O’Leary: I had been looking at The New York Times…god, I had wanted to work there since I was 17. I’d been working in public radio, and back in 2006, I think, I wrote them a cold letter saying, “Hey, you don’t know it yet, but you need something like me.” They didn’t answer that letter, of course. I sent that letter totally over the transom and didn’t hear anything back, which I half expected.

Then, a year later, I was making freelance radio and there was this job opening for an audio producer at The New York Times. It was this little moment in media where everyone thought the future of media was the audio slideshow. I was hired by The New York Times to make audio slideshows and to teach other people how to do that. I would make over 50 audio slideshows a year, I trained like 200 people on audio recording. I really spent the first 12 months of my existence doing that.

Then, of course, it became clear to me that the future of journalism was not, in fact, audio slideshows.

O’Leary: I know, who could have guessed?

So I started moving into doing more project management of interdisciplinary multimedia work — things that incorporated video and interactivity, working with the multimedia team and some of our awesome developers and designers. That’s how I got more broadly involved in digital storytelling, and then pretty quickly was asked to be a digital editor for the website for four of the news desks.

That was much more into the mainstream in terms of thinking about how do we bring The New York Times into a more digital place. I think I’ve said this in a bunch of places, but I had a different job every year I’ve worked here, which fits with my philosophy. I really think if you’re working on digital change in media, you should have an expiration date to your job. Whatever you’re working on, you should be able to complete and help leave behind a newsroom that’s better equipped to handle its digital work. I was really happy to be like: That job is done with, now we can move on to another project-based challenge.

O’Leary: That’s right. Historically, the Times has always moved around people to grow them and keep them fresh. I’m totally grateful that they were able to do that for me in a digital role and give me so many opportunities to learn little corners of the building and how different desks work. I think I’ve had a really unusual career in that I’ve probably worked directly at one time or another with almost every department in the newsroom.

O’Leary: There’s certainly some, but most of the people who’ve had that range of experience had long and storied careers here. People who might have started out on the copy desk at Metro and moved around in a more traditional way. I think just because the digital part of the newsroom hasn’t been around as long, there are fewer people who have had such a range of experience.

O’Leary: I think that if you’re working on digital change you need a combination of both deep specialists — people who understand, let’s say, analytics or audience development — and you need people who are good generalists and translators, the kind of people who can swim between different parts of the newsroom and communicate what’s happening as all this change is manifesting. That’s probably one of the most helpful roles I’ve been able to play at the Times, to serve as a communicator and translator between groups.

O’Leary: When you’re talking inside the Times, the work is really about helping people understand how their work fits into the larger direction of the paper. If you’re talking to an individual reporter or correspondent and you’re talking about the role of social media, you’re going to talk very individually to that reporter about their beat and what works or makes sense or is a good use of time for them in particular. So it’s a very tailored message to any individual or group within the building.

Outside the group, I’ve loved talking outside the building, because I feel like that’s where I’ve had the most creative freedom to kick around ideas about storytelling and the future of digital news. Within the building, we have so many people working on this question that you’re often collaborating with big teams and you’re part of a larger group who’s having that conversation. Having the opportunity to speak outside the Times to speak to journalists and students was a remarkable way for me to almost make recommendations for the future, which, within the Times, I was hesitant to do absent of broad collaboration. When I’m talking at a conference, I can be more speculative and creative and talk about what I think might happen in two or three years. That’s where I feel I’ve been able to do some of my most interesting thinking.

O’Leary: There’s a speech I gave in 2012 which has come out of a lot of my thinking about multimedia; that’s the one that Nieman Lab covered that I livetweeted.

In that, there were two arguments I was making. One was that we had to think about the promotion and distribution of our stories, and two, that we had to do storytelling in an integrated way. The way I talked about it there was: We have to close the exits on our stories. In a post Snow Fall world, that seems obvious, but in 2012, people were still creating — at the Times and at many other places — print articles that then would have a link to some interactive somewhere else. The idea to have a single integrated story using multiple formats was something most people had not yet considered. Having the freedom to talk about those ideas out in public space was really liberating.

O’Leary: I think if you look at the Times’ focus on audience development — audience development is another word for promotion and distribution. We’ve certainly matured in our understanding of all the levers and tools you can use to do that with. But I think now most of the media industry understands that you can’t be content just to make a great story, you also have to aid that story’s ability to travel in digital space. Those were ideas I got to first toy around with while I was speaking.

O’Leary: The biggest difference between 2007 and today is, if in 2007 I were approaching a traditional reporter or editor and talking to them about some digital idea, I would start the conversation like this. I would say: “Hey, you’re working on this incredible story and I can’t wait to be a part of helping you out with it, but what we’re going to do is not to take any of your time or in anyway disrupt your reporting process. That is sacred, and we want to protect that.” Then we’d have two very quick meetings — a half hour now and a half hour in a month — and we would make an interactive piece that was complementary to the article. In 2007, as digital people, we were expected to be 100 percent deferent to all traditional processes. We weren’t to bother reporters or encourage them to operate differently at all, because what they were doing was the very core of our journalism.

That was a really different conversation than today, when we work with all kinds of reporters and editors who are thinking really proactively about, How do we tell the story differently? What do we livetweet? What do we do in a liveblog? What kinds of digital storytelling would work best for this? In many cases you’ve got reporters and editors who have more ideas than the Times can even possibly produce online. The nature of the conversation has completely changed.

O’Leary: I think the culture and the process are one and the same. I think the process, which is the way we do our work, is intrinsically intertwined with the culture of who we are. Whether that’s the quasi-religious — and I say this in a good way — that The New York Times is committed to getting the story right, that’s a huge part of our culture that informs our process. Seeing the impact already that our new audience development team has had on getting our stories to more people is changing the way that we do story planning. When we have a story idea, we are trying to involve those people really early so every story can have its maximum impact. So I think those two things are really woven together.

O’Leary: One of the things about the Innovation report week that we couldn’t have anticipated was that it really put the entire newsroom on the same page. Everyone was really able to read it and reach a similar place where we all believe that these stories that are so important should reach their maximum possible audience. I don’t think you have grumpy people grumbling in the corners about: Oh, why are we trying to get readers for our stories? Everybody wants readers for our stories, so that’s been a good place of consensus to start this period of change from.

O’Leary: Of course buyouts and departures are really painful and hard for everyone to live through. It’s always hard to see incredible talent leave The New York Times. But if you step back a little bit…I’ve often said the process of change in a place like The New York Times is a thirty-year marathon. It’s really tempting for people to zero in one event or one moment and try to make some judgment about the entire process of change at The New York Times. I think we’re about 15 years into that marathon. There’s about another 15 years ahead of us. While that was certainly a sad and challenging time, I don’t think it reflects broadly on the directional course The New York Times is taking.

O’Leary: There have been a lot of us who have been carrying that baton. There were smart digital leaders who were carrying it before I was in some of these roles, people like Jon Landman or Jim Roberts. We have some incredible new talent that has joined us recently; Alex MacCallum is a total powerhouse. Everyone is really excited about Kinsey Wilson joining us from NPR. One of the things we talk about in the Innovation report is it’s a good thing to have more digital DNA circulating among places like the Times and startups and other media organizations. The whole industry is learning right now; we’re all figuring this out. The more we can cross-pollinate our knowledge among different companies and approaches and strategies, I think the better off all journalists will be.

O’Leary: Of course it’s a hard decision. I love The New York Times, and I feel like I grew up professionally here. But there were really two main reasons I felt like this was the right move for me at this time.

One is that I feel the Times is in an incredibly strong place, digitally. I feel like the work on the Innovation report, the incredible progress the audience development team has made, and an overall sense of openness that I feel in the newsroom everyday to the process of digital change, it feels like now is a good time to pass that baton on.

The second thing was I was just incredibly excited by the chance to do the work that Upworthy and I are planning to do together. As I’ve said in my speeches, I’ve long been a real nerd about how to structure digital stories to get and keep people’s attention. That’s exactly what Upworthy has been focused on. Their data infrastructure is really exciting to me. The ability to test out new ideas with them is a dream for me.

So it was a combination of feeling that things were in a great place at the Times and having this incredible opportunity in front of me. Of course, it was a hard decision, but it was one that just felt right.

O’Leary: So some of the recommendations in the report were really easy, because some of them were just a policy proclamation. Do we as a newsroom embrace the use of data judiciously to support our journalistic mission? To implement that, you can answer yes — and then all the people who have been wanting to work on those problems or are engaged in questions about data were unleashed to be even more effective in implementing what they’d been wanting to do.

The other thing that was really easy was one of our recommendations was to redefine our relationship with teams on the business side. That the wall of church and state was an important metaphor to declare our desire to avoid any conflict of interest — which is still totally in place, by the way — but that working with teams like Technology or R&D which happened to, by an accident of history, exist on the “business side,” that we should be allowed to do that more fluently. Once you say that’s allowed, you have more developers coming into the newsroom, more people meeting with their colleagues in groups like Product.

All those things have happened because there was a natural desire for them to happen, which is really what we uncovered reporting out the Innovation report. We said: What needs to change? And they said: We need to be able to talk to our colleagues. Once that declaration was made, those things were easy to implement.

One of the more challenging things, because it’s brand new for us, was to create an audience development team. That would be hard for any newsroom to snap its fingers and create out of thin air. But you know, damn it, if anybody’s done it it’s The New York Times. The fact that Alex MacCallum is on the masthead, the fact that she has built this incredible team in record time and that they’ve already seen these amazing audience gains in a very limited period. That’s hard to do, but they’re doing it.

O’Leary: Yes, I certainly was. I don’t think everyone has been, but as someone who’s worked towards the goal of digital change for seven years, the speed at which these changes have begun to take place after the Innovation report were like nothing I’ve seen in my entire career.

O’Leary: It really goes back to what I mentioned before: the fact that this document ended up being a public one really got everyone on the same page.

O’Leary: No one has really figured out the secret to mastering what it means to be a media organization in the digital age. So the critical thing is that places like The New York Times dive head first into a strong culture of experimentation. And by that I don’t mean throwing everything to the wall and seeing what sticks. I mean rigorous, studied experimentation, where new ideas are tried with excitement and with ease and are studied to learn what works and what doesn’t. I mean that taking risks and trying new things are celebrated even when they may seem, at the outset, like a failure. And that the definition of success for a new idea should be whether or not we learned anything from it, not whether or not it became the future of media.