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Because what people feel safe doing matters as much as what they’re allowed to do

Welcome back, aspiring and current Chiefs of Staff! 👋

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🚨 Don’t Miss Us at Boston & New York Tech Week!

Tech Week is one of my favorite times of year! And this spring, Ask a Chief of Staff is showing up again in a big way. We have two panels and two happy hours across Boston and New York, and I would love to see you there! 💜

📍 Boston Tech Week (May 26-31)

🎤 How Chiefs of Staff Grow & Scale | Tuesday, May 26, 6–8pm

Co-hosted with Industrious. A panel conversation about what it actually looks like to expand your scope, build leverage, and evolve with your organization as it scales. Real talk, real examples. RSVP here.

🥂 Boston Chief of Staff Happy Hour | Wednesday, May 27, 6–8pm

Skip the small talk and come meet people who actually get the role. Good conversation, good company. RSVP here.

📍 New York Tech Week (June 1-7)

🎤 How Chiefs of Staff Build Knowledge Systems That Scale | Tuesday, June 3, 6–8pm

Co-hosted with Notion. A deep dive into how high-performing Chiefs of Staff design systems that keep teams aligned, informed, and moving fast. RSVP here.

🥂 NYC Chief of Staff Happy Hour | Wednesday, June 4, 5–7pm

Co-hosted with The Malin. Same energy as Boston, different skyline. RSVP here.

Full Tech Week Calendar

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👶 What Does Your Company's Parental Leave Policy Really Say About Its Culture?

This week’s issue is guest authored by Ellise McDonald, Chief of Staff and certified EOS Integrator^TM at a Series C company where she has spent nine years building systems, shaping culture, and integrating all the moving parts. A Brown University graduate with a background in public health, Ellise brings a human-centered lens to operations and strategy. She also serves as an Ask a Chief of Staff Mentor.

Returning from parental leave changes more than your schedule. It changes how you see work, how you prioritize, and how company policies really impact families.

Parental leave is one of the clearest signals of how a company actually supports the people who work there.

Let me explain.

About a year ago, I returned from maternity leave and hosted a small fireside chat called From Strategy to Sippy Cups. What started as a casual conversation about returning to work quickly turned into something deeper. We ended up talking about how parental leave policies shape families, careers, and company culture in ways that are often invisible until you experience them yourself.

Before becoming a parent, I understood parental leave mostly as a benefit. It was a line item in a handbook or part of a recruiting conversation. After living through it, I realized it is much more than that.

📋 Policy vs. Reality

One of the first things that came up during that fireside chat was the imbalance that often exists between maternity and paternity leave.

In many workplaces, mothers receive longer leave while fathers or non-birthing parents receive only a few weeks. Even when policies appear generous, culture sometimes tells a different story.

My husband experienced this firsthand when we lived in Massachusetts. The state offers Paid Family and Medical Leave that allows parents to take up to twelve weeks after the birth of a child. On paper, that meant he could have taken significantly more time. In practice, his company only offered two weeks of paternity leave. The rest technically existed through the state program, but taking it would have felt risky for his role and reputation. Like many fathers in that situation, he took the two weeks and returned to work.

Policies exist, but cultural signals determine whether people feel safe using them.

There is often an unspoken fear that taking the full leave available to you could quietly impact how you are perceived, the opportunities you are given, or how quickly you are trusted with critical work again. Nothing about that experience was unusual.

🌍 A Global Perspective

Another lens that often changes the conversation is looking beyond the United States.

Our team has colleagues in Montreal, and parental leave there looks dramatically different. In Canada, many parents can take close to a year of leave. In the United States, twelve weeks is often considered generous. Even that is not guaranteed for everyone. Some workers rely on saved PTO to cover their leave. Others take unpaid time away from work.

The comparison is not about saying one system is better than another. It simply highlights how much of the responsibility often falls on individual families to figure out how to make it work.

💼 The Return to Work Reality Check

The biggest lesson for me came after returning to work.

Before having children, I remember noticing a group of parents who were often back online later in the evening. After bedtime routines were finished, emails would start moving again and messages would pop up. Sometimes it was catching up on work from earlier in the day. Other times it was simply the reality of leadership roles that do not always fit neatly into a nine-to-five schedule.

After becoming a parent, I understood that rhythm much better. Many people are balancing competing priorities throughout the day and then finding pockets of time to finish what needs to get done.

I came close to falling into that pattern myself. I remember a stretch of a few nights in a row where I logged back on after bedtime to catch up. By the third night, I paused and thought: this cannot become my normal.

There are seasons when late nights are unavoidable, and leadership roles sometimes require it. But one thing I realized during parental leave is that evenings had become something I wanted to protect. After a full day, reading bedtime books and winding down with family became an important way to reset.

For me, that meant focusing more during the day so that logging back on at night became the exception rather than the rule.

Work had always been a huge part of my identity. In many ways it felt like my first baby. Then my actual baby arrived and quietly reordered my priorities.

The shift was both disorienting and clarifying. For the first time, I felt a real need to put guardrails around my time. I became more intentional about how I spent my day, more focused on what actually moved things forward, and less willing to let work expand into every open space.

It also changed how I thought about my role. Instead of being in the middle of everything or constantly firefighting, I started thinking more about how to build systems that could run smoothly even when I was not there.

My job is still important. But it is no longer the center of everything.

💛 If You’re In It Right Now

If you are reading this while preparing to go on leave, or just coming back from it, this part is for you.

One of the hardest things to accept is that the job and the company will move forward with or without you. Decisions will be made. Priorities will shift. New dynamics will form. And when you return, there may be moments where you feel out of sync or like you missed more than just time.

That feeling is real. And it is more common than people talk about ❤

There can also be a quiet pressure to stay close to work while you are out. To check in. To keep context. To not fall behind. But what I wish someone had told me is that this time is finite, and it matters in a different way than anything happening at work.

You will rebuild context. You will find your rhythm again.

The time with your child, the time to recover, and the space to step fully away is harder to get back.

✨ The Quiet Influence of Chiefs of Staff

This is where Chiefs of Staff often play an unexpected role.

We are not always the ones writing formal HR policies. But we are often in the room when leadership teams discuss benefits, productivity, and culture. We see how policies are interpreted in practice.

That proximity gives Chiefs of Staff a quiet kind of influence.

I was reminded of this after the fireside chat, when a soon-to-be dad reached out to me. He asked a simple question on the surface: should he take all of his paternity leave at once, or split it up?

But underneath that question was something else. He was trying to understand what was actually safe to do. What would be supported. How it might be perceived.

It was not really a policy question. It was a culture question.

Moments like that are where Chiefs of Staff can have an outsized impact. Sometimes it is not about rewriting a policy. It is about helping leaders recognize the signals they are sending, and helping individuals navigate the space between what is written and what is practiced.

The most meaningful changes often start by paying attention to those moments and asking what they reveal. Over time, patterns emerge around who takes leave, how long they take, and how supported they feel when they return.

And those patterns say far more about a company’s culture than any policy ever will.

Whether you are the one heading out on leave, just finding your footing on the way back, or the person in the room when these decisions get made, you have more influence than you might think. The culture around parental leave does not change all at once. It changes one conversation, one exception, one moment of paying attention at a time.

Thanks for reading! This post is public so feel free to share it.

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