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Tamara Hinckley leads the Enterprise Tools Product team at Pinterest. She’s passionate about health & wellness and is the author of Half Moon Hustle. Before Pinterest, Tamara completed her MBA at the Harvard Business School where she co-founded a consumer products company. She’s committed to advancing diversity within the Tech industry and founded the Women In Product group at Pinterest. Tamara is also a certified vinyasa yoga teacher. She’s the mother of an almost two-year-old, with a newborn baby girl.

Tell us a little bit about your career journey, your family and what you like to do.

I'm originally from Ukraine, but I grew up on the East Coast and moved to the Bay Area about seven years ago, where I currently live with my husband and almost two-year-old daughter. I started my career in finance, working in investment banking and private equity, and then realized that wasn't really my passion. So I went to business school and ended up moving into tech. I joined Pinterest and have been here ever since. 

I've had a number of different roles over the last seven and a half years, most recently working in different parts of the product organization. I currently lead a team focused on helping advertisers with media buying. 

On the personal side, I love yoga. I've been practicing yoga for a long time. I'm a certified instructor, though I've never taught. My goal is to teach a class once the kids are older. I love to be outside, hiking or just going to the beach. A few years ago, I started a newsletter on Substack called Half Moon Hustle.

How did you become so interested in holistic living?

My newsletter is called Half Moon Hustle because it combines my professional side with my love for natural, holistic living. Growing up as an immigrant, I was taught to work really hard, hustle to get things done, and put in all the hours. I was working crazy 100 hour weeks in banking and private equity and life was really about the hustle for me. Eventually, I realized that wasn't giving me joy. 

I went through some health challenges when I was trying to get pregnant with our first kid and realized the toll that this hustle lifestyle had been taking on my body. And so that was the turning point when I realized, okay, I need to reset my priorities here and yoga and holistic living were a big part of that. 

I ended up revamping my whole lifestyle—which meant managing stress more effectively and being more clear with my boundaries around work. I still have the hustle component and the ambition, but the way it manifests is a little different in terms of the hours and the mindset. I'm hopefully managing it a little bit better than I used to. It's always tricky.

Where were you in your career journey when you found out that you were pregnant?

I'd been at Pinterest for over five years and I was really hoping to become a manager. I was trying to make that big transition from individual contributor to manager. That's where a lot of women get stuck on their path to becoming more senior. So I was very focused on that. 

I actually found out I was pregnant during the interview process for a new manager role that had just opened up. I really struggled with whether I should even continue with that process. If I got the role, should I take it? At what point should I tell the hiring manager that I was pregnant? 

I ultimately ended up getting the role and ended up telling my manager pretty soon afterward.  That’s just the way timing worked out, but he was super supportive. It didn't end up making any of the impact that I thought it would in a negative way, but I was nervous because Pinterest offers a very generous six month maternity leave, and so I felt guilty taking on a new role, managing a team of three to four people, and then leaving for so long. It felt like that wasn't fair to them, which, if a man were in a similar situation, I don't know that they’d think about it in the same way. They probably wouldn’t feel guilty like that.

Do you remember what your manager said or did that put you at ease?

He has young kids, and recently had his second child and had gone through the parental leave process. So his main reaction was just that he was super happy for me personally and reinforced that I was the right woman for the job and that my maternity leave and my job performance weren't really connected. He made it clear that they hired me because they thought I’d be excellent in the role and that didn’t change because I was pregnant.

We worked together on my coverage plan and how to manage and when to tell the team. I was doing a lot of hiring at the time. He helped me think through how to do that. And since he had just gone through it himself, he brought a lot of empathy, which made me feel very safe having those conversations and ultimately going on leave for a while.

So how did you approach planning for maternity leave, telling your team, and all of those sorts of things that first time?

The first time we were still dealing with COVID-19, so I was working remotely and that gave me a lot of agency for when to share the news. It was a high-risk pregnancy, so I really didn't feel comfortable sharing the news even with my manager until I made it to 20 weeks and had that big 20-week anatomy scan. I told my manager shortly after that. 

Then he and I worked through who to tell and in what order. The tricky thing was that I was a newly minted manager and there weren't many examples of other women who had gone on leave within the product organization at the company. So I talked to the few that existed in different parts of the company and got the tips and tricks and things to avoid. 

And maybe not surprisingly, there was this unspoken language about what to do that I found really helpful. So I talked to certain people in a certain order—my manager, then eventually my skip level, and my team a little bit later, once we had a plan. There was an unwritten checklist that I didn't realize existed. 

I ended up writing it down and publishing it in Lenny’s Newsletter so that other people could benefit because it felt like it was this unspoken agreement of how to do it and there wasn't much public information about it. I didn't have that many people to view as an example, so I wanted to take those conversations from behind closed doors and make them public.

Any high-level advice for other moms trying to navigate preparing for maternity leave?

A couple of things come to mind. Every company has a different policy and we can talk at length about why they should be longer and more consistent, but I'm assuming you're working within the confines of what exists. I think giving enough notice is important. So I think a good rule of thumb is at least three months. Try to give notice sometime in the mid-to-late second trimester so that you can work with your manager on your coverage plan.

I felt like the second time around my coverage plan was a lot more thoughtful because I was able to bounce ideas off my manager and collaborate with them on creating it versus having to come up with an answer right away. And I think that’s because they had a lot of time to give me input and for us to make decisions together. So give everyone enough time so that there's an opportunity to create a plan that is effective.

The other small tip that people tend to overlook is if you happen to be out during a performance review cycle, which I have both times, then it's important to think about what that means. Write your own self review before you go down out on leave and make sure that your manager knows what's important to you. Have those career conversations about compensation and whatever else matters because they won't remember if you don't put it down on paper and you won't remember if you're not there. 

I think advocating for yourself and making sure that your voice is represented during that review process and asking for what you deserve is important. I'm really glad I did that last time and I'm hoping to squeeze it in this time before I give birth.

What advice would you have for women who are feeling guilty or shy about advocating for themselves while they're out on leave? 

Well, I think there's a couple things. Part of advocating for yourself is about the past and that has nothing to do whether you're out or for how long. When you write your review, it's about what you accomplished over the year and those are things that you delivered for the company. 

I think people need to be comfortable advocating for the impact that they drove and that should be the case no matter how long they're going to be out. 

Companies that provide leave understand that people have babies and they need time to be there with their families—and they will probably come back and be happy if that leave is generous. The company is investing in you by giving you this opportunity to spend time with your family. So your plans to come back and drive impact for the company are valuable. 

I think advocating for yourself is hard, but it's all about the value you're driving for a company and when you come back, you'll continue to do that. And if that's the case, then the company should value and recognize that.

How has motherhood impacted your career progression? Was balancing the two different than you thought it would be?

Oh gosh, I don't think I could have prepared for motherhood, but I don't think anyone really can. And everyone's experience is different. You know, I think what's hard is a lot of people talk about it as something that will likely slow your career down. And I think there is some truth to that, which I'm really sad to admit. Men often don't take the leave that women do. So just logistically, when I'm being calibrated against my male peers and I've been gone for six months and they were not, then the hours that they put in versus what I did are going to be different. 

This actually happened to me, where I was being compared to someone who became a manager the same day that I did and then was able to progress more quickly than I did because they were around more. That was really hard for me to swallow.

I think one of the biggest things that is holding women back is actually men not being offered or taking the same amount of leave. So that's what it is. It’s the time away that you don't necessarily make up. 

How has motherhood changed the way you view your career?

The bigger impact for me has been the opportunity to see what's most important and gain a lot of perspective. That shows up every day when I'm looking at my phone instead of playing with my daughter and then realizing this Slack message can wait but she can't. I’m a lot more present because I don't wanna miss the few hours of the day that I'm actually with her when I'm not working. It also shows up at work where if I'm working, I need that time to be really effective because logistically I just have fewer hours to be there at my job. That means I have to be more ruthless about what I can take on. 

I become a lot more deliberate about how I prioritize my time and also more explicit with other people that I work with about my priorities and what I'm not doing. And I think that makes me more effective. It's not a bad thing. The company doesn't want me spending time on things that aren't important either. 

I think motherhood has been challenging in a lot of ways and rewarding in a lot of ways. And I think navigating that while rising up the ranks professionally has been a learning opportunity. It’s all about learning how to make it work. 

Motherhood really can make it clear for someone that they don't want to work. And that's a choice that I think we should all respect. But I think people who decide to stay do have to make a lot of sacrifices given that we're sleep deprived and pulled in all these different directions. And the reason we stay, I think, is because we care about the work and the impact. And that means that we're actually very dedicated and passionate employees. I would love to hire people who are excited about the work, even if it's done in a more constrained time frame.

So now, baby number two, you have a bigger team. What has been different this time?

Well, the pregnancy has actually been a lot harder, which I was not expecting. It was just more intense with all the symptoms, nausea, fatigue, et cetera. So that has been physically very limiting throughout and harder to balance while having another kid already at home,  which means I have much less time to rest and relax. 

But at the same time, it’s been familiar, which has been nice. I knew the checklist for how to work through my coverage plan and when to tell my manager. And I'm trying to take a different approach to the time that I'll be with my child, meaning I want to be more intentional about how I spend the time away from work. 

Last time I was feeling really antsy towards the end and actually came back a little early because I was going crazy being at home with a baby. I really missed the intellectual stimulation of work and feeling productive. This time I'm trying to lean into that quiet non-doing mode more and take some time to prioritize myself. So I’ll spend more time writing, connecting with other moms, even just getting comfortable not being productive, which is really uncomfortable for me.

How has your team been? Have they been super supportive?

My team's been great. Actually, some of them were on my team the first time around. And so I think for them, this wasn't that different because they knew they were in good hands while I was out. I take being a manager really seriously. And I think my team values all the thought and care I put into setting them up for success before I went on leave. I spent a lot of time talking with them about their goals and making sure that I had a good transition from me to their interim manager. I wrote up their performance reviews in advance before I went out, so that was documented. My priority was setting them up for success before I went on leave. 

Have you had anyone on your team go out on maternity leave while you were their leader?

I had someone go on paternity leave earlier this year, actually. It was a really interesting experience being on the other side, but he told me pretty far in advance. We worked on the coverage plan together. We made sure that he was ready early, which was helpful because the baby came early, and that he had a good transition back. I hope that he would say that he felt very supported. I think having gone through the experience myself made it a lot easier to guide someone else through the process.

Do you have any career advice for moms who are navigating this time without adequate leave? 

Oh gosh, I have so many thoughts. I have a lot of anger that people have to be put in that position. I personally think that we should have at least three, ideally four months of minimum leave for both parents. I think having that conversation with your employer, advocating for it to be paid, using all the data that exists out there is hard and uncomfortable, but important because it'll never change if we don't ask. Maybe employers would be open to it, but haven't really heard the need. So there's a piece of speaking up and trying to make it easier for yourself or the people that go after you. 

That said, you can only change what you can change. Then I think it's a matter of looking at your whole village and figuring out what you can do within the system you’re in. How much time your partner can or can’t take off is a big factor. While I have a very generous leave policy at work, I don't have family nearby. I didn't realize how valuable that was until after I had kids. So lean on the help from your community. 

One thing that has been really beneficial for me is meeting mom friends. While I was on leave I met a lot of moms who were also on leave and we've formed this amazing neighborhood group where we support each other and ask for advice and share tips and tricks. And I think that support network is really important. 

So even if you can't extend the leave or make it longer, I think commiserating can be helpful and so can getting suggestions from other people that are going through it. Lean into your village of support, both people who can help come and help take care of the kid, and peers who are going through that similar experience just to make sure that you don't feel as alone.

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