We all assume we’ll handle it professionally—until we’re in it. Or worse, until it’s one of our co-founders. Or someone too close to the center of decision-making. That’s when things start to fray in places you can’t quite name. And by the time you notice what’s broken, it’s not about the relationship anymore. It’s about your team’s trust in how you lead.
You’ve probably seen the headlines. A CEO and his HR head caught sharing an intimate moment at a Coldplay concert. A viral video. Public backlash. Suddenly, an entire company’s culture gets questioned over one evening of poor judgment. In that moment, it’s easy to roll your eyes and think, “That would never be us.” But if you’re a founder building in the early stages, the question isn’t whether workplace relationships are ethical or not. The question is whether your team knows what boundaries look like—and whether you do.
A new Milieu Insight survey shows that older workers in Singapore are most likely to find love at work. Thirty-eight percent of baby boomers say they met their most recent partner at the office. For Gen X, it’s still nearly 30 percent. That’s significantly higher than other groups. But the interesting part isn’t just how people meet—it’s how each generation defines what’s acceptable. While 38% of boomers say workplace relationships are fine in any context, most millennials and Gen Zs only agree if HR is informed and clear boundaries are respected.
That generational shift matters. Because the people joining your team today—your first hires, your future leaders—don’t want policies that ignore power dynamics. They want clarity. And if you’re not ready to give it, you’re already behind.
In the early days of building a startup, everything feels personal. You’re moving fast. You’re huddled over the same laptops, pitching the same deck, eating late dinners while debugging code or prepping a pitch. You share wins, losses, long nights, and longer weekends. Emotional proximity becomes the default operating mode. It doesn’t take long for those lines between professional respect and personal connection to blur.
It’s not unusual. It’s human. And in some cases, it even works out well. But here’s the hard truth most founders won’t say out loud: every workplace relationship introduces a shift in power. And in a small team, there is no such thing as “this is private.” Even if the relationship is between peers. Even if no one’s hiding anything. Once trust starts to feel conditional—once team members begin to second-guess how decisions are made—it doesn’t matter if your intentions were good. The damage has already begun.
The breakdown doesn’t usually come with a bang. It starts in the silence. A colleague notices someone getting more leeway on deadlines. Another team member stops volunteering ideas in meetings. Someone else withdraws from after-work socials. Then one day, a high performer quits—and the reason they give doesn’t add up. But if you talk to the rest of the team, they’ll tell you what really changed: the feeling that things weren’t fair anymore. That what mattered most wasn’t work. It was access. Access to the right person. Access to the inner circle. And that’s the kind of drift that kills a team’s energy long before it kills their output.
That’s what happened to me years ago in one of my early ventures. I wasn’t in the relationship. But my co-founder was. And for months, I ignored the shift. The partner in question wasn’t even in a leadership role. She wasn’t making big calls. But slowly, things tilted. She’d sit in on meetings she didn’t need to be in. She’d push back on decisions that weren’t hers to make. The worst part? My co-founder didn’t see it. Or maybe he didn’t want to. He’d just say, “She’s being protective,” or, “She’s giving good input.” And because I didn’t want to start a fight, I said nothing.
What I didn’t realize then was that silence is a decision. Every time I let it slide, I was teaching the rest of the team that proximity trumped contribution. That relationship status mattered more than role clarity. And when two of our earliest hires left within the span of three weeks, I finally had to admit it: we hadn’t failed at execution. We’d failed at culture.
In a corporate setup, you can write a policy and bury the problem under compliance. But in a startup, there is no place to hide. Culture isn’t in your employee handbook. It’s in every decision you make when no one’s watching. It’s in who you promote. Who you listen to. Who you shield. And once your team starts feeling like those rules change depending on who’s involved, you lose something you can’t buy back.
The Milieu survey found that 63% of Singaporeans across all age groups believe leaders should be dismissed if they breach company policy or behave inappropriately in a personal context. That number should make every founder pay attention. Because it’s not just about public scandals. It’s about how your team perceives accountability. And if your leadership team—yourself included—can’t model what ethical boundaries look like, then it won’t matter what product you’re building. You’re already scaling rot.
So what do you do if something starts brewing on your team?
First, drop the fantasy that you’ll deal with it when it comes up. You won’t. Not cleanly, at least. Because by the time it lands on your desk, someone’s already uncomfortable. Someone else already feels cornered. And you’re already too late.
You need to set the standard early—before it gets personal. And I’m not just talking about a boilerplate HR policy downloaded off the internet. I mean a founder-level clarity statement. What does your company believe about workplace relationships? When should they be disclosed? What safeguards exist to ensure fairness, especially when the power gap is wide? And most importantly, how will you protect your team’s ability to speak up if something feels off?
This isn’t about punishing people for falling in love. It’s about making sure that love doesn’t come at the cost of psychological safety. Because in a small team, even one perceived imbalance can shift the whole emotional terrain. You might not feel it immediately. But you’ll see it in your next round of hiring. In your performance reviews. In how your leadership gets challenged—or doesn’t.
And if you, as the founder, find yourself in a relationship with someone on the team, that clarity becomes even more critical. Step back from managerial duties. Reassign performance reviews. Make sure someone else—not your partner, not you—owns the key decisions involving each other’s work. It’s not about shame. It’s about demonstrating that power won’t be abused, even when no one’s looking.
The truth is, in an early-stage startup, everyone’s watching—even when they pretend not to be. They’re watching who gets pulled into strategy discussions. Who gets second chances. Who gets left out. And if they see favoritism, or worse, fear that speaking up will get them isolated, you won’t just lose good people. You’ll lose your culture’s integrity.
Workplace relationships aren’t new. They’re not inherently bad. But the context matters. In big companies, layers of hierarchy and HR procedures create buffers. In startups, the lines are too thin. One blurred boundary can distort everything. That’s why the damage feels outsized. Not because founders are more flawed. But because the system is more exposed.
When people say “it’s just gossip,” they’re missing the point. Gossip happens when truth is unclear. When people don’t trust the formal process, they create their own version of events. And those narratives, once set, are nearly impossible to unwind.
Fifty-four percent of Singaporeans in the Milieu survey said workplace relationships stir gossip and create uncertainty. That’s not a call to ban romance. It’s a call to build cultures where gossip doesn’t need to fill the gaps.
And that starts with founders who are willing to say the quiet part out loud: that love and leadership don’t always mix, and when they do, it has to be managed with more—not less—intentionality.
Because what you model becomes your culture. Not your values poster. Not your team offsite. What you permit. What you protect. And what you pretend not to see.
If I could go back to that early-stage company, I wouldn’t have waited. I would’ve had the hard conversation sooner. Not to shame anyone. But to protect what we were building. Because startups don’t die from one big blow. They die from erosion—of trust, of clarity, of shared belief in the mission.
So if you’re a founder reading this and thinking, “We’re good. Nothing’s happening on my team,” I’d still ask: have you set the rule? Do your people know what happens if it does? Not because you expect it to. But because you understand that culture is proactive, not reactive.
Love can happen anywhere. That’s not the problem. The problem is what happens when no one knows who’s in charge of protecting the rest of the team from the fallout. And if that’s you, don’t wait for the fallout to start asking the right questions.
Start now. Set the rule. Say it out loud. And mean it.
Because the strongest companies aren’t the ones that avoid every misstep. They’re the ones that don’t flinch when clarity is called for. Even—especially—when the lines get personal.
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