On his list: Harmonize and consolidate disparate IT shops, break down silos and question every process in place.

"When I got here, we had an IT organization focused on TV, one on radio and one for publishing. There were multiple instances of PeopleSoft running different versions in different business units," he says. "We had three to four flavors of phone systems and routers and databases that weren't talking to each other. We needed to consolidate, so we started with people, then processes and worked our way to systems."

In the first nine months on the job, O'Brien successfully consolidated the IT groups into one. With the people part of the consolidation complete, O'Brien and his team looked next to processes and systems. That's when it was time to scrutinize Journal Communication's contract with Microsoft.

O'Brien, who was always a proponent of cloud computing, had good experiences in the past with Microsoft in the BPOS environment. Journal Communications was about halfway through its agreement with Microsoft when he and his team had to take a close look at it.

"We looked at its investment and what it was going to take to upgrade the legacy productivity tools and legacy email and collaboration systems, and it was substantial," O'Brien says. "There was going to be a lot of hardware and software to repurpose and replace."