There's several times in conversation where you have the option of a speech check, and if you succeed you'll be met with a second speech check. The most recent example for me was with the Kuo-Toa. I passed a DC 15 check during the conversation with their priest to figure out that their god is a conman. But rather than being able to tell them that I needed to pass a persuasion or performance check, the DC for which was 10. To avoid a fight in this situation is a .25*.5 = .125 chance. Seven times out of eight a fight happens.
A single hard check would be better than multiple moderate to hard checks. A player can feel a bit cheated when the succeed a check only to be hit by another role of the dice. Multiple checks should really only be needed if the player choses to abandon their current plan and swap to another, if you're heading towards the same goal then you shouldn't need to keep rolling for anything but really hard tasks.
Related to this I hope in future we'll get options to smoothly choose which member of our party attempts a check. The great thing about the tabletop is having different players contribute by jumping into situations with their own skills.
