Employee frustrated after boss questions her for not working during leave

We don't talk enough about what boundaries actually cost in small teams. On paper, everyone says the right thing—“of course, take your leave,” “disconnect, we’ll manage,” “just hand over anything urgent.”
But when it’s your boss texting you during your break, asking for updates on supplier research that takes hours of legwork, the rules shift. Suddenly, silence feels like disobedience. Rest feels like a risk.

That’s the tension at the heart of a Reddit post that recently struck a nerve in the Singaporean work community. The story was simple. A team member took two days of approved annual leave. Her boss texted her with a request anyway. When she didn’t deliver by the time she returned, he made a snide remark: “Wah, so busy ah?” She had barely stepped through the office door.

This wasn’t about poor planning or negligence. It was about permission that wasn’t real. Boundaries that weren’t respected. And a system that pretends to care about rest—but punishes people for taking it seriously.

Let’s be clear. The employee had followed all protocol. Her leave was approved in advance. Her supervisors signed off, including the one who would later message her.

The request came on her first day off. It wasn’t urgent—just a standard procurement task. Research suppliers for a few items. Time-consuming, yes. But not mission-critical. She chose not to respond that day, wanting to preserve her time off.
On the second day, the boss followed up. She replied politely: “Allow me to follow up tomorrow.” That was her boundary, drawn clearly.

And yet, the moment she walked back into the office, she was questioned—mocked even—for not jumping straight into work the second she arrived.
Less than a minute into her day, the comment came: “Wah, so busy ah?”

This isn’t just rudeness. It’s a breach of a deeper agreement. The unspoken pact that if you plan, hand over, and disconnect as intended—you won’t be penalized. But here, she was. And that’s where things start to fray.

In a startup, we like to believe we’re informal. Chill. No hierarchy. But a comment like “so busy ah?” isn’t casual. It’s not a joke. It’s power play dressed in sarcasm.

Because what it actually communicates is this:
“I was waiting for you to work—even when you weren’t supposed to.”
“I’m disappointed you didn’t do more.”
And worst of all:
“I won’t say it directly, but I will remind you that you don’t fully control your own time.”

These moments accumulate. Quiet jabs. Passive pushbacks. And over time, a message forms in the team: being unreachable, even with permission, is frowned upon.

You start to see it in behavior. People say “I’m on leave” but still check Slack. They respond to texts on Sundays. They downplay sick days. Because the system has taught them that disconnecting—even temporarily—comes with relational risk.

This isn’t about one rude comment. It’s about founders and leads using tone and timing to reassert control when they feel discomfort. When someone else holds a boundary they wouldn’t dare hold themselves.

Here’s the thing. Most founders don’t intend to violate boundaries. They simply haven’t built systems to hold people when they’re away. So when they need something, they default to the same behavior that’s always worked—texting whoever knows the answer. Except this time, that person is on leave.

And instead of planning ahead, handing off properly, or waiting a day—they push. Softly. With a “hey, can you take a quick look?” And when they don’t get the speed they want, they respond with sarcasm. Or skepticism. Or withdrawal.

I’ve seen this pattern over and over. And every time, the team member wonders: Was I wrong to take leave? Did I let someone down? Am I being too rigid?

The founder, meanwhile, wonders why their team doesn’t take initiative. Doesn’t go the extra mile. Feels “checked out.” But what really happened is this: trust was broken under the surface.

The founder mindset often rewards responsiveness. We’re trained to believe speed is loyalty. That being always reachable is a sign of ownership. But in reality, it creates emotional debt in the team.

Every time someone responds to a late-night message or skips lunch to answer a Slack ping, they’re saying yes to you—but no to themselves.
And every time they do that without acknowledgment, their trust erodes a little more. Eventually, that’s what drives disengagement. Not pay. Not policy. But the unspoken expectation that you’re never really allowed to stop.

When your team starts treating leave like a “soft availability window,” you’ve already lost the culture you thought you had.

Let’s be brutally honest here. Most founders don’t have a boundary problem. They have a control problem. They trust their team’s talent. But not their absence. They trust delivery. But not systems. They approve leave. But still want replies.

Why? Because they never learned to design for unavailability. They never built workflows that assumed people would be offline—not just “delayed.”
So when someone’s off the grid, they panic. Or get passive-aggressive. Because now they feel the system isn’t working.

But it is working. It’s working as designed. The real failure is that there was no system—just people compensating for gaps with responsiveness. And that doesn’t scale.

If you're building a team, here’s your wake-up call:
If you can’t let someone disappear for 48 hours without getting itchy, you don’t have a team. You have a dependency network.

So how do you fix it?

Start here:
Assume every team member will be unreachable for two full days, every month.
Now ask: What breaks?

If the answer is “nothing,” your system is strong. If the answer is “I’ll need to text them anyway,” you have fragility disguised as flexibility.

Next, implement a true handover model—not just a Slack message. Assign a human fallback. Document key actions. And say this out loud:
“Unless it’s life-threatening, please do not contact [Name] during this window. If it’s urgent, speak to [Backup].”

And mean it.

Then, when they return, don’t greet them with “What are you busy with?”
Instead, say, “Welcome back. Hope you got a real reset. Let’s sync when you’re ready.” That line alone rebuilds more trust than any performance bonus ever will.

If your team hesitates to take leave, it’s not because they’re hardworking. It’s because they’re scared of the consequences of absence. That’s not dedication. That’s cultural dysfunction.

And here’s the hard part to hear:
If your team feels guilted for being offline, it’s because you trained them to feel that way. Through small messages. Weekend pings. Sarcastic comments. You didn’t have to say “don’t take leave.” You just had to act disappointed when they did.

And if you’re reading this and thinking “I don’t do that,” but you’ve ever made a team member feel nervous about being away—you need to look closer.

When you build a team, your role isn’t to be everywhere. It’s to ensure that everything doesn’t fall apart when you’re not there. That means creating systems that survive absence. That means modeling the behavior you expect. That means not messaging people when they’re off—even if it would take just five minutes.

You think that message is small. But your power makes it large. And if you don’t take that responsibility seriously, you’ll break your team without meaning to. One message at a time.

When I was a younger founder, I expected everyone to respond fast. I thought being always reachable was what built trust. Now I know it does the opposite. I’ve seen how people slowly check out after being “pinged one too many times.” How sarcasm replaces safety. How approved leave turns into quiet resentment.

If I had to do it again, I’d start with this principle:
Design your team around rest—not in spite of it. Because what breaks most cultures isn’t failure. It’s exhaustion pretending to be commitment.

If your startup can’t survive someone’s two-day leave without tension, it won’t survive your own burnout. Respecting boundaries isn’t soft. It’s structural integrity. Build like you mean it.