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How to take family leave if you're the boss

This piece originally appeared on Amanda Litman’s Substack, and we're so glad to share it here. Amanda writes thoughtfully about leadership, parenting, politics, and much more. You should learn more about her, subscribe to her Substack and grab her book When We’re in Charge. Don't delay, go buy the book. Image by Naima Green.


Scott Galloway, notorious podcaster/marketing professor/capitalist/masculinity influencer, has been stirring up a debate by saying something really really stupid.

From Jessica Grose’s excellent piece on the controversy:

Scott Galloway said, “I think dads are mostly a waste of time or space” for the first few months of a child’s life. He continued:

I think there should be mandatory maternity leave, because I think the species needs to propagate. I’m not sure there should be mandatory paternity leave. I think it sometimes creates resentment. I think sometimes it’s abused. And so I’m a bit of a capitalist here. I think it’s between the company, but I don’t know if I immediately default to oh, the father needs to be there.

Galloway also commented that he doesn’t think men should be in the delivery room. “I thought that was so disgusting and unnatural,” he says.

I don’t think Scott Galloway is wrong on everything. I listen to him on Pivot pretty regularly, and I often appreciate his perspective, even if I don’t agree with them. I think he can be a really effective messenger on lots of topics to an audience that needs to hear them from someone like him. (I also think his Resist and Unsubscribe campaign is grounded in a smart theory of change and if you’re looking for a way to push back on big tech, it’s worth checking out.) I’m not #cancelling him — after all, a “big tent” means including having allies who sometimes say stuff I disagree with.

All that’s to say, read this from a place of generosity:

When it comes to the importance of taking paternity leave — for the company, for both parents, for the kid, and for the family as a unit — Scott Galloway is 100% wrong.

It may seem ridiculous or privileged to debate whether men should take family leave in the context of a country where, somehow, barely a quarter of workers of either gender have access to paid leave, and fewer than 60% have access to unpaid leave.

The United States is the only industrialized nation to not have a national paid family leave program, and at the local level, only 23 states have paid leave programs.

And while family leave should not be a problem for individual companies to solve, alas, it is, and bad news, individuals are also failing. According to BLS statistics, only 40% of employers offer paid parental leave.

I can’t find data on this, so take it with a grain of salt, but I would venture a guess that many of the companies that do not have paid leave policies are coincidentally run by leaders (probably men!) who’ve never felt they should or could take time off themselves.

See: Scott Galloway! And he is not the first older wealthy man I’ve heard make the case that paternity leave is a waste of time.

The first time I heard it, my immediate reaction was “wow what a boomer-coded opinion.” Scott and those who agree with him have a definition of fatherhood that doesn’t reflect how a newer generation of dads (including most of the dads I know!) seem to understand their role in the family unit.

Consider that in 1982, 43% of fathers admitted (I hope with some embarrassment) that they’d never changed a diaper. By 2018, thank god, that number plummeted down to 3%.

That’s a good thing, and also, a thing that complicates work life for everyone. As the expectations for dads (and, sigh, always for moms) have gone up, millennial and gen Z working dads are starting to experience what working moms have always known: trying to do it all is really really hard.

Lots of other writers have responded to Scott’s bullshit claims — I especially liked expert fatherhood researcher Darby Saxbe’s explanation on the role dads can and should play during childbirth.

Jessica’s excellent piece sums up the economic and moral argument against him, as does Paige Connell’s response, and I liked economist Corinne Low’s, too. (Even TX Congressman Greg Casar got a swipe in through an op-ed on how he took family leave after his kid was born.)

Meanwhile, Eve Rodsky (of FairPlay fame) used it as a reason to kick off a series of conversations with men about their role during labor and the newborn days.

Over in my little corner of the internet world, I want to focus on one specific question that I hear from both men and women alike who have kids and also access to leave: How to actually do it if you’re the boss.

I get it. I’ll confess didn’t quite realize how complicated this would be until I had my first daughter.

Early on, Run for Something established a family leave policy that included twelve weeks fully paid. We’d had one team member take leave over the years but not since the organization had scaled in size—so when I got pregnant with my first daughter in 2022, I prepped for my maternity leave with the knowledge that how I did it would set the tone for how all current and future employees would think about their ability to access leave for themselves. I took that example-setting seriously.

I scoured the internet for advice on how to set up a leave plan — it’s not as simple as “hand off this project to that teammate” and “call this person for that question” when the projects are things like “raise the money, speak publicly on behalf of the organization, think long-term about where we’re going and how we’re going to get there, and solve crises as they arise.”

Everything I found online was either (sadly) guides on how to convince your boss or HR department you deserve paid family leave or how to write a coverage plan to give to your boss.

There was little out there about how to take leave if you were already the boss and even less about how to prepare myself and my team for my eventual reentry.

So I queried the group-chats. I found a few peers who’d been in my shoes — leaders who also became new parents while they were in a big job.

Almost all of them simply told me: Take the leave!

“I wish I’d actually logged off,” one said to me, explaining even as she ran her own company and maybe could have (or should have) taken the time, she felt compelled to be back at work within a few weeks of delivery.

Another explained how she was half-in, half-out during her maternity leave and ultimately found it more challenging (and frustrating) both for herself and for her team than helpful.

I didn’t need convincing on that front. I wanted to take the time — for healing, for my growing family, and to show my team that we meant it when we said we had a leave policy. (Also, like all benefits, the paid leave was literally part of my compensation.)

So I had to figure it out myself. Since then, I’ve codified some advice for any person in a position of leadership who’s preparing to go on leave. (All of this and many more details are in When We’re in Charge, FYI!)

I realize this might feel crazy to write out, especially given the stats on how few people have access to leave in the first place.

But I do this because I don’t want anyone who has a baby or a caregiving responsibility to have an excuse not to take the time they need. If the boss (and especially, ahem, a male boss) doesn’t go out when they have a reason to, employees might not feel like they can either.

So consider this your playbook.

A leader’s guide to taking leave

(1) If this is within your control, ensure your company has policies that support paid family leave.

This is not always possible depending on your role, but if it is, make it happen. If you need to advocate to HR, take on the fight. If you need to argue with a board of directors, make the case.

There are countless resources online about how providing paid leave benefits to both the company and the employee is undeniably net positive.

Ideally you should do this before you have to avail yourself of this policy, but if you have to be the first to push the limits, go forth and know that caregivers everywhere have your back.

(2) If you’re preparing for a new member of your family or for taking on caregiving responsibilities in some way: I know I said this already, but I’ll say it again: Actually take the leave.

Every piece of research known to mankind shows that taking parental leave in particular is better for families, better for parents (both birthing and otherwise), and better for companies because losing employees who leave for companies with better family leave policies is extremely expensive in the long term.

If you have caregiving obligations—maybe an aging relative or a sick family member—that require your full-time attention, don’t fool yourself. Trying to do it all is not going to work for anyone; you’ll be both a bad caregiver and a bad leader in the process.

(3) If you’re wary of it, or have a member of your team who is wary about it, or anyone is under the impression they’re irreplaceable, I promise you, you’re not. Just make a plan.

As early as possible, start a running list—I just kept one in my Notes app—of all the things that made up a month of work: meetings you ran, documents you reviewed, decisions you made, crises that came up you had to solve, and silly things like, whoops, turns out your cell phone was set up as the two-factor authentication for a particular social media platform, or you’re the only one who was authorized to call American Express and add new users to the credit card account.

This is a useful exercise both for preparing for leave but also more broadly for auditing how you’re spending your time and whether or not you’re actually the best person to be tackling a particular project.

Once that list feels exhaustive, do some sorting. Which decisions could be categorized by expertise needed? Which tasks need to be handed off or sorted out now, before you go out? Whom would you need to provide context to in order to make certain decisions and who should they be consulting when they do so?

You’ll end up with various buckets of work, perhaps including categories like strategic decision-making, HR issues, external and internal communications, and more.

Then each bucket—and sometimes each individual item within the bucket—gets a new owner, along with relevant documentation or context necessary for that person to take on the work.

Do this for every single project. All of them. Even the silly ones.

In addition, lay out what things you want to be called in on.

Keep your list small. Mine included: (1) a serious personnel issue with one of my direct reports, (2) a financial problem that would have meant immediate structural changes to the organization, (3) a lawsuit, or (4) a headline or story about us bad enough in a big enough outlet that would have my grandma calling me asking me what’s happening at work and if everything’s okay.

Finally, while you should obviously prepare an out-of-office message, if you can, tag in someone to fully monitor your work email. If you have an assistant, great. If not, pick someone on your team you can trust and empower with internal materials.

They should be responsible for keeping an eye on anything incoming that should be forwarded to someone else for response or forwarded to your personal email that absolutely must be reviewed before your return.2 This person (and maybe even this person only!) should also have permission to call or text you if your attention is necessary.

This kind of rigorous prep will be exhausting. But it will give you the space to actually step away.

I found a silver lining of all this is that it allowed me to hand off all kinds of things that probably shouldn’t have been mine to begin with and to have some advanced thought into what would happen in the case of an emergency.

In retrospect, I’m glad I spent as much time as I did on this process, and I’m glad I was wrapped up with the prep about a month before my due date, since, surprise, both my daughters were born three weeks early.

(4) Prepare for reentry.

As part of your leave prep, ask someone to keep running lists of what you’ll need to review upon your return, along with any emails that you absolutely need to see and big updates you might miss. Start gut-checking with yourself before you come back to clarify where you’re at and what kind of flexibility you might need— when do you want your days to start, travel restrictions, any accommodations you might need, etc.

On your actual first few days back, if you can, keep your schedule light.

Reenter your inbox gently and review the documents prepared for you, and if relevant, debrief with the appropriate top staff. From there, schedule one-on-ones with each team member— over the next month, reenter the working world on your terms, gently and with grace for the new person you are.

I’ll say it one more time: If you are in a position of power with the ability to do so, establish policies for paid family leave. And if you or your partner are having a baby, actually take advantage of it.

If you’re the one giving birth, do it because phew your body will need it. Your brain will need it. Your baby will need it. Take as much time as you can.

If you’re the dad or non-birthing partner, take the leave because your partner will need you. Your baby will need you. Begin as you mean to go on: As a good parent!

The more people (and especially the more dads) take leave, the more normalized it becomes for all parents and the less penalties people will face.

Do it because it’s a rare period of time where you can simply focus on your family. Leave with a newborn is absolutely not a vacation — but it does narrow the spectrum of things you have to care about for a little while, and that is a form of a break.

One last piece of advice: While you’re on leave, take that baby to the movies. Check the theaters near you — lots of places have “baby days” or “baby showings” (Alamo Drafthouse and Nitehawk both do if you’re in Brooklyn!) and it’s really nice to see something on the big screen with a bag of popcorn and a baby snoozing on your chest.

This was crossposted from Amanda Litman's Substack - subscribe for more!

Leaders ready to step in when you need to step out

We embed experienced former founders into startups to maintain operational continuity during founder absences.

Leaders ready to step in when you need to step out

We embed experienced former founders into startups to maintain operational continuity during founder absences.

Leaders ready to step in when you need to step out

We embed experienced former founders into startups to maintain operational continuity during founder absences.

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Take the leave you actually need.

Your business is covered.

Take the leave you actually need.