How caregiver support strengthens teams

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We didn’t think we were building a company for caregivers. We were building a startup for ambitious people—fast learners, full-stack problem-solvers, folks who could roll with ambiguity and own outcomes. We thought we had the right idea, the right timing, and the right team.

What we didn’t realize was this: the moment someone became a caregiver—whether for a child, parent, or partner—they became invisible to our systems. Not intentionally. But structurally. The assumptions we made about work hours, meeting cadence, urgency culture, and even communication tone—none of it had space for someone juggling care. And the worst part? We didn’t notice the cracks until someone quietly opted out.

When our first product manager went part-time after maternity leave, we thought we were being flexible. We let her set her own hours, dial in remotely, and skip late meetings. But beneath all the understanding, we hadn’t changed anything about how her team worked. Standups were still at 9:00 AM. Deadlines didn’t shift. Everyone else assumed she’d reply within the hour, just like before.

She kept showing up. But with a newborn who wasn’t sleeping, a house running on caffeine and white noise, and a brain stretched thin across feeds, charts, and strategy decks—she was drowning quietly. Three months later, she resigned. Not because she wasn’t committed. Because we made her choose. At the time, I chalked it up to “a tough season.” But seasons pass. And in the following year, we lost three more team members who were caring for elderly parents, special needs siblings, or dealing with burnout from constant juggling. This wasn’t random. This was systemic.

Most early-stage teams plan for the typical risks—market changes, tech delays, investor fatigue. But few founders factor caregiving into their hiring or operations logic.

In Southeast Asia especially, where extended family support is both assumed and fractured by migration or cost, many team members carry invisible loads. They wake early to prepare meals for parents. They schedule doctor appointments between product demos. They lose sleep over a relative’s diagnosis but show up smiling on Zoom.

And because we rarely name this load, we fail to design around it. We assume performance dips are personal. That absences are unfortunate but isolated. That if people cared enough, they’d figure it out. What we don’t realize is this: people are figuring it out. They’re managing hospital runs between Slack pings. They’re skipping lunch to avoid judgment. They’re rationing their energy so that no one sees the price they’re paying. Eventually, that price becomes unsustainable.

Here’s where we got it wrong: we thought caregiving looked like sudden leave or temporary absence. Something you bounce back from. But caregiving, especially for the sandwich generation, is a permanent background process. It doesn’t announce itself. It just demands more of your margin every month. A preschool illness becomes a recurring disruption. A parent’s fall becomes a string of hospital visits. A child’s diagnosis leads to new routines, assessments, therapy logistics.

The shape of caregiving is endless adaptation. And when a startup’s pace doesn’t allow for that adaptation, caregivers do what they’ve always done: deprioritize themselves, until their performance drops or they quietly step away. You don’t see it in exit interviews. You feel it in the emotional fatigue that creeps into your culture. You feel it in how your team avoids certain topics or tries not to ask for help. And eventually, if you’re paying attention—you feel it in your attrition data.

The shift for us began with one brutally honest conversation. A senior engineer asked for a call to talk about “her long-term fit.” That’s startup code for: “I’m thinking of leaving.”

But what she said next wasn’t about compensation or promotion paths. It was this: “My mom’s dementia has gotten worse. I’m the only child. I can’t do this job at 100%. But I also can’t afford to lose it. I just need the kind of support I can rely on—not the kind that makes me feel like a burden.” She didn’t want special treatment. She wanted predictability. And dignity.

That conversation forced me to confront a hard truth. We’d built a culture that praised “family first,” but penalized anyone who took that literally. We offered flex time, but judged people who weren’t “available.” We said people could take breaks—but only if they caught up later. Support, in our world, still looked like: “Just let us know what you need.” But that’s not support. That’s outsourcing the emotional labor of asking for help to the very people already stretched thin.

Real support doesn’t start with an HR doc. It starts with how leaders behave, what meetings are actually necessary, and what expectations we set without realizing.

We did four things:

First, we replaced default meetings with async updates. This removed the pressure of real-time performance and gave people autonomy over when and how they work.

Second, we normalized camera-off culture. This wasn’t about hiding—it was about giving people back agency and privacy. You can be present without being performative.

Third, we rewrote performance reviews to measure clarity, not just presence. If someone can move work forward with fewer touchpoints, that’s a strength—not a red flag.

Fourth, we made caregiving visible in our internal conversations. We stopped pretending it was “personal stuff” and started treating it like any other constraint to design around.

Was it perfect? No. But the tone shifted. People started volunteering ideas for how to support each other. Managers asked different questions. And we stopped losing great people to silence.

Let me say this clearly: supporting caregivers doesn’t mean compromising on excellence. It means acknowledging that excellence looks different across seasons—and building a system that doesn’t punish that difference. A caregiver who can deliver critical outcomes with limited bandwidth is often one of your most strategic assets. They manage time with military precision. They navigate complexity daily. They know how to prioritize under pressure—and let go of perfectionism when needed.

But if your org only rewards the loudest, the fastest, the most visible—you’re systematically sidelining that talent. And you’re sending a message that productivity matters more than people. That message costs you more than attrition. It costs you trust. It costs you institutional wisdom. It costs you the kind of team cohesion that can’t be faked in an all-hands.

If you’re a founder, here’s the real test: how does your company respond when someone needs to step back? Do you rally—or do you reassign quietly and hope no one notices? Do you adjust workflows—or do you overcompensate and guilt them later? Do you ask, “What do you need to stay?”—or do you assume they’re already halfway out?

This isn’t about optics. It’s about operating maturity. If your system only works when everyone is at full capacity, you don’t have a system—you have a dependency trap. And that trap will break your team the moment life happens. Which it will. Because caregiving isn’t a niche issue. It’s universal. It’s just unevenly distributed at any given time.

We’ve reached the point in startup culture where burnout has become a badge and overwork is still seen as a phase. But caregiving changes that calculus. You can’t hustle through a parent’s decline. You can’t mute a toddler meltdown. You can’t treat chronic illness management like a side quest. What you can do is build a company that assumes these realities and adapts with grace.

That starts with operational flexibility, not vague empathy. It means structuring goals around outcomes, not availability. It means redistributing work intentionally, not punitively. It means building systems that allow people to pause, return, pivot—and stay. Because when caregivers stay, you retain experience. You build culture resilience. You send a signal that work is part of life—not a replacement for it. And you create the kind of company people don’t just join. They grow with.

Don’t wait for the crisis. Build care into your company design from day one.

Ask yourself:

  • What happens when your top performer becomes a caregiver?
  • How would your system bend—or break?
  • What would it take for them to stay?

Then go build that version now. Make support real. Make flexibility structural. Make care a feature, not a bug. Because when you support caregivers, you’re not just being kind.

You’re being smart. You’re building a team that reflects the world as it actually is—not the world we pretend to operate in. And that kind of team? It’s the one that lasts.


Culture Singapore
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