Upon checking in, ask if your Wyndham Diamond Status came through on the reservation. Most times they don’t pay attention to status. This not only makes them check to make sure your reservation is tied in with your account, but subtly notifies them of your status. Once they say yes it’s on here — ask them if they have any suites available for the dates of your stay. Don’t ask about upgrades. If they say yes, then basically say, great! I’d like a diamond upgrade. If they refute the ability to do it, politely and playfully remind the desk agent it’s policy and that while you don’t want to be a bother, you would be happy to have the diamond desk call the hotel if it would help you.

I travel two weeks a month for work, and always stay in Wyndham properties. Rarely do I get voluntarily upgraded, but if I’m friendly, remindful of my status and the policy, and play it right — I usually always get the upgrade.

Ive only once had to actually call the Diamond Desk — the Desk agent said she didn’t have the authority to do upgrades — so I called, immediately got a diamond concierge member who immediately called the hotel and instructed her to make the change.