In my previous campaign, when the Players were making up a new group of characters after a near TPK, they all decided as a group to have the human bard PC be the leader of the group. He was the only one with a positive Charisma modifier. Unfortunately, even though the Player initially agreed to act as leader, she had not the personality for it and always shirked the role. The PC ended up dieing, and the group never again had anyone to be leader.
The next campaign, the group of PCs came together as individuals (not a team from the start). The dwarf monk tried to act as leader. When an NPC human cleric joined the group, the cleric supported the monk in whatever decisions and actions he made. Ironically, when the monk was virtually incapacitated on one adventure, the other PCs "made" the NPC cleric party leader. After the cleric died (on that adventure), and the monk was "recovered", the monk came out less wanting to be leader but the group was more willing to follow him. Such irony.
Now, the monk has left the group, replaced with a PC cleric with the Leadership feat. The Player is trying to be a leader, but the group just doesn't follow very well. They've actually nominated the PC's bard cohort as party leader. The bard defers to the PC cleric, but the other PCs actually listen and follow the cohort. Strange, indeed.
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Then, in a game where I was a Player, I tried to play my human paladin as a leader type (knowing the group really needed a leader). I did moderately well asking everyone's opinion/advice and then making a fast decision and moving on it. But then we had an "incident" that wasn't a proud moment for me.
We had encountered two groups of enemies that ended in a three-way battle. There had been some conversation between some PCs in the party and the orc group of enemies. My character was the only one to not speak Orc. The conversation was passed around in notes around the table for the ones who spoke the language. (A common thing for how we handle such things.)
After the major battle, I tried to get everyone to move out of the danger area, with a prisoner. No one wanted to move with me. I was getting, "Why?", "I don't think we should.", etc. I got forceful and finally got everyone to move. When we got out of the area, I started to let the captive go free (as I thought appropriate under the circumstances). The other PCs didn't want to let him go, but no one gave a reason why. We broke the game session there.
During the next week, we discussed the game via e-mail. That's when I learned what the orcs had said. I learned why the group didn't want to let the captive go. So there had been all this good information that *nobody* thought to inform the leader of. The whole group knew what was going on except for the one trying to act as leader -- and no one told him anything. All the effort they put into fighting against my attempt to lead, they never bothered to explain the information they had but I didn't. I was completely flabbergasted. I gave up trying to act as leader from then on.
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And then, another time, much longer ago, I had joined a new group. In the first game session, I learned how badly the group needed a leader -- anybody to lead. They spent 2 hours debating the next course of action! After the game session, through e-mail and in person, the DM and I discussed the situation. He told me he knew the group needed a leader, and directly asked me to take it on. He asked me to change characters from my rogue to a paladin or similar character to be leader. I agreed and brought in a paladin with the Leadership feat (and a cohort and some followers). The DM introduced my character as a leader-type, and I tried to fill the role.
But leading this group was like trying to ride a bucking bronco. Plus, after the initial game session, the DM didn't support me in any way. In fact, after a few game sessions, a new PC came in (a new character for a returning Player) -- this character was a blackguard! What!? Yes, that's right: the DM, after directly asking me to bring in a paladin and be group leader, allowed a Player to bring in a blackguard to the group.
So the two times that I've tried to be a leader failed miserably. I'll never do it again.
Quasqueton