The former managing director of the Evening Standard seems to like making bold, brash gestures, which extend to his hiring strategy.
While at the Standard, Anderson parachuted in his own ad team, led by the former agency Mr Smooth Alan Brydon, and introduced a radical new sales policy (which was quickly dismantled following his departure).
Anderson is now the managing director at News Group and his appointment of Yahoo!'s very own Mr Smooth, Mark Chippendale, as the media director also comes out of leftfield. Not for Anderson the hiring of a rival newspaper sales director or an agency press director to fill the role.
Unlike some of the changes at the Standard, Chippendale's appointment makes eminent sense and ties in with a broader strategy at News Group's News Corporation parent to integrate revenue from newspaper sales, online and mobile phones. Chippendale's is a new role, combining the old ad director role vacated by David Emin with responsibility for this "new" revenue.
Anderson explains: "I felt that we didn't need a classic newspaper ad director sitting on top of Liam (Reynolds - the deputy ad director) and Robbie (McIntosh - director of strategy). They're doing very well in a difficult market so there are no problems there. I wanted somebody who can embrace the three identifiable platforms and lead the different groups into a multiplatform play."
On the face of it, Chippendale seems the ideal man to pull this off.
Before joining Yahoo! as its European vice-president of sales just nine months ago, Chippendale had cut his teeth in the supposedly "old" media world of Sky's sales operation, where his experience of selling interactive TV advertising brought him right into the digital world. Then came the online baptism at Yahoo!, an experience that Chippendale describes as like "drinking from a fire hydrant".
Chippendale's chief assets are said to be his charming demeanour, enviable contacts book and understanding of how different advertising platforms work. Anderson also believes he has landed a consummate media practitioner with leadership skills and an understanding of the agency planning process. That may be so, but Chippendale still faces an uphill challenge to knit diverse platforms together in a print-dominated culture, and to encourage agencies to engage in this joined-up thinking.
And, who knows, greater co-operation with Sky could be part of the plan.
News Group has made a slow, solid start to reinvesting in its newspaper websites and products such as online bingo and the online classified service Sun Local (Leader, page 20). It has one of the country's most famous brands to work with, but the real effort will start now.