Planning for parental leave is a crucial step in ensuring a smooth transition—for everyone. Yes, this includes you. You might have a million questions or you might be drawing a blank. Whatever the case, here are the maternity leave questions to ask (and why!)
Download the 40 Questions Printable Guide
Now that you’ve shared the news that you’re pregnant, it’s time to get to work.
Proper preparation helps minimize disruptions, maintain productivity, and ease your reintegration into the workplace after your leave. Asking (and, in some circumstances, answering) certain questions also helps you to proactively problem solve, forecast, and really envision what your leave will look like—for you and for your colleagues.
By asking the right questions, you can set clear expectations, delegate responsibilities effectively, and feel confident stepping away to focus on your growing family.
And there’s a very real parenting lesson here, too. Ask questions, make plans to the best of your ability, and ask even more questions. Things will go sideways, but it’s always helpful to plan for whatever may come.
Caileen Holden, a content director for Career Contessa, spent months asking questions, creating a transition plan, and getting everything in line to prepare for her son’s March 2020 arrival.
Spoiler alert: while the plans went mostly awry, the planning process did help provide clarity in those early Covid months.
These questions will help you cover key areas—from discussing expectations with your boss to preparing your colleagues and direct reports.
This is also a great time to reflect on your own needs and career goals. Speaking to others can help you get set up for success both during and after your leave.
Let’s get to the Qs.
Download the 40 Questions Printable Guide
Questions to Ask Your Boss
Your boss is one of the most important people to align with before your leave. If your boss is a parent, their answers (and support) will likely be even more informative and helpful to your planning process.
Clear communication ensures that work continues seamlessly in your absence.
This is also a great time to start setting expectations around availability, responsibilities, and your return-to-work plan are well defined.
Coverage and Expectations
The following questions will be the most formative, so they can be as basic or as nitty-gritty as you need.
This is an opportunity to establish responsibilities for your transition plan, temporary replacements, and urgent matters that arise during leave.
Some companies have strict policies about communication during leave. Before asking these questions, consider reviewing your agreement for clarity. In the case that information isn’t included in your employee handbook or contract, here are some clarifying questions to ask
- To ensure continuity during my upcoming absence, I’d like to start building out a transition plan. May we discuss coverage of my responsibilities? Would you prefer I outline the process with some recommendations, or do you have specific preferences?”
- Why to Ask: Understanding the coverage plan helps ensure continuity and reduces stress for you and your team.
- What to Look for in an Answer: A clear delegation of responsibilities, assigned backups, and contingency plans for unexpected issues.
- What are your expectations for my availability during leave?
- Why to Ask: This question clarifies whether you are expected to respond to emails or attend occasional meetings.
- What to Look for in an Answer: Clear boundaries regarding work contact and agreement on what constitutes an emergency.
- How should we handle urgent matters that only I have knowledge about?
- Why to Ask: Asking this question ensures that critical knowledge is transferred before your departure.
- What to Look for in an Answer: A plan for documentation and identifying a go-to person for urgent matters.
Communication Plan
Take it from a parent who has done this a couple of times. This is not the time to get caught up in over-promising.
At WRK/360, we have a few recommendations about creating a high-level communication plan. Typically, we advise clients to check in about two-thirds of the way into your leave to confirm return dates, ask for any urgent updates, and begin discussing accommodations.
Feel free to throw a reminder on your calendar. If your due date is May 1st and you have 12 weeks of parental leave, set a reminder 8 weeks after your due date.
- How often should we check in during my leave, if at all?
- Why to Ask: Helps set realistic expectations and prevents unnecessary disruptions during your leave.
- What to Look for in an Answer: Agreement on whether check-ins are necessary and at what frequency.
- What’s the preferred method of communication during leave?
- Why to Ask: Defines how and when communication should happen if necessary.
- What to Look for in an Answer: A preferred method such as email, text, or a trusted intermediary.
- Will you or another point of contact inform me of any critical changes or updates during my leave?
- Why to Ask: Asking this question ensures that you remain informed about major changes without being overwhelmed. It also gives you the opportunity to define critical. For example, do you want to know about team or leadership changes? Updates with key clients or stakeholders?
- What to Look for in an Answer: A designated contact person who will summarize key updates for you.
Return Strategy
The return-to-work can be a scary time on many levels. Emotionally, physically, mentally, professionally—it’s a lot.
At WRK/360, we like to think of return-to-work as an opportunity to “re-onboard.” If it works for your life and type of work, asking for a phased return may be ideal. Depending on your office setup and its stance on flexibility and remote work, there might be a way to design a hybrid return, even on a temporary basis.
- Would a phased return be possible?
- Why to Ask: Asking this question helps ease the transition back into work.
- What to Look for in an Answer: Flexibility in return options and openness to a gradual reintegration plan.
- How will my workload be transitioned back to me and managed upon my return?
- Why to Ask: Ask this question to build a manageable workload and prevent overwhelm and burnout upon return.
- What to Look for in an Answer: A structured approach to redistributing tasks and a transition period.
- When should we discuss my return-to-work plan?
- Why to Ask: Asking this question helps set expectations for your reintegration.
- What to Look for in an Answer: A scheduled time before your return to finalize your transition plan.
Administrative Details
The details are important, especially when it comes to your paychecks, bonuses, and any benefits you might be able to access as an expecting or new parent. Make sure to have these conversations with your boss or with human resources.
- What paperwork needs to be completed before leave?
- Why to Ask: Avoid last-minute surprises and ensure compliance with company policies by asking this question
- What to Look for in an Answer: A list of required forms and deadlines.
- How does parental leave affect my benefits, bonuses, commissions or review cycle?
- Why to Ask: Ensures you are financially and professionally prepared by reviewing the policies in place for benefits, bonuses, commissions, and reviews.
- What to Look for in an Answer: Clarity on how leave impacts salary, bonuses, commissions, and performance evaluations. Bonus points for getting this in writing so there is no doubt upon your return to work.
- Are there company resources available to support new parents?
- Why to Ask: Asking this question helps you access useful resources like lactation rooms, back-up child care benefits, parenting workshops, or employee assistance programs.
- What to Look for in an Answer: Information on benefits, programs, and support groups.
Pro Tip: Set up an initial meeting 6-8 weeks prior to your expected leave to discuss these details. A written summary of agreements can help prevent miscommunication.
Utilize WRK/360’s Parental Leave Transition Workbook to help guide the conversation.
Questions to Ask Your Colleagues
Your coworkers will likely absorb some of your responsibilities while you’re away. Preparing them ahead of time fosters collaboration and reduces stress for everyone involved.
Knowledge Transfer
This is the part where you give up the most important keys to the kingdom, the knowledge and access that only you (usually) have.
- Which of my projects will you be covering and need information about?
- Why to Ask: Ensure your teammates have the necessary knowledge to manage ongoing work.
- What to Look for in an Answer: Specific projects or processes that require documentation or handover.
- What documentation would be most helpful for you while I’m away?
- Why to Ask: Use answers to this question as the basis for creating resources that ease the transition for your team.
- What to Look for in an Answer: Requests for process guides, key contacts, or troubleshooting documents.
- When are you available to start taking on a more proactive role in this project/with this client?
- Why to Ask: Understand how overwhelmed or excited your colleague is for taking over your work. This will help determine if you need to revisit coverage with your manager.
- What to Look for in an Answer: Timing is everything. Yes, you have a due date and an anticipated leave start date, but babies have their own timelines! You don’t want to find yourself in labor trying to download your colleague on everything they need to know!
Pro Tip: Make sure that you give access to any software or accounts needed to get the job done. Start the transition early, about 4 weeks prior to your due date to ensure coverage is ready to go.
Collaboration
Before heading out, make sure to inform any collaborators (including freelancers or partners) and make the appropriate introductions.
- How can I best prepare shared projects before my departure?
- Why to Ask: Asking this question can help you to create a smooth project progress while you’re away.
- What to Look for in an Answer: Suggestions for timelines, documentation, or additional training.
Support
Pro Tip: Consider creating a shared document with key information and FAQs to help colleagues reference important details easily.
- What concerns do you have about my absence?
- Why to Ask: Asking this question uncovers potential pain points before they become major issues.
- What to Look for in an Answer: Honest feedback about workload or knowledge gaps.
Questions to Ask Yourself
While it’s easy to focus on logistics and team dynamics, don’t forget to check in with yourself. Ensuring your own needs are met is just as important as preparing your workplace.
Career Considerations
- Is it important to maintain visibility while I’m on leave? If so, how will I maintain that visibility while on leave?
- Why to Ask: Asking this question helps ensure you remain engaged and connected to your workplace in a way that aligns with your goals and priorities.
- What to Look for in an Answer: Opportunities for periodic updates, networking, or continued professional development.
- How involved do I want to be while on leave?
- Why to Ask: Asking this question helps you to gauge what you really want to know, and whether you want (or can have) a clean break from your work during parental leave
- What to Look for in an Answer: There is no right or wrong answer to this one! It is deeply personal and it is okay if you change your mind! The key is to give yourself time to explore how you truly feel about staying connected while on leave.
Personal Preparation
- Have I properly documented all critical information?
- Why to Ask: Asking this question encourages a smooth continuity of work in your absence.
- What to Look for in an Answer: I have created a comprehensive transition plan for colleagues covering key responsibilities.
- What does a successful leave look like to me?
- Why to Ask: Help define your personal and professional goals for leave by envisioning an ideal leave (and return to work!) What does true support look like from your workplace?
- What to Look for in an Answer: Clear expectations for balance and well-being.
Conclusion
Download the 40 Questions Printable Guide
Thorough preparation for parental leave benefits your mental well-being, your team’s productivity, and your organization’s overall stability.
While it’s impossible to anticipate everything, having clear conversations, setting expectations, and staying flexible will help make the transition smoother.
Remember, plans can be adjusted as needed, and keeping an open line of communication ensures that both you and your team are supported throughout the process.