Kirk did it Starfleet style and with all due vehemence in "Journey to Babel" after capturing the fake Andorian agent:
"He's been subjected to questioning under verifier scan and truth drug. He reveals nothing. I suggest his mind has been so conditioned as part of a preconceived plan."
We don't know what was done in hopes of inducing the prisoner to talk, but we can assume that the "verifier scan" (probably similar to what we saw in "Wolf in the Fold") and "truth drug" would massively increase the reliability and value of the information gained. They would also make the process much more efficient and thus perhaps more humane, as the prisoner could not engage in falsehoods and thus misdirect the interrogation.
Indeed, it might be that there would be little or no need to coerce the victim when these apparently near-perfect truth-verifying means are available. Unless specially and very carefully trained, the prisoner would quickly reveal his deepest secrets even when only uttering a few initial phrases. The interrogators could now ask the exact right questions, and under the scan, a refusal to answer a question would tell almost as much as an answer.
In contrast, Klingons in "Errand of Mercy" used their "mind sifter" or "mind ripper" at what they thought was sufficient setting against Vulcans, yet failed to get through Spock's cover story. Spock knew something of the device in advance, but this experience would probably lead Starfleet to completely dismiss this and related techniques. What good can mindreading technology be when it so utterly fails even in the hands of the most ruthless operators?
Romulans and Cardassians are credited with classic interrogation tactics, many of which take a lot of time to be effective. Nothing futuristic there, and although the Federation might engage in similar tactics, those wouldn't much help our covert ops team which presumably is in a hurry.
However, a couple of novels, short stories and an ENT episode have dabbled in the use of virtual reality in futuristic interrogation. I guess any TNG era interrogation would automatically take place on a holodeck where reality could be subtly or grossly manipulated to enhance the process.
There's one aspect that has never quite been explored in onscreen or printed Trek yet, but might affect 24th century interrogations: the advanced state of the healing arts. Future medicine might not be useful only in the form of truth drugs - it might also be applied in a more sinister manner. The victim could be essentially skinned alive, cut to pieces and burned to crisp, and then restored to perfect health afterwards... Perhaps a Federation covert ops team in a hurry would proceed simply by applying a sledgehammer on the victim and promising that the effects will be reversed the very moment he, she or it talks?
Timo Saloniemi