“Think about what constitutes performance in [your] job,” he says. In some fields and industries, like marketing or financial consulting, performance is typically tied to a specific project rather than the number of hours an employee spends on the clock. Many freelancers do this by charging flat fees: The amount of time they spend on a project doesn’t matter, so long as they get it done.
In those cases, Friedman says, you might be able to arrange for a four-day workweek or flexible hours. “If the job is amenable, it has nothing to do with time, it’s not client-facing, you don’t have meetings—then absolutely, you should go and ask for it,” he says. “But you’ve got to have a plan.”
4. Start with a discussion—not a negotiation
After all your reflection and research, it may be tempting to rush into your boss’s office and lay out your terms. Kaila-Gambhir advises against that—at least initially. Instead, she says, talk to your boss about the possibility of working less. That way, “you’re not committing to anything. You’re not giving them what your optimal, ideal scenario is just yet,” she says. “You just want to have a discussion—to explore options and see what may be possible.”
This phase isn’t just about gathering more information for your proposal. It also lets your boss see that you understand their position as an employer, one who needs to consider their own business needs alongside your request. Then you can book a follow-up conversation to ensure you keep the conversation going, Kaila-Gambhir says.
If your boss isn’t open to the idea of a hard-and-fast change to your work schedule, this is also a good time to suggest a trial run of your proposal. A conversation, rather than an ultimatum-driven negotiation, can feel less intimidating for an employer.
5. Be prepared to walk away
While it’s tempting to imagine that absolutely everything about a job is negotiable, that isn’t always true. For instance, it would be very difficult for an intensive care unit nurse to convince an employer to allow remote work. Same goes for the manager of a community centre or a barista.
In fact, most Canadian jobs have never been worked remotely. In April 2020, at the height of the first wave of COVID-19, it felt like everyone was at home. But the Statistics Canada Labour Force Survey reported that 40% of Canadian workers were mostly clocking in from home. As of last November, it dropped to 20%.
To Friedman, asking for flexibility when your job cannot easily be done through alternate arrangements is a bad strategy. It won’t convince employers, he says, and might come off as entitled. If all else fails, finding a new job that will accommodate your desire to work less might be the best option. Some job postings include information on working from home, flexible hours, part-time status, etc.
“Do you want a flexible job? Then maybe you ought to apply for another position that has more flexibility,” he says. “I’m not telling you that’s right or wrong—I’m just saying that’s what an employer will say.”
Understand what you’re up against
You may have to accept the reality: a request to work remotely or outside of office hours may not be a possibility in your current job, or your boss may not see your working less as good for their bottom line.
But in his experience in coaching executives, Friedman says many are open to changing the ways their employees work. Negotiating a four-day week, a flexible work arrangement, or the ability to disconnect from email at the end of the day is totally possible, so long as you do your homework and know how to ask.
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