Andrew Smolenski

In true top-down culture, parents in leadership have added pressure to set a precedence for others. Andrew Smolenski, now Vice President of Business Operations & Strategy at Willow Innovations, was at Airbnb when he faced tech’s stigma surrounding parental leave.

Andrew was excited to become a father. He looked forward to taking the time to care for his child, but wasn’t sure if and how he should. Airbnb had a family-friendly culture with competitive benefits, but he still faced a conundrum: signal a perceived lack of commitment to superiors, or set an example for his team?

With help from a trusted career mentor, he decided the worst thing he could exemplify to others was “success at this company means not taking leave.” Detailed coverage planning ensued. Leadership and direct reports knew what to expect and what needed attention while he was out – and it went smoothly.

Andrew joined Willow Innovations in 2020 as Vice President of Business Operations and Strategy, where he focuses on the operations needed to scale the business. Parenthood is now part of his work and home life.

He says joining the breast pump company was exciting after becoming a parent, because he loved the idea of joining a company helping parents, especially moms, after living through the trials of early parenthood and seeing firsthand how much of an uphill battle it can be.

Andrew recently welcomed his second child while at Willow. He felt supported, prepared and, most of all, unapologetic about boundaries. Having navigated the ropes twice, he now encourages his team members to take their allotted time off - which is 16 weeks at Willow.

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<p class="content-highlight">Andrew’s story is chock full of golden nuggets for parents preparing for leave and the leaders who support them. Read his Q&A to see what Andrew learned from two parental leaves at different-sized companies, including the tactics that made him successful both times.</p>

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What did you do in preparation for parental leave to help set yourself up for longer term career success?

Both times I went on leave, I sat down to talk about it (early) with my manager with a plan. In our conversation, I focused on a couple of things:

• My proposed leave timeline – how I was planning to break it up
• An overview of all the open items that I was currently leading charge on, as well as a list of recurring items that I owned (as part of business as usual). From there, I broke everything down, into…
  • Items I was planning to close out before leaving. Our subsequent conversations then focused on my progress closing out that list.
  • Items that would be ongoing, but I shared where I had already arranged coverage while I’d be out
  • Remaining items that needed coverage with a couple of suggestions for it. (This became an action item for the discussion: to decide on a path forward)
• The specific places that I needed my manager to lean in while I was out. Assume best intent here, but also recognize that your manager is busy. You make everyone’s life easier by taking the guesswork out of it and help relieve the anxiety that they are very likely feeling about your absence (but are trying not to show) by breaking things apart into manageable pieces.

What mistakes did you make? Are there things you wish you had done differently before, during or after your parental leave?

After my first child, I made the mistake of thinking that I could go back to my old way of working when I returned from leave, where I would just outwork any problem. It took me some time to realize that I needed new paradigms for working smarter and setting boundaries for myself.

What was the most challenging part of taking parental leave and how did you address or overcome it?

Wondering if I was allowed to take it. I know that this is common for a lot of parents,
and a concern that I’ve heard almost all of my dad friends express to varying degrees. I think the challenge here is that ours is the first ‘generation’ (using that term very loosely) that has had access to more generous paid leave policies in the workplace since a lot of these policies have only been put into place in the last few years.

I was fortunate that I had a very supportive business partner/mentor who helped me look at the situation differently. She asked me to consider what signals I was sending by not taking the leave; in particular, to my direct report and more junior team members. Not taking the leave would have sent a very real signal to those team members that ‘success at this company means not taking leave.’

After all, it’s normal to look around your workplace for the signals of what success at the company looks like and what actions are valued. Just like I was looking for signals, they are doing the same. If there is a policy and you don’t take it, it sends a very clear message. Whereas my fear that someone will view me as uncommitted was an assumption and one that is either 1) incorrect and only in my head, in which case it should be challenged, OR 2) if true, a sign that the company and its leaders don’t live their values on paper and not a place that I want to work.

What worked really well in your re-onboarding experiences? What helped you feel good and up to speed faster?

I stacked my first days back with one-on-ones with my manager and other team members and asked each a series of questions to reorient myself, e.g.,

• How are you and your team doing since I’ve been out? What is morale like?
• Of the goals / work plan that we laid out before I left, what was accomplished? What’s still open?
• What roadblocks are you running into?
• What unexpected things happened while I was out? Any surprises?
• While I re-onboard, what are 2-3 things that I can do to be helpful to you? (Could be removing roadblocks, workshopping an idea, etc.)

Those meetings allowed me to get reacquainted to the landscape and any shifts. I then worked to develop and communicate my plan for my first few weeks back, including what my priorities were and where I would be focusing. This is always important for expectation setting, but helped to also serve the purpose of giving me a north star to stabilize myself, while I was re-orienting.

What did your manager or company do that was really helpful to your success transitioning back to work?

I was fortunate that both times, my company offered a re-onboarding benefit of working 4 days a week for the first few weeks back. This is extremely helpful, because it’s during that transition period that you need to learn how to balance work and parenting. With a first kid, this can come as a shock, if you are like me and want to do everything at 110%+. With subsequent kids, things are a bit easier, because you have a system that works for you (and your family) already in place (or likely you would not have gotten to the second kid,) however that system still needs a re-think as you adjust to the increasing complexity of family logistics as parents of multiple kids.

While the re-onboarding benefit is helpful, it’s a pretty rare one. For managers working in companies without it, I think we can still be understanding that our employees are going through a meaningful life transition and look for other ways to help support them, e.g., share stories of your own transition, encourage them to go to those pediatric doctor’s appointments with their partner who may still be on leave, etc.

If you had to name one thing (something you do, something you buy, something you have) that has had the greatest impact on your ability to manage working parenthood, what would it be?

They say it takes a village to raise a child, but unfortunately for those of us who don’t have family nearby, the village can be hard to come by. As someone who made a transition to the parenting space after the birth of my first kid, it’s been refreshing to see the rise of products designed for moms and dads to make things easier when you are trying to do it all. The Willow breast pump has been a game changer for my wife, which in turn is a game changer for me. (Note: I’m certainly biased here, but it was great to experience firsthand how much of a difference it made from the traditional pump we used the first time around.) There are others too – Snoo for sleep, Hatch nightlife for our toddler, etc.

Many parents say that once they had children their “bar” became higher. They no longer tolerated wasteful work, unproductive meetings, etc. What else would you say changed as it relates to your career or work style once you had kids?

It’s definitely changed my approach to work – my default is no longer, ‘I can outwork anyone or any problem.’ There are still times when that is necessary, but it’s not my primary tactic. Rather, I think more about breaking problems into pieces. Determining what I should do vs delegate. I spend more time planning my approach and framing the problem vs. just diving in.

Personally, I think having kids has made me a better people manager, since pre-children, there was always this lingering doubt about whether I should ‘just do it myself, since it will be faster.’ Today I’m much better at investing the time to teach, since ultimately everyone wins.

How would you describe the difference between returning to work after your first child vs. your second child?

Returning after the first child was a daunting task, because none of the systems that I had in place to be successful at work translated well to also being a successful partner and dad at home. I needed to overhaul everything (on very little sleep.)

With the second leave, there were systems in place already that supported working and raising a child. So it was more about adjusting them to figure out how they scale with another kid – and how to deal with the hurricane of getting two kids out the door in the morning…

What boundaries do you maintain as it relates to work/home? How have these boundaries shifted over time?

Learning to set boundaries was one of the hardest transitions in becoming a parent. I remember the first few months back at work with my first child, I felt like I was constantly taking work brain home with me and home brain to work. Without boundaries between the two, they blurred together and no one benefitted from this arrangement. I realized that I needed to create space between the two where I can transition from one focus to the next by mentally wrapping up one “to do” list before opening the other.

Pre-COVID, that time was during my commute. When I got on the train, I would start transition time – I’d review my to-do list for the day, check things off, review what was open, and determine what could wait for tomorrow vs. what absolutely needed to be done. I’d then block time on my own calendar after putting my son to bed to re-engage on those critical items. With the list compartmentalized, I could walk into the door at home and be fully focused on being at home without the nagging feeling that I was forgetting something or the urge to check email.

I also set communication guidelines that I shared with my team, e.g., I have email alerts and Slack messages turned off after hours, but if you need to get a hold of me urgently, do this. I was a bit worried that turning off alerts would cause me to miss something critical, but I experimented with it and it didn’t. What it did do was break the cycle of unnecessary late night responses. I learned from my team that when they saw an email from me in the evening, they felt pressure to respond, and if I responded to that even later, the cycle restarted and fueled this sense of being always on. In the end, everyone was happier.

Did you ever consider taking less than the total parental leave you were allowed? What made you feel confident that you could take extended time away from work for parental leave?

Definitely – I did consider taking less time. Ultimately, my decision to take the full leave was very much the result of the encouragement of my business partner/ mentor at the time who helped me shift my mindset around the signals that I was sending by not taking it.

I still remember that conversation well and have since tried to pay it forward. I’ve been fortunate in my career since my first child – I’ve had the opportunity to have similar conversations with new parents in my own team and I always tell them the same thing: If you don’t take the leave, consider what signals you are sending to more junior team members. We have the leave policy for a reason and I’d encourage you to take it, so that you can support your partner (who is probably also wondering how much leave to take and how they’ll manage by themselves if you don’t) and immerse yourself in this new life experience.

You recently had your second child (congrats!) while at Willow Pump which is a much smaller company than Airbnb. How has this experience been different (planning, strategizing for leave, etc.)?

The biggest difference between the two is the need to be really thoughtful about my leave coverage plan, since a much smaller company has a lot less functional redundancy, i.e., there isn’t likely to be one person to hand over everything to. I found that it doesn’t make it impossible to take the leave, it just requires more planning on who / what should be handed over, which has a silver lining in that it can create opportunities for people or the chance for someone to get exposure to a new area of the business.

It’s great to see though if a company our size can make space for all new parents to take 16 weeks paid with their newborns, then it’s definitely possible at larger institutions.

You’re one of the “lucky” fathers in the U.S. who has received extended paid parental leave. How have you and your wife utilized your leave to benefit the entire family? How did you think about when to take leave and how to best spend your time?

I’m definitely in a fortunate position to work at a company that provides a generous parental leave benefit. Having the time has really allowed my wife and me to both more equally share the burden of childcare, while also sharing in the highlights and joys of the early days together.

Most parents that I know wrestle with whether both parents should take their leaves simultaneously or sequentially – both have merits. Simultaneous allows sharing the load of those first really tough weeks, whereas sequential allows parents to have the longest coverage before needing to find full time childcare. The extended leave benefit allowed us to have the best of both worlds – sharing the ups and downs of the first ~8 weeks together and then allowing us each to go back to the office without worry that the homefront was in control.