The leadership that took Upworthy from unknown to “off the charts”

Innovation does not begin or end with the new technology or service a company brings to the world; it begins and continues with the way the company’s people think and operate. So while some companies solely make a quality product, others are shaping our experiences, our mindsets, and the way we live our lives - leading by their own example.

You may have heard of Upworthy - founded in 2012, it’s already one of the fastest growing media companies in history. They’re changing the way media is done in the digital/mobile/social moment of the 21st century, bringing attention to issues that matter. And it’s working; with tens of millions unique monthly visitors to their site and user engagement far surpassing their competitors’, Upworthy already has an impressive list of feats - including the innovative way they’ve structured their company. Built as a distributed team from the very beginning, Upworthy’s people can work from anywhere.

But Upworthy isn’t just leading the media industry and public opinion; they’re also shaping the future of how we work and live. To find out how they do it, I talked with co-founder Peter Koechley and Upworthy’s Director of People, Anitra St. Hilaire.

At Upworthy, where does the role of a leader begin and where does it end?

Peter: Leaders set the strategies in consultation with their team. They give their team direction and context about what we're doing and why, and then they give people freedom to pursue great work with as much agency as possible themselves. I think there's a tendency among some managers and leaders to micromanage, to get involved in decisions they should empower their teams to make; we watch out for that pretty carefully.

Anitra: In terms of managers, at Upworthy your manager is your mentor, coach, and support. They’re leveraged for information and context. There is none of that hierarchal, everyone-defers-to-the-biggest-title-in-the-room dynamic, which allows for a continuous feedback loop.

It’s an open, transparent environment where people share and get to know one another as individuals, so they’re able to bring their concerns to the table and help affect change in the ways they want.

Peter, as a co-founder, what kinds of decisions do you typically make and what do you delegate to others?

Peter: I default to extreme trust, delegating aggressively and early, and then go from there to find the right balance. I would rather assume someone is going to be able to run their team and craft their strategy, and then look for the places where it feels like there might be a gap, at which point I can step in to provide some helpful guidance or advice.

Would you say managers are always leaders?

Peter: No, leadership vs. management is strategy vs. tactic. So leaders describe vision and point to where you’re going, whereas managers enable their teams to figure out tactically the best way to accomplish that vision.

Anitra: Also, unlike management, leadership can happen at all levels of the organisation as people step up and identify opportunities, which is what happens at Upworthy.

When you're hiring, how do you assess if someone is a great leader?

Peter: We look a lot at their capacity for empathy and self-awareness. I think the ability to put yourself in different shoes and be aware of different points of view is a great predictor for success

How much flexibility and self-direction do people have at Upworthy?

Anitra: It's about people being responsible, self-driven adults who know what they need to get their work done and meet objectives. We are a distributed team so you can work from anywhere, at least within US time zones. There are some core hours when people tend to be more available and, of course, people should show up to their meetings, but people can choose when they do their independent work. So if they need to take two hours in the afternoon to workout, or maybe take a workshop, etc. they have the flexibility to do that and then get their work done at another time, as long as they keep their commitments to their team. This level of flexibility, autonomy, and trust comes from our fundamental principle that we care about individuals as humans who have lives and things they need to do, and not just as providers of a service to make Upworthy great.

Read: Are leaders born or made?

Peter, why did you and your co-founder choose to build this flexible culture?

Peter: We started from a foundational principle that we ought to treat people like responsible adults and then expect great work from them in exchange. So rather than demanding everyone shows up and clocks in at a set time, we encourage people to look for ways to optimize their own performance and hack their own work lives, and trust they'll do so in a really brave way. This came from my own life. I have two young kids and I know I do great work when I’m able to customize my work arrangements. For example, I know I can get two additional hours of good work in the day if I don't commute at rush hour, or at all. This does mean we have to hire people who are very self-directed, adaptable, and driven.

How does collaboration work with people distributed across different locations and time zones?

Anitra: At its core, there needs to be a level of trust in the organisation and the culture, so at Upworthy people feel free to ask anything. We’re also very proactive about creating environments where people can get to know one another in more casual, comfortable ways. We use different slack channels, like the "Water Cooler" where people can chat about their weekend and send photos. Recreating the kind of interactions you would have in an office makes it much easier when you work and engage with someone you've never met in person.

Peter: We have to be more intentional about communication, but I think that being mindful about how you craft a creative process, how you collaborate, and what input you get at what points, leads to really great creative product. We’re big users of collaborative technologies like Slack and Google Hangouts, and we’re constantly looking for new tools that capture the real time, in-person essence of early ideation and collaboration.

How well is this flexible, distributed model working for Upworthy?

Peter: Great - our average story is more shareable than any other publisher's, and our video engagement is just off the charts. We recently shifted our focus to video; early last year we were doing about four million video views a month; this month we'll do over 300 million views. The fact that we're able to drive these huge engagement numbers, despite being online in different locations, is something we're really proud of.

Anitra: And I think these incredible results are due to the fact that we’re getting the best of people, that they can contribute their best selves, because we value results and not hours spent working. The fact that I can plan my life around the things I need to, while being very available for work, definitely allows me to bring my best self to my work.

Do you think most, or all, companies would benefit from this kind of model?

Peter: There are lots of pros and cons to a distributed work model. I think it nets out slightly ahead, but probably for particular types of workers and particular industries. I think the broader principles of giving your team the context they need to make their own strategic decisions, and giving them meaningful work and exciting goals to run at, are applicable no matter what type of office set up you have.

And I really believe you can almost never go wrong with treating people like responsible adults and full human beings, so every company could benefit by doing that more. I also think there's a complacency that comes from doing things in the so-called "normal" way of having a central office and a traditional company culture that causes people to not re-examine the way they're setting up their business and their company.

At Upworthy, we sort of have the blessing and the curse of having to invent a lot ourselves about how to do work in this distributed, flexible way. We're not the first or the only, but the norms and best work structures are still being defined. I think we strive to be the Google of creating a great distributed workplace that gives people freedom and responsibility, yet allows for creativity, work-life balance, flexibility, and creates great lives for our people all-around.

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