The simple answer is to make the game a good enough experience that you don't care if you fail a check. Most games are quite shallow once off the critical path of successful checks, but if the game has many ways to progress, it matters less if you fail a check. Obviously if you then proceed to die because of the failure you reload anyway; and if you are on a replay ( or following a guide, or want to min-max ) you may reload to experience a different path or follow a particular path.
While I don't like DnD 5e combat, Larian do seem to be building a game I will want to play, partly because they want to build variety into the basic engine.
