+1

With all due respect, is this a theory or do you actually do this and what is your success rate?

I think you're more likely to hit the lottery then dialing up the top person, cold, at a major facility, get right through directly, find him/her at the desk, engage about the weather then lower the boom for an upgrade. I was a mid level executive for 30 years and stopped answering the phone 15 years ago if I didn't recognize the caller ID. 95 times out of 100 it was a peddler I didn't want to waste time with.

Email may be impersonal and new school, but it's how business operates and I've had decent success with little intrusion on both parties time...

best way i've gotten an upgrade...paid for it when I made the reservation.

You raise good points. Personally, I almost never care about an upgrade so don't go out of my way to seek one. But when I'm with my family, and really want a great view or extra space, I generally use calguy77's technique--I pay for it in advance!

But when I want to finagle a better room than I'm willing to pay for, my approach is to call the hotel and ask to speak with the rooms controller. Ultimately, that is the person who assigns rooms and has the direct power to make or break my stay. Yet they're not high enough on the food chain to be screening calls or not usually in the office during normal hours. I make my case, sprinkling in some humor and trying to find ways to establish a personal connection. And I'll not-so-humbly report that my success rate is phenomenal. But again, I only do this on the very rare cases when I care about an upgrade and can't/won't pay for it.

just call the hotel and ask the front desk directly, but from experience if you ask for the manager i would expect something like " the manager is busy or out of the office at the moment, would you like to be transferred to her voicemail?" Plus most front desk agents have enough empowerment to decided who to upgrade while the manager has better things to do than to take another call from just another guest asking for an upgrade.

Rooms controller or concierge (via the virtual method) has worked decently in the past. Like you I only request for special stays (family, new romance stays). Of course they can't outright grant but often they ask permission of the GM who are only happy to accommodate when they can. A little buttering up about being PP, LTP, Marriott loyal, etc help too.

I always ask on Twitter, they give me the email, I send a nice note, and 80% of the time I get a great reply with a nice upgrade.