He's goal oriented
In the first movie, he had a clear objective and never lost focus. Everything he did inched him closer to recovering the Black Pearl. Similarly, guild leaders need to come up with reasonable goals for their members and then hatch a clear plan on how to reach them. It could be raid progression, but it doesn't have to be solely that. In fact, if raiding is a little out of reach, leaders can set smaller goals, like getting everyone to a certain tier of gear, or leveling up the guild for helpful perks. Those are clear objectives that help put a guild into position to tackle a larger goal that's more difficult.
He's a great reader of people
Jack is a manipulator, and that's not exactly something that a guild leader should aim for. But then again, his ability to read people is a valuable skill to have. Guild leaders who can understand their guild members can usually anticipate issues ahead of time and hopefully resolve them before they blow up into major drama. And despite Jack being dishonest at times, he avoids hurting innocent people (as much as a pirate can of course). It's easy for a guild leader to get wrapped up in the power and forget to be compassionate. But leaders who show that they care for every member of the guild are the ones who tend to get the most loyal members in the long run.
He's not the best fighter, but he knows how to win
There's a tendency to assume that the guild leader also has to be the best player. But what's more important is that he knows how to get the guild as a whole to reach goals and win. Jack isn't a great fighter, and he's run from many battles, but he's smart in knowing when to fight, when to negotiate, and when to flee. Guild leaders need to also know which battles their guild members can handle, and which are beyond reach.
There's nothing more frustrating than marching a raid force into a zone that they have no business being in, and having the guild leader insist on everyone banging their heads on content that they can't beat even with perfect execution. Good guild leaders have a good handle on the morale of the guild, and they can pick good targets to match as a result. Some nights might be perfect for those new "stretch" targets, while other nights might be better for taking on content that's safer. And on those nights when things just aren't working out, a good guild leader knows when to call it a night and try again another time.
Jack Sparrow is weird, but endearing. I'm not saying guild leaders need to be weird, but I do think that they're very visible, and their personality trickles down throughout the guild. If you think about good guild leaders you've played with, they're usually people who are interesting or have a very distinct personality. Guild leaders are in a unique position because much of what goes on in guild revolves around them, so those leaders who have a unique personality to match are ones that players might connect with easier.
When Jack Sparrow takes on the British, he does it with such dramatic, over-the-top flair that he usually leaves half the town in shambles. He almost goes out of his way to do things big, and it makes him entertaining and appealing because you don't know what he's going to do next. I think guild leaders need a little of that too. Guilds can sometimes get stuck in a monotonous rut, and it's refreshing to have a guild leader log in and shake things up a bit.
I'm not sure it's good to do it as often as Jack does, but every now and then, why not announce a planned event but keep it a secret as to what it is. Maybe it's a new target for a raid, maybe it's a player event or a guild party, but whatever you choose, it'll create a buzz and generate some fresh excitement that's needed in guilds.
One of my favorite memories in game was in EverQuest
. There was a command that allowed guilds to declare war on each other, and players in each guild were flagged as PvP any time they came across a player in the other guild. It wasn't used often, but we decided to have some fun and try it out against a guild we associated with. We lined up in Paineel and it looked like a scene from Braveheart, with the two guilds running towards each other at full speed. I can't tell you what content we were raiding at the time, but I can tell you that the change of pace from going to war really energized the guild, and even though we lost badly, we had a lot of laughs that night.
He doesn't get too wrapped up in the power
Jack Sparrow will insist that people refer to him as Captain Jack Sparrow, but he's actually not what you'd consider power hungry. He enjoys playing a leader, but he seems to put more value on the fun that comes with it. Even though he wants his boat back, he won't pass up an opportunity to have some fun even if it slows him down in reaching his goal. Good guild leaders are ones who can walk away from the role and be OK with it. If they had to choose between running a guild and having a fun guild, they'd choose the latter every time.
Jack Sparrow might not be the easiest guild leader to follow, and he probably would leave you wondering what the heck was going on. But you'd reach your goal, and have an unforgettable time getting there. In the end, isn't that what guilds are all about?
Do you have a guild problem that you just can't seem to resolve? Have a guild issue that you'd like to discuss? Every week, Karen Bryan takes on reader questions about guild management right here in The Guild Counsel column. She'll offer advice, give practical tips, and even provide a shoulder to lean on for those who are taking up the challenging task of running a guild.