Or more accurately.
4e was an attempt to rejigger the rules to how it was played. But redesigning D&D from the ground up, especially with its combat system and lore, takes a long time and the designers ran out of that time.
So 4e was released with only 80% of its combat design finished and a lot of it core and fundamentally aspects not fleshed out enough. And they didn't get to playtest it enough.
Were 4e a videogame, they could go back an patch it. But it as a TTRPG. The best you could do was errata and errata has limits.
I'll give a more specific example: Skill Challenges
Even ignoring the math, I found that how they were advised to be used didn't work as well as how I started building Skill Challenges.
Part of the concept was to avoid 1 roll from making a situation binary. Why then were they still defined in a binary pass/fail way?
I got away from the idea of X successes before Y failures. Instead, I had better results by having a set number of rolls. The results would then depend upon margin of success or margin of failure and include several possible outcomes.
For sake of a generic example, let's use the cliche "Trying to Convince The Duke" challenge that was mentioned upthread. The PCs are trying to convince Duke Doe to let them borrow a magic weapon to use against a demon being summoned by a cult in a nearby swamp cave. In this challenge, there are 5 possible rolls.
Instead of Pass/Fail from X before Y, the results might be something like the following:
•More than 5 successes (possible with critical success): The Duke is convinced of the seriousness of the situation and pledges the service of some of his men (squad of Minion allies) in addition to allowing you to borrow the weapon.
•5 successes: The Duke allows you to borrow the magic weapon.
•4 successes: The Duke is convinced of the seriousness of the situation, but is hesitant to hand out such a powerful item. He agrees to send the item, but only if it is carried by one of his trusted retainers, who will accompany you.
•3 successes: The Duke listens intently and nods his head, as he takes in your story. Finally, he raises a hand to signal that he has something to say. He believes that the threat of the demon is a real and serious thing, but such a threat means his duty is to protect his people first. He offers supplies for your journey, the use of a lesser item from his treasury, and rooms to stay for the night, but he will not allow you to borrow the item.
•1-2 successes: The Duke is either unconvinced by the PCs or has some other reason for not aiding the PCs. You are politely asked to leave.
•0 successes: You have in some way managed to insult the Duke (or he has some other reason to be against helping the PCs). You are asked to leave.
•More than 5 failures (possible with critical failures): You have gravely insulting the Duke in some way (or he has some reason to be actively against helping the PCs): You are escorted to the city gates and told to leave the settlement.
Depending on the situation, there may still be times when I would still use the the X before Y way of doing things, but I preferred a range of possible results.
In some situations, the amount of rolls might be open ended. For example, I had a fight take place within an enchanted room that functioned a little bit like a tesseract and a little bit like versions of Bowser's Castle from Super Mario. To leave the room(s) and advance to the next area required choosing doors in the correct order.
I vaguely remember that the skills involved were Insight (to correctly guess or surmise which door should be next), Arcana (to pick up on mystical energies and deduce which way was correct -kinda like magical footprints), and a Wisdom Ability Check to pick up on some sort of pattern. The PCs also had to choose Endurance or Wisdom after a certain number of rounds to physically/psychically withstand constant exposure to the disorienting magic involved.
This also took place as various traps and encounters were able to be activated in the room. There was no set amount of failure because the consequences for failure involved the room becoming more dangerous as more traps activated and more creatures joined the room.
That last example is a bit complex and likely not the type of thing that could be easily suggested in a DMG. However, it stands out as a positive experience because I successfully combined combat encounters with an ongoing Skill Challenge without the clunkiness that trying to combine them via some of the DMG examples produced.