This past weekend, I took part in Ottawa Web Weekend. The event was an opportunity for entrepreneurial minded people in the Ottawa area to get together for a weekend and launch a web product in just 48 hours.

On Friday evening about thirty-five of us got together at The Code Factory collaborative workspace in downtown Ottawa and started brainstorming product ideas. For four hours we pitched, debated, voted and re-pitched ideas until we had something that everyone could agree on; a reservation swapping service targeted at event organizers. I’m proud to be a part of Ottawa’s newest startup, reBookMe.com!

For me, the most fascinating aspect of the evening was to watch which ideas were chosen and how they got chosen.

About a week before the event, event organizer Marc-Andre Plouffe set up a private site where the participants could exchange ideas, track down competitors and discuss the pros and cons of each one. By Friday afternoon, there were ten or so ideas posted on the website with a couple clear favorites including my own location-based idea called “LastSeenAt”.

On top of the ten ideas from the website, we had another ten or so ideas which people came up with on the spot and pitched to the group. By the time everyone had finished pitching their ideas, we had about twenty ideas split among thirty-five people. This posed a difficult problem since, assuming most people would vote for their own idea, no single idea was likely to get a significant share of the votes.

There was a wide range of ideas on how to cut down the number of options and in the end we decided to group together similar ideas. This meant that we could reduce the number of options without throwing out anyone’s idea right off the bat. It also had the unintentional side-effect of taking some of the more specific ideas and grouping them into more generic clusters.

This brought us down to about ten general clusters of ideas. We then went around the room and asked people to defend the potential of each idea or take it off the list. This proved to be a time-consuming process which didn’t do much to reduce our options. Without any competitive analysis, it was hard to say one idea was more likely to succeed than any other idea.

Our next approach was to further reduce the field by doing a round of multi-voting. In this stage, each participant got three votes and had to choose their top three ideas from the ten or so general clusters from the previous round. Luckily, the results of this vote produced two clear leaders: “How green are you” and “Appointment scheduling”. Since both of these ideas were either loosely defined or aggregates of several ideas, we split the group into four parts to further refine the ideas. Two teams tried to refine each idea and then all four ideas were pitched to the group.

Predictably, when you ask people to come up with ideas and then vote on which one they like the most, they’ll often vote for the idea they had a part in developing. So when we asked everyone to choose which of the four products they liked the most, just about everyone stuck with the idea they came up with. This meant that appointment scheduling won by virtue of having slightly more people in their group. In the end, everyone seemed happy with the choice since most people seemed to agree that they were both equally good ideas.

So how did we end up with appointment scheduling? How did such an extremely unlikely experiment in startup incubation produce such an ordinary product? For that, I think you need to look closer at how the ideas were pitched.

It was interesting to note that ideas which seemed popular on the website didn’t attract as much attention in person. In fact, both of the final two ideas were ideas which were thought up and pitched on the spot. Of course, this could be because some people didn’t visit the website beforehand, but I think it has more to do with how large groups choose ideas.

Another clue into how large groups brainstorm was that loosely defined ideas seemed to generate more discussion and therefore more awareness than very specific ideas. This leads me to believe that people don’t want to be presented with complete ideas. They would rather be pitched a general concept and then come up with the complete idea as a group. This gives everyone a stake in coming up with the final idea rather than feeling like they are just implementing someone else’s idea.

Another trend that I noticed was that although two-thirds of the group presented ideas, the ideas pitched by business and marketing people seemed to be received better by the group. Now, you could say that this is because business people are better at coming up with new products and marketing people are better at getting their ideas across but I think there’s more to it than that. Take for instance, the fact that all three organizers of the event pitched ideas which struggled to gain any traction. Wouldn’t an event organizer have some of the same advantages as the business and marketing people?

The key here is to look at what types of ideas people were pitching. While the programmers, designers and organizers tended to pitch more specific implementations, the marketing and business people tended to pitch entire markets. For example, “there’s a lot of money to be made in being green these days” or “anyone who has a limited number of resources could use something like this”. In the end, I think these types of open ideas encouraged more participation and led to a much more involved group because everyone felt that they had a hand in defining the final product.

On Saturday morning, the business and marketing folks further refined the concept so that the designers and developers had a specific concept to work with and by Sunday night we had a working prototype to demo. More importantly, when the question came up on Sunday night about who wanted to stay on and finish the product, we had 100% of the group on board. I think that’s a testament to how well we brainstormed on Friday night and how well we were able to come up with an idea where everyone felt they were part of the solution.