Recently I watched TED talk by Tim Ferris detailing his process for defining your fears. The video (embedded below) is well worth watching, but what struck me about it is how similar it is, albeit at a macro scale, to a project planning process to which I'd recently been introduced: the pre-mortem.
I'm not sure what what I should attribute that I had not previously encountered a project pre-mortem, as it's been discussed since at least 2007. The exercise, though, is brilliant in its simplicity. Early in the project (and the earlier the better), ask the team to imagine the project is done. The site has launched...and it's been a total failure. Then each person presents what they believe killed it*. In the particular project where I saw the technique used, we came up with a gamut of causes: technological and architectural failures, organizational politics, failure to get consensus from the wide array of stakeholders, even funding being yanked due to shifting priorities. For each person on the team, the identified cause was indicative of their biggest concern about the project.
Once that list is generated, the next step is to come back to the present and, similar to what Ferris describes in his talk, think through what can be done to prevent or mitigate each of the identified project killers. From that point, we're back in the realm of more common project risk management.
* In theory, you could get the same list from the team by asking them what the biggest risks to the project are. That approach, though, keeps the whole exercise in the intellectual sphere. My experience actually doing the pre-mortem exercise was that imagining the future and projecting ourselves into it made the whole thing more visceral and, I think, lead us to risks we wouldn't have come up with in the more traditional "what are the risks" approach.