What are the best ways to incentivize people to use "Enterprise 2.0" knowledge management / collaboration tools in an organizaton?

Bottom line up front: Show the benefits and make it easy. External incentives might work to get traction (e.g. some award or ‘badge’) but the only sustainable incentives are those that are inherent to the process.

So first, focus on the problem for which the tools are to be employed. Most people don’t care about enterprise wikis, they care about being able to do their jobs, about finding the right information and the right people. Make sure you understand the process you’re trying to fix, improve, or even replace with your enterprise 2.0 tools. Replacement is key because it’s easy to take new tools and “improve” a process that’s inherently broken or unnecessary, with or without new tools.

Provide people with a working demonstration of an existing business process. You’ll have busy people and you’ll have technologically disinterested or just plain unsavvy people. Work up an example that makes it obvious how the new system works and where the benefit is. This should be a real working example, i.e. take a process in your business and actually change how it’s done using the new tools.

Especially in a large organization, you should actively help people figure out how their processes, tasks, etc, can be accomplished with the new tools. Sometimes this means rethinking tasks and entire processes. Oh, a dozen people are all contributing duplicate copies of a PowerPoint presentation to be updated for hours on end and then printed off to brief the admiral? Why not just collaborate in a central location on the content… hell, why not just brief from that location, and skip the PowerPoint wankery altogether? If you want to spread the idea of indoor plumbing you must go from village to village showing people how it can work for them, and helping with the initial implementation.

Get people up the ladder using the new tools. Grassroots efforts to use new tools can be successful, when they’re led by people who just want to use the tool. But if you want to achieve pan-organization adoption you need leadership to show that they’re using it, too. Unfortunately, in large organizations you often have to work to the tools and styles of management. When the VP is working from the shiny new enterprise 2.0 tool, so can - and will - everyone else (eventually).

Be careful about overestimating how easy the tools are for everyone. And not just the interfaces, but changes in underlying concepts. Even tech savvy users approach tools and systems using preconceived notions. If you’ve ever read anything by a developer complaining about the transition from Subversion to [name your DVCS] you’ll understand.