Back to School: 3 Critical Employee Leave Considerations and Tips

For many businesses and organizations, fall and winter are “busy seasons.” The lull of summer is gone, and demands pick up. For employees with children, autumn also means the return of school and many scheduling obligations (along with the increased spread of germs). Employees without children can also face an uptick in personal issues in fall and winter, given increased illness and family obligations. 

Excused time off from work, therefore, is an essential component of every workplace. Nonetheless, there is no nationwide requirement for paid time off. There are, however, several statewide requirements that require paid time off for personal and family-related illness. Locally, Maryland’s Family Medical Leave Act (deductions start January 2027 with leave use effective January 2028), D.C. Universal Paid Leave (currently effective), and Virginia’s new Paid Sick Leave and Paid Family Leave Acts (deductions starting in December 2027 with leave available for certain employers in 2028) all require that employers with teams of all sizes provide paid time off for illness.

How do employers reconcile the need to provide employees with time off and productivity needs? I recommend that employers consider the following tips:

  1. Identify the legal requirements for leave and what your organization would like to offer in addition. 

    A good starting point for any policy is identifying what is legally required for a particular workplace. Legal requirements typically stem from where a team member works – and the number of total employees that the employer has. The federal Family and Medical Leave Act (FMLA) requires up to 12 weeks of unpaid leave for qualifying events for teams with 50 or more employees. Employers with only one employee in DC (and soon to be Maryland and Virginia) will need to provide up to 12 weeks of paid leave. These requirements relate only to employee and family illness, with payout stemming from the localities. Employers should therefore consider how much leave they can offer for personal (but not illness-related) reasons. 

  2. Identify a reasonable way to implement a policy and communicate any updates. 

    Policies work for the entire team if they are reasonably implemented and regularly communicated. Each component of a policy should align with legal requirements (i.e., 30 days’ notice for MD and VA PFML when the request for leave is foreseeable, such as with childbirth or a scheduled surgery, or the need to track the number of days used). Moreover, communicating a policy or its updates eliminates ambiguity.  

  3. Attempt to be flexible while clarifying how unapproved leave is treated.

    Both Virginia PFML and Paid Sick Leave implementation details are forthcoming. Therefore, employers will need to be flexible in clarifying or updating policies moving forward. Similarly, employers should plan to be flexible in addressing employees’ unforeseen (or last-minute) leave requests – while balancing legal and operational requirements. For example, employers can make clear that requests of all types can be denied while also clarifying when leave without pay might be permissive. 


Theodora Stringham focuses her practice on bringing solutions-oriented representation and zealous advocacy to complex issues impacting individuals, organizations, and businesses. Ms. Stringham seeks to understand clients’ concerns and provide thorough and strategic options aimed at achieving their goals. She has been recognized for her work in the Real Estate, Labor and Employment, and Commercial Litigation practice areas, providing counseling and litigation support for a wide variety of concerns.

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