Paul James, global brand leader at St. Regis Hotels and Resorts, estimates that he spends no less than 150 nights a year in hotel rooms. His experience goes well beyond his own company's brand; he often checks out the competition by staying at other hotels.

Over time, Mr. James has developed a number of tricks to make sure his hotel stays are comfortable. For instance, after booking a room online, he immediately follows up with a phone call to the hotel's concierge. His aim: to request a room that will suit him.

"Unless you're at an airport hotel, you'll find that there are a vast number of shapes and designs of rooms within the raft of standard or deluxe rooms," he says. Sometimes he wants to ensure there's a large work table; occasionally, he wants extra room with a crib for his son. And because he's over six feet tall, he always makes sure to ask for a king-sized bed.

Paul James, global brand leader at St. Regis Hotels and Resorts. Ramsay de Give for The Wall Street Journal

"It never hurts to ask" if you have a special need in mind while checking in, whether it's a specific view, a larger sofa, a mini refrigerator (not all hotels provide them), or a room on the executive floor—"even if it's just a bowl of fruit," Mr. James says. "It's surprising how much a hotel generally can do and can provide for you once you get there," he says.

One key to getting what you want is making a convincing argument for it. "It's those people who tend to have a good reason who get what they want—whether it's getting a larger room because you're going to be meeting some people in your room or you're celebrating a birthday or an anniversary," he says.

When Mr. James is checking into a hotel, he always makes sure he's nicely dressed. Typically he'll show up in a suit or slacks and a jacket. "If you look the part, you'll tend to get looked after a little bit better," he says. But he notes that some guests can look like they "just walked off the tennis court" and still get five-star treatment if they "talk and communicate" well. It helps if a guest "engages with the person that they're talking to as a human being, being pleasant and engaging and not overly demanding or difficult or obtuse or overly distracted," he explains.

He doesn't usually request an upgrade unless something is very wrong with the room, noting that members of good loyalty programs can get regular upgrades without having to ask.

Throughout his stay, Mr. James goes out of his way to be nice to the concierge. "That's rule No. 1," he says, noting that he'll often stop at the concierge desk to thank the staff after a recommendation has paid off.

Such positive reinforcement typically results in the concierge staff offering better service and sightseeing advice over the course of a trip, he says. "If you reward them with a, 'That was great—more like that, please,' it could help open up a whole raft of new access points to the city," he says. Your feedback will also give them more clues to what you're looking for.

If the concierge has performed a significant task for you, it's nice to tip him or her that day, he says, but tipping at the end of the stay is perfectly acceptable, too.

When Mr. James is staying in a U.S. hotel, he generally tips the concierge $10 to $20 a day, depending on how much he has used the service. Bellhops who carry his luggage get $2 to $5, and he always leaves $2 to $4 a day in an envelope for housekeeping.

Mr. James leaves the total tip for housekeeping in the room just before he checks out, rather than leaving it out as a daily amount. At the end, he says, "you just have a better idea of how you've been looked after."

—Cheryl Lu-Lien Tan