Video: How to Score the Best Hotel Upgrades

I got a lot of great feedback on the videos that Conde’ Nast Travel posted with my advice on the best time to book award travel, the best hotel perks for business travelers, and the best first class rewards.

I don’t have video production skills, and don’t figure that most readers actually want to look at me.

But videos are a popular way to convey information, and many of you find it useful to listen to advice and not just read it.

So while I’ve written up my advice on how to score the best hotel upgrades, and redeeming hotel pooints for upgrades, I thought I’d also share a video that I recorded last year on getting hotel upgrades.

Production quality isn’t as strong as the Conde’ Nast videos. But I think Sean Colahan did a great job.

I also hate watching myself — I’m sitting in a chair funny, my jacket is bunchin up — but hopefully the advice is useful. 🙂

Appreciate your thoughts. Is video a useful supplement to the blog?

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About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. I feel the video supplements are VERY helpful!! I hope you will continue to use them!! Thanks for the great blog!

  2. Jacob Tomsky (author of “Heads in Beds”) also mentioned politeness and the $20 bribe, but for him, passing the desk clerk $20 along with your credit card (folded once as you did) works in the cities that he’s clerked in – New York and New Orleans. Unclear if these were chains or not. One of his other suggestion is to book the room through the chain’s web site as they’ll have more of your money and thus value you more.

  3. Video is only useful if it’s captioned or there’s a transcript I can read. Being hearing impaired I get frustrated when I see any video without that.

  4. Great video, Gary. Video was of good quality and informative, but for whatever reason I still like to have the script, or at least the highlights, as TPG does on his Sunday videos.

  5. Very nice job. You are too hard on your on yourself. Best explanation and demonstration of the $20 trick I’ve seen.

  6. Video is helpful but I sometimes I simply don’t want it. I appreciate it when the video is transcribed as well.


  7. I meant to ask – how did you produce the nice graphics? Certainly a step above ppt.

  8. Gary – I really enjoyed it, and look forward to more in the future. Also, your jacket dilemma reminded me of the scene from Broadcast News where Bill Hurt is advising Albert Brooks on how to overcome that very problem.

  9. Great Video. One thing I think is missing is FHR and virtuoso which come with a room upgrade if booking through them.

  10. Great video post, and very useful information, but my two cents, take them or leave them, are to stick to just text for the bulk of the content.

    One of the most useful things about blog posts is that I can go back and skim them and pick out the useful bits or get a refresher at a point when I might need one on a given subject. With video, it’s just not anywhere near as easy to do – was that one good part 2 minutes in, or 6?

    Also, there are always the logistical issues with videos (Using airport wifi? Forget it), and the fact that certain portions of your readership might not be inclined or able to watch videos with sound for certain long periods of certain days not falling on the weekends 😉

  11. Great video! I found it more informative than just the print would have been. Thanks!

  12. Great video! Much better quality then the LIAT response to Richard Branson! Very informative and it was also great to put a face to all of the posts. 🙂

  13. Good job Gary. The key, that you certainly hit on, is to be willing to ask, supplement it with a gratuity, and most important of all, to just be plain nice. These people see loads of a$$holes every day and it’s sad to say but apparently, being nice can make you stand out!

  14. The video was fine production wise. I do production for a living and it worked because you had great information to share. Thanks! Nice demo of the bill trick. I always have a couple denominations folded and ready so it’s less awkward when it’s my time at the counter.

    My tip back to you: close the blinds or curtain to your right next time. If it’s too dark open them partially. The camera will auto iris to a better setting if you have it set that way and it will take some of the brightness off your face.

  15. I was prepared to say, “nope, I like print” but indeed, getting your information in a video reinforces the print material and was very useful. Nice production job also. Thanks.

  16. Gary, enjoyed the video for a change of pace. thanks for the effort you go to for your readers benefit

  17. Gary, I loved your video! Your blog is the one I read religiously of the 4 I follow (Lucky’s is 2nd, followed by The Points Guy & Million Mile Secrets). I thought the video was a great addition! Only 2 suggestions from my opinion: (1) Have it be shorter, I’d say 5 minutes max. (2) Write out the key points in your blog for those who can’t watch the video or for the times when I cannot access my audio but can still read (like on an airplane when I don’t have my headset).

  18. Very nice and useful Gary!

    Question regarding the cash tip up front – if you are tipping $100 to get the penthouse, and only an entry level suite is offered, how do you handle?

    I’ve done it with two $20s, making it easier to tip $20 for a basic upgrade.

    I also got someone giving me a view of the HVAC shaft on the 7th floor of the Venetian and expecting $$ for the “upgrade”. It was a “best in category” upgrade, which is not an upgrade (although sometimes a very worthwhile and nice gesture, but not that time).

  19. Second question stimulated by your great video:

    What type of upgrade could one expect in high season (early October) at the Andaz 5th avenue with only Platinum status using 50% extra points? Will there be a door separating the bedroom and living room

    (That’s my #1 criteria, followed by it not being in the dormers at #2).

  20. Nice job, Gary!

    Somehow my first question vanished into the ether:

    How do you handle having $100 bill out for the Penthouse and getting an entry level upgrade offered?

    I’ve had two $20s before (for flexibility), but Ben is more persuasive than Andrew.

  21. Really liked the video: easy to follow, key points noted on the transition screen, and having you focus on certain points through your talking was great.

  22. Nice job in front of the camera. It isn’t easy and that’s why you can edit them! However, it’s not an effective way of communicating. Why spent 9+ minutes on something you can read in 2min<? Most of us read your blog to get information. On a related note, most of us are more interested in the tips and tricks related to upgrades. It felt as if you spend ~1/2 of the video demonstrating the size of your hotel-penes. Less nobb measurement info and more practical info.

  23. I personally hate videos. It has nothing to do with the content or the quality just that I would simply rather read that watch. I learn better by reading instead of hearing. If you did them here and there, it would be fine, but I would be disappointed if they were a regular item.

  24. Great video Gary! Have you ever had the $20 trick backfire on you in a smaller city?

  25. Hey Gary – I think that they videos are useful, especially to people who tend to learn through audio/visual methods as opposed to reading. I just started experimenting with video on my site and while I’m not sure it will ever replace writing, it does allow you to tell a more in depth story and connect on a deeper level with your audience.

  26. Great video – very entertaining and informative. A really nice addition to your blog

  27. Gotta give it to you, excellent video and you are a natural in front of the camera.

    But where was Emily? ( kidding, of course I know…) 🙂

  28. I kept thinking of that scene in the 1987 movie “Broadcast News” where William Hurt tells Albert Brooks to pull down his suit coat from the back and sit on the tail.

  29. I’m against the video-on-the-blog thing. I can generally read much faster than I can sit and watch a clip. Also, I’m in Afghanistan, trying to plan trips for when I get back, but the network blocks all videos due to bandwith issues. So whatever great tips were offered in these videos pass by me unseen & unheard.

  30. Gary,
    Concerning the 50% upgrade cost for a Hyatt suite… Does this option show up when making online reservations or do you need to do it over the phone?

  31. How old are you??
    You look horrible, fat, double chin etc. What kind of medicine are you on by now? Your cholesterol?
    Sport? I probably making a joke here.
    You will be surprised but I am writing this as a friend who cares and likes your blog A LOT.
    You are the result of years of awful eating that I read time and again in your blog.
    You are not evil? But your decisions create a lot of pain and suffering.
    Most likely you will brush it off and of course not publish.

  32. Just wanted to flag that you indicate you work for PETA and are making a political point with your video.

  33. was never a huge fan but after a a out loud chuckle at “Frank Sinatra” I’m plugging back in. Nice tips. Good vid. A great deal can be said for the personal touch.

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