Seems like the key to making this work is having done the legwork beforehand to know you're making suggestions that won't wind up being tone deaf.

That legwork probably looks like having several conversations beforehand with people on the inside beforehand, so you actually have a basis for thinking you know what sort of problems are relevant for the decision makers.

On average, that's probably something college students looking for their first jobs aren't well positioned to do (especially if they're looking for their first job through formal recruiting channels at huge corporations).

And on average, for people with a few years of professional experience, its a matter of realizing that hanging out at conferences, happy hours, and other informal situations where you're around other similar professionals is low hanging fruit for these sorts of conversations, and recognizing that these situations present these sorts of legwork opportunities is a big advantage.

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I said students don't typically do that well, but I don't think that has to be a rule, lots of advice talks about trying to do 'informational interviews'. I think this is sort of what they're getting at, what you want to get out of an informational interview, is to sort of be able to frame the problems a future interviewer might have, and be able to do an interview like this.

There's probably a lot of trial and error that goes into getting this right. And also, probably a lot of investment in having conversations where the payoff doesn't seem very obvious.

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couple book suggestions:
1.
http://www.svastralwind.com/uploads/2/7/2/6/2726225/the_2-ho...

gives a method for setting up informational interviews, good read overall

2. I've suggested this books a couple times, I think its actually really deep when contemplated on

Spin Selling by Neil Rackham

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Let me do a quick breakdown on why I think Spin Selling is really deep.

Its basically a method for asking questions that elicit deeper responses

its breaks down all sales questions into 4 categories:

SPIN Selling proposes there are four types of questions, thus SPIN stands for :

1) Situation Questions deal with the facts about the buyers existing situation.

2) Problem Questions ask about the buyer's pain and focus the buyer on this pain while clarifying the problem, before asking implication questions. . These give Implied Needs.

3) Implication Questions discuss the effects of the problem, before talking about solutions, and develop the seriousness of the problem to increase the buyer's motivation to change.

4) Need-Payoff Questions get the buyer to tell you about their Explicit Needs and the benefits your solutions offers, rather than forcing you to explain the benefits to the buyer. Getting the buyer to state the benefits has greater impact while sounding a lot less pushy. What these questions do is probe for explicit needs.

The quick takeaway, is that sometimes situation and problem questions are sometimes needed to make sure you know what everyone is talking about, but those questions are boring for the person being asked them. The basically amount to giving information to someone who clearing doesn't know as much as they do.

What you really want to do, are minimize those question (probably by googling extensively before hand), and ask implications questions and need payoff questions, those are the questions that will lead the listener to consider things they hadn't previously considered.

When you start asking those questions, you'll start having conversations where you learn things other people don't know.

This is presented in the context of making sales calls, but its actually good advice for a huge range of conversations where what you're trying to determine "what does the other person want?" "why do they want it?"