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Something I'd like to point out is that any discussion of "Say Yes" needs to be predicated on the assumption of another rule being in play: "Don't be a dick." The issue of a player who wants their PC to dual-wield repeating crossbows or to avoid challenges by narrating their own easy victory is not a "Say Yes" issue. That's a "Being a dick" issue. You can't even talk about "Say yes" if that kind of stuff still needs to be resolved.

Second, here's the actual passage from the DMG, p.28:

Originally Posted by 4e DMG

Saying Yes
One of the cornerstones of improvisational theater technique is called “Yes, and . . .” It’s based on the idea that an actor takes whatever the other actor gives and builds on that.

That’s your job as well. As often as possible, take what the players give you and build on it. If they do something unexpected, run with it. Take it and weave it back into your story without railroading them into a fixed plotline.

FWIW, this is somewhat different from Vincent Baker's "Roll the dice or say yes" (the usual source credited for the concept).

Originally Posted by Dogs in the Vineyard, p.91

Drive Play Toward Conflict

Every moment of play, roll dice or say yes. If nothing’s at stake, say yes to the players, whatever they’re doing. Just plain go along with them. If they ask for information, give it to them. If they have their characters go somewhere, they’re there. If they want it, it’s theirs. Sooner or later—sooner, because your town’s pregnant with crisis—they’ll have their characters do something that someone else won’t like. Bang! Something’s at stake. Launch the conflict and roll the dice. Roll dice or say yes. Roll dice or say yes. Roll dice or say yes.

So, they serve slightly different purposes, given the different focus of D&D vs. DitV. However, in both cases, they're encouraging you the get to the good stuff and give players appropriate input that invests them in the situation.

In the context of D&D's more traditional setup, I think this passage from Spirit of the Century better conveys how "Say yes" works in terms of die rolls:

Originally Posted by Spirit of the Century, "Setting Difficulties"

Before you – the GM – call for a die roll, it is critically important that you stop and do two things:

1. Imagine Success
2. Imagine Failure

It sounds simple, but it can make a critical difference. Success is usually the easy part, but failure can be bit trickier. You want to make sure that both outcomes are interesting , though interesting certainly doesn’t need to mean good.

If you cannot come up with a way to handle either outcome, you need to rethink the situation.

It’s as simple as that, because there are few things more frustrating to a player than making a skill roll and getting told that it nets them no new knowledge, no suggested course of action, no new development for the story, and so on.

So, whenever you call for a roll, be absolutely certain you understand entails. If one or the other branch does not suggest a course of action, then calling for a roll is probably a bad idea.

It doesn't obviate saying "no"; saying "no" is still a valuable tool in the DM's arsenal. But the point is to focus on what's interesting and moves the game forward. You err on the side of "yes" because "yes" is positive and collaborative, while "no" is too often exclusionary and obstructionist.