Here’s another one from my meetings this week: a couple of people asked me about how to contribute to a wiki without looking stupid. This is a question I get quite often when meeting with organizations to talk wiki adoption. Some people will say that the biggest obstacle keeping them from participating on the wiki is fear of breaking it, looking stupid, or doing something wrong.

My take: If you’re silent, you’re not interesting. When you talk, even if you say something controversial or seemingly “stupid”, you’re much more interesting. Also, what you think sounds stupid might sound brilliant to someone else. Bear in mind that pop culture and the media tend to quickly pass judgement on things people say, whereas within an organization people are likely to take a different approach and pay closer attention to what people they work with have to say because it has value to them.

Regarding the notion of doing something wrong, Peter Himler recently blogged about IBM distinguished engineer Mike Moran’s new book Do It Wrong Quickly, and Himler says of the book, “He turns the old “plan then execute” mindset on its ear, favoring a non-stop cycle of refinement where failure (or “doing it wrong”) is a necessary and accepted step on the road to marketing nirvana. I mean in the old marketing paradigm, one can spend beaucoup bucks and still see a campaign fall flat. Whereas on the Web, if the messages don’t mesh, pull ‘em down and try something else til you get it right. Makes sense.”

Himler happens to be applying this to marketing, but the idea applies to everything, including collaboration. Trying to massively plan something and then expect it to be successful is more risky in my opinion than applying a flexible, iterative approach and making smaller mistakes along the way. In fact, the even bigger risk is that with the old approach the people whose reputations are staked on its success will do whatever it takes to appear successful.

I once worked at a firm that invested $100K in a content management system and to justify the expense they had to demonstrate that a certain number of new groups were using it every six months. So the group in charge of getting teams to use the system signed teams up for spaces that they never used (in fact, they’d even tell the people that they were signing up that they didn’t have to use the spaces (no one in senior IT leadership ever actually looked at the content – they just wanted to see a higher number each time they checked!)