The five digital freedoms – the freedom to connect, contribute, create, challenge, and choose – portend change for all organizations regardless of industry or geography. There is no stopping people from expecting the same opportunities in their work life as they experience in the personal lives. These freedoms are in direct opposition of many currently-accepted management practices and will usher in a more humanized approach for getting work done—whether we like it or not.

During the recently concluded Gartner Symposium, my colleagues and I ran two workshops exploring how the five digital freedoms will change how organizations work. CIOs and their teams chose one of the five freedoms and examined its positive and negative consequences. They crafted an action plan to take back home and implement so they could capitalize on the selected digital freedom without losing control. With every freedom comes the responsibility to use it wisely.

Remarkably, most of the teams zeroed in on the freedom to choose. They wrestled with the issue of how they could create more choice in employees’ work lives and still meet commitments. In many ways, this is the most basic freedom of all—and yet, it seems in short supply in the workplace. I’ll bet if I did a post-workshop follow-up interview I’d learn that people feel constrained, told what to do more often than they’d like, and seldom consulted during decision making.

If we genuinely believe that these freedoms will define the best workplaces going forward, all leaders must examine their mindset and behaviors to understand where they are constraining these freedoms—and what they can do to unleash more openness, more participation, and more choice in their organizations. We must ask the questions: “What will encourage more employees to reach out to each other when they have a problem (freedom to connect)? What can leaders do to demonstrate to employees that it’s okay to speak up, to offer an insight, to make a contribution—even when it’s not in their job description? How can we design more opportunities for collaboration—and even invite in a little dissent?”

Here’s my pick for a powerful first step toward building more freedom into your organization: advocate and support the freedom to iterate.

Iteration is built on the premise that we won’t get it right the first time, but we’ll learn from our experience and do better next time. The practice acknowledges that progress requires risk taking, a dose of courage, some calculated bets, and the understanding that you’re more likely to sidle toward an answer rather than marching toward a goal in a straight line.

The organizations that are respected as serial innovators – those that establish an innovation competency rather than just looking for the “big win” – cite the freedom to “fail” as a key factor in their success. And most often they put the word “fail” in quotes because they know it takes many tries to get the results they want. They don’t believe that the successive tries were failures so much as opportunities to learn.

So leaders, look for situations when you can encourage those working with you to “give it a go” and see what happens. Just as important: model this behavior yourself. Look for opportunities for teams to make decisions. This is different from delegating decision making while retaining veto power; it is stepping out of the leader role and letting others take charge. The socially centered leader knows that sometimes it is better to lead from the back.

Are you experimenting with any of the five freedoms? What’s your idea for building the freedom to choose, to contribute, to create, to challenge, and to connect into our organizations? Share your stories and ideas in the Digital Freedom Challenge over at the MIX.

Carol Rozwell is vice president and distinguished analyst at Gartner, and the architect of the Digital Freedom Challenge.