Let’s face it, there is a whole lot more enthusiasm for making organizations more open, dynamic, and free than there is progress. Why? Control has been the iron fist behind too many organizations for too long. And unleashing freedom inside them requires dismantling deeply-embedded management principles and practices. Of course, it’s not an either/or proposition. The real trick—and the far greater degree of difficulty—is reimagining organizations, redesigning work, redefining leadership and rethinking the measure of value in a way that transcends the tradeoff between freedom and control.

Thanks to the emerging ecosystem of digital, mobile, social technologies and the principles that undergird them—including openness, community, collaboration, experimentation, meritocracy, and autonomy—we can imagine organizations that are both large and human scale, efficient and flexible, disciplined and inspiring. And thanks to the participants in the Digital Freedom Challenge, we don’t have to just imagine them—we can explore dozens of real-world case studies and bold new approaches to dramatically expanding individual autonomy at work without compromising the ability to scale, coordinate, and get important things done together.

Today we are delighted to announce the winners of the Digital Freedom Challenge. But first, we’d like to thank the ten finalists for their inventive and important approaches to expanding autonomy at work. We owe a huge debt to everyone who contributed to the challenge—and to everyone with the guts, grit, and ingenuity to take on the status quo (and the generosity to share what they’ve learned in the process). Thank you all!

Now, meet the winners (in alphabetical order):


First up, Aaron Anderson deserves congratulations for his brave experiment in “open-sourcing” his job, redesigning his approach to work, and reimagining the work of leadership in the process. In his story, Working in Plain View: Using a Wiki & Social Media to Broadcast as you Work, Anderson recounts his adventures in blowing up the traditional, rigid boundaries of “the job” as he took on a newly-created role as director of strategic organizational initiatives at San Francisco State University. His first move: he invited his colleagues to help define the role, and involved them and the wider university community in the work itself by doing it “in plain view” via a wiki and other social tools.

Over the next year, Anderson effectively turned his work into a lab, not just for devising new strategic organizational initiatives, but for making work itself  more open, fluid, transparent, and collectively determined. His approach is straightforward: he uses free, widely available tools (such as for his wiki) and shares new projects, initiatives, and milestones as they occur. Rather than spending his time refining memos and reports, polishing PowerPoint presentations, or leading closed-door sessions, Anderson posts his work as an invitation to his colleagues and relevant contributors to take part.

“Instead of turning on my computer and creating word documents or spread sheets,” he says, “I open a browser and create web pages or Google docs.  A word document stuck on a hard drive doesn’t do anyone much good, particularly if you need others to collaborate on it. A web page or Yammer post or note or Google document has a URL and can be set to allow others to edit as soon as they log in.” Rather than simply documenting the work, Anderson is creating a space for collaboration and connection. The office as wiki effectively puts everyone on the same team—and moves the strategic agenda from the executive to the collective realm.

The result: the emergence of a genuine culture of collaboration where individuals have the freedom to connect with whomever they want, to choose what work they do and with whom, and to contribute beyond the strict confines of their job role. While Anderson’s experiment in working in public is still unfolding, it offers up a several powerful lessons about the nature of work and leadership today. For example, Anderson learned that while failing in public stings, it’s the fastest road to a genuine fix. And, true power comes from sharing information, work in progress, and the credit for it, not from hoarding and controlling it. Read more here.


In his winning hack, Self-Build Job RolesKeith Gulliver (along with co-authors Claire McCartney, Cassie Lloyd Perrin, Hendrik Dejonckheere, Kubatova Jaroslava, and Kukelkova Adela) pushes the boundaries of self-determination and flexibility when it comes to defining “the job” further still. It’s a simple idea (but not an easy one) and a hack of the fundamental flaw in the industrial system of management: a design that treats flesh-and-blood human beings as interchangeable parts in a machine. Gulliver, a 26-year veteran of IBM’s talent and HR operations, offers up a powerfully detailed approach to making jobs as adaptable as the individuals who do them and as dynamic as the external environment in which they work.

The hack presents a model with a “core role” at the center surrounded by an overlapping ecosystem of activities—including learning, external secondments, stretch assignments, special projects, experimentation, and sabbaticals. That universe of options sits in a cloud-based system which operates like a marketplace where individuals can exercise their freedom of choice during an annual “self-build window.” Over time, individuals build value for themselves and for their organization by becoming masters at “flexing” their job roles in response to individual needs, inspiration, and the changing marketplace. Gulliver and team address the practical implications, challenges, and share a step-by-step experimental recipe for trying this at home.

In a world where half of the job openings are for roles that did not exist before 2005, the Self-Build Job Roles hack represents a powerful shift from a conversation about the “workforce” and “worker engagement” to one about “productive, creative people doing something meaningful . . . as members of a working community.” Read more here.


Alanna Krause goes further still to drive a stake through the heart of top-down, formal hierarchy with her story, When Business Met Occupy: Innovating for True Collaborative Decision-Making. It’s a remarkable tale of the creation of a practical and peaceful tool for overturning established ways of leading, governing, and managing—and institutionalizing people power in the process.

That tool, a collaborative decision-making application called Loomio, grew out of a shared need: Krause’s organization, Enspiral, a cooperative of social entrepreneurs based in New Zealand, and the local organizers of the Occupy movement were both struggling with the challenge of wrangling a diverse community to make truly collaborative and effective decisions. The two entities joined forces to develop Loomio, a strikingly intuitive and accessible approach to direct democracy.

Inspired by the Occupy movement’s “General Assembly” approach to engagement, consensus building and conflict resolution, the disarmingly simple online application allows for any individual in a group to start a discussion—whether it’s a family member initiating a conversation about managing a joint property, a team member suggesting a new initiative, or a citizen advocating for an approach to community policing. Then members of that group can post comments, critiques, links, pictures and interact with them as they might on Facebook or Twitter (likes, @mentions, comment threads). Out of the discussion, potential solutions arise and anyone can offer a proposal. Individuals can react with a simple thumbs up, thumbs down (“I think we can do better, but I can live with it.”), abstain, or block (“I have serious concerns.”), along with short, Twitter-like statements about their vote. The result is a very clear, quickly digestible overview of where the group stands, what the main issues are, and the reasoning behind them. Areas of conflict and even failed initial proposals become constructive steps toward a better, shared solution in this transparent, tightly-designed environment.

The beauty of Loomio is that it transcends the tradeoff between efficiency and engagement. And, unlike most conflict-based, majority-rules approaches to group decision-making, it gives a truly diverse mix of perspectives and voices a meaningful role in the conversation, builds a deeply shared understanding of the issue at hand, and generally leads to higher-quality outcomes.

But, as Krause and her colleagues would attest, this approach is bigger than a software tool—it’s about fundamentally rethinking how you mobilize and organize people to productive ends. In very short order, Enspiral eliminated countless hours of meetings and downsized the (already streamlined) core management team from five full-timers to one part-time role. More important, Krause and her colleagues underwent a crash course in effective collaboration and distributed leadership, which they’re happy to share along with the open-source Loomio tool. Today, Loomio has more than 10,000 registered users in over 30 countries, with groups as diverse as the Wellington City Council, the Wikimedia Foundation, entrepreneurial businesses, the Greek Pirate Party, and youth groups around the world among them.

As Ben Knight, one of Loomio’s founders says, “Democracy doesn’t need to be this abstract thing that we only get access to once every four years, managed by a professional class far away. With the right tools, it can be a skill that we practice together every day, in our schools, our workplaces and our communities.” Read more here.


In contrast to the activist approach to expanding freedom at work, Stephen and Raynah Remedios propose a more reflective model in their hackThe Digital TOOT (Time out of Time). The hack addresses the twin challenges of the difficulty of developing a comprehensive and shared understanding of what is going on across an organization (what they call the “Pulse”), and the lack of capability or motivation for reflection (what they call the “Pause”) in the context of relentless short-termism inside organizations and accelerating, disruptive change outside them.

Their solution: a simple, engaging, online tool to create a “view into that layer of organizational life that is so rarely available (and hardly ever as a whole): the landscape of individual feelings, intention, and interpretation.” The Digital Toot (as in “time out of time”) is a simple interface that prompts people to answer a question a few days a month with a single word (e.g. What is your world like? How are you feeling today? One word to describe X Function/Customers/Brand?). This five-second, anonymous exercise yields a rich set of feelings, perspectives, and insights that, when quickly aggregated and presented back in a variety of immediately “readable” views (time-based charts, key-word visualizations, functional perspectives, etc.) offer up a global (and bracingly honest) snapshot of the soft underbelly of the organization.

The “pause” is built into the pulse check—literally a moment to stop, reflect, and record a deep, true feeling. Beyond the obvious mental health benefits, the Digital Toot lays the groundwork for the “five freedoms” (the freedom to connect, to chose, to contribute, to create, and to challenge). Equipped with a total and nuanced view of the organizational mood—and the greater equanimity that grows out of the habit of reflection—individuals and teams have the opportunity to act with more empathy, generosity, agency, and creativity. The even better news: it’s a cheap, quick and dirty experiment that any organization or group could try based on the approach outlined here.


Finally, Stelio Verzera, takes on nothing less than the challenge of “liquefying” the rigid, industrial-era controls and structures that create bottlenecks, silos, disengagement, misalignment, and a host of other organizational pathologies, in his hack, Liquid Organizations: Building the Next Evolutionary Stage of Anti-Fragility. The “liquid organization” grows out of a set of fundamental principles, including: serious transparency, agile, iterative experimentation, co-creation as the fundamental means of engagement, a meritocratic system of decision-making authority and compensation, and “radical waste elimination” (e.g. lengthy and laborious job interviews are replaced with trial runs for candidates).

These principles are brought to life via a platform of tools and processes. While the digital tool set is flexible, the critical four pillars of open-governance are: 1) a common “working board” on which all work in progress is visible, limited, and collectively approved and prioritized; 2) a credits accounting system that converts self- and peer-reported value creation into compensation; 3) a toolbox of decision making approaches—ranging from lazy majority voting to a simple dot-voting tool, to a multi-phase envisioning and selection process; and 4) a reputation tracking system that offers a view of individual activities (both “healthy” behaviors and “pathologies”), the relationships between people, and a broader view of the whole community.

If  this seems like a wholesale transplant of the conventional organizational operating system, it is. But it’s not just an abstract model. Verzera and his colleagues at Cocoon Projects are conducting an ongoing experiment in liquefying their own organization. According the Verzera, the liquid approach has yielded a multiplex of deep benefits, from pushing everybody in the organization to “embrace a proactive trial and error operational attitude” that strengthens meritocracy and turns the organization into a magnet for the best talent, to the amplification of creativity, leadership, and operational skills in a dynamic, control-free work environment, to the overthrow of the idea of an “employee” advancing up the org chart in favor of individuals boosting their impact and mastery in the flow of a liquid organization. It’s the ultimate freedom: determining your own destiny—and playing a meaningful role in determining the destiny of your organization. Read more here.

Congratulations to all of the winners of the Digital Freedom Challenge—everybody wins when we make progress on making all organizations more resilient, innovative, and inspiring.