How to make a painless guild transition?

[Chickenpox]

First ill explain the situation I'm in
So I've been in a guild that I joined while leveling after taking a long break from wow. Ive been in this guild for a bit, and am even a highest ranked officer (I'm fairly sure this is just because i was the only one that used the vent for socializing).
The leader has tried to / is in the process of transforming it into a raiding guild. But were just not getting anywhere, we get around 1 or 2 people other than me and the GM showing up to raids, and having to pug the rest. This isn't a case of not enough members, were running near 100, and a good 75% are 80's, its just noone is dedicated enough. This has been after 3/4 weeks of trying. Were blocked on Saurfang, and I want more progression, I want more raids.
I have applied to another guild, and am hoping to get in, but what I am asking is, Whats the least painful way of making a transition from 1 guild to another, with the least amount of pain to everyone?

[Acheronia]

1) Be honest. Tell your guild leader your frustrations and what you want out of the game. Tell him you have/want to apply to another guild.

2) If you're not too impatient, tell the guild leader that you'll stick around for 1/2/3/.. week/month/year and you'll give it your best shot to help him convert the guild.

3) There's plenty of advice in the posts below how to transform a leveling/social guild into a hardcore/casual raiding guild.

4) Good luck!

[Voddy]

You should really have told your Guild Leader that you were planning on applying to join another guild, before actually applying. If they find out, they will probably feel betrayed and upset that their 2nd in command has gone behind their back and applied to a different guild. Your best bet is to be upfront and honest about it, and say you can always return if things don't work out in the new guild you are hoping to get in.

[Bashal]

Just a thought: was there an attempt to pin down exactly who is interested, and schedule raids at a time when most of those people are available? Or did you guys just start throwing stuff up on the calendar?

[Dreador]

You should really have told your Guild Leader that you were planning on applying to join another guild, before actually applying. If they find out, they will probably feel betrayed and upset that their 2nd in command has gone behind their back and applied to a different guild. Your best bet is to be upfront and honest about it, and say you can always return if things don't work out in the new guild you are hoping to get in.

That's a bad idea. Reason is, if you don't get into the new guild you've now created a resentment toward yourself in your current guild, and if I was the GM as soon as you came to me with that I'd probably just kick you for it. Just app silently, when it's accepted then approach the GM. If he/she knows anything about management he'll/she'll understand. It may not sit right with them but there won't be any unspoken aggression that you will have to deal with while you stick it out waiting to be accepted. Think about RL jobs. Do you tell you're boss you're planning on leaving the company before applying? Good luck, because he'll start recruiting your replacement and regardless of whether or not you get the job, you are now fired.