Designing digital democracy is hard. The structures and conventions that have evolved for deliberative democracy, as messy as it can be offline, don’t transfer perfectly into machine code. Many different companies, civic entrepreneurs, nonprofits and public servants are working to create better online forums for discussion that make better use of technology. This morning, New York City’s new chief digital officer, Rachel Sterne, asked how NYC could use technology to serve citizens. In 2011, the White House is using an unprecedented mix of Web 2.0 platforms at its new State of the Union page for tonight’s speech, integrating graphs and other elements to the WhiteHouse.gov livestream.

Tonight, a new alpha feature in Google Moderator is adding some social signals to help identify the questions that citizens want President Obama to answer in his YouTube interview on Thursday night. Every tweet with an #askObama hashtag will be added to the Google Moderator instance at YouTube.com/AskObama. And every retweet of an #AskObama tweet will count as vote in the Moderator instance. (For the uninitiated, a retweet on Twitter is when a user reshares another user’s tweet. To count as a vote on Moderator, the retweet has to be a “native RT,” not the older manual version where text is copied.)

It’s a simple tweak but it’s one that could make the tool more useful for people who wish to crowdsource questions. “There’s a lot of experimentation going on with Gov 2.0,” said Ginny Hunt, product manager for Google Moderator. “There’s a lot of people on all sides trying to figure out how to involve people in a more useful, participatory, exciting way.”

Hunt looks at Moderator as a way to aggregate and rank answers from many different places across the Web. “We don’t see Moderator as a Q&A platform in quite the same way that you might look at Yahoo Answers or Quora,” she said. “We see it as a way to have an ongoing conversation with constituents in a way that’s efficiently organized. That’s why it fits so naturally with YouTube, because there’s a very clear connection with engaging content.”

Hunt emphasized that what people will see on Moderator tonight “is really alpha” and isn’t available on the standard module on YouTube. “It’s a small step in the evolution of social engagement,” she said. “The more we can simplify the process for government and partners, the better. What you’ll see with Twitter tonight is just the first step. Tweets will get integrated into Moderator with your Twitter identity. It’s just a tiptoe into how we can aggregate ideas in a smarter way and is highly experimental, which is why it’s in Google Labs.”

Part of that process is in making the Google Moderator API available to developers. For instance, Google Moderator powers 10 Questions, which the Personal Democracy Forum relaunched in an effort to reboot citizen to candidate engagement.

“We’ve now used the API to kick of something called YouTube World View, which will be a monthly interview with a world leader,” said Hunt. “You can use the API to plug into anything you want to socialize to allow ranking. We made it open because we expect people to be more innovative than we can anticipate in terms of easily crowdsourcing within a community.”

The content from a Moderator series can also be exported as comma-separated values (CSV) files, which allows developers and designers to take the information and do analysis with the raw data.

There are many challenges in creating platforms for civic discourse, including building in incentives for participation, mitigating identity or privacy issues, addressing vocal minorities overwhelming the system, or ensuring systems scale under heavy traffic. (On that last count, Google’s servers have had little trouble keeping up the load: the Google Moderator instance for last year’s YouTube interview on the CitizenTube channel received over 11,600 questions and over 660,000 votes.)

Even as the role of the Internet as a platform for collective action is growing, however, the technical challenges of getting this right include numerous design, community and cultural challenges. The ways that connection technologies can be turned to governance, versus campaigning, will become increasingly critical as more people go online. Many of the social platforms that are in current use give their users substantial ability to personalize what information or conversations they receive.

Clay Shirky, speaking at this year’s State of the Internet Conference, said that government and technologists have systematically undersigned social spaces where hard choices are addressed. “We have, thanks to James Madison, lots of well designed systems to do that [offline]” he said. “We don’t have as many online. The tendency to rant or opt out prevents the kind of bargaining or horsetrading that’s important.”

The Google Moderator team has made an effort to address some of those issues. “We’ve tried to address that by giving everyone a way to let their voices be heard and to weigh in on the process. Ideally, a small, loud, organized group wouldn’t block the virtual room for others,” said Hunt. “The online systems haven’t caught up to the checks and balances that exist in an in-person town hall. Sometimes, they can be more disruptive. We’re still figuring that out. We do care that people have fair space to have their voice heard.”

Hunt posits that when you ask community about not just what they want to say but what they care about, you’ll get more useful results. “We’re not just inviting people here to post something. We’re asking them to contribute and then vote on something they care about. Freedom of speech in a representative democracy can be messy but that’s part of the process that makes it what it is. The challenge is getting closer to giving people who are busy, with a lot on their minds, a way to get involved.”

The real time Web needs to become the right time Web for most of those citizens to find it relevant in their everyday lives, as it did today when a new geolocation app launched that connected trained citizens with heart attack victims. People need actionable intelligence. Geeks hacking smarter government to make asking questions and gathering feedback simpler can and will make a difference. “If we can make it simpler for folks to plug in, that’s a good thing for everyone,” said Hunt. For those that want to #askObama a question about his plans for 2011, that Moderator instance closes at midnight on Wednesday.