Are you afraid to ask for flexible work arrangements to deal with family issues? Or, do you think your employees aren’t forthcoming about their work-life needs; and if they are do you worry requests for alternative work schedules could impact the bottom line?

Discussions about using flexibility in order to make work “work” better for employees and employers can be difficult and that’s why some people try to avoid them. But what if you were forced to sit down and talk?

One politician in San Francisco – David Chiu, the city’s Board of Supervisors’ President — decided employees and employers needed a “nudge,” so he introduced an ordinance to mandate such conversation, an ordinance that recently passed and goes into effect on Jan. 1, 2014. And the new edict is being closely watched by municipalities, and by employers, beyond the City by the Bay.

“This is starting a discourse,” said Enzo Der Boghossian, a partner at employment law firm Proskauer’s California office. “This is going to be a great exercise, a social experiment.”

Indeed, other towns are considering getting in on the experiment. “We have heard from administrations of mayors in other major cities about doing the same thing in their cities,” Catherine Rauschuber, Chiu’s legislative aide, told me last week. She declined to disclose which cities have reached out.

San Francisco is the first city to pass such an ordinance. Vermont passed a similar law earlier this year that also kicks in the first of the year; a law Rauschuber said the city’s ordinance was partly based on. The legislative team, she added, also used as a framework the late Ted Kennedy’s Working Families Flexibility Act, which would have ensured employees’ right to request flexible work arrangements.

Comparable federal legislation was introduced by ‘congresswoman Carolyn Maloney (D-NY-14) in 2009, and was most recently referred to subcommittee last year.

Der Boghossian doesn’t expect movement toward passing such a law on the federal level any time soon, but he believes many city governments will be watching San Francisco to see how the ordinance plays out and follow suit if things go well.

In order to enforce the law, he explained, “It’s going to take a lot of manpower.” And with so many local governments strapped for resources, he’s doubtful any city will be able to enforce such an edict effectively.

He does, however, expect the ordinance to trigger many requests by employees.

“Are employees going to feel comfortable, improve morale and increase productivity, or will it create a negative situation for employers because so many employees are asking for so many accommodations, and they lose the ability to standardize their workforce and work schedule,” he asked. “It’s a very progressive piece of law making. And it will be interesting to see in implementation if this actually works out.”

Clearly, the ordinance will have some growing pains, and city officials expect as much.

In industries where there’s a lot of shift work, including manufacturing, retail and the restaurant industry, Rauschuber said, it will be more challenging to get a “yes” answer when it comes to flexible work requests. To help find solutions, she added, Chiu put together a “scheduling predictability taskforce” to work on the issue, including employee advocates and employers.

The city also worked early on with the business community, including the Chamber of Commerce, to find out their concerns, and modified the ordinance as a result before it was presented.

One of the big concerns from businesses was a provision in the law allowing the Labor Standards Office to review business decisions for denying workflex. “They didn’t want the city questions business decisions,” Rauschuber said, and subsequently that provision was taken out of the ordinance.

What did stay was a ban on retaliating against someone who requests a flexible work arrangement, she pointed out. “We heard from worker advocates that those types of conversations weren’t happening,” she said, adding that some employees were fearful that it could lead to a negative impact on their jobs.

“Our workplaces haven’t caught up with our changing society. Our society hasn’t caught up with changing families,” she said. So, the ordinance, she maintained, “nudges companies in the direction of work flexibility.”

In the end, an us-against-them mentality won’t be productive, whether it’s a nudge or a big stick approach, stressed Ellen Galinsky, president of Families and Work Institute. “The point is it shouldn’t be a we/they,” she continued. “It’s shouldn’t be just a nudge to get flexible work, it should be a nudge to get solutions that work for both employers and employees.”

For more information about San Francisco’s ordinance, check out this fact sheet.

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