#17: How to improve your parental leave policy & program

Apr 17, 2024

E17_Jessica Winder (feed)

About The Episode

At most organizations, there is an HR leader responsible for the employee experience of parental leave and leave of absences more broadly. 

But what happens when the person in charge of this experience takes their own parental leave? 

To answer this question and more, we brought Jessica Winder, career coach, author of The Hidden Gem Within and fractional Chief People Officer onto the podcast. 

Jessica was previously the SVP of People at a marketing organization where she brought Parentaly in as a benefit for expecting parents

One year later, she found out she was pregnant with twins and would soon become a mother. 

We talked about why she decided to invest in parental leave programming that specifically addresses career and business implications even before she became a parent. 

She also shared her experience with parental leave - as both a manager and expecting employee - and how she personally benefited from a program like ours.

Links & Resources


Disclaimer: This podcast transcript is autogenerated and may contain minor errors or discrepancies

Allison: Hi, Jessica, thank you so much for joining me today.

Jessica: Hi, I'm so excited to talk to you.

Allison: We have a lot to cover because we've known each other for a while. You actually brought Parentaly into your last organization before you were a mother. So before you had parental leave, you realized that there was a challenge with parental leave. I want to get to your parental leave experience in a minute. 

But I wanted to start this off by saying you come in, you're leading the people function at a 200-person company and you and I connected. Right away you had a lot of questions and a lot of thoughts. Bring me back to that moment in time. How did you think about parental leave from the perspective of an HR leader running the people function in that moment?

Jessica: Yeah, I instantly knew from past experience, and mind you, I've been in HR for almost 13 years. I've seen people leave a company that were amazing because we did not set them up correctly to come back or we did not make them feel welcomed back.

And so I instantly knew when I heard about [Parentaly], I thought, oh, this is amazing. Like you're coaching people, you're giving people resources and not just them, but their managers, because I have absolutely seen where managers did not know what to do about parental leave. And they treated it as something that they were just not meant to deal with. Like this is HR's problem. Like, go talk to HR, you're pregnant, good luck, go talk to HR, congratulations. And it's like, why? Why can't it be interactive? 

And so when I started with that organization, I knew because also the demographics, so we were an early stage startup. Most of our employees were between the ages of 25 to 35. That's like prime years for most people that are thinking about family planning. And so I knew, and even when I joined, I think we already had like three people that were pregnant. And so I'm like, okay, this is something we need to address, especially because we don't have a lot of coverage. So it's not like we have people that could just cover people when they went out on leave.

I knew it was important because we wanted people that were leaving to come back. And so I always thought about it, like, how can we make sure that they come back and they feel welcomed? And so that was really, really important. And yeah, I will say that it was a great decision. I'd do it again. I plan to do it again, any company I go to. So yeah.

Allison: I love to hear it. How did you make a business case to leadership to invest in parental leave, both from a policy perspective? You extended the policy, which many company leaders will say, oh gosh, we can't afford that. You were able to do it on the policy side and you convinced leadership to bring in parental leave and to pay money for a service that sometimes leaders will say, like, do we really need that? How did you make the business case for those two things?

Jessica: Yeah, I very strongly leaned in on if we don't do this, this is what will happen. These people will leave. And another thing, at the same time, we were working on diversity and inclusion. And so I put it all together, which I think that diversity needs to be a part of every, it needs to be woven into everything.

And so when I was making the argument to implement these new things, what I said was if we do not have this, then we're going to lose, and I was particularly talking about working mothers, and I was like, we are going to lose these people, and that will then impact our future leaders. Like, how are we growing people from within and all of these things? I can't lie and say there was not resistance, because there absolutely was. There was resistance to say we cannot afford this, we are a small startup.

Allison: Mm -hmm.

Jessica: And my pushback was, we cannot afford not to do it because how much does it cost you to replace these said people? And so if we don't do it, this is what's going to happen. And it took persistence. I am nothing if not persistent. If you tell me no, I'm coming back to you with more data. And so it definitely took several conversations to get this in place. It was not easy.

And so I want the listener to know that it wasn't just like I asked and I received. That was not the case. I had to keep coming back with more data, I am a big person on research. So I kept researching like what are other startups doing? So another thing with business leaders is they want to know what their competitors are doing. I'm like, well, our competitors are actually offering more time. And so like if we can't get to what they're offering, what's the in between? 

And so one of the things that I think was a win and I've learned this in HR is like, even if you don't get everything you want, did you get something? So I didn't get all the time that I wanted to give, but I got an extra two weeks. I didn't get some things, but I got some things. And I'm going to keep building on that. So start from somewhere. That's what I would say, start from somewhere.

Allison: I thought you did a really great job. Back when we first met, you were really transparent about, here's where we want to get, but it's going to take me some time and I'm going to pick away at this. And so, and I feel the same way. I also run a small business and we would love to offer so much more across so many different benefits. And I found that it can be helpful to talk about that and to say, that's where we want to get to. And here's how we're going to get there step by step. 

And it was so cool for me to watch you do that because you actually did then get there piece by piece building towards something that is much better. And I think you're right that a lot of people, they're scared and paralyzed. Like if I can't get it all, it's just, it's like this huge mountain to climb.

Jessica: Yeah, it's like an all or nothing mentality and I'm like, absolutely not. I'm gonna get something out of this. I was like, even if I just get a week and then next quarter I'm gonna come back and get more time. So just keep being persistent.

Allison: Yeah. So then you became pregnant. So, you know, you rolled this out actually quite a while before you would need the parental leave policy or the parental leave benefit. You also happen to be a career coach yourself. And so I was really excited when you were pregnant for all of the obvious reasons, but also because I was like, wow, this is going to be interesting to hear her perspective as a career coach going through a career coaching experience with parental leave. What was that like for you?

Jessica: Oh my goodness. A whole new world - like Jasmine. And I mean that in an awesome way because you're right. Like I'm a leader, I'm a coach, but I was in deep waters of the unknown. You think that you're ready and obviously the family planning was something that was on my mind, but it was something that once I got pregnant, ample disclosure, I had twins and I'm a black woman. So there were just so many complications and so many fears that I was very transparent about. I am on an unknown road and I am very scared.

I was very transparent with my leadership team about it even. It's funny because I have absolutely coached people on when to tell their employer that they're expecting and how to go about it. And even when I had to do it, I knew my leader would be excited for me, and I was still nervous like I was still like, oh my goodness, like what do I say and like how do I say it and am I going to feel differently and you know, there was there are a lot of emotions. 

Allison: Yeah! Same.

Jessica: And I think being in the thick of it after I have coached people from the perspective of HR, not from the perspective of I am also a mother. So it was very, very different for me. And I did not, I'm gonna be honest, I didn't expect to feel all the emotions that I felt. I thought like, I know this, this is how you do it, step one, two, three. But then when you have to do it, it doesn't feel that way.

Allison: Right. What were your fears in that moment? Explain more why you felt that sort of fear anxiety.

Jessica: I think for me the fear I felt was that I had coached women that were more junior in their career and at the time I was a senior vice president and I didn't know any other senior vice presidents that were like in my position and I had recently been promoted. So that was another thing. Like I had recently gone from a VP to a senior vice president and gotten more responsibilities and I thought, oh, I don't want this to quote/unquote get in the way or I don't want them to feel like I'm not as committed as I was.

You know, two weeks ago when they didn't know that I was pregnant. So I think it was the fear of like, I want to remain to be a good leader and be seen as a good leader and that I'm going to take this time for myself and for my family, but I'm still committed. I think it was the factor of, am I still committed? Which I absolutely was, but I was scared that they would feel differently about it.

Allison: I totally resonate with that feeling because I felt the same way. Like even with our investors, I had two of my children after I started Parentaly and I knew they would be happy. I knew they knew what they were signing up for when they invested with us. And still I felt like I had to approach that conversation, even though we coach people not to feel this way, that I had to justify and I had to like to overly verbalize my continued commitment to the business.

Jessica: Yes. Mmmhmmm.

Allison: And I could almost feel myself coming out of my body in that moment being like, what are you doing? You know, like you're coming in with this lack of confidence when I'm very, this is the business model that I run, you know? And so I totally hear you that there's something about it that just sort of stirs up these emotions that quit from you.

Jessica: Mhmmm, yes. You can coach people all day, but when you have to do it for yourself, you have to like to find this power from within. And I had even, this is funny, I'm a really big sticky note person. I had put a sticky note for when I was about to tell my leader, mind you, I absolutely adored her and loved her and knew she was going to be happy for me. But in the moment, I literally wrote on a sticky note, like, this is positive. This is something you've always wanted.

Allison: Right.

Jessica: I had to remind myself that even though I'm scared, I wanted this family, I wanted these daughters, I want this and these people are going to support me, But in the moment I was absolutely afraid.

Allison: Oh, I hear you. So then you started the Parentaly program. Tell me what that experience was like and what surprised you about doing that work through Parentaly.

Jessica: I think what surprised me was very much all of the templates and all the things that I just had not thought of. Like in my mind, even though I  have done this for other people, I thought, oh, I'm a leader. I'm just going to write down everything I do and somebody's going to do it. Well, no, no, that's not how it works. 

And mind you, I only have one person on my team. So I was very much concerned. I think that's my main thing. I was very concerned for her, like, what is she gonna have to take on while I'm not here? Not thinking of it like, there's some stuff that we could just pause, like she doesn't have to do everything I'm doing on top of her work. And so when I joined, I really did try to come into it from the mind frame of I am not an expert in this. Like I am a leader in HR, I'm a leader in coaching, but this is outside of my realm, so I'm gonna come into this with a very open mind, open heart of like, teach me, help me, guide me. 

And so my energy from the very start was like, don't think of me as the leader in this, like treat me like everybody else because I don't know what I'm doing.

Allison: Yeah, your, your Parentaly coach was very nervous because she said, Oh my gosh, Jessica's this force of nature. She's so wonderful. She is a career coach. You know, it's very intimidating when you are a career coach coaching another career coach. But then she said, at least her feedback to us was, it was wonderful, you know, and you could almost make the case that someone who understands coaching almost gets even more out of a coaching experience. Like they understand how this is supposed to work.

Jessica: Yes!

Allison: How did going through that pre-leave period impact your thoughts from an HR perspective? Or did it not?

Jessica: It absolutely did. It really enforced that the prep work is needed. And I will give insight that my daughters were premature. So I was not ready like I should have been, if I'm being honest. I absolutely think my coach did everything she could to get me ready. But I think mentally, I was one of those people that was manifesting that, no, they're going to come on this date. I didn't even have a hospital bag. That's how much I refused to prep. I was like, no, I'm not doing this. This is what's going to happen. I'm going to will myself into my due date. Well, it didn't quite happen like that. 

But the prep work was so important, especially when it came to getting my manager ready. So getting my manager ready and then also getting my employee ready to take over my work. So I think that was the added layer for me. If you're a leader, making sure your leadership team is ready and then making sure that your actual department, your actual team is ready. And I was very focused on my department being ready, not necessarily the leadership team, which I absolutely had to put more work into, particularly with my peers. 

So thinking about how my leave is going to impact my CFO? How is it going to impact everyone else? Because when I went on leave, it was the time that we were doing performance reviews, we were doing employee engagement, we were doing all these things that were annual that we needed to be ready for. So, I was just not prepared for thinking about it both ways, thinking about employees in your leadership team.

Allison: Looking back, what is one thing you did really well before you went on leave and one thing you wish you would have done more of?

Jessica: With my coach, we documented like all the templates. I absolutely utilized them. We wrote everything down. Everything was in writing. The timeframes were ready. When I text my team and said, Hey, I'm on the way to the hospital. They were like, got it. Good. We have all the documents. Like we have folders. We had everything that we needed in that sense. 

Allison: Good.

Jessica: I actually think when I think about preparing myself, I wish I would have took more time

to think it through for myself. Like I was so, so worried about getting everybody else ready that I don't think I actually sat down and got myself ready if I'm being really transparent.

Allison: Yeah, I've thought a lot about that, like, I worked up until with my second and third child, I had induction dates. And so I did the same thing where I worked up until I went to the hospital and I look back and I think, well, why did I just take like a couple of days to myself to really get in the head space? Because then you have these babies and everything is about them at that point in time.

Jessica: Oh, yeah, everything changes, but I wish I would have done that. And I actually, ironically, probably a month before I had the babies, I did take like a week off and I just read books that whole week and it was amazing. And I was so happy that I did that. But the day that I actually ended up having the babies, I worked that morning. I was sending out emails and then I was like, oh, you know what, my blood pressure is high. My midwife said I should go to the hospital, so I'll be back later. And they're like, wait, what?

Allison: Oh my gosh. So let's talk about the return to work experience, which must have been very difficult, especially with twins. I've never had twins. I have heard it's much harder than just having a singleton. What was that return to work experience like?

Jessica: For me, my team was so amazing because I had set a strong boundary that I did not want to be contacted. So I, especially because my twins were premature and they were in the NICU for a while, I really, really needed to focus on my family. So even before I left, I had said, Hey, I want to have this boundary that you do not contact me about work stuff. Like you guys are going to figure it out. I believe in you, but I have a strong boundary on this. And my team absolutely respected that. 

There were two times that actually me and my manager got together, but it was like literally just for her and I to talk. We didn't talk about work. We talked about the babies and how I was doing with my mental health and my physical health. Like it was more of a friend, you know, to talk than it was about work. And so that was really, really important to me to set that boundary and my team respected it and it was something that I valued. So yeah, that worked out perfectly for me in that sense.

Allison: And was that pre -planned catching up with your manager? Okay.

It was pre-planned before I went out that I wanted us to still be able to talk. I consider her to be, especially now that I've left that organization, she is absolutely a close friend. And it was also pre-planned that I was going to be talking to my team, not about work. So I would send them baby photos, or I would say, hey, ladies, not sleeping, or just quirky things that were going on, but we did not talk about work.

Allison: I love that. We have heard from a lot of people that they like maintaining social connections. And even for some folks, especially abroad, where people tend to take 6-12 months, that people really like being brought in on the social team outings or things like that, that doesn't bring on stress, but allows that continued connection. And so I love that you were able to plan for that. I think one of the hardest parts with parental leave, especially with your first, is not knowing how you'll actually feel in the moment. So I'm impressed that you knew you would want that boundary. And then you did actually want it in the moment, right?

Jessica: Oh yeah, I was very, very...I think part of it is that I'm a recovering perfectionist and I knew that if they asked me about work, if they asked me to do something, that I would do it. And so I knew from my own mental health that I had to say, I can't do anything or I'm going to do everything. And I knew that.

Allison: Mm-hmm. Yeah, so you return to work and you return to work in an environment where there was a lot of change going on. We hear that a lot from people who go through a coaching program, whether their manager was switched out while they are on leave or they returned to an environment where there are layoffs happening or the business has totally pivoted or their project has been deprioritized or, you know, and it can be very scary and sort of disorienting. What was that experience like for you to walk back into a scenario that felt very different from what you left?

Jessica: So another thing that my coach was amazing at was talking about the re-onboarding. So one of the things that my team did, and I think this is amazing because obviously I work in HR, was my direct report did a re-onboarding plan for me. So there was a phased in approach. I came back quote unquote part -time, whereas I wasn't going to every meeting, but I was still like logged in. We have a new hire spotlight, and  she spotlighted me. We talked about the babies and sent it out to the whole company.

I was reintroduced to meetings knowing that I was just going to be there to listen and I wasn't going to have to participate, but joined just to listen and get caught up. So that part of it was absolutely amazing.

But I can say the week before I was going to come back I was riddled with anxiety. Mind you, knowing that like my situation, I have a nanny, I want to be honest about that. Like she's in my house with me and I was still, and my twins are upstairs, I'm downstairs, I could go up, you know, at any time. And I still had so much anxiety. I think the first day I logged in, I had a meeting for 30 minutes and then I logged off and started crying. Like I was just so filled with emotion. And I think my team was so kind to me. And even out of all the things that they did, they gave me space.

That's one thing that I would say. And most of the people on my team were mothers already. And so they knew and they were checking in with me throughout the day, like, how are you feeling? What's going on? So they gave me space that first two weeks to where I did not feel pressured to be quote unquote back on. I did not feel pressured to be back being like a strong leader. I was very much in a soft girl era.

Allison: Yeah. That's so important. And it's just even when things are exactly as planned and you know what you're coming back into, it is such an emotional experience. And you're right. You are in a very good position where you have a nanny and the babies are right there. And even still, it's so hard, the context switching to go from this lifestyle of you're doing something totally different. And now all of a sudden you sort of flip that switch back on. 

In hindsight, if you were to start a new role today as chief people officer somewhere else, what would you do differently or what are the things that you would be investigating to make sure that that company is set up successfully to support new parents?

Jessica: I think the first thing I would do is contact everybody that's gone on leave and I would want to do a session or like tell me what it was like when you came back. Were you welcomed back? Did anyone acknowledge that you were even back? You know what I mean? Like were you thrown back in and had expectations set for you? I think it's really, really important within that first couple of weeks that they are not expected to quote unquote be back full time and whatever that means to that person, whether that's meetings, whether that's if they're client facing, are they expected to be back and like presenting the clients on day two? Like what does that actually look like? So I think even setting them up that first 30 days is so, so important.

Allison: Right. I think that's so incredibly helpful. I want to jump into hot topics. So we started doing this recently and we love it. This is not a gotcha, so don't sweat. So I'm gonna go through a few hot takes. I'll throw something out at you, answer in like a couple sentences and we'll get through a bunch of these. So, ready?

Jessica: I like it. Okay. Yeah, let's do it.

Allison: Okay, best benefit you've ever received as an employee.

Jessica: This is a hard one, like, oh, there's so many good ones. I definitely think parental leave, so making sure that I had enough time to spend with my twins. And actually another thing that I will point out is that my twins were in the NICU for two weeks and they gave me that time back. So they allowed me to have those extra two weeks back once the babies got home with me.

Allison: That's amazing. What is the right amount of parental leave an employer should offer?

Jessica: Oooh, this is a hot one. I was actually ready to go back so I will say that I was off for four months and at four months, I was ready to go back…so it is very personal. I know some people that that would not have been the case But for me, I was ready. I was ready even though it was emotional. I was ready. So, can I say I don't believe that it should be standardized amount?

Allison: That's fine. No, I can hear you. I know it's not a real question. It's kind of an impossible one. What's the one misconception about the HR profession you wish you could change?

Jessica: Oh, I think this is a funny one. And I posted about this one on LinkedIn where people are like, HR is not your friend. No, finance isn't your friend either. Neither is any other department. So I think thinking about HR as like an adversary or like they're an extension of legal. I tell people all the time, I'm not a lawyer. I'm married to a lawyer. I'm not a lawyer. And I don't want to be. So just that perception of being the gatekeeper, I think, you know, HR can be creative. I think of HR as an ability to be creative. Even utilizing this type of service is a step in being creative in how you think about your employees.

Allison: Best and worst advice you received before or after your twins arrived.

Jessica: Oh my goodness. People loved to give me twin advice when they had never had twins. So that was really fun about what I should do with them and all this fun stuff. And I'm like, but you don't know.

This is an interesting one. I think the best advice, and this was actually recent advice, was to put them in the same crib together now that they're 6-months. And it has been a game changer for us. And they comfort each other. It is amazing and the sweetest thing to watch. I cry watching them sometimes. They're in the same crib together. And it is amazing. They sleep much better.

Allison: So cute. What was the worst advice or are you not able to share? Probably the worst advice is anything you heard from non-twin parents, right? That is so funny. I cannot imagine giving advice to someone given that I have not had twins on that. 

Jessica: Exactly.

Allison: Okay, last hot take. Number one thing you've learned about yourself since becoming a mother.

Jessica: This one makes me emotional. I've learned that I'm resilient, that no matter what, I'll figure it out. It's not gonna be perfect, but I'll figure it out.

Allison: Oh, I love it. All right, that is all we have. But before we go, we are going to share a link to your book and we will point folks towards where they can find you on LinkedIn. We love all of your posts. You have so many good perspectives. Are you also career coaching? If people are looking for a career coach, is that still something you're doing? 

Jessica: Oh yeah, I absolutely am. I have some new clients. I'm doing resume writing too, so absolutely reach out.

Allison: I love that. Well, thank you so much for sharing all of your experience here and congratulations on the babies. I know they're six months old, but they still count as babies. And thanks for joining me today.

Jessica: Oh, yes. Thank you so much. I really had a great time talking to you.