In January, news broke that Amy O’Leary, the deputy international editor of The New York Times, would be leaving to become editorial director at Upworthy. O’Leary’s role at the Times, where she had worked for eight years, mostly involved helping the paper adapt to the digital world. Most famously, she co-authored an “innovation report,” leaked last May, that concluded the paper has struggled to make that transition. Yet, given the Times’ prestige and Upworthy’s reputation for offering breathlessly headlined but often hollow content designed to go viral, it was a move many found surprising. CJR’s Christopher Massie asked O’Leary about the newspaper she left behind, as well as about her new gig.
Did the Times make any strides in its transition to digital in the months between the release of the report and your departure?
Absolutely. Everyone read the report, everyone was aware of its primary recommendations. So you had this massive alignment, where everyone from the most seasoned reporters and copy editors to the newest hires working on analytics were all suddenly on the same page and able to move forward together.
How did that new attitude manifest itself?
The most obvious way you saw it in the newsroom was that, in addition to all the traditional conversations that editors and reporters have about a story’s content or how we were attacking a certain line of coverage, there was also this new conversation that started in a really robust way about, How are we going to make sure people are reading it? After reading the report, people realized there were simple things the Times could undertake that would carry our journalism much, much farther into readers’ lives and homes. And who at the Times would be against that? That’s why we go into journalism. No one’s going to be against thinking more smartly about an email newsletter strategy if we’re going to reach a million new readers. No one’s going to be against thinking a little bit more sharply about search-engine optimization or social media if it brings us huge new readership.
The report observed that the separation between the newsroom and the company’s business and technology departments created mistrust and a simple lack of information on the editorial side. Did that wall erode during the months after the report came out?
We fervently believe that you need some of those walls of separation to protect the newsroom against conflicts of interest. But what happened was that, by an accident of history, these other important groups like research and development, technology, the group that studies and does research about Times readers, all of these groups were just considered to be “business side.” The guy who built the breaking news alert system wasn’t talking to the news desk that was writing the breaking news alerts. That’s just, frankly, kind of crazy. But again, once it was pointed out, everyone was like, of course, that’s crazy.
Last month, you told my colleague Alexis Sobel Fitts that all media, from The New York Times to BuzzFeed to Upworthy, are “in a battle for people’s attention now.” In a battle, there are winners and losers. Are you switching sides?
It’s not that The New York Times versus BuzzFeed is the battle that’s happening for every minute of someone’s attention. It can be between Candy Crush or YouTube videos or whatever app on someone’s phone has their attention this minute. What I’m fighting for is that high-quality news and information, the stories that people care about, the issues that matter most actually win in that fight for attention, and that more people are paying attention to those kinds of important stories than are playing a stupid game on their phone. So I’m still on the same side.
If your ideal vision for Upworthy is fulfilled, what will it look like?
My ideal vision for Upworthy would be that any time you encounter a story from Upworthy, you are genuinely surprised and moved about an issue in the world that really matters.
Christopher Massie is a CJR contributing editor.