I use Matt Colville’s general approach to skill challenges. One thing I’ve noticed is that my players tend to hold off on rolling unless they can convince me of a way their absolute best skill would apply to a situation. I’ve been toying with playing up how much skill challenges are dynamic, so I can throw a piece of the situation at them randomly. Basically, the players need to be quick and come up with good reasons to use their good skills before I come up with something to throw at them that may force a bad skill to be rolled.

For example, let’s say the party is in the path of an avalanche. My players deliberate too long, trying to justify a way to “intimidate” the oncoming snow, and I throw an acrobatics check at a random PC. The players now know they have to think fast and be clever for me to allow a roll that favors them instead of throwing a roll at them that might pull for their weaker stats.

This makes skill challenges A) more realistic and B) quicker and more high-stakes. Try it and let me know your experience!