Freedom: There’s a difference between having it and knowing what to do with it.

In the workplace, giving employees the room to reach their objectives in the ways they see fit can be a solid leadership move — if done right.

But as challenging as it can be to define what exactly freedom means, it can be equally challenging, and weirdly paradoxical, to define its boundaries.

Freedom in the workplace can be the ability to keep non-traditional hours, work from home, take unlimited vacation days, exercise creativity in how to approach immediate job goals, or otherwise.

As far as why companies both large and small are considering or embracing employee autonomy, the reasons run the gamut.

Charlie Harary, partner at venture capital firm H3 & Company and a business professor at the Syms School of Business at Yeshiva University said some have taken cues from successful companies like Google, whose reputation for innovation has been linked with less conventional work environments.

He also talked about the ever growing millennial workforce — the way Baby Boomers and Generation X view what work is, is different than millennials.

“Because of their life experiences, these Millennials have very high expectations for learning, development, transparency and flexibility on the job. Providing them with the freedom to manage much of their own work and to determine when and where they do that work is fundamental to their satisfaction,” said Donna Wells, CEO of Mindflash.

Another force is more advanced technology that makes something like telecommuting a more viable option. Being open to hiring telecommuting employees can open up a talent pool previously limited by geography, a well as reduce costs associated with having employees on site. Plus, tools like Skype (and other free video calling apps) now exist and make being away from the office more manageable.

What it takes on the part of managers is the willingness to let go somewhat and adjust the metrics they use to determine if work is getting done, Harary said. The question is not whether a boss can see an employee sitting at a desk for eight hours, but whether the employee is producing the work they’re supposed to and meeting expectations.

For Wells, many of her employees work remotely or have schedules specific to their needs. One developer spent a month in Mexico with his wife’s family after having a baby.

“Honestly, since he usually works from Seattle, many HQ employees didn’t even know where he was that month, which, in my opinion, is a great measure of the success of this experience,” she said.

Beyond punching in and out, there’s the idea of allowing employees the control how how they do their jobs. Dane Atkinson, CEO of supports the idea of getting out of the way, as a manager. His longtime mentor, David McBride, had a theory called the Gandalf management theory (think The Lord of the Rings) which essentially said to put together a diverse team — not everyone can be a warrior — and help them figure out what they’re good at, and then don’t interfere. Just as Gandalf disappears a few times during the story, “trust [employees] to take whole legs of the journey on their own,” Atkinson said.

When managers talk about freedom, part of the hope is that the yield is positive. Mark Thompson, author and senior executive coach, said that in interviewing people from Fortune 500 companies, Inc 500 businesses, and even Warren Buffett, he lighted on what he calls the 2×3 rule.

Managers want:

1. Innovation – “Creativity by its nature requires that they have the freedom to experiment a bit.”

2. Reciprocity – “You’ve got to feel that you can make some choices on the job so that you ‘own’ it as your responsibility. It’s the only way to be fully emotionally committed. And if you give people some freedom, they’ll reciprocate by supporting their co-workers more too.”

3. Loyalty – “If you want people to stay after all the training you’ve invested in them, then you’ve got to reward them with some freedom.”

But to give some shape to this nebulous idea of freedom, managers should make sure that it’s exercised in three ways, Thompson said:

1. Purpose – “Your team has to be clear about what customers want from your company’s products or services — use your freedom to understand how your customers want freedom too.”

2. Passion – “What is it about the job that gets that employee up in the morning? What flips their switch? If you don’t have an answer for that, then the freedom you give is pointless.”

3. Performance – “Give your people freedom to find creative ways to meet your objectives — they’ll come up with ideas you’ve never imagined — without doing at the expense of all their co-workers’ lives. But make sure the performance metrics are objective and obvious so you can all celebrate the win.”

Both Wells and Harary emphasized that with the decision to give employees more freedom, comes the need to view the manager as being the the responsible party for employee engagement.

“It’s the responsibility of the manager to create an environment where employees can thrive,” Harary said.

Communication, Wells said, is key. “Both may have to learn new skills to successfully perform or manage non-traditional work schedules and locations without the crutches of a 9-to-5 appearance at the head office. In my experience, communication between manager and employee in the first two months is the difference between success and failure.”

Another deciding factor, Atkinson said is whether managers are fully giving freedom or instead giving “just enough rope” for employees to hang themselves as they get caught between making certain choices and not others. It’s important to go all in.

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