Ask an Expert: How Can I Ask My Boss for Flexibility at Work?

Woman working from home


Carmen Dahlberg
Carmen Dahlberg33
Founder of Belle Detroit Creative Solutions
Whether you are transitioning to a caregiving role or are a childless worker looking to manage burnout with a schedule that better fits your needs, flexibility at work is the hallmark of a conscious workplace and can lead to more engagement.

What if your boss doesn’t know this? You can help her see the benefits of a flexible schedule without having to hide out under your desk when the conversation is over. Below, read four tips for making your case for flexibility — without the awkwardness. 

1. Make a business case for flexibility.

Your boss might be concerned about flexibility’s potential to become a company time-thief, but you can assuage her fears by showing the benefits the practice can offer your workplace as a whole. Remind her that flexibility in your schedule will allow you to become more productive because it will require you to take more ownership over your projects and shifting your mindset to be more results-oriented rather than focus purely on the hours you work. In other words, it will help you work smarter, not harder. It will also push you to hone your communication skills and help you handle a greater degree of autonomy in your work, all of which are crucial to develop if you plan to pursue future leadership opportunities at your company. Your workplace, meanwhile, will benefit from this investment: it doubles as skill development and a retention strategy. If your boss wants to see the numbers, the statistics are in your favor: 67% of businesses offer flexible scheduling and employees who work from home are 87% more likely to love their job.

 2. Speak to the ways flexible scheduling will augment your specific strengths.

Consider the ways that flexible scheduling will encourage the development of strengths unique to you. Are you a natural connector? Explain how flexible scheduling will challenge you to find more and better ways to communicate with your team. Do you introduce new technologies to your office? Demonstrate how remote software can make your company more effective. Finding ways to align your talents to aspects of flexible work can help shift your boss from general concerns about flexible scheduling to an understanding of why you are the right person to ask for it.

3. Anticipate the counterarguments. 

Doing your research on the benefits of flexible work is important, but equally crucial is anticipating the different directions your conversation can take. Approach the meeting as a dialogue — not a place to air grievances or list demands — and think ahead of time of the reasons your boss might hesitate to allow more flexibility. For example, if your boss worries that she might feel pressured to offer flexible work to everyone, including team members who could potentially abuse it, respond by speaking to her strengths, such as, “Actually, one of the things I respect about your management is your ability to identify individual team members’ strengths and guide us accordingly.” If versatility is actually a weakness, consider her other skills or values that honestly align with a vision for flexible scheduling. 

 4. Have a plan – and suggest a trial run.

Before you meet, create a plan that demonstrates your ability to handle the responsibility of flexible work. The plan should show specific ways you will communicate with colleagues while offsite or on a different shift. Additionally, consider offering to start with a 30-day trial period. Working together throughout the trial period will help give your boss more ownership while easing her into a more indefinite commitment. The temporary season can help you identify blind spots and may even allow the two of you to build out a flexible policy for future employees.

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As the founder of Belle Detroit Creative Solutions, Carmen Dahlberg advances opportunities for working mothers by creating accessible, flexible jobs in the design ecosystem and promoting a culture of caregiving across American workplaces.