iserith
Magic Wordsmith
This isn't fair to 5e. From the Basic Rules:
I think there must be a lot of DMs out there that read this and think "hmm, well there is *always* a *chance* of failure, so I'll have them role for everything." But even those DMs don't really play like that. They don't have PCs role for every footstep, because there is always a chance of misstepping.
If I were writing the rules, I would likely say a "reasonable chance of failure" or give some more guidance, encouraging DMs to limit check to important, thematic moments.
One thing I do that some folks may consider homebrewing (but I argue it isn't because *the DM* decides whether there is a change for failure--how the DM decides this is left largely to the DM's discretion): if the DC is Very Easy (5) or Easy (10) I will grant an auto-success to someone with proficiency in that skill. In some circumstances, I'll do that same even for DC 15 (medium). I like to reward players for their character-building choices. Obviously, their class, races, background, and feat selections tell me as a DM a lot about how they see their character. Letting a character proficient in acrobatics with a background as a circus entertainer bypass rolls to jump over some of the smaller pits makes sense, is within the RAW, speeds up gameplay, and honors the player's vision of his or her character.
So, 5e could try to give more guidance in this area, but it is not fair to say that 5e reduces all character play to the rolling of dice.
Couple of side notes for everyone's reference since I (sadly) have them memorized:
Check out DMG 236-237, "Role of the Dice" and "Using Ability Scores." It talks about different approaches, including once where the DM calls for a lot of ability checks, and their respective drawbacks. (The drawbacks mentioned to the "Roll With It" approach are interesting.) The latter section explains the guidelines for when to call for a check, that is, when the attempted task is somewhere between impossible and trivially easy, and when there's a meaningful consequence of failure. Add that to the section in the Basic Rules (page 58) as to the DM determining there's a chance of failure/uncertain outcome and, voila, there's your completed checklist for determining whether a roll is appropriate.