I almost quit my job after parental leave

We’re taking a step back to share Allison’s founding story.

Why did she almost quit her job after returning to work after her first child was born?

Everything was great on paper.

Her company offered a generous paid leave policy and even promoted her soon after she returned.

So what happened?

Spoiler: It definitely wasn’t because she wanted to leave the workforce.

In this episode, Allison shares why she left a great career in sales to start a company to solve the very challenges she faced after her first child was born.

We also went through the very first “Ask Me Anything” segment where she answered five questions about parental leave and working parenthood we received this week - including topics like:

• What can parents do to overcome the biases they’re subjected to at work?
• How can employees maintain professional relevance and skills while they’re on leave?
• What’s the right way to tell a new manager I’m pregnant at a job I just started?
• How can I set boundaries now that I’ve returned to work without seeming like I can’t keep up?
• What can I do to make my parental leave a positive experience being the first at my company to take it?

It's 2017, and after 10 years of working in investment banking and going to business school, I'm now leading the enterprise sales team for a tech startup in New York City. And that's when I found out I was pregnant.

I was absolutely thrilled. I wanted to be a mom my entire life. And my company offered great medical benefits and a good paid parental leave policy. So all things considered, I felt incredibly privileged and excited for this next chapter.

Unfortunately, and little did I know at the time, my parental leave was about to be an incredibly disruptive force on my career and professional identity. Fast forward to my return to work after parental leave, I returned to an absolute nightmare situation.

In my absence, my direct reports weren't managed well. Key deliverables slipped through the cracks and we missed our goals. And a direct report even quit as a result of her negative experience while I was on leave.

Further, leadership was making assumptions about my career aspirations. Things like, “She probably won't want to travel,” or, “Adding this to her plate would be too much right now.” I missed out on high-impact projects, all because I was struggling to get my feet back underneath myself after being out on parental leave.

So what did I do? I honestly considered quitting. Not to drop out of the workforce, but to take a similar role at a similar company. Because the idea of starting fresh elsewhere…it felt easier than digging out from the hole my parental leaf had created.

But I didn't quit. I worked overtime to get back to a good place at work. It was exceptionally challenging and painful. And somewhere in that messy middle, I had the epiphany. For all of the great medical and new parent support I had, how was there nothing to support my career trajectory, team, and business across this important time in my life?

And I got really determined to figure out, am I unique? Or did this happen to others too?

So I decided to survey my network, fellow business school grads, many of whom were in consulting, finance, retail, and technology companies. And I just asked them, “How was your experience?”

And almost 100% had the same story.  They said, “I would never give back the time that I took, but it negatively impacted my career.”

Turns out my experience was not unique at all. In fact, it was almost the universal experience across everyone I spoke to.

And this is why Parentaly was born.

After becoming a parent, I was more ambitious than ever, and I knew there was a way to fix the avoidable outcomes I and many others faced in their careers by putting intentional support in place. So I got to work and built a program to tackle these specific work challenges. We tested and tested and tested, tried various iterations to create the right formula of support. A program that not only supported the employees going on leave, but also helped businesses minimize the disruption the rest of the team feels when an employee goes on leave.

And it worked!

Fast forward to 2023, and we've built a new category for career-focused parental leave support. We're now supporting thousands of employees and managers, including some from massive companies like Zoom, PwC, and Hershey, as well as smaller, fast-growing companies.

And that's my story.

I feel incredibly fortunate to get to spend every day focused on how to make life better for working parents everywhere. And that I now have a phenomenal team alongside me on this journey to supercharge our growth.

And to think it all started because I saw firsthand that parental leave should be a positive inflection point, if only someone could help companies get it right.

Now that I've shared my founding story, let's dive into the “Ask Me Anything” segment.

At Parentaly, we get tons of questions every single day from people about how to improve the parental leave and return to work experience.

And so my team thought it would be fun and possibly hilarious to put me on the spot and ask me five questions that came in this week and have me respond to live right now.

To be clear, I haven't read these questions in advance, so you're getting the real unscripted Allison response here today. So with that, let me read off the first question.

Q1: I co-lead my company's parent ERG, and the topic of motherhood bias comes up every now and then. How would you advise parents and companies or ERGs looking to overcome or combat the biases that they may be subjected to?

AW: Ah, of course they threw societal bias issues as the first question. This is a really tough one. Motherhood bias is real. So is the fatherhood bonus. There is plenty of research that proves this out.

And just before I answer the question, and maybe this is me stalling, I think it's worth it to define what this means. So what this means is that you take two people that are virtually identical on paper, right? They have a child, one is a woman, one is a man.

The woman ends up making less money over time versus the man simply because of societal bias that her number one priority now is her child and therefore she will not work as hard. His priority is now his child, and so he will work even harder to provide for that child.

So the exact same thing happens to people who have, you know, look the same on paper, and because of our gender bias or motherhood, fatherhood perceptions, expectations, they get treated differently, and therefore the mother is penalized, and the father actually receives more money over time. So that is what this is in reference to. This comes up all the time.

What can people and companies do? If I had the answer to that, I would be extraordinarily wealthy. This is a big problem.

So in all seriousness, my recommendation is you've got to start somewhere. And the first thing that I think every single company should be doing is they should be doing manager training for anyone who has people going on parental leave, or quite frankly, even around working parenthood in general.

If you are a manager at an organization, you should understand what the motherhood bias is. Because so much of how we begin to counteract the motherhood bias, fight against it, is simply being aware of its existence so that we as society, as humans, as managers, as coworkers, we can catch ourselves when we feel ourselves making assumptions about someone and what their work will be like or not be like because they have these other people in their family, i.e. children.

The beginning of this is recognizing that bias. And so that's the number one thing. Of course, I believe that every company should provide manager training, especially to managers who have people going on parental leave. But that's the first step.

And I think unfortunately, too many people just don't even know about this bias. And so they aren't able to even counteract this because they are unaware of its existence.

And then of course, there are other ways for companies in terms of standardizing performance reviews, making sure that people who go on parental leave do not get looked over for their promotion pathing, performance reviews, things like that. But I think a lot of this begins with really recognizing that this exists.

Q2: I've never taken more than two weeks of vacation, so as excited as I am that my company offers six months of leave, I'm nervous about how it might impact my work, especially in such a competitive job market. Any advice on how I can maintain my professional relevance and skills during this extended parental leave?

Okay, so my initial reaction is, this is interesting that the question is about maintaining my professional relevance and skills while I'm on parental leave. I don't think you should have to.

And what I mean by that is, six months of leave is both a very long time and nothing at all. It's a very long time in terms of what you are potentially missing at work, right? Like, things will change, you will come back to an environment where everything feels and looks differently, most likely.

But it's nothing in the scope of your life. I think even asking what I need to do to continue to be relevant, I think that's the wrong question.

I think a better question is, “What can my team and manager and company do to help me come back and be successful?”

You're not going to be irrelevant by stepping out for six months. So I'm a little bit triggered by the question of professional relevance. I think it's more, yes, this will be difficult to come back to work. Six months is a long time to be gone from work and from your projects, but it's not about your relevance.

It's about getting back, understanding what your new world looks like, having a really clear plan, aligning with your manager on what you need to do, and really staying in tune with where the organization has shifted and what brings you joy, what will get you excited to go to work after six months. You're not going to become irrelevant.

So don't ask that question! And I mean that in the nicest possible way. Don't worry about it. Go out on leave, focus on how to have a really strong re-onboarding, because it's not about you. It's about the systems in place to help you re-onboard.

Q3: I am 24 weeks pregnant with my second, and I just accepted a new job. I'm really excited to start, but I'm feeling unsure about how and when to tell my new manager that I'm pregnant. If you have any advice or resources for parents making a career change mid-pregnancy, I would be so grateful.

AW: First of all, good for you. I think a lot of people really do want to make a change while they're pregnant and they don't because they are scared or worried. It is definitely more challenging for all of the obvious reasons to start a new job as you are trying to ramp up and ramp out at the exact same time.

So, good for you. You obviously made a choice that was very in line with your career ambitions, and just wanna give you kudos for that.

In terms of my advice, I think it's really all about planning. You know, you're trying to do a lot in a very short window of time, and you can actually get a lot done in the 10 to 16 weeks that you have at your new job before you go on leave. And so what I would do right away, it sounds like you haven't disclosed to your manager, I think you should.

Now, of course, it's a personal decision, but I do think at this point, and given the short timeframe and the fact that you're new, the most powerful thing you can do is say, “Hy, I've got approximately 14 weeks. How do we get the most out of this?”

And my personal opinion as an outsider, of course, this depends on your industry, your function, the size of your company, etc. What I would focus on is to be really clear on how long it's gonna take you to ramp, be really clear on your goals, and set really concrete deliverables…and goals, quite frankly, milestones, for what you want to hit before you go out.

Make them realistic, but start delivering.

Q4: I returned to work a few weeks ago and it's been a lot harder than I thought, almost like the team forgot that I just got back. I wish I did a better job setting expectations because the way things are going is not working for me. Do you have any suggestions on how to approach this without seeming like I'm unable to keep up?

Here's another thing where I always feel bad when people say I returned to work and…what I can hear from this question is lack of confidence and feeling like it's your fault, when the reality is it is the manager's responsibility to support returning to work parents.

Think about when a new hire comes in. If they don't understand what's going on in week two, no one's ever like, oh, they're just not smart or they just can't cut it. No, of course not. It's...yeah, they're brand new, they're figuring things out.

This is equally as true for a returning to work parent. The company looks different, things are very different, and you need a proper re-onboarding. And so it is not on you.

If you return to work, you feel overwhelmed, you're not being given this re-onboarding experience. And yeah, okay, sure, you could have done a better job setting expectations, but really, that isn't how it should work. How it should work is that the manager should be setting the expectations with you.

They should understand that you need to re-onboarding, that you need some time before you begin to execute.

Given that, and it sounds like you don't have that situation, unfortunately, I think the biggest suggestion I have is to talk to your manager honestly about this and begin to talk about what you believe is an appropriate ramp up plan with really concrete milestones and due dates and deliverables.

We always recommend that people build a 90-day plan. So we recommend that you have a reading time where you're catching up on emails, you're reading any sort of materials that you missed out on. Then you go into a listening tour, you're having one-on-ones to find out what you missed.

And then you put together a 90-day plan because you wanna make sure that you and your manager align on what good looks like. Because if you are not operating with that, you have no idea what matters and what is most important and what is really your North Star.

So that is my recommendation: Talk to your manager and start building that ramp plan. Make sure you've done a listening tour and had time to sort of redraw all the materials and build out a plan.

Q5: I'm one of the first people to take parental leave at my company. How can I navigate this experience in a positive way knowing they may not fully support or understand the challenges or changes I'm facing and will continue to face as a working parent?

It's a bit of a loaded question. Just because you're the first doesn't mean that they won't understand you or your experience as a working parent. I guess it sort of depends, are there working parents at the organization?

I think going on parental leave as the first or second person is always challenging. Simply because the company has never built coverage plans before, people aren't used to being one person down.

I have a million and one recommendations. I would say you should go through our coaching program. We walk you through every single step for how to do this.

But I guess if I had to call out the number one recommendation, it would just be to build a strong coverage plan, which is actually very hard in practice. That's why I have a business around it. But any sort of plan that you can put together is incredibly helpful.

Because especially when people haven't done this before, they need to be able to see the plan and you need to make the implicit explicit. You need to write down everything as it relates to your offboarding, your coverage plan, training goals for what you want your coverage team to do and deliver on when you're out.

And you might need to build your own re-onboarding schedule because if your manager has never done this before, unfortunately, they probably don't know how. And while this shouldn't fall on your shoulders, it may be in your best interest to take that on.

All right. And with that, thank you so much for your questions. These were great and we would love to continue to answer your questions. So feel free to send in more and we will see you next time in the next AMA!

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