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Message: <blockquote data-quote="The Shadow" data-source="post: 4205672" data-attributes="member: 16760">Fair enough.  I will stand down... though I do sometimes get this urge to tilt at windmills. <img src="https://cdn.jsdelivr.net/joypixels/assets/8.0/png/unicode/64/1f642.png" class="smilie smilie--emoji" loading="lazy" width="64" height="64" alt=":)" title="Smile    :)"  data-smilie="1"data-shortname=":)" />A very interesting question.  An advisor *could* simply be fluff to explain failures ("I can't fault your logic, but on balance I like Baron Evillo's idea better.") or fluff to explain consequences of failures.  ("I don't ordinarily send annoying people to the salt mines, but Baron Evillo is right, you're too dangerous.")Alternatively, he could be an actual character rolling for successes and failures of his own.  Now, would he be on the same playing field as the players (his successes counting as their failures, and vice versa), or would he keep separate track of successes and failures?The easiest way might be to say, "Whoever gets to X successes first convinces the Duke.  Failures count as successes for the other side."On the other hand, it might be very interesting if *both* parties could win (the Duke sends his troops to help, but sends a spy to keep an eye on the PC's that the Baron has secretly ordered to assassinate them) or both could lose (the party doesn't get the Duke's help, but he's pissed at the Baron, who is now out of favor.)Interrogation:  While this obviously gives Intimidate a huge chance to shine, other skills could potentially useful...  Knowledge-type skills to be able to know when the guy's lying;  Streetwise in particular to know what to threaten him with, depending on the situation;  Diplomacy to play Good Cop;  Bluff to make him think you know everything already and spill something...  Perhaps Str vs. Fort rolls for torture.  (Yuck, but still.)Or, if the players feel like blowing some cash on the Detect Thoughts ritual, you can avoid a skill challenge entirely. <img src="https://cdn.jsdelivr.net/joypixels/assets/8.0/png/unicode/64/1f642.png" class="smilie smilie--emoji" loading="lazy" width="64" height="64" alt=":)" title="Smile    :)"  data-smilie="1"data-shortname=":)" />Overland Travel:  As simple or sophisticated as you want.  Getting to Example City might be a skill challenge, or maybe each leg of the journey could be.  Maybe most of the journey is fine, but you set up a challenge to get through a nasty section of forest.  Or, if you prefer, you can just say, "You get there after five day's travel.  What do you do?"One thing that might be fun is, rather than having "random encounters", the GM has some planned encounters along the way that can be circumvented by succeeding at challenges.CSI:  Again, as much or as little as you want.  Finding and interpreting a single clue could be a challenge in itself, but that would probably get old.  Whereas having a challenge out and out tell you who the murderer is could be a bit much too.I say, treat it like a cop show or a movie... the challenge is there to give you a significant lead, something tangible to follow up on.  Failing in it badly might mean that you just plain don't turn anything up;  failing marginally might mean you have a clue but haven't figured out what to do with it yet.</blockquote>

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