Why saying yes all the time can sabotage success

There’s a moment that stays with me from my early days advising a startup team in Kuala Lumpur. We were in the middle of a tense sprint, working on a partnership launch that had been fast-tracked by the CEO. The goal was clear: deliver within three weeks. No time to ask too many questions. Just execute.

But something felt off. The integration wasn’t fully mapped. The support team hadn’t been looped in. Even the partner’s expectations seemed vague. I raised a few concerns, carefully, in private. So did a few others. But in meetings, everyone nodded. No friction. No resistance. Just a series of yeses that kept the plan moving forward—toward what we all suspected would be a mess.

And it was.

The launch flopped. Customers churned. The partner complained. Internally, trust eroded. And the CEO? He was furious. But not just at the outcome. He was furious at the silence that came before it. “Why didn’t anyone say anything?” he asked. He meant it.

It’s a question that gets asked in every broken team, eventually. And the answer is almost always the same: “I didn’t think it was my place.”

Let’s unpack that. Because doing what your boss says without clarity or conviction doesn’t make you a great team player. It makes you a liability.

In early-stage startups, this pattern is especially dangerous. Small teams move fast. Roles blur. Founders carry enormous pressure. In that environment, obedience gets mistaken for alignment. And the habit of following orders without friction gets reinforced—until something breaks.

But here’s the truth: if your name is on the delivery, your judgment should be in the decision. Otherwise, you're not building a company. You're performing in someone else's script.

The situation I saw in KL wasn’t unusual. It happens everywhere. Founders with vision and urgency make bold calls. They speak with confidence, even when conditions are shaky. And the team, eager to execute and stay in good favor, falls into lockstep. Feedback softens. Questions stay inside heads. Everyone leans into the momentum. It feels efficient. But it's false efficiency. Because when the cracks show—and they always do—the cleanup is messier than the friction would have been.

I’ve learned to pay close attention to the “quick nods” in meetings. The quiet assent. The absence of second-order thinking. Those are warning signs. Not of laziness or apathy—but of emotional overalignment. The kind that confuses loyalty with obedience.

It usually starts from a good place. You believe in the founder. You trust their instincts. You want to move fast. And you don’t want to be “that person” who slows things down. But the problem is, when everyone avoids being that person, no one holds the line. The business starts making decisions with no internal challenge function. And you start accumulating silent debt—execution debt, trust debt, culture debt.

The real damage isn’t just the failed launch or the frustrated client. It’s the internal rot that spreads when people stop using their own judgment. Teams lose the muscle to disagree well. Founders lose visibility. Accountability becomes foggy. And suddenly, the company is running on vibes and velocity—not on clarity or conviction.

So let me say this plainly: your job isn’t to agree. It’s to think. And in high-accountability environments, that means pushing back when something feels off. Not rudely. Not performatively. But clearly.

In that KL startup, one product lead told me, “I felt it was wrong, but I assumed someone else had thought it through.” Another said, “I flagged it quietly in Slack, but I didn’t want to make a scene.” These are smart, capable people. But they’d been conditioned to execute, not to challenge. The founder, meanwhile, believed his team would speak up if there were issues. He thought silence meant support. He was wrong.

The misalignment between what leaders think they’re communicating and what teams feel they can say is a silent killer of startups. And the deeper problem isn’t always ego. Sometimes it’s structural. If your standups only ask for updates, not concerns, don’t be surprised when no one raises risks. If your leadership style rewards pace over process, don’t be shocked when shortcuts become systemic. If your culture glorifies the founder’s vision, don’t be confused when no one questions the map.

Here’s what I tell founders now: your team will take their behavioral cue from you. If you only ever want speed, they’ll give you speed—even if it kills the project. If you don’t ask for input before decisions are made, they’ll learn that speaking up is futile. If you say “my door is always open,” but never change direction based on team feedback, they’ll learn that the door is decorative.

And here’s what I tell team members: if you stay silent about a decision you disagree with, and it breaks, you are complicit in the failure. Your job isn’t to defer. It’s to co-own.

Ownership without voice isn’t ownership. It’s theater. And in a real startup, no one has time for performances.

The moment of clarity for the KL team came two weeks after the launch failed. The CEO pulled the senior team into a room and said, “From now on, if you see something wrong, I want you to speak it—directly, clearly, and early. I’d rather get into a fight than walk into another mess with fake harmony.”

It changed things. Not overnight. But slowly, the team learned to disagree in public. They built rituals—like pre-mortems and red-flag Fridays—to surface concerns. They added roles to meetings to ensure someone was always tasked with challenging assumptions. The culture got sharper. Not meaner—sharper. And results got better.

The founder had to learn to accept friction as a form of trust. The team had to unlearn obedience as a default setting. That’s the shift. It’s not about being loud. It’s about being responsible.

In Southeast Asia especially, this can be hard. Many teams are shaped by cultural norms that reward harmony, respect, and hierarchy. Challenging a boss—even with good intent—can feel risky. But startups aren’t traditional companies. They’re experiments in speed and risk. And the price of unchallenged hierarchy is too high.

I’ve mentored founders in Singapore, Indonesia, and Saudi Arabia who’ve struggled with this dynamic. Brilliant operators who can’t get their teams to push back. Talented teams who burn out trying to deliver flawed plans they never believed in. The root cause is almost always the same: a culture that treats obedience as virtue.

But the best founders I know? They don’t want silent yes-men. They want sharp co-builders. They want feedback, not flattery. And they know that disagreement isn’t disloyal—it’s protective.

If you’re in a team right now where you feel tension but aren’t speaking it, ask yourself: What would it take for me to say this out loud? What am I protecting—my relationship with my boss, or the future of this project?

And if you’re a founder reading this, ask yourself: What signals am I giving my team about disagreement? Have I punished people for challenging me? Have I rewarded the fastest yes over the most thoughtful no?

Because in the end, startups are built on decisions. And good decisions need friction. Not chaos. Not ego. Just friction—the kind that sharpens clarity and catches blind spots before they scale. Obedience doesn’t build resilience. It builds dependency. And dependency is fragile. Especially when the founder is tired, distracted, or wrong.

So the next time your boss tells you to execute something that doesn’t sit right, don’t freeze. Don’t disappear into Slack. Don’t whisper your doubts in DMs and move forward anyway.

Ask the hard question. Make your thinking visible. And if it’s still a go, then own it fully. Because that’s what high-trust, high-accountability teams do. They speak. They disagree. They commit. And they build better, faster, and stronger because of it.

No startup needs another obedient executor. What they need is someone willing to risk discomfort for the sake of clarity. Someone who knows that loyalty without judgment is just compliance in disguise.

So speak. Even if your voice shakes. Especially if the room is quiet. That’s not rebellion. That’s leadership. And if you’re a founder reading this, make it safe. Not easy—safe. Because safety creates voice. Voice creates clarity. And clarity? That’s where real momentum begins.