“Why?” should be the D&D version of “yes, and ….” It can move the action further and it can gt you to the place where you can say “yes, and.”
A few examples from recent play sessions.
Our half-orc barbarian asks, as they're preparing to leave town for an overland journey, “can I buy a bird?” The easy answer was “yes.” The town is big enough to support a stock yard. Heavily agrarian. At worst inquiries could be made and some opportunistic townie would go TRAP something for him. Why he didn't catch his own, or ask the party ranger to do so was beyond me, but so what? Table discussion then devolved into a discussion of Ogar owning a vulture. Or perhaps a falcon, but no sleeve. At THIS point I began imagining all manner of unintended consequences. So I asked why? He has several control/speak with animal spells and has been unable to use them. This would allow him to do that. So – a birdbrained scout. Not a familiar. Not a beast companion. Just extended scouting ability. So I said yes, but …. no birds of prey. A pidgeon. A dove. Maybe even a crow. I offered a chicken but was soundly rejected. And a duck or goose would be eaten too soon! But I already have PRICES for those three. He's flush with cash so that's not a problem. We agreed in principle to a non-stat-block bird (thus eliminating the temptation to use offensively) of yet-to be-determined provenance. Some quick research yielded the Red-billed Quelea. And everybody's happy.
The party has taken on a “Magnificent Seven” type task to protect a small village. Quite admirable. In prepping the defense the rogue asked to “walk the perimeter. Why? He explained his idea for locating the highest traffic means of ingress in order to narrow down what needed to be defensed AND to set up opportunities for enfilading fire. I could then provide him with the exact info he was looking for instead of waxing poetic about “the beautiful countryside lightly frosted with rime.” He didn't USE the enfilade opportunities, but that's beside the point. The question “why?” saved time and enabled the player to do what he wanted to do succinctly. Several other similar plans were attempted by other party members along the same track. Can I X? Is there any Y laying around? Why? Once I know why I can better answer the question and the players can actualize their plans. Everybody's happy.
Side note: Two new flavor mechanics got expanded this session. It's winter. Temps dropping. Party made sure to purchase winter clothes when the opportunity presented. Weather report is simply three words: one for precipitation, one for wind and one for temp based on the 10 degree range the wind chill presents (pleasant, cool, brisk, chilly, etc.) As conditions worsened the party realized their winter clothes wouldn't protect against ALL cold. A couple frosty nights threw the party into disadvantage. Staying close to the fire and within a windbreak were helpful but they know their movement is now limited by conditions.
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