick google search, look at the drivers behind a recent deal or two and say “I noticed you guys just completed ____. that was a pretty cool deal. did you work on it? If so, how did ____(insert potential complicating factor) influence the deal/the valuation”?

 

That is a good point, I've been on other side of that a few times. A person asks me about a project our firm is involved in that they found via google/news/etc, but it is not one that my business unit had anything to do with. Honestly, I really don't care or think much about it and just explain the details about our firm that make since, but it does signal a form of misunderstanding that could have been figured out (in fairness, not always easily).

If this is in just a general networking situation, this would be totally normal. If it was an interview, I think I may wonder how much the person knows what I/we do.

I think you should be fairly sure that this deal you want to ask about is 100% related to the person you are asking. In all honesty, unless there is something really noteworthy or unique or unique to YOU about this deal, I feel these "what was it like doing X deal" type questions are just boring and something you would only talk about with a student. Nothing wrong with it, but it is a missed opportunity in my personal opinion. YMMV

 

For interviews I always ask "Regardless of the outcome of this process, what advice can you give me?"

I've found that interviewers LOVE that question and it makes the relationship more personable (interviewer now feels like a mentor). You can also modify the question to suit the situation.

 

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