What would you do with unlimited vacation? One start-up tried it — and shares what happened

In a New York Times opinion piece, a local founder takes to task the traditional view of set vacation days. But does an “open leave” policy raise problems of its own?

Dharmesh Shah, co-founder and chief technology officer at HubSpot, argues that strict leave policies have a real cost and aim attention at micromanagement rather than innovation.

“Managing, monitoring and enforcing a vacation policy takes time, energy and money,” he wrote. “Right now, a talented engineer somewhere is trying to figure out how she’s going to squeeze her children’s doctor’s appointments into one afternoon or produce an entire day’s work in one morning so that she can leave work early to attend a friend’s wedding.”

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Shah said the policy has paid off big for his employees’ happiness, health, and creativity.

Having worked in some places that seemed to march only to the tune of the timecard to places that did offer open leave, I much preferred the latter — and I was more effective in those places, too.

Just as companies that automatically pare budgets based on previous year’s spending see employees suddenly “find” last minute expenses, those businesses that live by the timecard inevitably find employees find new busywork to keep the hours coming. That means there’s no ground-level support for automation, efficiency, or adaptation.

But one of the counter-points to Shaw’s post, from Levi Felix, is just as true: It’s up to companies, managers, and employees to set clear boundaries and make sure that employees really do take time to unplug — completely — from work, at least occasionally.

“Offering unlimited vacation time without set parameters or intentions for employees and management does nothing but exacerbate ... problems,” Felix wrote. “Create rules and clear boundaries for what it means to be ‘on vacation’ (both for management and for employees). Set expectations and empower team members to support one another in the effort to unplug.”

Neither open leave nor traditional vacation days offer a silver bullet: Instead, companies work best when they work with their employees to ensure that time off really is time off, while still acknowledging that the power of (almost ubiquitous) connectivity means we can be more flexible than ever before with how, when, and where we get things done.

What do you think? What’s the best arrangement of setting up vacation so it works for both employees and employers? Let me know at Hive@Boston.com, or onTwitter and Facebook.