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The core idea behind Gumshoe as a system is that 'Core' clues are successfully found with an appropriate use of an investigative skill.

There are a whole bunch of interpersonal investigative skills such as Flattery, Intimidation, Reassurance. Can an inappropriate use of one of these skills 'fail' or make a situation worse, or would the investigator instinctively know that now is not the right time to use Flattery for example?

As an example, lets say we have a witness to a crime who is petrified. They have a Core Clue that can be retrieved by the investigators. However, I would like to portray this guy as someone who hates to be intimidated and would rather fight back than be cowed by any such attempts.

In this circumstance what do I do if an investigator tries to intimidate them? Do I let them fail, making things worse (as long as the core clue is still obtainable some other way of course), or do I assume that their skill in Intimidation tells them this would not be a good time to use it?

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Not Mechanically Harder

Why?

The point of Gumshoe is that getting the clue is boring - but doing something with it is interesting.

If you have not described the witness' resistance to intimidation, why thwart the players' agency and go against this core tenet of the game? If you have described it, why are your players pursuing this avenue?

Since there is no roll required to get a clue, how will you penalize them? How will it be made harder when success is automatic?

Sure, you can roleplay the witness raising his hackles and refusing to be intimidated by Bad Cop and then Good Cop can flatter him and get the clue. But generally, Gumshoe isn't about the players guessing which skill you picked when designing the clue, it's about them describing their highly competent investigators getting information.

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This is a question that has bedeviled me, too. One solution I have used is a range of potential answers depending on the Interpersonal Ability used. If players use the "wrong" one it makes the information less useful or creates other bad conditions elsewhere. So the intimidated guy warns the police about the PCs.

Otherwise, when you roleplay witnesses you can telegraph the kinds of techniques that they will respond favorably to. I think it would be tricky to play a petrified guy who resists intimidation!

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Yes, they can fail to get the clue

The case you describe might be one where the investigator will not get the clue by trying Intimidation, but may instead need to use another ability. It's not worth spending much time on how the clue is retrieved, more interesting is to focus on what they do with the new information.

Sometimes I run into situations where an ability might be relevant but spending that Investigative point won't yield anything ('sure, you look imposing, but there's no more Intimidating to do here'). This might be a case where an ability should get the clue (you do want the story moving forward) but it won't get much else.

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