There’s a lot of talk about flexible schedules these days—working from home one day a week (or always!); working four-day weeks instead of five; or shifting the traditional 9-to-5 to something that works around your family, hobbies, or preferred working schedule, just to name a few.

But while you’ve probably heard of these options, you may have pushed them aside, thinking that a flexible work schedule “just wouldn’t work” for your job or company.

Well, I’m here to tell you that, in many cases, it can. And it can definitely make a huge difference in your life: Yes, it can improve your sleep, relationships, and hobbies, but it can also help you maintain your health and vigor on the job.

While it probably wouldn’t have worked in some of my previous jobs, like when I worked in investment banking or when I was on the buy-side, I recently took a corporate job, where it did. Here’s what I learned through the process of asking for more flexibility and a change to my schedule—and how you can do it, too.


1. Prioritize Your Most Important Needs

As you think about what type of flexible schedule will work best for you, ask yourself: What are the two most important needs in your life outside of your day job? What are the schedule adjustments that would most dramatically affect your stress level and happiness? Is it making time for your daily workout class, or is it needing to make calls during normal business hours for that startup idea you’re trying to get off the ground? Having two schedule changes to propose is often helpful because it allows room for a potential compromise to get at least one.

For me, I wanted to work from home on Fridays so that I could have less distraction from impromptu office meetings and friendly interruptions, thus leading to less of a to-do list over the weekend. Plus, I could get laundry and other tasks done while on conference calls, again leaving more time for purely my interests over the weekend. I also wanted to start my workday later than my boss, who has a long commute and gets into the office before 6 AM in order to leave in time to pick up her kids from school.

From there, you can strategize how your work schedule might be adjusted to meet these needs. If you are running a nonprofit on the side and need to be at some weekday events, say, maybe you can designate specific hours of being logged into your work later in the evening or on an off day to tie up your responsibilities. Or if you need to make a morning swim session to prepare for the triathlon you’ve been training for, instead designate a period of time before heading off to the gym, or an hour before bed, to pre-address anything going on in the morning while you’re away.

Of course, your schedule and preferences aren’t all you’ll have to think about, which brings me to…


2. Understand What an Appropriate Ask Can Be

Every workplace has a culture that allows for different types of flexibility. There will be some aspects that you will not be able to change, and that’s important to understand before you go any further.

First, read your employee handbook to see if there are major ground rules that you need to observe. At my job, for example, it’s acceptable to get a workout in during the day as long as you’re finishing your workload on time and not leaving during critical work periods. But if you’re on market hours, you probably won’t be able to leave during the middle of trading.

It’s also worth asking a couple veteran employees how they manage other priorities and view the company’s perception on non-work related activities and to pay attention to what others on your team are doing. If you have a group that runs at lunch, it’ll be easier to join them than to ask to leave early to go to the gym. Or if you have a group that leaves to make their children’s sports, you may be able to adapt your needs to coincide with their time away.

As part of this, think about what the culture of your team and the needs of your co-workers are, too. In my case, I built a relationship with my manager by caring about what her kids did and letting her know how important it was to me to have my parents there when I was young. Relating to her situation allowed her to relate to mine when I honestly told her that I was struggling to get enough sleep due to our early mornings, and I felt like it was making me far less productive for the first few hours of the day.


3. Set Up a Time to Talk

Once you’ve determined what an ideal—and workable—flex schedule might be, put a time on the calendar for you and your boss to discuss your needs. Offer to take him or her to lunch or coffee to get outside of the walls of your office and to be away from the disruption of incoming email pings and ringing phones.

I chose to have this discussion at my one-year review, as I felt that I had proven my value to the firm and run on its schedule for a year, building trust in my abilities and dedication to our work. The timing may look different for you, but it should be when you feel comfortable that you have had time to understand and assess your situation and go through a few runs of your main job responsibilities—say, two or three monthly cycles of publishing a magazine, or a couple quarters of preparing financial documents. This way you can feel out what “normal” is. And, of course, timing this conversation after producing some great work product is ideal to back up your value proposition.

When you sit down to discuss your needs, detail how your flexible work schedule will benefit your boss—will the flexible schedule allow you to take on additional responsibilities if you’re working instead of commuting a couple of days a week? Will it make you a more attentive project manager if you can clear your head in the middle of the day on a run? After all, the best way to get more flexibility is to prove that this schedule will actually make you more productive at work. (If you think your boss will be skeptical or want more information, bring some research that reinforces your point, like this.)


4. Ask to Do a Trial Period

One of the best ways to get your boss on board is to suggest a trial period—anywhere from a week to a few months—after which you and your manager can decide whether it will work.

Then, show that it will work! During this period, work harder than you would have otherwise, and don’t even attend the events you want the flexibility for. Use the time to take initiative on a new project, get ahead on your timelines, and check in more than usual. Importantly, keep track of your work—whether it’s the number of sales calls you made or the detail you added to a financial model, having tangible results that are stronger than your previous stats will be critical to showing that you can handle the flexibility and that it will in turn improve your work product. If you’re far more productive during your trial period, your boss will have a much harder time telling you no.


5. Maintain Open Communication

Once your boss agrees to your new schedule, don’t drop the ball. Being on a more flexible schedule probably means that you should check in and be in closer communication than you would otherwise to make sure your boss can trust you until it becomes the accepted “new normal.” Plan a checkin for a month after you start the new schedule to show your boss that you are committed and loyal to your word—not just asking for more free time—and be sure to ask for feedback on anything about your situation that might work better.



To be fair, my current boss was amazingly receptive to this process, and not all managers will be. But if you’re told no, be willing to compromise on what you want to begin with, or realize that you’ve laid the groundwork for another ask in the future.

Lastly, remember that being flexible means being adaptable. There will be times when you’ll have to alter your great new schedule, whether it’s a busy season or when a fire drill pops up. Keep a good attitude and be willing to take on these challenges, and you’ll find that it will drive even more flexibility for you down the road.

What’s my next ask? Working remotely in Italy for a month.


Photo of working from home courtesy of Shutterstock.