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When do you tell a guild member no?

Say you have this hypothetical situation. You’re in charge of a guild raid and since these are your friends, people you know who are kind, your looting system is just random rolling. You’re still master looter but anyone who wants an item can /roll and whoever is the highest gets it.

These are the people who will argue over loot in the fashion of “You take it, you need it more” “No, it’s okay, you won it fair and square so it’s yours”. It’s not uncommon for this to go on for several minutes, your guildmates are generous people.

So everything should go smoothly right?

Then say that a vanity item drops. Everyone can use it, and it’s not super rare but certainly not everyone has it. So several people roll on it and one wins it.

Now say that winner can’t use it right away when others who rolled could have. And say that their character won’t even been their main anymore in a month or so, as they have already announced they’re switching mains. What if this person has also been known to roll “need” for an off-spec item that another guildie could have used for their main spec?

This person has been in the guild for a long time and certainly doesn’t seem to be malicious, perhaps they’re simply unaware of how they appear. But either way, their actions can come across as rather greedy to other guildmates.

What would you do in that situation? Can you teach a grown adult how to think of others instead of just themselves? Or were they perfectly within their right to take something within a guild that’s more like a family?