As much traveling as I do, I've been able to figure out the best ways to improve my chances of getting a free seating upgrade. Here's how...
One of the keys to getting a seating upgrade is to find flights that are not full. These flights generally occur during odd hours, mostly late at night when people don't like to travel. So, rather than traveling early in the morning, consider catching a late night flight.
Check-in early on-line if you can so that you are higher up on the waiting list for an upgrade. The more miles you've flown (the more established you are), the better your chances of maintaining your position on the list. Your position could change depending on the frequent flyer status of the other passengers who are on the list. You could move up or down the list depending on your relative frequent flyer status.
If you've experienced a delay (e.g., with a connecting flight), consider asking for an upgrade especially if the airline was at fault for your delay and you have proof of missing an important meeting. The airline may at least give you higher priority on the upgrade list.