I'm hitting a ceiling two years into my first real job. I work on a 5-person team in a tight-knit organization where the average employee age is about 25. Last spring, I made a move and asked my boss (who's about three years older than me) for a raise and increased responsibility/title change. This was met positively, and (after three months of payroll issues) they processed the raise...
But it's now January, and my title change hasn't taken effect. My boss and I and our higher-ups worked for a couple months on a slightly expanded job description. Since last fall, my boss has asked me for "new title ideas" about three times and missed his own deadline to finalize my new title a few times. I've followed up via email and in person each time, trying to diplomatically push him to decide on a title and make the change.
I want to show growth on my resume and be empowered to do more with a new job description. I've been in the driver's seat of this promotion throughout the process, and it doesn't feel great to be fighting for my own recognition when it's entirely in my boss's power to just make it happen. I don't want to alienate my boss by going over his head (I'm comfortable talking to the people above us), but at the same time this is his first-ever management experience and it could be met as a good opportunity for feedback for him. I confided in the #2 on the team, and he suggested asking the boss to get a drink after work and bringing up my concerns in a less formal setting after some icebreaker conversation.
Would it be appropriate to ask him to backdate the change when it finally happens?
How should I get my boss to actually follow through with my title change?
EDIT: I am doing some of the new responsibilities, but a new title would empower me to do them better when interacting with other departments. I have already followed up with my boss in person and via email many times, (bringing it up without expressing frustration). This isn't "just be upfront with your boss," as suggested in the job duties thread — I need to do something to get his attention.