So You Want to Run Your Own Presentation Roulette

Presentation Roulette is returning to Learning Solutions, and this time Realities360 attendees can check it out too. Join in the weirdness on Monday, March 30th from 6:00-7:00pm and check out the lineup of 2020 speakers right now!


Presentation Roulette still holds the record for the weirdest idea I’ve ever gotten approved since I started working with the eLearning Guild.

If you’re not familiar with it, it’s our our hybrid improv comedy and presentation skills event that we’ve been running for the past few years the evening before Learning Solutions begins (this video explains it in a nutshell). True, it’s absolutely ridiculous, but that doesn’t mean it doesn’t also serve a purpose too. Having a bit of fun helps ease people into the event and also sets up an opportunity for them to get to know some of the other attendees.

While Presentation Roulette got its start at Learning Solutions, it’s absolutely something you can run yourself at your own meetings and get togethers too: all it really takes is some weird stock photos and a few people who are okay with looking ridiculous. That said, there are a few extra things I do that I think go a long way towards helping it be especially amusing… and also setting up your presenters for success.


Write weird presentation titles that are easy to make up stories about

The first place I start when preparing for Presentation Roulette is with brainstorming presentation topics. You want ideas that that aren’t just silly, but ideally are silly in a way that’s specific to your audience. So for Learning Solutions I tend to play with titles that poke some gentle fun at the L&D industry as well as technology on a whole (we are the eLearning Guild after all!). Here are a few of the titles I’ve used in previous years:

  • Collecting pointless data about your learners for fun and profit!
  • eLearning for pets: a new market for L&D
  • Not so musical chairs: Getting your seat at the table by stealing everyone else’s
  • Learning was so much easier when all we had were chalkboards: Why we should never do anything new EVER
  • Smell-o-vision! 4D video for learning!

This both narrows down your potential options and gives you a good jumping off point for ideas that are likely to click with the specific audience you’re putting this activity together for. Plus, by having a theme all your speakers have a connection to, that sets them up to do well no matter which title they have to improvise around.

Related to helping your speakers, you also want to ensure your titles have a good balance between enough details that they aren’t scrambling in the moment to come up with a place to start their presentation story, but not so many details that you aren’t giving the speaker room to play and make the presentation their own.

Find intense images that make you laugh

Presentation Roulette seems to work best when the stock images used for the slides are intense in at least one of two ways.

An example of a tacky stock image. A man in a suite stands on the right side of the image. On his left is a web of different people-shaped icons, all connected together with lines.

Intensely bad images are things that may have earnestly been trying to be good but either never actually were or succeeded at the time but have aged terribly. Think of some of the most awkward stock photos you’ve seen over the years or image set ups that you’ve seen over and over again. To find these kinds of images I tend to use more traditional stock photo sites. One lower cost option I found was DepositPhoto (AppSumo regularly does an inexpensive deal for 100 photo credits with them for around $50). For free photos, try out PixaBay and StockVault for some useful options.

Example of a silly stock photo. The image shows a man with many strips of tape twisting his facial figures around. He looks visibly uncomfortable.

Intensely weird images on the other hand may technically be high quality photos, but the subject matter is just super strange. You get the sense, though, that this weirdness is completely on purpose.

You can find photos like these on the previously mentioned sites as well as more consistently high quality free stock photo sites like Pexels and Unsplash (Try searching for terms like “weird” or “silly”). My most consistent source for beautifully shot but deeply strange photos, though, tends to be Gratisography.

What you’re going for here are images that are hilarious all on their own. That makes it way easier for your speakers to build a funny presentation around them.

Choose images that give your speakers some natural story threads

You can technically just choose 20 random images, throw them in a deck, and call it a day. That said, you can do a lot to help your speakers by carefully selecting the photos and order they come in for each topic.

What you want to do is have at least some of your images clearly connect to your topic, even if it’s a weird connection. For instance, if your topic was the eLearning For Pets one I mentioned earlier you’d want to make sure the deck had some images of animals. However, that’s not to say they couldn’t be the weirdest animal pictures you could find. It’s once again a careful balance of enough connection that it gives your speakers ideas but enough weirdness that you haven’t boxed them into a single story… and you even occasionally make them do double takes because an image is so unexpectedly odd.

Keep it short

These talks are funny, but usually only if they don’t go on too long. What’s worked well at our events has been having each presentation be 20 slides, each showing for 15 seconds – so 5 minutes total. Short works for a lot of reasons. If a speaker has a rough time connecting a particular slide image to their improv presentation, they just need to struggle for a short period of time before they get the next image. If one of your speakers isn’t the best at improv comedy after all, there’s not that much time until the next speaker is up. And, as SNL is a fantastic example of, some concepts are funny for a short period of time but stop being so if you drag them out for too long.

Assemble your Avengers

Part of what makes this work is finding the right people. They don’t need to be trained in improv or anything, but you do want people who are comfortable with the idea of potentially looking ridiculous in front of their friends and/or co-workers. That’s not going to be everyone’s comfort zone, so Presentation Roulette probably isn’t a good fit for an activity you want everyone to participate in.

One thing we’ve found works well is having speakers who are all funny, but all in different ways. Mix it up by having some speakers who are great at hamming it up and others who can nail a deadpan delivery. And take a few chances with you choose to present… you never know who might surprise you by being amazing at this.

Prep in advance

Finally, part of what I find helps make the event itself as fun as possible is getting as many of the boring parts set up before it starts. So before the event get all the slide decks in a single folder on one computer, give each file a name that references the topic so they’re easy to locate, and set up timing so each slide automatically advances after 15 seconds. I also pre-print the presentation topics on pieces of paper, fold them up, and pop them into a hat or sack in advance so everything’s good to go. These are all small things, but you’d be surprised how much not having them ready in advance can drag down the flow of the event.

Related note: our speakers also like it when they know what slide they’re on in the deck… time kind of stops working sensibly when you’re in the middle of improvising, so it’s easy to have no idea how many slides have passed and how many more you have to go. To help with this, just put a countdown number on the bottom corner of all of your slides so they know how many more they have to go.

A example of a slide with a countdown number on it. A small red circle has been inserted in the bottom left hand corner of the slide with a number 12 in it.

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