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How to Ask for a Flexible Schedule

A script for convincing your manager to let you work from home or deviate from traditional work hours

Photo: Thomas Barwick/Getty Images

IIt’s never been easier to get things done outside the confines of a 9-to-5 workday. Video conferencing, Slack, and a slew of productivity and project-management tools help blur the lines between time in the office and time outside of it.

This ability to work wherever, whenever, has obvious downsides, but it also comes in handy when life throws a wrench into a more traditional schedule. You might regularly have to pick up your kid from school at 3 p.m. You might have a chronic medical issue that requires regular appointments. You might need to care for an aging parent, or an ailing pet, or an apartment under bedbug attack, with exterminators set to spray every two weeks. Or you might need to move to a different location, and want to hold on to your job.

Life has a tendency to make demands that compete with work, says Jamie Klein, president and founder of the consulting firm Inspire Human Resources. “Anyone who’s human and an adult has responsibility in addition to work,” she says. “Period.” And then there’s the reality that some people work better outside of a traditional office environment. Whatever the reason, sometimes you need to ask your boss for some flexibility. And while some managers are fine with employees mixing it up, others will need a little convincing. Here’s how to make your case.

Gather data

Before you ask your boss for a schedule change — which, ideally, you should do in a private face-to-face meeting, and not over Slack or email, or on a video call — you want to make sure you’re armed with some cold, hard facts to support your case.

To start, Klein suggests researching whether other employees at your company have been able to take advantage of more creative work hours or remote work. “It’s always hard to be that first person,” she says. “If there is precedent [for someone] senior or junior to your level, that helps. If it’s a peer, it really helps.” Talk to these people about how they made it work, and point to their success in your own conversation, tailoring the salient points to your own situation. (Of course, if any of these people didn’t manage to make it work, you might want to steer clear of citing them as an example, or to point out what makes your situation different.)

You’ll also want to demonstrate that others think of you as a strong worker, particularly if part of your plan involves remote work. “Working from home is not for everyone,” Klein says. “It’s a match for people who are high performers, who are go-getters, the A-team. It’s not a match for low performers.”

Come to the meeting armed with specific examples of your past performance (reviews, emails praising your work) to prove you’re up to the challenge. This also reminds your employer that it’s worth accommodating your schedule, instead of risking losing you.

State your terms up front

Let your boss know exactly what you need, and why, without digging too deep into the emotional details — they don’t need to know the intricacies of your personal life in order to make a decision, and bogging them down with extra information will just distract from the issue at hand. Instead, be straightforward: “Once you get into the room, say, ‘The reason I want to talk to you today is, I need some flexibility and I’d like to talk to you about some ideas I have around how that could look,’” says executive coach Meg Myers Morgan, an assistant professor of public administration at the University of Oklahoma and the author of Everything is Negotiable. “It’s totally okay to state up front, ‘I have an aging parent, I have to pick up my kids,’ etc. You should always be transparent and authentic.”

Provide a concrete plan — or three

The number one thing you don’t want to do is make your boss figure out a solution to your predicament.

“Your leader is thinking, I have 100 things in my inbox that I have to solve this week, and you’ve given me one more problem to solve,” Klein says. “It’s always appreciated when the employee has done the thinking for you.”

Maybe you’ll be offline from 2 p.m. to 3 p.m. in the afternoon for school pickup, but you plan to make up for that lost time with additional evening hours. Or maybe you have a standing therapy appointment on Friday afternoons, so you’ll work a dedicated chunk of time on Sunday evening to bring yourself up to speed for the week ahead.

People like options, and it’s easier to edit a list of options than to draw up a plan from scratch.

Whatever the situation, be specific about your plan — or even better, have a few different plans in mind to offer up, and let your manager choose whichever one fits best with the team’s needs. People like options, Klein says, and it’s easier to edit a list of options than to draw up a plan from scratch.

Anticipate and address your boss’s worries. “The thing that will go through the leader’s mind is, ‘How the heck is the work going to get done when you’re offline? We’re not used to working this way,’” Klein says. “To get in front of that, the employee could say, ‘Here are five concerns I imagine you might have. I’ve given some thought from your perspective. Here’s how I plan to handle these.”

Promise to work hard

This sounds like an obvious one, but it is actually important to reiterate. Despite the growing prevalence of remote work, there’s still a perception that it’s easy to slack off when your boss can’t stop by your desk. It’s also easy to seem like you’re slacking off — if you’re working from home and not responsive right away, your employer might not be able to tell that you’re on a call, or stepped away momentarily to use the restroom.

“When you reach out to [someone working remotely] and they’re not there, you have a visual of them sitting on a couch watching General Hospital and eating bonbons,” Klein says. “You don’t know if they’re on a conference call or heads down on a project.”

“The bulk of your ask should be around how this is going to make you a better worker or make the results better for the team.”

It’s worth mentioning to your boss that there’s plenty of research linking remote work and flexible schedules to increased productivity. “The bulk of your ask should be around how this is going to make you a better worker or make the results better for the team or company,” Morgan says. For example, you could say something like, “I’ve found that I’m at my most productive early in the morning. Starting the day working from home, rather than wasting that time on commuting, would let me take advantage of those hours to get more done.”

It’s also a good idea to be specific about the ways in which your flexible schedule will benefit your boss. It might, for instance, be helpful for your company to have someone on the clock during the hours when the office is empty.

At an old blog job of mine, I offered to sign on early from home and write the first few posts of the day, in exchange for being able to come into the office in the afternoon. This meant my boss had some help getting stories up before the rest of the staff was online, and I was able to get more work done during my more productive early morning hours.

Offer a trial basis and set a date for a check-in

Of course, this isn’t an option if you are moving to a new city, but your boss might be more inclined to grant your request if you offer them a rip-cord option. “Say, ‘Let’s try it for three [or] six months, and if at any point this isn’t working, the deal is done,” Morgan says. “It gives them assurance that you’re going to try really hard. You set up a situation where they know that you’re auditioning for the permanency.”

If you take this approach, Klein says you should set a specific date for a check-in. “It’s helpful for a leader to hear, ‘I’d like to have a check-in with you at X number of weeks/months, and if at that point we’re not meeting expectations, we can talk.”

If your boss agrees to your proposal, don’t count on them remembering all the details. Instead, follow up with an email, outlining everything you discussed and the conclusions. “We think our boss is thinking about us all the time, but they may agree to something and never think about it ever again,” Morgan says. “Getting the plan in writing is a good idea.”

Rebecca Fishbein is a writer in Brooklyn & the author of GOOD THINGS HAPPEN TO PEOPLE YOU HATE, out 10/15. Find her on Twitter at @bfishbfish.

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