This is part two in a two-part series on parental leave and return to work. If you’re planning a parental leave, or gearing up to return from one, this conversation is for you.
Prefer Spotify? Listen to the episode on Spotify here.
Most of us spend countless hours preparing for the arrival of a child - from birth or adoption plans to getting the home ready. But far fewer of us plan for how we’ll return to work, and how we’ll adjust to working life with a new child at home.
Today’s episode features two of the foremost experts on parental leave, to help anyone navigating this time:
Allison Whalen is the founder and CEO of Parentaly, which prepares employees for leave and supports their return. She built Parentaly after living through her own difficult return to work.
Erin Grau is co-founder of Charter, a future-of-work media company, and previously led the effort to overhaul the parental leave policy at The New York Times after having her first daughter.
Both have spent years talking to parents about what actually helps, what doesn’t, and pioneering new approaches to parental leave. If you’re in the middle of this transition yourself, or supporting someone on your team, here’s what they say you should know.
The Fear Is Normal, Even When Everything Else Goes Right
Allison had a healthy first pregnancy, a job she loved, and none of the medical complications she’d braced for. What caught her off guard was a different kind of fear entirely, one about her career.
"How can I step away for months and not have everything I've poured my
heart and soul into in my career just crumble at my feet?"
Most women who go through leave, especially the first time, express a fear about what will happen when they are away. A lot can change at companies during time away - and while this is normal, it also can feel scary when it is outside of our control.
When Allison asked colleagues and peers about her own fears, she found she wasn’t alone. Business school peers described a similar version of parental leave over and over, summarizing it as:
“I loved every second of my leave, wish I would have had more time, but I had to pay for it in terms of what happened to my career and to my team.”
This experience inspired Allison to start Parentaly, and to focus on creating real solutions for those returning. If you’re feeling this same fear right now, it’s worth knowing that most people who eventually leave a job after parental leave aren’t leaving the workforce. Of new parents who leave their company after returning from leave, only 4% do so to exit the workforce entirely. The rest move to a different job.
Both knowing the fear is normal - and knowing that even if you move on from your company, it’s usually for another work chapter - is helpful for anyone going through early parenting years. If you’re worried a leave will end your career: for most people, it doesn’t. More often, a specific employer doesn't work out, or the leave becomes a springboard to the next chapter.
You’re Allowed to Ask for the Policy You Want
Erin’s parental leave advocacy started in a cafeteria at The New York Times, comparing notes with other new mothers about what leave could look like. They wanted to advocate for something better and treated it like a real project: they gathered data, surveyed employees, and built a formal proposal for the CEO and COO.
Importantly, the policy they created applied the same way to every new parent, regardless of how they became one.
“Whether you became a parent by birth or adoption, whether you personally gave birth or your partner gave birth, you all got the same leave.”
This created an environment where leave was not just supported, but encouraged, for all parents. As a result of Erin and her colleagues’ effective business case, they improved both the duration and terms of parental leave for all employees and helped inspire change in countless other organizations.
If your company’s policy feels unequal or incomplete, Erin’s experience is proof that a well-documented case, built with real data and real stories, can change it. She and her colleagues also open-sourced everything they built, so other employees could use it too.
Going on Leave Looks Different for Everyone - and You Don’t Have to Disappear Completely
One thing Allison has learned from working with thousands of parents: full disconnection isn’t automatically the kindest option, and it’s not required. What matters more is that the person going on leave gets to decide how much they want to hear from work while they are out.
During Allison’s own leave, a COO reached out a few weeks postpartum to update her on a project she’d spent months on, and gave her the choice of when to engage.
“I care about you. I’m thinking about you. This was an important thing that you spent a lot of time on. I wanted you to hear the resolution.”
For Allison, she did not want to engage fully, but she appreciated the opportunity and outreach - it made her feel considered while she was away and alleviated some of the fear.
Before you go on leave, it’s worth telling your manager exactly what you want. Do you want to be looped in, and in what circumstances do you want updates? Do you want total silence? Either is fine, but naming it removes the guesswork for everyone.
Allison also has advice for a specific trap: don’t lock in big decisions, like whether you’ll want reduced hours, based on assumptions around how you’ll feel once you’re back.
“Don’t make decisions based on a future you that may or may not exist.”
This is one of the most common misperceptions, she says. High achievers like to have a plan, but planning for what you will want on the other side of a child - whether it’s your first or third - is almost never necessary so it’s best to wait until you return.
The Confidence Dip Is Real, and It Passes
Erin’s return to work came with a psychological hit that had nothing to do with logistics.
“My confidence was so rocked. I went back to work thinking: are they finally onto me?”
Her actual transition back was also rocky, something Erin describes as not sufficiently intentional. She didn’t feel fully back to her previous level of confidence for a full year, and then had a second child and went through it again.
Then, one day she approached her husband, and floated the idea of staying home full-time. He stopped her right there, saying something that would help Erin shift out of her confidence drop and back into herself:
“If you didn’t work, our daughters would never know who you truly are.”
I loved this story from Erin. Her husband saw her work as essential to who she is and a great use of her talent, something to embrace rather than shy away from. That support gave her permission to be fully herself, even in the toughest parenting moments.
If you’re in this dip right now, both Allison and Erin want you to know it’s common, and it’s temporary. You don’t need to make permanent decisions based on how a tough period of parenting feels.
What to Ask For When You Return
There are a few specific things worth requesting before your first day back, based on Allison’s work with parents across many companies.
Ask for a casual check-in with your manager a few weeks before you’re back.
Ask for a written re-onboarding plan, almost as if you were a new employee. According to Parentaly, employees with a strong, written re-onboarding plan are 3X more likely to find their return easier than expected. It’s a small ask that makes a real difference.
If you have flexibility on your start date, consider a Wednesday instead of a Monday, since it’s less overwhelming.
Finally, try out your childcare arrangement before your actual first day, not on it. Having a childcare routine down before you jump back into work can ease the transition period.
It’s also worth asking your manager to hold off on any big career trajectory conversation for the first few weeks. Almost everyone is overwhelmed during that stretch, and decisions made in that state don’t always reflect what you’ll actually want once you’ve found your footing.
Policy: The Sobering Bigger Picture
The United States remains one of the only countries in the world that does not guarantee federally mandated paid maternity leave. It is a sobering reminder of how much falls to moms - and the companies they work for - to get through what should be one of life’s best moments.
Erin points to childcare access and workplace flexibility as the two biggest factors pulling mothers of young children out of the workforce, and she’s concerned that some of the flexibility gained during the pandemic is fading.
Allison’s view of the US system is direct: as the only major developed country without national paid leave, the US is clearly far behind. But the bigger gap is within the US itself, between people whose employer offers generous leave and people whose employer offers none.
Erin also brings it back to the home, referencing something Gloria Steinem told her directly: “family is too often the birthplace of inequality.” Who takes on unpaid labor at home affects who has room to grow professionally, on both sides of a partnership.
Until leave policies catch up, it’s on all of us to push our companies for better policies and to use the time we have wisely. Allison and Erin show that when we do, we can create real change, both in our workplaces and for the next generation of working moms.
Allison & Erin’s Tips for Leave:
Define how you want to engage while on leave, before you go. Whether it’s full disconnection or occasional updates, tell your manager directly and agree on a plan upfront.
Ask for a written re-onboarding plan and a mid-week start date. Both are small requests that make the actual return significantly easier.
Give yourself real time before assuming a tough moment will be the new normal. A confidence dip or the urge to quit in the first weeks back is common, and it’s not a reliable signal of what you’ll want once you’ve settled in.
About Allison Whalen
Allison Whalen is the founder and CEO of Parentaly, a parental leave program that helps companies protect business and talent continuity when employees take extended leave.
She founded Parentaly after returning from her own parental leave and recognizing that even predictable leave transitions can create unnecessary disruption, performance gaps and retention risk when they are not planned well.
Today, Parentaly partners with global enterprises to operationalize parental leave through structured pre-leave coverage planning, manager enablement and return-to-work execution - helping companies close the gap between generous policy and business outcomes.
Allison holds an MBA from Wharton and previously led enterprise sales at Managed by Q, which was acquired by WeWork. In 2023, she was named to the Twin Cities Business Journal’s 40 Under 40 list for innovative leadership and her work building Parentaly.
About Erin Grau
Erin Grau co-founded Charter, a future-of-work media company backed by Bloomberg and the Financial Times. After The San Francisco Standard, founded by venture capitalist Michael Moritz, acquired Charter, Erin served as The Standard's Chief Operating & AI Officer. She is also an inaugural resident at Gloria Steinem's foundation, where she focuses on women, AI, and economic opportunity.
For two decades, Erin has guided organizations through transformation at the intersection of talent and operations. She was VP of Transformation and Digital Operations at The New York Times and led people, strategy, and operations at Away.
Erin holds a B.A. in Journalism from NYU and is a graduating fellow of the Sulzberger Executive Leadership program at Columbia University's Graduate School of Journalism, where she concentrated on women at work and change management. She lives in New York City with her husband and two daughters, who know her as both Mom and their Girl Scout troop leader.
