Gayle Karen Young may have the cat-herding-est job on the planet. Young is chief talent and culture officer at The Wikimedia Foundation, the San Francisco-based nonprofit that operates Wikipedia and other online collaborative projects. A psychologist and organizational leadership specialist, Young counseled corporations like Oracle and Virgin before fetching up at the idealistic, quirky, uber-collaborative Wikimedia. I talked with Young about managing in an environment with tens of thousands of constituents, all of whom demand to be heard.

What is the culture like at Wikimedia?

One way to get a handle on it is to think of it as a series of nested, interconnected cultures. There’s a bit of the spirit of the Enlightenment. Truth and knowledge are paramount. One of the things I notice consistently among our employees is that they love to learn and love to teach. We have a Syrian guy who is teaching Japanese on the side because he loves doing it. Our director of features knows-;on a scary level-;everything there is to know about McDonald’s hamburgers, the varieties and pricing differentials. So there’s this inordinate intellectual curiosity that is very much tied to Enlightenment values.

Also we’re in California, which is a free-to-be-me state. And we operate within the Internet’s why-wasn’t-I-consulted culture. So there’s that egalitarian sense where people feel they can voice their opinions and exercise control over their projects. And then you have some of that Silicon Valley entrepreneurial element.

Besides intellectual curiosity and a belief in Wikimedias mission, what else do you look for in employees?

We have to find people who are capable of thinking at a generational level rather than in terms of typical business cycles. Sue Gardner, our executive director, understands what it means to play a long game. In Silicon Valley, especially, a lot of people say they are long-term thinkers who really aren’t. But Wikimedia isn’t creating this repository of human knowledge for the current world. It’s creating it for the future. So we edit Chinese Wikipedia for its current incarnation but also for the day the Great Firewall comes down.

Was there an early experience that brought home to you what an unusual working environment this would be?

I had just redesigned our jobs page, and I was very excited about it. Then I got an instant message from one of my colleagues saying somebody took it down. I said, “What do you mean ‘somebody took it down?’” It turned out a community member had taken down the jobs page. I had to hunt this community member down--find somebody in the Foundation who knew him, find which IRC channel he happened to be on. He was like 17, lived somewhere on the East Coast with his mom. I engaged him in a conversation about why he took down my jobs page. He had issues with some of the privacy pieces. Because the page links to Jobvite, which is our backend applicant-tracking software, and Jobvite pulls the IP addresses of people who visit their site. I said to him, “First, help me understand this issue.” It turned into a lovely conversation. He had some good ideas for dealing with it. And he actually ended up rewriting the code for me.

How much does the community weigh in on matters unrelated to content?

They weigh in on absolutely everything. So when we talk about the design of notifications, talk about the design of the visual editor feature, when we post jobs that are available at the Foundation--everything. We invite them to do so because they will anyway. Some of their objections are very cogent and thoughtful and reasonable. Some are more just resistance to change. You have to discern which is which and then try to corral the voices. That’s what we did, for example, with our terms of use. They are among the few understandable terms of use on the Internet. They have gotten some awards. We invited community input on that. We had a period of taking it in. We closed the period for comments. And then we put out another version with a lot of those elements integrated and explained why we did things. People were very happy with that. Within limited time frames and limited context you can make a series of decisions, open it up for input, and still move forward with the underlying process.

How are the ideals of Wikipedia itself reflected in how the organization is run?

We very much prize transparency. For example, all our monthly metrics meetings are on Youtube, streaming live as we have them. We look at our strategic priorities and we invite staff to give an overview of what has been going on. It’s one way the whole Foundation gets communally grounded and informed on all our current initiatives. People ask questions from all over the world, live, as it’s happening. So when we talk about the rollout of a new feature, people say hey, have you thought about this.

So its not just community members watching? I could observe your meetings?

We publish when the next one is and the access information and the agenda. Anyone who is remotely interested can pop online with us.

Do the ideals of Wikipedia ever conflict with decisions related to efficiency or performance?

One issue we run up against is we are obviously big believers in free and open software. That’s an ongoing tension because some of the free software isn’t as good as some of the paid software. For instance, we use proprietary software to run our HR infrastructure because the free software out there has problems with privacy, ironically enough. That’s an issue we surface in public and have community discussions around.

Which of your skills has been most important to this job?

The ability to roll with things matters a lot. I need to operate in as wide-open a way as I know how. The metaphor that pops into my head is a camera lens when the aperture is very wide. Because you never know what is going to float through on any given day. Anything from mediating an interpersonal issue to wondering whether I will have to intercede with the French government because a Wikipedia editor in Paris was detained and questioned. You need the ability to parse out what is the core piece of work that needs to get done in an inherently noisy environment.

I expected that in this role I would build infrastructure and do the leadership development work and be a strategic partner for my fellow C-levels. I did not expect to draw as deeply as I have on my background as a psychologist. When [Internet activist and political organizer] Aaron Swartz committed suicide a number of months ago, that was very hard for our community. He was a prospective board member at one point; he was an active community member; a lot of people here knew and respected him. Often suicides happen in clusters in communities, and I have sat up with a couple of community members at 3 in the morning when they have felt suicidal and talked to them and found them help.

A few months ago, Sue Gardner announced she was stepping down. Has the Wikipedia community weighed in on who her replacement should be?

That’s just part of the process. We have asked for input as we put the job description together. It’s interesting, because the community is so brilliant in so many ways, especially in aggregate. But a lot of them don’t have familiarity-;and I wouldn’t expect them to-;with the kinds of leadership skills it takes to spearhead a movement and organization this complex and massive. Some of the names I’ve heard floated are lovely people but don’t have the skillset required for this role. It’s another of the ongoing tensions between different kinds of expertise. We value the input and we hope they see the value of the people we put forward.

When you are considering an applicant, is the first thing you check out their Wikipedia page?

 If they have one, that’s great. There’s every likelihood that they don’t. Their LinkedIn profile is useful, as is word of mouth among our personal networks. Wikipedia pages are factual-;they read like encyclopedia pages. They show what people have accomplished. But it’s hard to tell about a person’s leadership style from their Wikipedia entry. What’s their approach to collaboration and transparency? Some of the intangibles would be incredibly difficult to get from a Wikipedia page.

Do you see other organizations becoming more like Wikimedia?

I think the Wikimedia Foundation is actually a good blueprint for what’s happening in Silicon Valley. This distributive, immersive, interactive, boundary-less, fluid staffing and structure is becoming more and more relevant. Distributed leadership models are becoming more relevant. Leaders need to be able to see others’ perspectives and discern soft boundaries because the Internet is never off. This is a place where the leadership challenges of the next century are being born.

Dont you mean the next decade? 

The next decade, for sure. But I wouldn’t be surprised if it was the next century. Like I said, we are in this for the long game.