Bumping into Roadblocks While Accessing Benefits for a Leave from Work?

3 Advocacy Tips from 2 Employment Attorneys

Is taking a leave from work ever seamless? Hopefully the need for your leave is positive – but even a low-key pregnancy “with no complications” has at least some layers of unpredictable timing and mental gymnastics when giving notice to a manager or HR. And then there’s deciding when to share your plans with colleagues or clients and the awkward dance of knowing when to transition projects off of your plate – to avoid an early exit impacting a project or your reputation – but also not appear like you’re checking out too early.

Whether it’s needing a medical leave for an injury, taking time to care for a relative, or using parental leave, the very nature of planning a leave from work has a lot of decisions that come along with it.

That’s why questions around accessing benefits during this time should be expected. And yet…even as attorneys and women in our mid-30’s (who had watched many coworkers, friends and family members go on parental leave), we naively assumed that our offices’ human resources professionals would hold our hands and walk us through the process of taking parental leave. 

To be clear – this was not our approach to life in general. We’re natural problem solvers and chose a professional path of advocacy because we believe in using our voice to add value in tough situations. But parenthood felt like a milestone that so many people went through… so surely it would be simple. There had to be a process set up. We’d just follow the path? Right?

If you’re reading this and nodding because that was your actual experience - well, that makes our hearts sing with relief.

If your experience was more confusing than straightforward, you’re not alone! For most of our clients, accessing employment and/or state-provided benefits and getting answers to related questions takes a lot of time and mental energy to sort through. (Our firm works with businesses and individuals in Massachusetts, often advising on challenges that arise when healthcare situations and employment terms are impacted at the same time.)

Here are 3 tips to consider if you’re running into problems while accessing benefits (whether these are benefits administered through personal insurance policies or benefits offered through your job, or through state-administered programs like the Massachusetts Paid Family and Medical Leave program).

  1. Review the policies (or programs) relevant to YOUR situation. This means requesting copies of the policies and reading them (or having someone you trust read them in detail and summarize them for you). Oftentimes employees receive a “summary of benefits” or a quick snapshot of an employer’s offerings (intended to make things easier to understand at a high level). But if you have questions about the specifics, or things don’t seem to be working the way you understood them – it’s on you to ask. And if the response includes a document that again doesn’t address your question, and your instinct is that there’s more behind the answer – ask again, in writing. 

    The interplay of benefits across different categories of policies (for example, accessing a short-term disability policy for certain weeks of your leave and then utilizing a state-benefit program for other weeks of leave) can get confusing, for anyone. Our informational tip is to review each of your  policies, calculate out your expected financial benefit by week, and get someone from each benefit provider/policy to confirm your understanding before taking leave. 

  2. Review the amount of weekly/monthly benefits you receive during leave to confirm these are consistent with your expectations. We understand that this topic might not be on the top of your list. The decision to take a leave from work assumes that something important in your family or personal life is requiring a lot of your attention. That said, schedule reminders to check what financial benefits you received and/or tap in a family member to help verify that the actual benefit checks/deposits are consistent with your expectations. 

  3. Follow-up for answers to your questions until they make sense to YOU. We frequently work with clients who are told one thing from an employer and another from a third party benefits administrator or insurance provider and then get stuck in a loop back and forth trying to get a straight answer and explain WHY they are taking a certain position on an issue regarding a benefits and/or insurance policy. It is not uncommon for confusion around the practical application of these policies - and per the suggestion above, if the answer isn’t consistent – then what does the actual written policy say? And if you can, consider adding another layer of review, like requesting to involve another colleague or manager in the discussion.

We are cheering you on as you track down the answers to your questions and take charge in accessing the benefits that apply to your situation. We always say that we hope you don’t need our consulting services – but we’re here if you do!


We’ll continue to share practical tips about advocacy for employers and individuals in Massachusetts. If you’re interested in our educational content, sign up for our newsletter here.

Please note: The information reflected on this website or blog is not, nor is it intended to be, legal advice. Use of this website or blog does not create an attorney-client relationship between the user and Scully & O’Leary LLC. 

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Bundle of Joy, Bundle of Benefits: Remember to Review Your Insurance Benefits Before Baby Arrives