Run a pilot

Introducing a new schedule as a three- or six-month trial gives you an out if reality proves your staff--or you--can't stomach it. "If you have to roll back a flexible schedule that employees think is set, retention can take a real hit," says the Society for Human Resource Management's Lisa Horn.

Protect time off

Education technology startup Treehouse allows its 85 employees to set their own hours and work from wherever they want. But making sure people aren't stuck fielding emails on their private time requires planning. Employees are expected to upload files that might be needed and share updates so their colleagues can act in their absence. "Everyone has to think about being a good team player," says founder Ryan Carson.

Break rules, occasionally

When Basecamp's Jason Fried first rolled out the 32-hour workweek, employees enjoyed the reduced hours year round. But after two years, the delight began to fade. "I think it's more appreciated and more special when it comes and goes," he says. Now the shortened weeks are a seasonal treat, allowing employees to squeeze in extra outdoor time during Chicago summers and then burrow into longer weeks during the winter.

Timing is everything

Within a year of starting her Austin-based tech company, SchooLinks, Katie Fang decided to implement a four-day workweek. She thought the longer weekends would recharge her five-person team, but, she concedes, "it failed so badly." As the founder and CEO of a new startup, Fang didn't have the time and manpower to manage the communication kinks that came with the transition. When SchooLinks geared up for launch, trying to squeeze a massive amount of work into four days ended up making a stressful period even more onerous. "Maybe when we're more established, we can embrace a shorter week again," she says.