How to Get Your Maternity/Parental Leave Squared Away

Squared Away’s playbook for leveraging your assistant as you prepare for maternity/paternity/parental leave.

Kelsey Opel
4 min readOct 23, 2020

Maternity and parental leave is an exciting time in your life, and it can be chaotic as you prep for a life-changing experience. We’re sharing our playbook for how to leverage an assistant while on maternity or parental leave.

Step 1 — Plan Ahead at Work

Be proactive in outlining what you handle day to day. Identify the items your team will be handling for you, and find what your assistant can take on as reoccurring tasks.

This planning period is a great time to take inventory of the low-risk work-related items you can permanently hand off to your assistant. Planning at work may include:

  • Inbox management: We will work to keep your inbox clean and organized.
  • Calendar management: We will rearrange your schedule as needed to ensure you have ample time with your family and for new parent/new baby appointments. We will ensure your calendar stays clean and move meetings out if you need to extend your parental leave.
  • Monthly reporting: Templates and previous examples are excellent, then do a test run a few times before you are out for your leave period.
  • Social media maintenance: We can keep your social media presence active on both work and personal social media accounts. We recommend informing your assistant of this plan at least a month before your leave date so posts and plans can be prepped.

We can work with other teammates, too.

  • If you won’t have many work tasks for us to handle, have us work with your team members.
  • Working with your teammates keeps our work continuity and ensures we don’t miss a beat when you return!
  • If you handed off your work to other team members while you are out, we are happy to help them.

We can be your “middle man (or woman)”

  • With your assistant being well integrated into your day to day and business work, we can summarize the needs of your team/essential updates from your team, and report back to you on questions that cannot wait to return.
  • From there, you can respond to our summarized list, and your team can continue working effectively while you focus on your family.
  • We will manage your calendar and schedule as needed so you don’t return to a flooded calendar with an overwhelming number of meetings.

Step 2 — Plan Ahead at Home

If you are working with a Chief Executive Assistant, that means we handle it all. These are ways we recommend you leveraging your assistant while on maternity or parental leave:

  • Grocery delivery and prepared meal delivery
  • We can set up and maintaining a cleaning service.
  • Allow us to manage both your work and personal calendar(s). We are happy to also set appointments for you/your partner/your child.
  • Baby gear research (anything from top strollers and car seats to new vehicles).
  • Assistance with planning for any visiting relatives, baby showers/baby sprinkles, sip and sees, etc.

Baby Gear Tips from the Squared Away Team

These are the top items the Squared Away team recommends as you plan for your new family member’s arrival!

*This list is not sponsored nor endorsed by Kelsey Opel or Squared Away, we are sharing baby gear that we genuinely use and enjoy.

Step 3 — We’ve Got Your Six

We strive to be a constant in your life; while your personal life may be in flux, we are here to help you stay on track with your plans and goals.

Set Times to Connect with Your Assistant

We are here to support you. We recommend connecting with your assistant every two days on Slack or a scheduled day each week for a phone call.

  • The regular contact period is a great time to discuss any urgent matters and updates from the company. We will keep a running list of what needs to be handled, discuss it on the 1:1 contact times, and update you as the items are completed.
  • We can help you with your personal life, too. If you need a cleaning service setup, meals delivered, sending flowers or gifts to social contacts, find you need a sleep consultant, or need to schedule self-care.
  • Once you’re ready to return to work in a limited or more involved capacity, we can work with you on a work from home schedule that we will aim to support your new parenthood life along with your work life.

We want this to be a special and memorable time for you and your family. We are here to support you and help you keep your life organized while taking care of your new family member.

If you’re ready to get Squared Away, visit us at GoSquaredAway.com or grab some time for a call.

Drop by our social media and say hi👋 Instagram, Twitter & Facebook.

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Kelsey Opel

Startup Operator // Snowboarder // Taco connoisseur. Follow along for my journey in operations and lessons learned in this territory.