I’m Jessica Lessin, Editor-in-Chief of The Information, and This Is How I Work

If you work in media, you know The Information to be something of a scoop-factory, capable of producing the kind of scrupulous investigations that move markets, and vying for clout with the likes of the New York Times. If you merely consume journalism to be better informed, you’ve probably been privy to some of the site’s work, which regularly echoes across your Twitter feed and occasionally sends shockwaves through Silicon Valley and the larger tech industry.

At the helm of the subscription-based publication is Editor-in-Chief Jessica Lessin. As the site’s leader, she has her finger on the pulse of everything her team of reporters and editors does. Recently we talked to Lessin about the demands of running an investigative news outfit from her home and how she detaches from the nonstop churn of news.

Running an investigative news outfit remotely is certainly feasible in this day and age, but what’s been the most difficult aspect of the switch, and what have you done to overcome it?

We’ve had to work very hard to keep everyone on the same page, not just about the day-to-day strategy or the next big scoop, but the big picture strategy stuff too. Ironically, since we’re all writers, we had more of a meeting/discussion culture than a document/notes/memo culture. But we’ve added some written stuff in, too, to good effect. The pandemic drove that, but so does our growing scale of a company. We’ve hired more than two dozen people since the start of the pandemic, the vast majority of whom we had never met.

How unpredictable is your day-to-day? News is unpredictable, but in many ways I feel that management might not be as frenetic and out of your hands. How do you strive for regularity in your daily routine?

I’m actually trying to go in the opposite direction. When my schedule is too regimented, it’s consumed by meetings that may not reflect what needs to be done in the moment. And then there’s no time to do the other stuff, whether it’s helping edit a major story or chasing an important new hire. Right now I’m aiming for a mix of recurring meetings that resemble a routine, and then a lot of unstructured work time. It’s been a bit easier to find the unstructured time when I haven’t had to travel frequently for work.

What do you do to detach from news and keep your mind fresh? Has the upheaval of the last year made this feel like more of a necessity?

Being outdoors helps so much. I write my best columns, come up with my best ideas and feel at my best when I step away from my desk—even for a few minutes. Music has also been helping lately. In a remote work culture, you can be chained to your desk and the internet and the news cycle for hours. I think it’s drained some of my creative thinking.

Is your organization considering transitioning to a hybrid setup? How integral is it for you all to collaborate in the same physical space?

Our plan is to be back in the office in the fall, with some remote days and some team members working fully remotely, as we have always had. Most importantly, we’re going to try things out, see how they go, and revise. Our culture thrives in-person, so yes, we believe strongly in spending time together, whether it’s discussing articles, working on a new product or simply learning from each other’s reporting techniques.

Moving forward, how do you see The Information developing and evolving?

More reporting on more subjects without losing our signature depth. Technology is changing every business, and today only 49 percent of our subscribers work in the tech industry. We are excited to serve professionals across industries who need to understand how tech companies operate and the technologies (AI, AR/VR, cloud) that are going to change the face of business.

From a product standpoint, we are excited to build new news products for our large and loyal community—stay on the leading edge of how people follow the news and build communities around it.

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